Title: Holiday Rentals Winchester from £151: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [Hotels in Winchester](https://expedia.co.uk/Winchester-Hotels.d3000447144.Travel-Guide-Hotels)[Winchester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winchester.d3000447144.Car-Hire-Guide)[Winchester Holidays](https://expedia.co.uk/Winchester.d3000447144.Holidays-City-Breaks) ![Winchester, New Hampshire in winter ](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [27 Feb - 1 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=3000447144&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [10 Apr - 12 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=3000447144&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [8 May - 10 May](https://www.expedia.co.uk/Hotel-Search?regionId=3000447144&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [5 Jun - 7 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=3000447144&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester holiday rentals ![Exterior detail](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/fb54d968.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/8c094e30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/06a81bab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/57c0c927.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town. [](https://www.expedia.co.uk/Peterborough-Hotels-Studio-Apt-With-Full-Kitchen-1-Minute-Stroll-Over-Picturesque-Bridge-Into-Town.h102238328.Hotel-Information) Peterborough 9.8/10 Exceptional (31 reviews) "Fully equipped kitchen, comfortable open floor plan, easy walk to downtown and very hospitable—thank you—we’d like to stay here again next year!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark £123 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Peterborough-Hotels-Studio-Apt-With-Full-Kitchen-1-Minute-Stroll-Over-Picturesque-Bridge-Into-Town.h102238328.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/01ff54d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, offices](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/512b2604.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/d695e72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/7e27ff2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovely 2nd Floor Apartment [](https://www.expedia.co.uk/Greenfield-Hotels-Lovely-2nd-Floor-Apartment.h102386531.Hotel-Information) Greenfield 10/10 Exceptional (48 reviews) "Very cute apartment, clean and nice furnishings, bed was very comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew H. £151 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Greenfield-Hotels-Lovely-2nd-Floor-Apartment.h102386531.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/a4ec6964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Books](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w960h638x0y1-6a5c7328.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w2207h1242x0y0-824667c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Books](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w1125h1933x0y49-6292efb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Friendly Hilltop House In Putney Vermont [](https://www.expedia.co.uk/Putney-Hotels-Pet-And-Family-Friendly-Hilltop-House-In-Putney-Vermont.h19887179.Hotel-Information) Putney 9.4/10 Exceptional (59 reviews) "The property was beautiful--great views, super peaceful, and fabulous hosts. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Louis T. £232 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/Putney-Hotels-Pet-And-Family-Friendly-Hilltop-House-In-Putney-Vermont.h19887179.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/126000000/125300000/125300000/125299924/f2b21706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/126000000/125300000/125300000/125299924/88c9bc33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/126000000/125300000/125300000/125299924/94e00bfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/126000000/125300000/125300000/125299924/5d550d48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy & Bright Guest Suite [](https://www.expedia.co.uk/Peterborough-Hotels-Cozy-Bright-Guest-Suite.h125299924.Hotel-Information) Peterborough £142 includes taxes & fees 24 Feb - 25 Feb [](https://www.expedia.co.uk/Peterborough-Hotels-Cozy-Bright-Guest-Suite.h125299924.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/3696f739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/6c4ecd64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/e7a2f4c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/d2180d1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Adirondack Cabin with Sauna on Lake Monomonac [](https://www.expedia.co.uk/Rindge-Hotels-Beautiful-Adirondack-Cabin-With-Sauna-On-Lake-Monomonac.h106335693.Hotel-Information) Rindge 9.8/10 Exceptional (25 reviews) "This is a great property, and Jim is a wonderful host. He accommodated all our requests for sauna use and provided helpful tips about the area. We hope to return again one day!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leigh C. £261 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/Rindge-Hotels-Beautiful-Adirondack-Cabin-With-Sauna-On-Lake-Monomonac.h106335693.Hotel-Information) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/9b2c42ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/18e29612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/ad9f4a52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/c66c8a42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock [](https://www.expedia.co.uk/Rindge-Hotels-2-Bed.h88302089.Hotel-Information) Rindge 10/10 Exceptional (23 reviews) "The cottage was a great place to stay. Very conveniently located to where we wanted to travel to. It has a great view of the lake, very clean and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole B. £250 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Rindge-Hotels-2-Bed.h88302089.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/262afaed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/41130fc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/d458659b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/c9f7c522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy apt in beautiful secluded spot 15 mins from Mt Snow [](https://www.expedia.co.uk/East-Dover-Hotels-Cozy-Apt-In-Beautiful-Secluded-Spot-15-Mins-From-Mt-Snow.h113155266.Hotel-Information) Dover 10/10 Exceptional (4 reviews) "Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica H. £152 includes taxes & fees 28 Feb - 1 Mar [](https://www.expedia.co.uk/East-Dover-Hotels-Cozy-Apt-In-Beautiful-Secluded-Spot-15-Mins-From-Mt-Snow.h113155266.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/9530dfe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/40c2e2d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/962a1a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/c459a4e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning Glass House nestled in the Vermont wilderness! [](https://www.expedia.co.uk/Brattleboro-Hotels-Stunning-Glass-House-Nestled-In-The-Vermont-Wilderness.h111133438.Hotel-Information) Guilford 10/10 Exceptional (1 review) "The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Grant D. £312 includes taxes & fees 18 Feb - 19 Feb [](https://www.expedia.co.uk/Brattleboro-Hotels-Stunning-Glass-House-Nestled-In-The-Vermont-Wilderness.h111133438.Hotel-Information) ![TV, books](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/8f769c56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/4c6a2082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/d16d9700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, eco-friendly toiletries, hair dryer](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/17c13c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro [](https://www.expedia.co.uk/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.Hotel-Information) Walpole 10/10 Exceptional (8 reviews) "Beautiful cozy cottage. Very clean. Wonderful host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gloria A. £187 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/1ec609e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/b0490e8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/0997d6b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/b4e38c32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Whitingham & Mount Snow Area Village Apartment [](https://www.expedia.co.uk/Jacksonville-Hotels-Lake-Whitingham-Mount-Snow-Area-Village-Garden-Apartment-2-BR.h108320042.Hotel-Information) Whitingham 10/10 Exceptional (1 review) "This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anicia K. £224 includes taxes & fees 4 Mar - 5 Mar [](https://www.expedia.co.uk/Jacksonville-Hotels-Lake-Whitingham-Mount-Snow-Area-Village-Garden-Apartment-2-BR.h108320042.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120420000/120414900/120414848/4f40d5b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120420000/120414900/120414848/8031ab01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120420000/120414900/120414848/724bdf50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120420000/120414900/120414848/1f82fc7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Terrific 3-bedroom unit in charming Leverett with AC [](https://www.expedia.co.uk/Leverett-Hotels-Terrific-3-Bedroom-Unit-In-Charming-Leverett-With-AC.h120414848.Hotel-Information) Leverett 10/10 Exceptional (1 review) "The apartment is lovely, so comfortable and quiet!! Caitlin was a wonderful host, very responsive. Would absolutely stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anna B. £344 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Leverett-Hotels-Terrific-3-Bedroom-Unit-In-Charming-Leverett-With-AC.h120414848.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/a6a78255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/1ce3fb4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/bcfc0861.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/f2b8d538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet Mount Snow/Stratton Skiing/hiking [](https://www.expedia.co.uk/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information) East Dover 9.8/10 Exceptional (10 reviews) "Easy to find! Clean! Cozy!! Would definitely stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy-michael G. £321 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/25e52beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/c6092f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/9396f37e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/6faf555f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Finnish Cabin with Sauna on Lake Monomonac [](https://www.expedia.co.uk/Rindge-Hotels-Finnish-Cabin-With-Sauna-On-Lake-Monomonac.h106476934.Hotel-Information) Rindge 10/10 Exceptional (11 reviews) "Amazing place. We really enjoyed our brief stay. Great host. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary S. £205 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Rindge-Hotels-Finnish-Cabin-With-Sauna-On-Lake-Monomonac.h106476934.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/84000000/83070000/83064100/83064044/bb59d3ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83070000/83064100/83064044/af204105.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83070000/83064100/83064044/ee57533b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83070000/83064100/83064044/0e213458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Enjoy your stay in an antique home in an antique toy museum! [](https://www.expedia.co.uk/Winchendon-Hotels-Enjoy-Your-Stay-In-An-Antique-Home-In-An-Antique-Toy-Museum.h83064044.Hotel-Information) Winchendon 9.4/10 Exceptional (8 reviews) "What a fun stay! Great communication with the property manager Don, cute town, lots of American history to be discovered, fun stay. 10/10 highly recommend!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katja Z. £373 includes taxes & fees 14 Feb - 15 Feb [](https://www.expedia.co.uk/Winchendon-Hotels-Enjoy-Your-Stay-In-An-Antique-Home-In-An-Antique-Toy-Museum.h83064044.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/8d9f525d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/4e846ae7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/e0a6d5c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/6cc8f8eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails! [](https://www.expedia.co.uk/Keene-Hotels-The-Leverett-House-In-Charming-Keene.h117913271.Hotel-Information) Keene 10/10 Exceptional (2 reviews) "Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Xilin J. £373 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Keene-Hotels-The-Leverett-House-In-Charming-Keene.h117913271.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/019323ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/b4c71f0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/89c4c4df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/31e9eac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Downtown 12ppl Hot Tub Fire Pit Games [](https://www.expedia.co.uk/Keene-Hotels-Downtown-Hot-Tub-Escape.h97317603.Hotel-Information) Keene 9.6/10 Exceptional (22 reviews) "Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jack P. £226 includes taxes & fees 26 Feb - 27 Feb [](https://www.expedia.co.uk/Keene-Hotels-Downtown-Hot-Tub-Escape.h97317603.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/1a650c93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, video library](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/18ad0df8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/4c5c4ab9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/e3b7abc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9 [](https://www.expedia.co.uk/Keene-Hotels-Charming-Updated-Farmhouse-In-Historic-Picturesque-Walpole-NH-And-Sleeps-8.h33961365.Hotel-Information) Walpole 10/10 Exceptional (50 reviews) "We had a very lovely stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) mary c. £456 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Keene-Hotels-Charming-Updated-Farmhouse-In-Historic-Picturesque-Walpole-NH-And-Sleeps-8.h33961365.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/5dd08019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/94d9ae76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/303ca4c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/14aa4f5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grey Cabin with Sauna on Lake Monomonac [](https://www.expedia.co.uk/Rindge-Hotels-Grey-Cabin-With-Sauna-On-Lake-Monomonac.h106489950.Hotel-Information) Rindge 7.6/10 Good (4 reviews) "Great location host was on it.anything u needed he was there.no ac was the only thing.but it was unusally hot.i would go again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian £256 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Rindge-Hotels-Grey-Cabin-With-Sauna-On-Lake-Monomonac.h106489950.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/9832d1e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/6d3522c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/6c18250e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/76bef906.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Twin beds on 1st floor with En-suite bathroom. [](https://www.expedia.co.uk/Shelburne-Falls-Hotels-2-Twin-Beds-On-1st-Floor-With-En-Suite-Bathroom.h120039334.Hotel-Information) Shelburne Falls £135 includes taxes & fees 3 Mar - 4 Mar [](https://www.expedia.co.uk/Shelburne-Falls-Hotels-2-Twin-Beds-On-1st-Floor-With-En-Suite-Bathroom.h120039334.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/126000000/125510000/125509100/125509057/c518608e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/126000000/125510000/125509100/125509057/fe0b5860.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/126000000/125510000/125509100/125509057/567302b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125510000/125509100/125509057/fa19e387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large 3BR Apartment in Marlborough NH: Sleeps 8-10: Close to Keene! [](https://www.expedia.co.uk/Marlborough-Hotels-Large-3BR-Apartment-In-Marlborough-NH-Sleeps-8-10-Close-To-Keene.h125509057.Hotel-Information) Marlborough £263 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Marlborough-Hotels-Large-3BR-Apartment-In-Marlborough-NH-Sleeps-8-10-Close-To-Keene.h125509057.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.co.uk/Hotel-Search?startDate=2026-02-25&endDate=2026-02-26®ionId=3000447144&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=VR_SPRING_PROMO_3000447144) ## Find holiday rentals that suit your style Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America®ionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CABIN) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America®ionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=APARTMENT) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America®ionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=COTTAGE) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America®ionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=VACATION_HOME) Chalets [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America®ionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CHALET) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Holiday-Rentals.d3000447144.Travel-Guide-HolidayRentals)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Holiday-Rentals.d3000447144.Travel-Guide-HolidayRentals) ## Top Winchester Hotel Reviews ![Four Columns Inn](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/be42824d_y.jpg) ### Four Columns Inn 10/10 Excellent "We stayed in the John Fane room which is in the main building. It is cute as a button. Perfect for couples. " [](https://expedia.co.uk/Newfane-Hotels-Four-Columns-Inn.h83257793.Hotel-Information) ![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg) ### The Putney Inn 10/10 Excellent "For the money it was very decent in the clerk was nice also" [](https://expedia.co.uk/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Vikings Villages Resort](https://images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/6c062779_y.jpg) ### Vikings Villages Resort 10/10 Excellent "My husband and I really don’t know where to begin about this place. It was just absolutely fantastic. In every way. The entire facility is a work of art.!!!!! " [](https://expedia.co.uk/Brattleboro-Hotels-Vikings-Villages.h92078509.Hotel-Information) ![Latchis Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Spotless room -- all the basics. Friendly & helpful staff" [](https://expedia.co.uk/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![Holiday Inn Express Hotel & Suites Brattleboro by IHG](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/b5010c60_y.jpg) ### Holiday Inn Express Hotel & Suites Brattleboro by IHG 10/10 Excellent "The staff, amenities and room were a high standard. Although we only stayed one night we had everything we needed to be comfortable and cozy " [](https://expedia.co.uk/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) ![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg) ### Colonial Motel And Spa 10/10 Excellent "Amenities were great!" [](https://expedia.co.uk/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0_y.jpg) ### The Covered Bridge Inn 10/10 Excellent "Good" [](https://expedia.co.uk/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) ![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 10/10 Excellent "What's clean staff was friendly food was good bar was nice the buildings a little bit old " [](https://expedia.co.uk/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![The Inn At Crumpin Fox](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/b4ead30a_y.jpg) ### The Inn At Crumpin Fox 10/10 Excellent "The room was very spacious and exceptionally clean. We enjoyed the sitting area by the large bay window. The gentleman at the counter was very friendly and helpful. He even shoveled the snow from my vehicle." [](https://expedia.co.uk/Bernardston-Hotels-The-Inn-At-Crumpin-Fox.h4570044.Hotel-Information) ## Find out more about Winchester **Everything you need to know about** **Winchester** **holiday rentals** Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Winchester holiday rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Winchester holiday rentals we have selected for you start as low as £151 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Winchester rentals** At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. ## Explore a world of travel with Expedia - Trending destinations on Expedia.co.uk ### Trending destinations on Expedia.co.uk - [Holiday Rentals in the Cotswold ](https://www.expedia.co.uk/lp/b/vr/cotswold) - [Holiday Rentals in Lake District ](https://www.expedia.co.uk/lp/b/vr/lake-district) - [Devon Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Devon.d6046196.Holiday-Rental-Destinations) - [Norfolk Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Norfolk.d6046223.Holiday-Rental-Destinations) - [Bedfordshire Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Bedfordshire.d6046189.Holiday-Rental-Destinations) - [Dorset Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Dorset.d6046198.Holiday-Rental-Destinations) - [Northumberland Holiday Rentals ](https://www.expedia.com/Destinations-In-Northumberland.d6046225.Vacation-Rental-Destinations) - [Herefordshire Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Herefordshire.d6046203.Holiday-Rental-Destinations) - [Essex Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Essex.d6046201.Holiday-Rental-Destinations) - [Cumbria Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cumbria.d6046194.Holiday-Rental-Destinations) - [Yorkshire Holiday Rentals ](https://www.expedia.co.uk/Yorkshire-Holiday-Rentals.d6342462.Travel-Guide-HolidayRentals) - [South Wales Holiday Rentals ](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals) - [North Wales Holiday Rentals ](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals) - [London Holiday Rentals ](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals) - [York Holiday Rentals ](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals) - [Blackpool Holiday Rentals ](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals) - [Isle of Wight Holiday Rentals ](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations) - [Scarborough Holiday Rentals ](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals) - [Edinburgh Holiday Rentals ](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals) - [Bath Holiday Rentals ](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals) - [Bournemouth Holiday Rentals ](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals) - [England Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations) - [Scotland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations) - [Cornwall Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations) - [Wales Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations) - [Northern Ireland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations) ## Frequently asked questions ### Can I find a holiday rental in Winchester? ### What are some of the best holiday rentals that Winchester has to offer? ### What’s there to see and do in Winchester? ### What’s a holiday rental in Winchester like? ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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