Title: Sheffield Holiday Homes from £233: Search Holiday Homes in Sheffield | Expedia.co.uk [Hotels in Sheffield](https://expedia.co.uk/Sheffield-Hotels.d157238.Travel-Guide-Hotels)[Holiday Rentals in Sheffield](https://expedia.co.uk/Sheffield-Holiday-Rentals.d157238.Travel-Guide-HolidayRentals)[Sheffield Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Sheffield.d157238.Car-Hire-Guide)[Sheffield Holidays](https://expedia.co.uk/Sheffield.d157238.Holidays-City-Breaks) ![FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA](https://images.trvl-media.com/place/157238/14d96789-8e82-406f-8456-70392b70b95e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/157238/14d96789-8e82-406f-8456-70392b70b95e.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 [17 Apr - 19 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=157238&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [29 May - 31 May](https://www.expedia.co.uk/Hotel-Search?regionId=157238&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [26 Jun - 28 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=157238&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [24 Jul - 26 Jul](https://www.expedia.co.uk/Hotel-Search?regionId=157238&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Sheffield holiday homes ![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/665b8282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/3e6e58ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/4ce0af29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/8f9296e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheerful 3-bedroom cottage with woodstove [](https://www.expedia.co.uk/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information) Sheffield 10/10 Exceptional (42 reviews) "The property was centrally located for skiing, and was a comfortable stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly R. £372 includes taxes & fees 6 Apr - 7 Apr [](https://www.expedia.co.uk/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/dba15cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/8425e45e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/807b3960.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/22ef1826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing [](https://www.expedia.co.uk/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information) Sherwood Forest 9.8/10 Exceptional (14 reviews) "Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew F. £291 includes taxes & fees 6 Apr - 7 Apr [](https://www.expedia.co.uk/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/52bc41a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/dcb799f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/caf5dd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/6137aab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home in Great Barrington [](https://www.expedia.co.uk/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information) Great Barrington 9.8/10 Exceptional (28 reviews) "The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) maureen k. £242 includes taxes & fees 13 Apr - 14 Apr [](https://www.expedia.co.uk/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/83d3f833_edited_d758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/2e0581f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/a133e616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/0e4076ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires! [](https://www.expedia.co.uk/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information) Sherwood Forest 10/10 Exceptional (5 reviews) "We loved it! Lots of local hiking trails and a wonderful relaxing place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon K. £282 includes taxes & fees 6 Apr - 7 Apr [](https://www.expedia.co.uk/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/3db87cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/bf37a122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/38f44943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/68707c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CT Gate House Goshen CT, Gate House Goshen CT [](https://www.expedia.co.uk/Goshen-Hotels-Gate-House-Goshen-CT.h106031055.Hotel-Information) Goshen 9.4/10 Exceptional (9 reviews) "The property was great and the house was huge even for all 12 of us " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan L. £527 includes taxes & fees 14 Apr - 15 Apr [](https://www.expedia.co.uk/Goshen-Hotels-Gate-House-Goshen-CT.h106031055.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105270000/105261400/105261396/aedce656.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105270000/105261400/105261396/dc64a392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, music library, stereo](https://images.trvl-media.com/lodging/106000000/105270000/105261400/105261396/3e8fa497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105270000/105261400/105261396/9477bd21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3-Bedroom Cabin Getaway With Rustic Charm [](https://www.expedia.co.uk/West-Cornwall-Hotels-3-Bedroom-Cabin-Getaway-With-Rustic-Charm.h105261396.Hotel-Information) Cornwall 8.4/10 Very good (6 reviews) "Absolutely beautiful cottage exactly as pictured inside and out. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michaela C. £405 includes taxes & fees 2 Apr - 3 Apr [](https://www.expedia.co.uk/West-Cornwall-Hotels-3-Bedroom-Cabin-Getaway-With-Rustic-Charm.h105261396.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Games room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/cc4451e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/9af2b9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, electric kettle](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/52345b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Riverside Berkshires Retreat [](https://www.expedia.co.uk/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) Great Barrington 9.0/10 Wonderful (12 reviews) "Close to a great bakery and near to a farm market and shopping mall. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cristine C. £234 includes taxes & fees 8 Apr - 9 Apr [](https://www.expedia.co.uk/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/w2439h1242x124y0-c2be86b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/9046d578.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b86b4635.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/d970b68c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk into town, soak up sun on enclosed porch & steps away from nature trails! [](https://www.expedia.co.uk/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information) Stockbridge 10/10 Exceptional (35 reviews) "A very special, well equipped, and comfortable house with a great kitchen, bedrooms and bathrooms as well as a lovely enclosed porch and outdoor area in an amazing location. Wonderful home with all amenities and thoughtful details provided for guests. A short walk to charming town and across from a beautiful hiking area. Excellent stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan £536 includes taxes & fees 29 Apr - 30 Apr [](https://www.expedia.co.uk/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/2802a7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/f0716890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/e715a827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/58aa3713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Barn Retreat — All-Season Escape Awaits! [](https://www.expedia.co.uk/East-Chatham-Hotels-Spectacular-Barn-With-1-Bedroom-1-Loft.h108908975.Hotel-Information) East Chatham 10/10 Exceptional (2 reviews) "Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy S. £536 includes taxes & fees 2 Apr - 3 Apr [](https://www.expedia.co.uk/East-Chatham-Hotels-Spectacular-Barn-With-1-Bedroom-1-Loft.h108908975.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/e3f04cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/d96d2729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/c8b2ae4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/dc4b2063.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Treetop Hideaway in Tyringham [](https://www.expedia.co.uk/Lee-Hotels-Treetop-Hideaway-In-Tyringham.h92899508.Hotel-Information) Monterey 9.0/10 Wonderful (10 reviews) "This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah B. £425 includes taxes & fees 22 Apr - 23 Apr [](https://www.expedia.co.uk/Lee-Hotels-Treetop-Hideaway-In-Tyringham.h92899508.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/8c6e7df7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/w1079h1080x0y0-daba01fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/21b3ce2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/3a5ebff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### rural, serene + sophisticated space [](https://www.expedia.co.uk/Red-Hook-Hotels-Rural.h36245067.Hotel-Information) Red Hook 10/10 Exceptional (8 reviews) "Beautiful property with unique accommodations in the Hudson Valley" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) BRIAN PATRICK M. £319 includes taxes & fees 8 Apr - 9 Apr [](https://www.expedia.co.uk/Red-Hook-Hotels-Rural.h36245067.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/cd1323be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/621adf1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/25e02c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/412632db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sun Filled Lenox Retreat - Minutes to Tanglewood! [](https://www.expedia.co.uk/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information) Lee 9.8/10 Exceptional (6 reviews) "Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paulo I. £345 includes taxes & fees 2 Apr - 3 Apr [](https://www.expedia.co.uk/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information) ![TV, fireplace, printers](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/4d94597a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Games room](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/dc9a1bf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, printers](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/69c2e8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/772f14ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room [](https://www.expedia.co.uk/Great-Barrington-Hotels-Berkshires-Best-Large-Deck-With-Hotub.h120149051.Hotel-Information) Great Barrington 10/10 Exceptional (4 reviews) "Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roberta £998 includes taxes & fees 2 Apr - 3 Apr [](https://www.expedia.co.uk/Great-Barrington-Hotels-Berkshires-Best-Large-Deck-With-Hotub.h120149051.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/8b34823f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/b9c0be0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/9510eac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/636f9a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 5-bedroom house in charming Lee with WiFi [](https://www.expedia.co.uk/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.Hotel-Information) Lee 8.8/10 Excellent (3 reviews) "House was clean and made our Thanksgiving great with it's size and amenities. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Khalil S. £601 includes taxes & fees 7 Apr - 8 Apr [](https://www.expedia.co.uk/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/dc6494b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/47a45e10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/fa10adc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/34a7dcb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renovated house. Built in 1890s. No neighbors in sight. [](https://www.expedia.co.uk/Chatham-Hotels-Renovated-House-Built-In-1890s-No-Neighbors-In-Sight.h124466418.Hotel-Information) Chatham 8.0/10 Very good (1 review) "Mark was very communicative and helpful, answering all questions quickly and accurately" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim S. £233 includes taxes & fees 2 Apr - 3 Apr [](https://www.expedia.co.uk/Chatham-Hotels-Renovated-House-Built-In-1890s-No-Neighbors-In-Sight.h124466418.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/105000000/104760000/104752000/104751955/6b3841f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104760000/104752000/104751955/6584c339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/105000000/104760000/104752000/104751955/cc6d7fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/105000000/104760000/104752000/104751955/fc31b289.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The George is an elegant restored home in the Hudson Valley [](https://www.expedia.co.uk/Stanfordville-Hotels-The-George-Is-An-Elegant-Restored-Home-In-The-Hudson-Valley.h104751955.Hotel-Information) Stanfordville 9.4/10 Exceptional (6 reviews) "This our 3rd stay at the property and once again we thoroughly enjoyed the house and the grounds. We had an opportunity to enjoy horseback riding on site and would definitely recommend that to any visitors. The hosts were very kind and hospitable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric L. £840 includes taxes & fees 8 Apr - 9 Apr [](https://www.expedia.co.uk/Stanfordville-Hotels-The-George-Is-An-Elegant-Restored-Home-In-The-Hudson-Valley.h104751955.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/60ca61c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/99099166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/93b387f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/6dacf3a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whispering Estate Guest House - A Romantic Countryside Getaway [](https://www.expedia.co.uk/Goshen-Hotels-Whispering-Estate-Guest-House-A-Romantic-Countryside-Getaway.h118467341.Hotel-Information) Goshen 10/10 Exceptional (5 reviews) "Beautiful property and great location. A true retreat. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea B. £677 includes taxes & fees 8 Apr - 9 Apr [](https://www.expedia.co.uk/Goshen-Hotels-Whispering-Estate-Guest-House-A-Romantic-Countryside-Getaway.h118467341.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711133/ba8bc3b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711133/50598ac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711133/cd7f7955.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711133/643478da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded escape w/ hot tub + pizza oven+ fireplace [](https://www.expedia.co.uk/Craryville-Hotels-Secluded-Escape-W-Hot-Tub-Pizza-Oven-Fireplace.h123711133.Hotel-Information) Taghkanic £723 includes taxes & fees 6 Apr - 7 Apr [](https://www.expedia.co.uk/Craryville-Hotels-Secluded-Escape-W-Hot-Tub-Pizza-Oven-Fireplace.h123711133.Hotel-Information) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/4f2c31bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/b9e06e08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/803c069e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/6873f6f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy. Clean. Free bagel shop. 3 Fireplaces. [](https://www.expedia.co.uk/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop-3-Fireplaces.h120045407.Hotel-Information) Great Barrington 10/10 Exceptional (1 review) "The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary R. £381 includes taxes & fees 13 Apr - 14 Apr [](https://www.expedia.co.uk/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop-3-Fireplaces.h120045407.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34910000/34909900/34909812/c91d8041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34910000/34909900/34909812/bb73a401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34910000/34909900/34909812/0c61e6f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34910000/34909900/34909812/335992a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Country Lodge Straight Out of the Pages of a Great Novel [](https://www.expedia.co.uk/Pine-Plains-Hotels-A-Country-Lodge-Straight-Out-Of-The-Pages-Of-A-Great-Novel.h34909812.Hotel-Information) Pine Plains 10/10 Exceptional (13 reviews) "Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hessie S. £1,113 includes taxes & fees 2 Apr - 3 Apr [](https://www.expedia.co.uk/Pine-Plains-Hotels-A-Country-Lodge-Straight-Out-Of-The-Pages-Of-A-Great-Novel.h34909812.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=2026-04-15&endDate=2026-04-16®ionId=157238&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=APART_HOTEL) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=VACATION_HOME) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=APARTMENT) Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=CABIN) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=COTTAGE) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=CONDO) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=VILLA) ![](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%2FSheffield-Private-Holiday-Homes.d157238-aaPrivateHolidayHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSheffield-Private-Holiday-Homes.d157238-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ## Top Sheffield Hotel Reviews ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Everything was great will definitely be coming back very soon " [](https://expedia.co.uk/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Clean, quiet, spacious, comfortable, and lovely furnishings! It was a very relaxing overnight." [](https://expedia.co.uk/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Quality Inn Great Barrington](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/ed6ed4e8_y.jpg) ### Quality Inn Great Barrington 8/10 Good "The Quality Inn in Great Barrington is a good value play. The room we had was clean; the staff was friendly and knowledgeable; and the heating was welcomed on this March day. Breakfast was a weak point, but the coffee was good and available throughout the day. And yes, I would stay there again. " [](https://expedia.co.uk/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb_y.jpg) ### Berkshires Untold 10/10 Excellent "Easy check-in, secure and clean" [](https://expedia.co.uk/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "Breakfast is excellent, quiet place is peaceful you can relax really well it has an Indian cuisine restaurant inside also a bar the restaurant is excellent all you request they will do it as long that they have it they will do everything is excellent to this In. Friendly staff." [](https://expedia.co.uk/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 8/10 Good "Nice, easy access, and good price" [](https://expedia.co.uk/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Room was comfortable and quiet. Staff accommodated a request to change rooms after check-in as we discovered there was someone next door who was constantly on the phone speaking loudly in a voice that carried on something business related. Relocating us was very appreciated." [](https://expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![The Whitlock](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/f0d9797c_y.jpg) ### The Whitlock 10/10 Excellent "The facility is unfortunately only staffed 2-8pm daily. None of exterior doors lock at night. Front desk staff was very helpful. The place was very clean and convenient to shops and restaurants." [](https://expedia.co.uk/Lenox-Hotels-The-Whitlock.h66244754.Hotel-Information) ![Interlaken Inn & Resort](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/dbbfdf3a_y.jpg) ### Interlaken Inn & Resort 10/10 Excellent "Overall great amenities and great price" [](https://expedia.co.uk/Torrington-Hotels-Interlaken-Inn-Resort.h19679605.Hotel-Information) ## Find out more about Sheffield ## Sheffield Holiday Homes information | Number of reviews | 204 | | ----------------- | ----------------- | | Accommodation | 437 Holiday Homes | | Lowest Price | £233 | | Highest Price | £1,113 | ## Explore a world of travel with Expedia - More ways to book - [Book Holiday Homes in Sheffield on Expedia.com ](https://www.expedia.com/Sheffield-Private-Vacation-Homes.d157238-aaPrivateVacationHomes.Travel-Guide-Accommodation)