Title: Sheffield Vacation Home Rentals from CA $357: Search Top Private Vacation Homes for Rent | Expedia.ca

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![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)

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## Check prices for these dates

In two weeks

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=157238&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 four months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Sheffield vacation homes

![Exterior detail](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/3db87cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/979641d4.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)

![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/68707c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Goshen

[](https://www.expedia.ca/Goshen-Hotels-Gate-House-Goshen-CT.h106031055.Hotel-Information)

9.4/10

Exceptional

(8 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.

CA $148

CA $904 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Goshen-Hotels-Gate-House-Goshen-CT.h106031055.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)

![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/c729995e.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)

![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)

### Vacation Home in Sherwood Forest

[](https://www.expedia.ca/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information)

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.

CA $203

CA $523 total

includes taxes & fees

Jan 27 - Jan 28

[](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)

![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)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/8c55822c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/af01e53f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sherwood Forest

[](https://www.expedia.ca/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information)

9.6/10

Exceptional

(10 reviews)

"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."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

James D.

CA $223

CA $548 total

includes taxes & fees

Jan 21 - Jan 22

[](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/85000000/84680000/84672900/84672833/6137aab0.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)

### Vacation Home in Great Barrington

[](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information)

9.8/10

Exceptional

(26 reviews)

"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cameron M.

CA $203

CA $345 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.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)

![Exterior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/d3c8327e.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)

![Interior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/25e02c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Lee

[](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information)

9.4/10

Exceptional

(3 reviews)

"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."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sarah D.

CA $250

CA $639 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/3bd0d6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/c34ecca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/399488d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/6339dfc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Housatonic

[](https://www.expedia.ca/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.Hotel-Information)

10/10

Exceptional

(3 reviews)

"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cheryl F.

CA $188

CA $371 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90540000/90533800/90533768/886f5b56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/91000000/90540000/90533800/90533768/2bced913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90540000/90533800/90533768/e5399220.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/91000000/90540000/90533800/90533768/1cca2542.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Monterey

[](https://www.expedia.ca/Monterey-Hotels-Hupi-House-Tranquil-Home-In-The-Hills.h90533768.Hotel-Information)

10/10

Exceptional

(1 review)

"Hupi House was the perfect location for our girls reunion weekend. It was a great mix of a quiet retreat in nature and good meals/shopping in town. The property and house are beautiful and updated. Beds and linens are top notch! Highly recommend."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kim H.

CA $1,180

CA $2,462 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Monterey-Hotels-Hupi-House-Tranquil-Home-In-The-Hills.h90533768.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)

![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)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/055ed8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/cc4451e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Great Barrington

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information)

9.2/10

Wonderful

(7 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.

CA $266

CA $394 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/79000000/78260000/78257600/78257590/b090eb5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78260000/78257600/78257590/9292b93f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78260000/78257600/78257590/7ecad611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78260000/78257600/78257590/277bbd12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Spencertown

[](https://www.expedia.ca/Quiet-And-Private-Accommodations-In-A-Country-Setting.h78257590.Hotel-Information)

10/10

Exceptional

(1 review)

"Fantastic place to stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

James

CA $296

CA $378 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Quiet-And-Private-Accommodations-In-A-Country-Setting.h78257590.Hotel-Information)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99770000/99761000/99760997/223b97ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99770000/99761000/99760997/fc7a38f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/100000000/99770000/99761000/99760997/b0fcb999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/100000000/99770000/99761000/99760997/ab7eeeee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hudson

[](https://www.expedia.ca/Hudson-Hotels-Tranquil-Victorian-On-Charming-Street.h99760997.Hotel-Information)

8.0/10

Very good

(2 reviews)

"What a darling house! We stayed with my mother and my adult kids for Thanksgiving and it was the perfect spot! The host was most attentive to all of our questions and request ex! It’s the perfect location for visiting the Hudson Valley and the house was so comfortable and accommodating for all of us! We loved everything about it!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mary R.

CA $346

CA $795 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Hudson-Hotels-Tranquil-Victorian-On-Charming-Street.h99760997.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/124000000/123030000/123028900/123028859/e6a8de71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123030000/123028900/123028859/07647859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123030000/123028900/123028859/9f6d0429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/124000000/123030000/123028900/123028859/4ac89d04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Goshen

[](https://www.expedia.ca/Goshen-Hotels-Sequoia-House-Charming-Goshen-Getaway-Quiet-Retreat-In-Litchfield-Hills.h123028859.Hotel-Information)

CA $333

CA $706 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Goshen-Hotels-Sequoia-House-Charming-Goshen-Getaway-Quiet-Retreat-In-Litchfield-Hills.h123028859.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/ac949794.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)

![Exterior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/3a77d3b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Goshen

[](https://www.expedia.ca/Goshen-Hotels-Whispering-Estate-Guest-House-A-Romantic-Countryside-Getaway.h118467341.Hotel-Information)

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.

CA $750

CA $1,238 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Goshen-Hotels-Whispering-Estate-Guest-House-A-Romantic-Countryside-Getaway.h118467341.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)

![Outdoor dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/d970b68c.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)

### Vacation Home in Stockbridge

[](https://www.expedia.ca/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information)

10/10

Exceptional

(32 reviews)

"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

cathy c.

CA $415

CA $903 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Stockbridge-Hotels-Walk-Into-Town.h77128037.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)

![Living area](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/7be72235.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)

![Private kitchen](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/b7d8032f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Chatham

[](https://www.expedia.ca/Chatham-Hotels-Renovated-House-Built-In-1890s-No-Neighbors-In-Sight.h124466418.Hotel-Information)

CA $243

CA $422 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Chatham-Hotels-Renovated-House-Built-In-1890s-No-Neighbors-In-Sight.h124466418.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)

![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/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)

### Vacation Home in Great Barrington

[](https://www.expedia.ca/Great-Barrington-Hotels-Berkshires-Best-Large-Deck-With-Hotub.h120149051.Hotel-Information)

10/10

Exceptional

(3 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

CA $790

CA $1,851 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Great-Barrington-Hotels-Berkshires-Best-Large-Deck-With-Hotub.h120149051.Hotel-Information)

![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)

![Exterior](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/1bcf2f0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/87b97def.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/d712468a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Great Barrington

[](https://www.expedia.ca/Great-Barrington-Hotels-Great-Barrington-Get-Away.h29615546.Hotel-Information)

9.4/10

Exceptional

(26 reviews)

"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elizabeth G.

CA $431

CA $768 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Great-Barrington-Hotels-Great-Barrington-Get-Away.h29615546.Hotel-Information)

![TV, DVD player](https://images.trvl-media.com/lodging/65000000/64120000/64114700/64114663/22e85ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player](https://images.trvl-media.com/lodging/65000000/64120000/64114700/64114663/ad619e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player](https://images.trvl-media.com/lodging/65000000/64120000/64114700/64114663/fd2d7d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/65000000/64120000/64114700/64114663/2719bd35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in New Marlborough

[](https://www.expedia.ca/Great-Barrington-Hotels-Peaceful.h64114663.Hotel-Information)

9.8/10

Exceptional

(22 reviews)

"A very nice post & beam Berkshire house, quiet, clean, great acerage and amenities.Lucas was very accessible to handle minor issues quickly."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

HARRELL O.

CA $700

CA $1,454 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Great-Barrington-Hotels-Peaceful.h64114663.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)

![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)

![Interior](https://images.trvl-media.com/lodging/105000000/104760000/104752000/104751955/0e1eb54c.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)

### Vacation Home in Stanfordville

[](https://www.expedia.ca/Stanfordville-Hotels-The-George-Is-An-Elegant-Restored-Home-In-The-Hudson-Valley.h104751955.Hotel-Information)

9.4/10

Exceptional

(6 reviews)

"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Polly J.

CA $1,000

CA $1,562 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Stanfordville-Hotels-The-George-Is-An-Elegant-Restored-Home-In-The-Hudson-Valley.h104751955.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/8f88ebfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/add10ec8.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)

### Vacation Home in Red Hook

[](https://www.expedia.ca/Red-Hook-Hotels-Rural.h36245067.Hotel-Information)

10/10

Exceptional

(7 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.

CA $415

CA $529 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Red-Hook-Hotels-Rural.h36245067.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)

![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/17bd9585.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)

![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)

### Vacation Home in Lee

[](https://www.expedia.ca/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.Hotel-Information)

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.

CA $660

CA $1,196 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.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=2026-01-31&endDate=2026-02-01&regionId=157238&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

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Cottages

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Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America&regionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=VACATION_HOME)

Apartments

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Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America&regionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=APART_HOTEL)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America&regionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=CONDO)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America&regionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=VILLA)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America&regionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=CHALET)

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## Top Sheffield Hotel Reviews

![Wilder House Berkshires](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/f0c223e5_y.jpg)

### Wilder House Berkshires

10/10 Excellent

"It was a very pleasant hybrid of a classic BnB with the privacy of an air BnB. Host was on point and communicative. We loved hanging out downstairs in the living room(s). Breakfast was fabulous "

[](https://expedia.ca/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.Hotel-Information)

![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg)

### Berkshires Untold

10/10 Excellent

"Great food, nice room, nice staff. "

[](https://expedia.ca/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/ca1036e9_y.jpg)

### The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"It’s an older property, but clean and comfortable. The staff was extremely friendly and welcoming. "

[](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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

"Clean, very nice bed and linens, pool, jacuzzi, in room fireplace. Balcony right outside of living room. The breakfast was ok, they offered a lot but not top quality. The waffles were very good and the bacon. Overall excellent stay. Conveniently located to everything."

[](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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

10/10 Excellent

"everything"

[](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)

![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg)

### Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"The room and amenities were amazing. "

[](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information)

![Courtyard by Marriott Lenox Berkshires](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/b4c52f47_y.jpg)

### Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"Our stay was great! "

[](https://expedia.ca/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information)

![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg)

### Quality Inn

10/10 Excellent

"excellent"

[](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information)

![Element Lenox Berkshires](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/c0933de7_y.jpg)

### Element Lenox Berkshires

10/10 Excellent

"Spotless rooms and the friendliest service at the front desk! "

[](https://expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information)

## Find out more about Sheffield

## Sheffield Vacation Homes information

| Number of reviews | 147                |
| ----------------- | ------------------ |
| Accommodation     | 437 Vacation Homes |
| Lowest Price      | CA $357            |
| Highest Price     | CA $1,851          |

## Explore a world of travel with Expedia

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