Title: Chester Holiday Homes from £188: Search Holiday Homes in Chester | Expedia.co.uk [Chester Travel Guide](https://expedia.co.uk/Chester.dx89014)[Hotels in Chester](https://expedia.co.uk/Chester-Hotels.d89014.Travel-Guide-Hotels)[Holiday Rentals in Chester](https://expedia.co.uk/Chester-Holiday-Rentals.d89014.Travel-Guide-HolidayRentals)[Chester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chester.d89014.Car-Hire-Guide)[Chester Holidays](https://expedia.co.uk/Chester.d89014.Holidays-City-Breaks) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.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 [10 Apr - 12 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=89014&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 two months [22 May - 24 May](https://www.expedia.co.uk/Hotel-Search?regionId=89014&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [19 Jun - 21 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=89014&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [17 Jul - 19 Jul](https://www.expedia.co.uk/Hotel-Search?regionId=89014&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester holiday homes ![Dining](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/4ae7b7c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/35c5b21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/c539eb47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/df792487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Chester Farmhouse near Near VT Slopes [](https://www.expedia.co.uk/Chester-Hotels-Charming-Chester-Farmhouse-Peaceful-And-Close-To-Everything.h101473310.Hotel-Information) Chester Depot 9.6/10 Exceptional (18 reviews) "House was in a perfect location. The town was adorable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle A. £310 includes taxes & fees 29 Mar - 30 Mar [](https://www.expedia.co.uk/Chester-Hotels-Charming-Chester-Farmhouse-Peaceful-And-Close-To-Everything.h101473310.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/d906295e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/98b36931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/0b80abe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/w1353h898x0y0-eb6e1bb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Vermont Cabin · Mountain Views · Near Okemo [](https://www.expedia.co.uk/Chester-Hotels-WhiSki-Cabin-12-Acres-With-A-Mountain-View.h105335886.Hotel-Information) Chester 10/10 Exceptional (4 reviews) "Clean, spacous house, good location and great scenes of the mountains." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) pauline £756 includes taxes & fees 7 Apr - 8 Apr [](https://www.expedia.co.uk/Chester-Hotels-WhiSki-Cabin-12-Acres-With-A-Mountain-View.h105335886.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99270000/99266000/99265952/w505h683x260y0-72ec8d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99270000/99266000/99265952/w509h683x258y0-02581c4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/100000000/99270000/99266000/99265952/b42bfe82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99266000/99265952/w507h683x259y0-21bbc4b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River [](https://www.expedia.co.uk/Newport-Hotels-Sugar-River-Treehouse-Relaxing-Escape-Among-The-Trees-On-The-Serene-Sugar-River.h99265952.Hotel-Information) Newport 9.8/10 Exceptional (21 reviews) "The treehouse was the perfect place to unwind and relax for a few nights. Seeing the pines covered in snow out of every window was truly magical. Clean, well stocked, and everything was in good working order. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley P. £279 includes taxes & fees 1 Apr - 2 Apr [](https://www.expedia.co.uk/Newport-Hotels-Sugar-River-Treehouse-Relaxing-Escape-Among-The-Trees-On-The-Serene-Sugar-River.h99265952.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/620d544b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/cea2d009.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, Internet, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/5f732777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/a4954c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts [](https://www.expedia.co.uk/Stratton-Hotels-Stratton-Mountain-Condo-With-Shared-Pool.h44577227.Hotel-Information) Stratton 7.8/10 Good (56 reviews) "Location was great, pool, hot tubs and sauna were great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lin M. £188 includes taxes & fees 7 Apr - 8 Apr [](https://www.expedia.co.uk/Stratton-Hotels-Stratton-Mountain-Condo-With-Shared-Pool.h44577227.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 (51 reviews) "We had a very lovely stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) mary c. £439 includes taxes & fees 30 Mar - 31 Mar [](https://www.expedia.co.uk/Keene-Hotels-Charming-Updated-Farmhouse-In-Historic-Picturesque-Walpole-NH-And-Sleeps-8.h33961365.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) ![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) ![Books](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w960h638x0y1-6a5c7328.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 host and her daughter were lovely and kind and very quick with all communication." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan O. £228 includes taxes & fees 29 Mar - 30 Mar [](https://www.expedia.co.uk/Putney-Hotels-Pet-And-Family-Friendly-Hilltop-House-In-Putney-Vermont.h19887179.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/81ff9d6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/83d1a856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/0592805f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, travel cot, WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/cba81200.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Front Family Friendly Escape [](https://www.expedia.co.uk/Newport-Hotels-Lake-Front-Family-Friendly-Escape.h100538389.Hotel-Information) Newport 10/10 Exceptional (4 reviews) "Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann R. £256 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Newport-Hotels-Lake-Front-Family-Friendly-Escape.h100538389.Hotel-Information) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/3e9df2f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/4c677d14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/29b5b165.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/098ed9b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Enjoy this authentic and cozy VT Barn with Brand New Hot Tub [](https://www.expedia.co.uk/Londonderry-Hotels-Enjoy-This-Authentic-And-Cozy-VT-Barn-With-Brand-New-Hot-Tub.h106674947.Hotel-Information) Londonderry 7.0/10 Good (2 reviews) "I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine M. £371 includes taxes & fees 30 Mar - 31 Mar [](https://www.expedia.co.uk/Londonderry-Hotels-Enjoy-This-Authentic-And-Cozy-VT-Barn-With-Brand-New-Hot-Tub.h106674947.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/4501ee4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/3902b9c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/w1170h1596x0y468-0a8fb230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/bdac3cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table. [](https://www.expedia.co.uk/West-Dover-Hotels-Fantastic-Location-Mt-Snow-Ski-Off.h101085488.Hotel-Information) Dover 9.8/10 Exceptional (15 reviews) "We enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.co.uk/West-Dover-Hotels-Fantastic-Location-Mt-Snow-Ski-Off.h101085488.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/128000000/127430000/127428300/127428264/30adea26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/128000000/127430000/127428300/127428264/7e0bff2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/128000000/127430000/127428300/127428264/5e2bec88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/128000000/127430000/127428300/127428264/54ecf1fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2-Bedroom Unit in Plymouth, Vt. Central to Killington, Woodstock & Okemo! [](https://www.expedia.co.uk/Plymouth-Hotels-2-Bedroom-Unit-In-Plymouth.h127428264.Hotel-Information) Plymouth £77 includes taxes & fees 14 Apr - 15 Apr [](https://www.expedia.co.uk/Plymouth-Hotels-2-Bedroom-Unit-In-Plymouth.h127428264.Hotel-Information) ![TV, books, stereo](https://images.trvl-media.com/lodging/124000000/123950000/123942400/123942314/668fb777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123950000/123942400/123942314/w1280h852x0y1-a2dcac1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books, stereo](https://images.trvl-media.com/lodging/124000000/123950000/123942400/123942314/1d81a334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books, stereo](https://images.trvl-media.com/lodging/124000000/123950000/123942400/123942314/88c2ea85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Vermont Chalet w/ Sweeping Mountain Views [](https://www.expedia.co.uk/East-Dover-Hotels-Secluded-Vermont-Chalet-W-Sweeping-Mountain-Views.h123942314.Hotel-Information) Dover £381 includes taxes & fees 30 Mar - 31 Mar [](https://www.expedia.co.uk/East-Dover-Hotels-Secluded-Vermont-Chalet-W-Sweeping-Mountain-Views.h123942314.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/fe1abb51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/ad47e382.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/344617b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/1516e7fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle [](https://www.expedia.co.uk/Ludlow-Hotels-Short-Walk-To-Shops.h22865847.Hotel-Information) Ludlow 9.8/10 Exceptional (108 reviews) "We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hannah M. £345 includes taxes & fees 30 Mar - 31 Mar [](https://www.expedia.co.uk/Ludlow-Hotels-Short-Walk-To-Shops.h22865847.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) ![Exterior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/6cc8f8eb.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) ![Interior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/4e846ae7.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. £370 includes taxes & fees 30 Mar - 31 Mar [](https://www.expedia.co.uk/Keene-Hotels-The-Leverett-House-In-Charming-Keene.h117913271.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/f5d0c9b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/ef649af5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/996bc915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/6beaf5ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft [](https://www.expedia.co.uk/Bondville-Hotels-The-Mountain-Escape.h96211209.Hotel-Information) Jamaica 9.6/10 Exceptional (25 reviews) "I stayed here for a few days in October with friends. We had some initial confusion with the door locks, but the hosts were able to resolve it quickly.Great location, tons of sleeping and living space, and the hot tub was a welcome addition. We had a great time and would recommend this spot." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan E. £663 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Bondville-Hotels-The-Mountain-Escape.h96211209.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/23000000/22770000/22769000/22768970/a93fa1dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22770000/22769000/22768970/67c634a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/23000000/22770000/22769000/22768970/a4957511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/23000000/22770000/22769000/22768970/1aff520b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route [](https://www.expedia.co.uk/Ludlow-Hotels-Beautifully-Updated-Unique-Village-Home.h22768970.Hotel-Information) Ludlow 9.8/10 Exceptional (85 reviews) "We had a great stay at this home for a long weekend skiing at Okemo. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa W. £345 includes taxes & fees 30 Mar - 31 Mar [](https://www.expedia.co.uk/Ludlow-Hotels-Beautifully-Updated-Unique-Village-Home.h22768970.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102380000/102376700/102376668/w1179h778x0y0-d3dfa0ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/103000000/102380000/102376700/102376668/9dbc4479.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/103000000/102380000/102376700/102376668/7ae24bbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102380000/102376700/102376668/550afcf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!! [](https://www.expedia.co.uk/West-Dover-Hotels-Amazing-4-Bedroom-Townhome-In-Mt-Snow-Village-With-Your-Own-Private-Hot-Tub.h102376668.Hotel-Information) Dover 10/10 Exceptional (13 reviews) "great location easy access to the mountain and the pool was outstanding." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jim f. £881 includes taxes & fees 7 Apr - 8 Apr [](https://www.expedia.co.uk/West-Dover-Hotels-Amazing-4-Bedroom-Townhome-In-Mt-Snow-Village-With-Your-Own-Private-Hot-Tub.h102376668.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/c3df7e46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/f1219ef1.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/91000000/90700000/90693000/90692944/9f5da7f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/22345953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large Killington Area Home | Sleeps 7 | Game Room [](https://www.expedia.co.uk/Bridgewater-Hotels-Bridgewater-Inn-2-King-Beds-Game-Room-Skiing.h90692944.Hotel-Information) Bridgewater 9.6/10 Exceptional (7 reviews) "My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Owen C. £408 includes taxes & fees 14 Apr - 15 Apr [](https://www.expedia.co.uk/Bridgewater-Hotels-Bridgewater-Inn-2-King-Beds-Game-Room-Skiing.h90692944.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120120000/120119000/120119000/b59ee24f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120120000/120119000/120119000/bf994535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120120000/120119000/120119000/23b2b069.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120120000/120119000/120119000/ca1442d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 3 Bedroom Condo in the Heart of Manchester VT [](https://www.expedia.co.uk/Manchester-Center-Hotels-Cozy-3-Bedroom.h120119000.Hotel-Information) Manchester 10/10 Exceptional (1 review) "Beautiful place Very spacious and super organized we love our stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rafael £410 includes taxes & fees 29 Mar - 30 Mar [](https://www.expedia.co.uk/Manchester-Center-Hotels-Cozy-3-Bedroom.h120119000.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/125000000/124540000/124538100/124538047/56942c8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/125000000/124540000/124538100/124538047/8eaa2151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124540000/124538100/124538047/d2d17c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124540000/124538100/124538047/d6484e37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stratton Woods · Secluded Vermont Cabin Retreat [](https://www.expedia.co.uk/West-Wardsboro-Hotels-Stratton-Woods-Secluded-Vermont-Cabin-Retreat.h124538047.Hotel-Information) Wardsboro 10/10 Exceptional (2 reviews) "Cabin was wonderful!Thank you,The Katz Family " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kim k. £293 includes taxes & fees 21 Apr - 22 Apr [](https://www.expedia.co.uk/West-Wardsboro-Hotels-Stratton-Woods-Secluded-Vermont-Cabin-Retreat.h124538047.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/77000000/76910000/76905900/76905876/61fb65d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/77000000/76910000/76905900/76905876/395f0ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76910000/76905900/76905876/2e63fc6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76910000/76905900/76905876/0e44f29d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE! [](https://www.expedia.co.uk/Bondville-Hotels-Mountain-Oasis-Hot-Tub.h76905876.Hotel-Information) Jamaica 9.6/10 Exceptional (28 reviews) "EXCELLENT location managed by an amazing host who was very communicative and helpful!Hottub was perfect, plenty of sleeping and activities available at the house and in the immediate area (local food was AWESOME)." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) s w. £690 includes taxes & fees 15 Apr - 16 Apr [](https://www.expedia.co.uk/Bondville-Hotels-Mountain-Oasis-Hot-Tub.h76905876.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=2026-04-10&endDate=2026-04-11®ionId=89014&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=CABIN) Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=APART_HOTEL) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=VACATION_HOME) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=APARTMENT) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=CONDO) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=COTTAGE) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=VILLA) Chalets [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&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%2FChester-Private-Holiday-Homes.d89014-aaPrivateHolidayHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Private-Holiday-Homes.d89014-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/b9b1ed95_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "There's a cute little town nearby with a great coffee shop. " [](https://expedia.co.uk/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/8d6bfa64_y.jpg) ### On The River Inn 10/10 Excellent " Very cozy. Lovely breakfast. Fun smores" [](https://expedia.co.uk/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Stone Hearth Inn and Eatery](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/52ce2be1_y.jpg) ### Stone Hearth Inn and Eatery 10/10 Excellent "Beautiful place. Rustic and restored beautifully to keep the charm. Talked with the owner over breakfast. Family business with an amazing restaurant. We will stay there again! " [](https://expedia.co.uk/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) ![Best Western Plus Keene Hotel](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-4a5edcca_y.jpg) ### Best Western Plus Keene Hotel 8/10 Good "Room was fine. Only stayed one night for a quick trip. Didn't realize that the restaurant was closed on Sundays. Was looking for a meal after a long drive, but there were plenty of places to eat in the area. " [](https://expedia.co.uk/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Hampton Inn and Suites Manchester](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg) ### Hampton Inn and Suites Manchester 10/10 Excellent "Every employee was incredibly friendly, even if only passing us in the foyer or hallways. Stacy, the operations manager, was especially engaging, knowledgeable and helpful as we were deciding what to do for dinner and what events and venues were worth visiting. We took all of her suggestions and were thrilled when she was spot-on across the board, from Ye Olde Tavern to the syrup-making tour at Dutton’s to the Vermont Country Store. She’s an asset to your operations." [](https://expedia.co.uk/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/10a69b41_y.jpg) ### The Covered Bridge Inn 6/10 Okay "Good job" [](https://expedia.co.uk/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) ![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/05f7e3bc_y.jpg) ### Colonial Motel And Spa 2/10 Terrible "What a dump" [](https://expedia.co.uk/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![Hideaway Inn Mt. Snow](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/c5bdc83b_y.jpg) ### Hideaway Inn Mt. Snow 6/10 Okay "The bath soap container was empty. I asked a hotel staff member if she could refill the dispenser and she said she would bring it to my room in a few minutes. She never showed up as promised. I passed her on the way out 45 minutes later. She look at me and went on her business. " [](https://expedia.co.uk/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.Hotel-Information) ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/06298210_y.jpg) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "It was great to have so many amenities on site. It felt like a home away from home. " [](https://expedia.co.uk/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ## Find out more about Chester ## Chester Holiday Homes information | Number of reviews | 335 | | ----------------- | ----------------- | | Accommodation | 944 Holiday Homes | | Lowest Price | £188 | | Highest Price | £881 | ## Explore a world of travel with Expedia - More ways to book - [Book Holiday Homes in Chester on Expedia.com ](https://www.expedia.com/Chester-Private-Vacation-Homes.d89014-aaPrivateVacationHomes.Travel-Guide-Accommodation)