Title: Browse the Best Sheffield Resorts from CA $87 | Expedia.ca

  

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# Search Resort Hotels in Sheffield from CA $87

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## Check prices for these dates

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Sheffield Resorts

We don't have any properties that match your exact search

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## Recommended hotels in Sheffield

![Wilder House Berkshires Room 3](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/f0c223e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![45-inch flat-screen TV with digital channels, streaming services](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/683afd1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![45-inch flat-screen TV with digital channels, streaming services](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/8660fa49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/7fea6163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wilder House Berkshires

Sheffield

9.8/10

Exceptional

(37)

"Highly recommend this beautiful bed & breakfast! The room was wonderful and overlooked the property, the breakfast was delicious, and the hospitality was amazing. I had a fantastic stay, and will definitely stay at The Wilder House again when I'm in the area."

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

Marina

CA $221

CA $247 total

includes taxes & fees

Nov 3 - Nov 4

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

![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)

![Dining](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/8f9296e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/f26544ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cheerful 3-bedroom cottage with woodstove

Sheffield

10/10

Exceptional

(40)

"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.

CA $275

CA $629 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/9fa6f837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/edf60411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/eca50f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/565807cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Guesthouse Cabin vacation rentals in Berkshire County

Sheffield

10/10

Exceptional

(9)

"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "

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

Tom S.

CA $544

CA $961 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/be126a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/e2e7e72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/11bb9318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

8.8/10

Excellent

(683)

"This motel was easy access right off the highway, super clean, and the staff was great. We would definitely stay here again. Breakfast options were good as well. "

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

Tina

CA $149

CA $167 total

includes taxes & fees

Nov 5 - Nov 6

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

![In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Bedrooms, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/723a5f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7f86e411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/a393dfb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

7.6/10

Good

(556)

"The staff were very friendly and accommodating "

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

Tom

CA $105

CA $117 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information)

![Garden](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, Private Bathroom (Garden - Pets Allowed) | Miscellaneous](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/c68ae4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Suite, Private Bathroom (Catamount - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/13717808.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment, Private Bathroom (Greylock - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/9aba043f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shaker Mill Inn

West Stockbridge

9.6/10

Exceptional

(432)

"Very casual and easy check in and out; lovely and substantial breakfast"

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

Jamie

CA $149

CA $164 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/9aabb83a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/05418243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/a831aba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn

Lee

8.4/10

Very good

(1005)

"Staff was very helpful - easy location - clean rooms!"

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

Karen

CA $129

CA $144 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gazebo](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/20495b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/7062b6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/5a6f7f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Howard Johnson by Wyndham Lenox

Lenox

7.6/10

Good

(816)

"Staff was very friendly and helpful."

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

Pamela

CA $110

CA $123 total

includes taxes & fees

Oct 31 - Nov 1

[](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information)

![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/4fd790fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Non Lakeside Superior Room, 2 Queen beds](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/d3eea453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ba9d3ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/53f3f179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Lee

9.0/10

Wonderful

(1002)

"Great Indian restaurant in the hotel!"

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

Chris

CA $148

CA $166 total

includes taxes & fees

Nov 5 - Nov 6

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

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/b51475ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/670699cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/74865ec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshire Mountain Lodge

Pittsfield

9.0/10

Wonderful

(740)

"Great stay, perfect "

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

Lawrence

[](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room, 1 King Bed, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f3c92221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3a8723ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/4ea5ab50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Yankee, Trademark Collection by Wyndham

Lenox

9.0/10

Wonderful

(1023)

"Fresh breakfast menu, clean and great location."

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

Gail

CA $149

CA $167 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information)

![Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/748b4faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/83dd2b57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/44ab9667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Monument Mountain Motel

Great Barrington

9.0/10

Wonderful

(780)

"Very convenient and we were happy that the little restaurant we'd chosen for dinner was right across the street (we drove anyway, as it's a busy street)."

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

Elizabeth

[](https://www.expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/c0933de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/754813dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Coffee/tea maker, dining tables](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/5fd0e723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/f1aeba62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Element Lenox Berkshires

Lenox

9.6/10

Exceptional

(9)

"New hotel very nice"

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

joel

CA $188

CA $210 total

includes taxes & fees

Nov 6 - Nov 7

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

![Property grounds](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/75f1ed66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/1ddc8409.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free self parking](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/46ab504c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed | View from room](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/6d6cf248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wagon Wheel Inn

Lenox

7.0/10

Good

(640)

"Beautiful area. Close to Mt. Greylock, Octobrr Mountain and Pleasant Valley Audubon."

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

Benjamin

CA $96

CA $107 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Lenox-Hotels-Wagon-Wheel-Inn.h1730144.Hotel-Information)

![Library](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/50a90cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/6349c6d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Library](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/e7ac793d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/d4318cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blackberry River Inn

Norfolk

9.4/10

Exceptional

(151)

"Very good breakfast.excellent waiter.love the atmosphere."

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

Marc

CA $229

CA $264 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/fb8a0016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/b28516d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/9c157bdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/fd1046f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Locust Tree Bed and Breakfast LLC

East Canaan

9.0/10

Wonderful

(409)

"Great breakfast! Had a wonderful stay!"

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

Michelle

CA $146

CA $168 total

includes taxes & fees

Oct 31 - Nov 1

[](https://www.expedia.ca/Torrington-Hotels-Locust-Tree-Bed-And-Breakfast-LLC.h7753947.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed, Non Smoking | Bathroom](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/18ef112b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/1d183ca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/1650f935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn

Great Barrington

8.4/10

Very good

(1000)

"Clean room, nice location "

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

Devron

CA $117

CA $131 total

includes taxes & fees

Nov 12 - Nov 13

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

![Interior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/9b4c64ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Untold

Lenox

9.0/10

Wonderful

(786)

"We had a nice room and the food was delicious. Great place to stay. "

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

Vincent

CA $129

CA $144 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/56630735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/2558ee66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/9b821fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/cdf64ef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pleasant Valley Motel West Stockbridge

West Stockbridge

6.8/10

(1001)

"good average place to stay."

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

Terry

CA $79

CA $87 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/West-Stockbridge-Hotels-Pleasant-Valley-Motel-West-Stockbridge.h3201405.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Villa, 3 Bedrooms](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/5aedd4f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/0fe63f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/4f7ca94f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

South Lee

9.0/10

Wonderful

(773)

"We enjoyed our stay and will definitely be back."

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

Howard

CA $163

CA $202 total

includes taxes & fees

Nov 18 - Nov 19

[](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.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=2025-11-13&endDate=2025-11-14&regionId=157238&adults=2&lodging=HOTEL_RESORT&sort=RECOMMENDED&openPlayBack=true)

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## Top Sheffield Hotel Reviews

![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg)

### Berkshire Mountain Lodge

10/10 Excellent

"Excellent all the way around"

[](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.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

"Very clean and roomy lodge (2 bedrooms); conveniently located; has kitchen; recreational facilities a bit dated. Will come back again. "

[](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)

![Holiday Inn Express Hotel & Suites Great Barrington by IHG](//images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg)

### Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"Excellent front desk staff. Ask for Steve. Very convenient to Monument Mountain and local ski resorts."

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

![Monument Mountain Motel](//images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94_y.jpg)

### Monument Mountain Motel

10/10 Excellent

"5 stars!"

[](https://expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.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

"View of the lake was lovely! Breakfast was fine—yogurt, eggs, pancakes and cereal. Coffee was plentiful!"

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

![Blackberry River Inn](//images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/50a90cdd_y.jpg)

### Blackberry River Inn

10/10 Excellent

"Charming place. No tv. Small room. Good breakfast. "

[](https://expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.Hotel-Information)

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

### Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "

[](https://expedia.ca/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.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 place. Friendly staff and very well located. Great breakfast options. "

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

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

### Quality Inn

10/10 Excellent

"Clean and convenient. Great front desk help. "

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

## Find out more about Sheffield

## Sheffield Resorts information

| Number of reviews | 11,819 |
| --- | --- |
| Accommodation | 5 Resorts |
| Lowest Price | CA $87 |
| Highest Price | CA $961 |

## Frequently asked questions

### What can I expect from a resort vacation in Sheffield?

> Longing for a relaxing getaway? Indulge in all the comforts of a resort, where you can find everything you need for your stay from convenient food and drink options to activities and shopping. Browse the resort options in the area and discover the right one for you, whether you envision yourself sipping drinks by a sprawling pool or hitting the golf course for an afternoon game.

### What's a top resort in Sheffield?

> Our highest-rated resort near Sheffield: [Holiday Inn Club Vacations Oak 'n Spruce Resort](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h13232379.Hotel-Information) - Ski resort. 12.2 mi (19.6 km) from Sheffield. Has a sauna, a fitness center, and a terrace.

### What can I do in Sheffield?

> Housatonic River, Magnolia Bluffs Casino, and Mount Everett State Reservation are a few of the interesting sights to visit. Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary are a few additional attractions in the area that you might like.

### What's the weather like in Sheffield?

> The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

### What's the best way to get to and around Sheffield?

> Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 22 mi (35.4 km) from the city center. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.9 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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