Title: Sheffield Vacation Home Rentals from CA $368: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Sheffield](https://expedia.ca/Sheffield-Hotels.d157238.Travel-Guide-Hotels)[Vacation Rentals in Sheffield](https://expedia.ca/Sheffield-Vacation-Rentals.d157238.Travel-Guide-VacationRentals)[Flights to Sheffield](https://expedia.ca/Cheap-Flights-To-Sheffield.d157238.Travel-Guide-Flights)[Sheffield Car Rentals](https://expedia.ca/Car-Rentals-In-Sheffield.d157238.Car-Rental-Guide)[Sheffield Vacation Packages](https://expedia.ca/Sheffield.d157238.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/0c91d6ccb27784bad8a181efd70e605a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Sheffield Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](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 [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Sheffield Vacation 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/76000000/75600000/75599900/75599864/99d3f85f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/af920cc8.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 Sheffield 10/10 Exceptional (39) "The property was centrally located for skiing, and was a comfortable stay." CA $331 CA $690 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.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) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/e729bc4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/1c3ab355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/31d52781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CT Gate House Goshen CT, Gate House Goshen CT Goshen 10/10 Exceptional (6) "Wonderful stay. It really is a gate house. The property is beautiful and the house is spacious. If I was eloquent,I could go on and on... " CA $140 CA $892 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Goshen-Hotels-Gate-House-Goshen-CT.h106031055.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/ecdea449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/51a25809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/162d61f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/4bbc4f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access! Sherwood Forest 10/10 Exceptional (3) "We loved it! Lots of local hiking trails and a wonderful relaxing place." CA $226 CA $556 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.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) ![Dining](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/80124d14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/347359ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/4e64ac0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking Sherwood Forest 9.6/10 Exceptional (8) "Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well." CA $248 CA $580 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/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) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/c50e9e6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/e0f691bb.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) ### Home in Great Barrington Great Barrington 9.8/10 Exceptional (23) "Enjoyed our stay!!!" CA $218 CA $368 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/a4dc2b95.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) ![Exterior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/d3c8327e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/32714507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sun Filled Lenox Retreat - Minutes to Tanglewood! Lee 9.4/10 Exceptional (3) "The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay." CA $311 CA $706 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/329257ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/a0287de3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/a7b21f81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/04c3bec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bungalow in the Berkshires Lee 10/10 Exceptional (3) "Great location, very clean and well appointed with everyth" CA $419 CA $578 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Lee-Hotels-Bungalow-In-The-Berkshires.h111821595.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/cb8efd3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/d975f5d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/0bc1df65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/3a77d3b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whispering Estate Guest House - A Romantic Countryside Getaway Goshen 10/10 Exceptional (3) "Beautiful property and great location. A true retreat. " CA $1,116 CA $1,693 total includes taxes & fees Oct 10 - Oct 11 [](https://www.expedia.ca/Goshen-Hotels-Charming-Retreat-At-Stone-Hill-Estate-Nature-Meets-Luxury.h118467341.Hotel-Information) ![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/406cc767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/59edf6fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, paper towels](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/780d89c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water" Great Barrington 10/10 Exceptional (1) "The host was exceptional and so kind. The location was in close proximity to 3 quaint New England small towns whose downtowns had many restaurants and local shops to enjoy-Great Barrington (GB Eats for breakfast), Stockbridge (best shopping) and Lenox (exceptional dinner at Frankie’s Italian). The house looked updated on the outside but inside looked like early 1900s with a hint of Victorian influence. My only caution is for anyone with mobility issues as all 3 bedrooms and the only (very small)... CA $314 CA $443 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/505c31c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/64f95c5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/53261c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/8d87241a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Great Barrington Get Away Great Barrington 9.4/10 Exceptional (23) "The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. " CA $398 CA $725 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Great-Barrington-Hotels-Great-Barrington-Get-Away.h29615546.Hotel-Information) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/93000000/92460000/92452800/92452756/4d036f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/93000000/92460000/92452800/92452756/725d323d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92460000/92452800/92452756/ec6797eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/93000000/92460000/92452800/92452756/e6b4678e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy. Clean. Free bagel shop. Great Barrington 10/10 Exceptional (10) "The perfect location for a stay in Great Barrington. The house is so well done and very comfortable!" CA $558 CA $926 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop.h92452756.Hotel-Information) ![1 bedroom, WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241164/23b3990f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241164/976df379.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241164/52586681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241164/0e806d18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Experience Timeless Elegance in The Edith Wharton Room! Lenox CA $289 CA $418 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Lenox-Hotels-Experience-Timeless-Elegance-In-The-Edith-Wharton-Room.h115241164.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/772f14ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/ee5ac04d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/61aeb8a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/f98a9691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room Great Barrington 10/10 Exceptional (1) "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!" CA $878 CA $1,965 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Great-Barrington-Hotels-Berkshires-Best-Large-Deck-With-Hotub.h120149051.Hotel-Information) ![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/636f9a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/d06b32cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, dishwasher](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/8b34823f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/171b6a68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 5-bedroom house in charming Lee with WiFi Lee CA $628 CA $1,145 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/105000000/104760000/104752000/104751955/cef7f580.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104760000/104752000/104751955/48ee7521.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) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104760000/104752000/104751955/6584c339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The George is an elegant restored home in the Hudson Valley Stanfordville 9.2/10 Wonderful (5) "Wonderful property." CA $804 CA $1,296 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Stanfordville-Hotels-The-George-Is-An-Elegant-Restored-Home-In-The-Hudson-Valley.h104751955.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/9eeeead4.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/121000000/120050000/120045500/120045407/4f2c31bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/w1424h960x16y0-bffb2a3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/0cd1f311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy. Clean. Free bagel shop. 3 Fireplaces. Great Barrington CA $558 CA $926 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop-3-Fireplaces.h120045407.Hotel-Information) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241207/4609a9c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241207/9a87bae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241207/1e673737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241207/2f1ef067.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Elegant Carriage House room with a queen bed and private patio. Lenox CA $312 CA $446 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Lenox-Hotels-Elegant-Carriage-House-Room-With-A-Queen-Bed-And-Private-Patio.h115241207.Hotel-Information) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241220/cab9849e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241220/67e04fa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241220/0ab2702a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241300/115241220/66c88863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Carriage House room with a double bed and private balcony Lenox CA $334 CA $474 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Lenox-Hotels-Cozy-Carriage-House-Room-With-A-Double-Bed-And-Private-Balcony.h115241220.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241178/5094c384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241178/8e547a0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241178/b9beadbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241178/4d1c49db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Susan B. Anthony Room - Cozy & Charming Stay Lenox CA $356 CA $502 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Lenox-Hotels-Historic-Susan-B-Anthony-Room-Cozy-Charming-Stay.h115241178.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241126/af794997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241126/w1301h728x0y4-b0569205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241126/64c22087.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels](https://images.trvl-media.com/lodging/116000000/115250000/115241200/115241126/31755c7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn Lenox CA $457 CA $638 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Lenox-Hotels-Experience-Timeless-Elegance-In-The-Niles-Johnson-Room-At-The-Cornell-Inn.h115241126.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.ca/Hotel-Search?startDate=2025-10-23&endDate=2025-10-24®ionId=157238&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true) ![](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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSheffield-Private-Vacation-Homes.d157238-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSheffield-Private-Vacation-Homes.d157238-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Sheffield Hotel Reviews ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Easy parking, great community spaces, beautiful decor! " [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Great lodge with 1 bedroom suites and fully stocked kitchens " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "Clean venue. Very quiet and I highly recommend renting a kayak. You might see a bald eagle:)" [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](//images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "This is a fun family resort... a great vacation place .. in a great location.. something for everyone. Perfect family reunion place.. All Ages happy.. " [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires](//images.trvl-media.com/lodging/1000000/920000/913200/913175/1d50a551_y.jpg) ### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires 10/10 Excellent "The property is very nice and the staff was extremely friendly and helpful." [](https://expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](//images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Great location, very clean!" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](//images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG 10/10 Excellent "Brand new property with friendly and helpful people." [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "Lovely historic hotel that we enjoyed but also knew going in not to expect modern…yes the floors creak and doors and windows dont fit snuggly. We loved it for all those reasns! Staff is wonderful! Enjoy the front porch while you are there!" [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "Very basic and affordable " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ## Find out more about Sheffield ## Sheffield Vacation Homes information | Number of reviews | 113 | | --- | --- | | Accommodation | 451 Vacation Homes | | Lowest Price | CA $368 | | Highest Price | CA $1,965 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in The Berkshires](https://www.expedia.ca/3Star-The-Berkshires-Hotels.s30-0-d6047665.Travel-Guide-Filter-Hotels) - [5 Star Hotels in The Berkshires](https://www.expedia.ca/5Star-The-Berkshires-Hotels.s50-0-d6047665.Travel-Guide-Filter-Hotels) - [Alford Hotels](https://www.expedia.ca/Alford-Hotels.d3000421226.Travel-Guide-Hotels) - 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