Title: The 10 Best Hotels Near Chesterwood, South Lee from CA $143 | Expedia.ca

[South Lee Travel Guide](https://expedia.ca/South-Lee.dx183343)[Vacation Rentals in South Lee](https://expedia.ca/South-Lee-Vacation-Rentals.d183343.Travel-Guide-VacationRentals)[Chesterwood Car Rentals](https://expedia.ca/Car-Rentals-In-Chesterwood.d6091841.Car-Rental-Guide)[Chesterwood Vacations](https://expedia.ca/Chesterwood-South-Lee.d6091841.Vacation-Attraction)

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# Find hotels near Chesterwood, South Lee from CA $143

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## Check prices for these dates

Tonight

[Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=6091841&startDate=2025-12-18&endDate=2025-12-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=6091841&startDate=2025-12-19&endDate=2025-12-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6091841&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6091841&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Recommended

Price (low to high)

Distance

Star rating

## Our top choices for Chesterwood hotels

![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/8494e5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room #10 Queen's Cottage | Private kitchen](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/bbf9b83e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/6cbad311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room #4 - Roosevelt Suite, 1 King Bed, Fireplace, not pet friendly](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/6fb5c35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Devonfield Inn B&B

[](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information)

7.5 km from Chesterwood

10/10

Exceptional

(134)

"The inn has an excellent location and amenities."

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

Christopher

[](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/edd6aeec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gilded Stage in the Mainhouse](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/76b1fb3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/1f3ef87e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/44792ad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Inn at Stockbridge

[](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information)

5.2 km from Chesterwood

9.8/10

Exceptional

(99)

"Well-run and elegant property. "

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

Steven

CA $346

CA $405 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/0ab8f96e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/284a1f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/ea4dc35f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/8eb2abf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Inn at Kenmore Hall

[](https://www.expedia.ca/Richmond-Hotels-Inn-At-Kenmore-Hall.h27551652.Hotel-Information)

12.1 km from Chesterwood

10/10

Exceptional

(27)

"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "

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

Margaret

CA $793

CA $869 total

includes taxes & fees

Dec 20 - Dec 21

[](https://www.expedia.ca/Richmond-Hotels-Inn-At-Kenmore-Hall.h27551652.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)

![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)

![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Element Lenox Berkshires

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

12.5 km from Chesterwood

9.8/10

Exceptional

(13)

"New hotel very nice"

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

joel

CA $186

CA $208 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![Front of property](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/bb8fdf64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/3d2d74c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fire Spa Suite | Room amenity](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/af4baaa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fire Spa Suite](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/de897732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chambery Inn

[](https://www.expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information)

8.7 km from Chesterwood

9.6/10

Exceptional

(373)

"Amazing customer service! Location was very good to explore the area."

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

Sophia

[](https://www.expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/1d50a551.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/32c535e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/9d0420c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/f2aaf746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

[](https://www.expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information)

8.6 km from Chesterwood

9.4/10

Exceptional

(758)

"Clean room, very courteous staff "

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

Thomas

CA $186

CA $208 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information)

![Loft, Private Bathroom (Skylight Loft)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/48ea2807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, Private Bathroom (Victorian Room)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/49947e81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/86910798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/eb4406db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Brook Farm Inn

[](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.Hotel-Information)

9.1 km from Chesterwood

9.4/10

Exceptional

(164)

"Everything was perfect - location and accommodation."

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

Christopher

[](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.Hotel-Information)

![Egyptian cotton sheets, premium bedding, down comforters, minibar](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/b42c4262.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/be4af91d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/9aaa75ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/549437da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Prospect Berkshires

[](https://www.expedia.ca/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.Hotel-Information)

12.8 km from Chesterwood

9.6/10

Exceptional

(15)

"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "

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

Laura

CA $292

CA $373 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.Hotel-Information)

![Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Private kitchen](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/61ae6bd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/22135a72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/c0c5a00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/fbd2cba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### East Rock Inn

[](https://www.expedia.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information)

10.1 km from Chesterwood

9.4/10

Exceptional

(36)

"We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again."

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

Laura

CA $173

CA $194 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information)

![Aerial view](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/c9940794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pines Duplex Suite | View from room](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/7bcf94fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/0fed38f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/ca0080b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Inn at Silver Maple Farm

[](https://www.expedia.ca/East-Chatham-Hotels-Inn-At-Silver-Maple-Farm.h17094013.Hotel-Information)

17.5 km from Chesterwood

9.8/10

Exceptional

(98)

"Great stay, comfortable place"

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

barry

CA $178

CA $199 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/East-Chatham-Hotels-Inn-At-Silver-Maple-Farm.h17094013.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)

![2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/3c0625c1.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)

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

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

6.6 km from Chesterwood

9.0/10

Wonderful

(804)

"Convenient location, very roomy, well equipped kitchen. "

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

Carolyn

CA $176

CA $224 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![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)

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

### Monument Mountain Motel

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

8.7 km from Chesterwood

9.0/10

Wonderful

(805)

"Yes it was clean & staff was very polite. "

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

Barbara L.

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

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/9b7b4cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d969459c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Queen Beds (Main Inn)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/5f2e6b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Red Lion Inn

[](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information)

3.3 km from Chesterwood

8.8/10

Excellent

(1004)

"Old time charm and hot tub under the stars"

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

Lori

CA $196

CA $281 total

includes taxes & fees

Jan 14 - Jan 15, 2026

[](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.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)

![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)

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

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

8.6 km from Chesterwood

9.0/10

Wonderful

(1001)

"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"

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

Elisabeth

CA $138

CA $154 total

includes taxes & fees

Jan 7 - Jan 8, 2026

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

![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)

![Garden](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/f8f74b93.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

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

19.9 km from Chesterwood

9.8/10

Exceptional

(39)

"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "

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

Allison

CA $194

CA $217 total

includes taxes & fees

Dec 21 - Dec 22

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

![Property amenity](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/b4c52f47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/cbf141ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/36a39838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/w4000h2033x0y0-e62570a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Courtyard by Marriott Lenox Berkshires

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

12.1 km from Chesterwood

9.2/10

Wonderful

(590)

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

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

Mingming

CA $186

CA $208 total

includes taxes & fees

Dec 21 - Dec 22

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

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

8 km from Chesterwood

8.8/10

Excellent

(707)

"Great hospitality "

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

regina maria

CA $147

CA $165 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![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)

![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f43c89bb.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)

### The Yankee, Trademark Collection by Wyndham

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

14.9 km from Chesterwood

9.2/10

Wonderful

(1004)

"Friendly staff, very clean room and super comfy bed"

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

Linda

CA $128

CA $143 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/ceca8706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/e55e7242.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One King Bed, Non-Smoking, Accessible | View from room](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/5d049cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn & Suites Berkshires-Lenox

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

14.7 km from Chesterwood

9.2/10

Wonderful

(1000)

"Clean, pleasant staff and good breakfast. "

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

Edward

CA $144

CA $161 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![Front of property](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/e8f22f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Suite, 1 Queen Bed | Living area](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/d32c867e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/a5a66acc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Suite, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/f3a87415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Cornell Inn, Lenox & The Berkshires

[](https://www.expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information)

10.7 km from Chesterwood

9.0/10

Wonderful

(1000)

"The Inn was very nice and the staff was super friendly and attentive."

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

Steven

CA $230

CA $265 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.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=2026-01-02&endDate=2026-01-03&regionId=6091841&adults=2&sort=RECOMMENDED&openPlayBack=true)

## Top Chesterwood Hotel Reviews

![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg)

### The Red Lion Inn

10/10 Excellent

"We had a very nice experience staying at the Red Lion Inn. Our room was upgraded when checking in which was a nice surprise. The hotel was beautifully decorated for the season. We loved the cozy feel of the fireplace in the lobby especially on such a cold day. "

[](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information)

![Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10](https://images.trvl-media.com/lodging/93000000/92110000/92100700/92100621/369ddb1e_y.jpg)

### Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

10/10 Excellent

"Spacious house with large, well designed kitchen Excellent location Responsive host "

[](https://expedia.ca/Stockbridge-Hotels-New-4500-Sq-Ft-Modern-5-Bed-55-Bath-On-Housatonic-River-And-Walk-To-Stockbridge.h92100621.Hotel-Information)

![A Grand property in Historic Stockbridge](https://images.trvl-media.com/lodging/34000000/33970000/33960400/33960335/222fc9b7_y.jpg)

### A Grand property in Historic Stockbridge

10/10 Excellent

"We were in Stockbridge for the first time for our annual family Thanksgiving and orienteering event. Most stayed at the inn, but some rented the Taggert House as a place where family could easily be together It was perfect and so conveniently located a short and beautiful walk to town. The house is huge, the kitchen is roomy and well-stocked, the beds were comfortable and each bedroom had its own bathroom. The pool table was a big hit. Parking was easy. The owners couldn’t have been nicer or more responsive. I highly recommend the Taggert House and, if your group is extra large, also rent their River House just behind it. Five stars plus. We will be back! "

[](https://expedia.ca/Stockbridge-Hotels-A-Grand-Estate-In-Historic-Stockbridge.h33960335.Hotel-Information)

![The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/587b0e23_y.jpg)

### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

10/10 Excellent

"It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!"

[](https://expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information)

![Secluded Family Home in Serene Stockbridge Woods](https://images.trvl-media.com/lodging/34000000/33670000/33660100/33660074/abf132cf_y.jpg)

### Secluded Family Home in Serene Stockbridge Woods

10/10 Excellent

"This place is beyond amazing. If you have a chance to book it, do it immediately."

[](https://expedia.ca/West-Stockbridge-Hotels-Tranquil-Getaway-In-The-Stockbridge-Woods-Warm.h33660074.Hotel-Information)

![Stockbridge Home, Come Experience The Berkshires!](https://images.trvl-media.com/lodging/88000000/87640000/87633700/87633659/b5ee0956_y.jpg)

### Stockbridge Home, Come Experience The Berkshires!

10/10 Excellent

"Our stay at the Stockbridge Home was fabulous! Lovely home! Clean, well stocked kitchen and beautiful comfortable bedrooms. The bathrooms were spotless and spacious. We loved the private backyard in the quiet neighborhood. We were able to walk into town on safe walkways. Short drive to hiking trails. We would highly recommend this home for your visit to the Berkshires! Thank you Lucas and Drew! Excellent hosts. "

[](https://expedia.ca/Stockbridge-Hotels-Stockbridge-Home.h87633659.Hotel-Information)

![Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay](https://images.trvl-media.com/lodging/106000000/105020000/105019600/105019545/a7b5f2d0_y.jpg)

### Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay

10/10 Excellent

"Clean "

[](https://expedia.ca/Housatonic-Hotels-Woodland-Zen-By-AvantStay-Modern-Design-Patio.h105019545.Hotel-Information)

![Lofted Hideaway on Pixley Hill](https://images.trvl-media.com/lodging/118000000/117640000/117636000/117635998/beed0775_y.jpg)

### Lofted Hideaway on Pixley Hill

10/10 Excellent

"The house was clean and cozy but large enough for a big family. We brought our dog and there were no problems doing so. The hosts responded to all of our inquiries very quickly. The house was on a hill so kids and dogs would need outside supervision. The kids rooms indoors were wonderful! The deck was the perfect place to read and unwind. "

[](https://expedia.ca/Housatonic-Hotels-Lofted-Hideaway-On-Pixley-Hill.h117635998.Hotel-Information)

![Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions](https://images.trvl-media.com/lodging/103000000/102010000/102001500/102001430/b9eabd0d_y.jpg)

### Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions

10/10 Excellent

"Lovely home, great location. The grounds, outdoor dining setup, etc. were all terrific."

[](https://expedia.ca/Stockbridge-Hotels-Charming-Cape-Cod-Home-In-Prime-Berkshire-Location-5-Minutes-To-Tanglewood.h102001430.Hotel-Information)

## Hotels near other Chesterwood attractions

### Norman Rockwell Museum

4.7/5 (252 reviews)

You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6091839)

### Berkshire Botanical Garden

4.0/5 (1 review)

Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621532665247)

### Mission House

You can spend time exploring the galleries in Mission House in Stockbridge. Wander the lakeside in this quaint area. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621560941222)

### Naumkeag Museum

3.5/5 (2 reviews)

You can spend time browsing the exhibits at Naumkeag Museum during your travels in Stockbridge. While you're in the area, stroll along the lakeside. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6091843)

### National Shrine of the Divine Mercy

4.5/5 (54 reviews)

Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621532665250)

### Schantz Galleries

You can spend an afternoon exploring the galleries in Schantz Galleries during your trip to Stockbridge. Wander the lakeside in this quaint area. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621532665248)

### Art et Industrie

You can spend an afternoon exploring the galleries in Art et Industrie in Great Barrington. Amble around this quaint area's gardens, or seek out the hiking trails. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621532665245)

### Berkshire Theatre Festival

You can get tickets for a performance at Berkshire Theatre Festival on your trip to Stockbridge. Wander the lakeside in this quaint area. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621532665249)

## Frequently asked questions

### What are the top-rated hotels near Chesterwood?

> [Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10](https://expedia.ca/Stockbridge-hotels-Taggart-Treehouse:-Modern-Luxury-Meets-Nature:-Stunning-river-views,-sleeps-10.h92100621.Hotel-information)
> 
>   
> Taggart Treehouse offers a luxurious escape with breathtaking river views, just 3.2 km from Chesterwood. Rated an impressive 10 by travellers, this modern retreat accommodates up to 10 travellers, perfect for larger groups. Guests can enjoy amenities such as a fully equipped kitchen with a dishwasher, oven, and coffee maker, along with a spacious patio and garden area for relaxation.
> 
>   
> [Vacation in a Berkshire Farmhouse](https://expedia.ca/West-Stockbridge-hotels-Vacation-in-a--Berkshire-Farmhouse.h33973032.Hotel-information)
> 
>   
> Located 4.7 km from Chesterwood, the Vacation in a Berkshire Farmhouse boasts a remarkable review rating of 9.8\. This historic hotel combines charm with modern comforts, featuring a well-equipped kitchen, outdoor play areas, and nearby hiking trails. Guests can unwind on the patio or explore local attractions such as wineries and ski resorts, making it a versatile choice for all travellers.
> 
>   
> [The Inn at Stockbridge](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information)
> 
>   
> The Inn at Stockbridge is a 4-star gem just 6.6 km from Chesterwood, rated 9.8 by travellers. Guests can indulge in complimentary cooked breakfasts and relax by the outdoor pool. With a variety of amenities, including a spa, fitness facilities, and beautifully designed rooms with premium bedding, this inn perfectly blends comfort and elegance, creating a peaceful retreat amidst the stunning Berkshire landscape.

### What hotels are within walking distance to Chesterwood?

> [The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information)
> 
>   
> The Stockbridge Country Inn is a charming 4.5-star bed and breakfast located just a 12-minute walk from Chesterwood, with an excellent review rating of 9.2\. Guests can enjoy delightful amenities such as complimentary breakfast options, an onsite art gallery, and a terrace for relaxation. Outdoor enthusiasts will appreciate the hiking and biking trails nearby, along with a golf course located just a short distance away. The inn boasts a luxurious historic design, complete with premium bedding and a fireplace, ensuring a comfortable and memorable stay.

### How much is a hotel near Chesterwood?

### What are the most popular family-friendly hotels near Chesterwood?

> [Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10](https://expedia.ca/Stockbridge-hotels-Taggart-Treehouse:-Modern-Luxury-Meets-Nature:-Stunning-river-views,-sleeps-10.h92100621.Hotel-information)
> 
>   
> Taggart Treehouse: Modern Luxury Meets Nature is only 3.2 km from Chesterwood and enjoys a perfect 10 travellers' rating. This unique hotel offers a cozy kitchen and a lovely patio, perfect for family gatherings. With a travel crib and stair gate for children, it ensures safety and comfort for younger travellers. The stunning river views and nearby nature trails make it an ideal retreat for families looking to connect and unwind.
> 
>   
> [Vacation in a Berkshire Farmhouse](https://expedia.ca/West-Stockbridge-hotels-Vacation-in-a--Berkshire-Farmhouse.h33973032.Hotel-information)
> 
>   
> Vacation in a Berkshire Farmhouse is a fantastic option just 4.7 km from Chesterwood, an impressive travellers' rating of 9.8\. This inviting farmhouse features amenities tailored for families, including a spacious kitchen, outdoor play area for children, and a variety of toys to keep the little ones entertained. With a beautiful garden and patio, parents can relax while kids explore. Guests also enjoy nearby hiking, skiing, and antique shopping.
> 
>   
> [Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)
> 
>   
> Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG, located 7.6 km from Chesterwood, offers a family-friendly environment with a review rating of 9.0 and a 3.5-star rating. Families will appreciate the onsite playground, arcade game room, and spacious rooms equipped with kitchen facilities and a crib at no extra charge. Guests can also take advantage of the indoor and outdoor pools, hot tub, and nearby skiing activities for a fun-filled family holidays.

### Which hotels near Chesterwood offer the best views?

> [Vacation in a Berkshire Farmhouse](https://expedia.ca/West-Stockbridge-hotels-Vacation-in-a--Berkshire-Farmhouse.h33973032.Hotel-information)
> 
>   
> Located just 4.7 km from Chesterwood, this charming farmhouse is rated an impressive 9.8 by travellers. Guests can relish breathtaking mountain views from the patio and enjoy outdoor adventures, including hiking and skiing nearby. The hotel features a fully equipped kitchen, a cozy garden, and ample parking, making it a perfect retreat for nature lovers who appreciate rustic charm.
> 
>   
> [The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information)
> 
>   
> Just a short 12-minute walk from Chesterwood, this 4.5-star inn is rated 9.2 by travellers. Guests are treated to scenic mountain views from the terrace and can indulge in complimentary full breakfasts. With amenities like a pool, hiking options on-site, and a charming historic design, this inn provides a cozy and luxurious feel, making it an ideal spot for art and nature enthusiasts alike.
> 
>   
> [Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)
> 
>   
> This 3.5-star resort is situated 7.6 km from Chesterwood and boasts a review rating of 9.0\. Guests can take advantage of the outdoor and indoor pools, hot tubs, and on-site tennis courts. The resort's balconies and patios offer lovely resort views, perfect for relaxation after a day of exploring. With family-friendly amenities and a variety of activities, it's a delightful choice for those looking to enjoy the Berkshires.

### What are the best affordable hotels near Chesterwood?

> [Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10](https://expedia.ca/Stockbridge-hotels-Taggart-Treehouse:-Modern-Luxury-Meets-Nature:-Stunning-river-views,-sleeps-10.h92100621.Hotel-information)
> 
>   
> Taggart Treehouse is a spacious retreat just 3.2 km from Chesterwood, rated an impressive 10 by travellers. This hotel features stunning river views and is perfect for families or groups, providing amenities like a fully equipped kitchen with a dishwasher and an oven, plus a cozy patio to enjoy the outdoors. Guests can also benefit from onsite parking and WiFi, ensuring a comfortable stay.
> 
>   
> [Vacation in a Berkshire Farmhouse](https://expedia.ca/West-Stockbridge-hotels-Vacation-in-a--Berkshire-Farmhouse.h33973032.Hotel-information)
> 
>   
> Just 4.7 km from Chesterwood, Vacation in a Berkshire Farmhouse boasts a remarkable review rating of 9.8\. This family-friendly farmhouse features an outdoor play area for children and is surrounded by opportunities for hiking, skiing, and winery tours. Guests can enjoy a kitchen equipped with modern appliances, a charming patio, and WiFi to stay connected during their stay.
> 
>   
> [Shaker Mill Inn](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information)
> 
>   
> Located 7.9 km from Chesterwood, Shaker Mill Inn is a cozy escape with a review rating of 9.6\. This inn offers a free breakfast and self-parking, making it a convenient choice for travellers. Guests can relax in their rooms featuring a kitchenette and enjoy the beautiful garden or the private hot tub. With contactless check-in and a warm atmosphere, it's a delightful option for a restful stay.

### Are there any hotels with pools close to Chesterwood?

> [The Inn at Stockbridge](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information)
> 
>   
> The Inn at Stockbridge, just 6.6 km from Chesterwood, is a sophisticated 4-star retreat with an outstanding review rating of 9.8\. This hotel features a serene outdoor pool surrounded by beautiful gardens, ideal for relaxation. Guests are treated to complimentary breakfast and access to a 24-hour fitness centre, ensuring a comfortable and energizing stay.
> 
>   
> [The Red Lion Inn](https://expedia.ca/Stockbridge-hotels-The-Red-Lion-Inn.h5780784.Hotel-information)
> 
>   
> Located only 3.7 km from Chesterwood, The Red Lion Inn boasts a charming 3.5-star experience with a review rating of 8.8\. Guests can unwind in the outdoor pool area, featuring comfortable sun loungers. This historic hotel offers a variety of amenities including a spa, 24-hour room service, and easy access to skiing and snowboarding activities, perfect for those looking to explore the nearby mountains.
> 
>   
> [Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)
> 
>   
> Situated just 7.6 km from Chesterwood, the Holiday Inn Club Vacations Oak n' Spruce Resort is a family-friendly gem with an impressive review rating of 9.0\. Guests can enjoy both indoor and outdoor pools, complete with sun loungers and a poolside bar for leisurely afternoons. Additional highlights include a hot tub, mini-golf, and on-site tennis facilities, making it an ideal choice for families and outdoor enthusiasts alike.

### What are the best pet-friendly hotels near Chesterwood?

> [Vacation in a Berkshire Farmhouse](https://expedia.ca/West-Stockbridge-hotels-Vacation-in-a--Berkshire-Farmhouse.h33973032.Hotel-information)
> 
>   
> Just 4.7 km from Chesterwood, Vacation in a Berkshire Farmhouse is an idyllic retreat for pet owners, allowing pets in-room. With an outstanding review rating of 9.8, this farmhouse boasts a historic charm and offers a plethora of amenities that include a kitchen, outdoor play area for children, and nearby hiking opportunities. Guests can unwind on the patio or explore local attractions, making it an excellent choice for families and travellers with pets alike.
> 
>   
> [The Inn at Stockbridge](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information)
> 
>   
> The Inn at Stockbridge, located 6.6 km from Chesterwood, is a charming 4-star hotel that welcomes dogs only. With a remarkable review rating of 9.8, this inn features an outdoor pool, spa services, and a lovely garden area, perfect for relaxing with pets. Guests can indulge in a complimentary cooked breakfast and enjoy comfortable accommodations with premium bedding and designer toiletries, ensuring a delightful stay for both you and your furry friend.
> 
>   
> [Econo Lodge Lee - Great Barrington](https://www.expedia.ca/Lee-Hotels-Econo-Lodge-Lee-Great-Barrington.h913013.Hotel-Information)
> 
>   
> Econo Lodge Lee - Great Barrington is just 8.0 km from Chesterwood and offers a cozy stay for travellers with pets. This budget-friendly hotel allows pets in-room, making it a great choice for those traveling with furry companions. Guests can enjoy amenities like daily housekeeping, free continental breakfast, and access to a mini-golf course on-site. Rated by travellers at 6.4, it's a convenient option for families looking to explore the beautiful Berkshire region.

### Can I book a fully refundable hotel close to Chesterwood?

### Can I find Expedia discounts for hotels near Chesterwood?

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- [Great Barrington Hotels ](https://www.expedia.ca/Great-Barrington-Hotels.d110336.Travel-Guide-Hotels)
- [Hotels near Hancock Shaker Village ](https://www.expedia.ca/Hancock-Shaker-Village-Hotels.0-l6091849-0.Travel-Guide-Filter-Hotels)
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- [Honeymoon Resorts and in Lenox ](https://www.expedia.ca/Lenox-Hotels-Honeymoon-Hotels.0-0-d8587-tHoneymoonHotels.Travel-Guide-Filter-Hotels)
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- [Hotels near Mahaiwe Performing Arts Center ](https://www.expedia.ca/Mahaiwe-Performing-Arts-Center-Hotels.0-l553248621532665242-0.Travel-Guide-Filter-Hotels)
- [Mill River Hotels ](https://www.expedia.ca/Mill-River-Hotels.d3000748895.Travel-Guide-Hotels)
- [Monterey Hotels ](https://www.expedia.ca/Monterey-Hotels.d6005411.Travel-Guide-Hotels)
- [Hotels near National Shrine of the Divine Mercy ](https://www.expedia.ca/National-Shrine-Of-The-Divine-Mercy-Hotels.0-l553248621532665250-0.Travel-Guide-Filter-Hotels)
- [New Marlborough Hotels ](https://www.expedia.ca/New-Marlborough-Hotels.d137834.Travel-Guide-Hotels)
- [Hotels near Norman Rockwell Museum ](https://www.expedia.ca/Norman-Rockwell-Museum-Hotels.0-l6091839-0.Travel-Guide-Filter-Hotels)
- [Pittsfield Hotels ](https://www.expedia.ca/Pittsfield-Hotels.d9478.Travel-Guide-Hotels)
- [Richmond Hotels ](https://www.expedia.ca/Richmond-Hotels.d151138.Travel-Guide-Hotels)
- [Sheffield Hotels ](https://www.expedia.ca/Sheffield-Hotels.d157238.Travel-Guide-Hotels)
- [Hotels near Ski Butternut ](https://www.expedia.ca/Ski-Butternut-Hotels.0-l6182072-0.Travel-Guide-Filter-Hotels)
- [South Egremont Hotels ](https://www.expedia.ca/South-Egremont-Hotels.d183341.Travel-Guide-Hotels)
- [Guest Houses in South Lee ](https://www.expedia.ca/South-Lee-Guest-Houses.d183343-aaGuestHouses.Travel-Guide-Accommodation)
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- [B&B in Stockbridge ](https://www.expedia.ca/Stockbridge-Bed-And-Breakfast.d162575-aaBedAndBreakfast.Travel-Guide-Accommodation)
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- [Hotels near Tanglewood Music Center ](https://www.expedia.ca/Tanglewood-Music-Center-Hotels.0-l503292-0.Travel-Guide-Filter-Hotels)
- [The Berkshires Hotels ](https://www.expedia.ca/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)
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- [Hotels near Tyringham Cobble ](https://www.expedia.ca/Tyringham-Cobble-Hotels.0-l553248621532665261-0.Travel-Guide-Filter-Hotels)
- [Tyringham Hotels ](https://www.expedia.ca/Tyringham-Hotels.d183347.Travel-Guide-Hotels)
- [Hotels near Ventfort Hall Mansion and Gilded Age Museum ](https://www.expedia.ca/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Hotels.0-l553248621532665270-0.Travel-Guide-Filter-Hotels)
- [Lgbt Friendly Hotels in West Stockbridge ](https://www.expedia.ca/West-Stockbridge-Hotels-LGBT-Friendly-Hotel.0-0-d173346-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in West Stockbridge ](https://www.expedia.ca/West-Stockbridge-Hotels-Luxury-Hotel.0-0-d173346-tLuxuryHotel.Travel-Guide-Filter-Hotels)
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- [Spa Hotels in West Stockbridge ](https://www.expedia.ca/West-Stockbridge-Hotels-Spa-Hotel.0-0-d173346-tSpaHotel.Travel-Guide-Filter-Hotels)
- [West Stockbridge Hotels ](https://www.expedia.ca/West-Stockbridge-Hotels.d173346.Travel-Guide-Hotels)

- [Flights to Lenox ](https://www.expedia.ca/Cheap-Flights-To-Lenox.d8587.Travel-Guide-Flights)
- [Flights to Stockbridge ](https://www.expedia.ca/Cheap-Flights-To-Stockbridge.d162575.Travel-Guide-Flights)
- [Flights from Lee ](https://www.expedia.ca/lp/flights/8572/flights-from-lee)
- [Flights from Lenox ](https://www.expedia.ca/lp/flights/8587/flights-from-lenox)

- [Visit Great Barrington ](https://www.expedia.ca/Great-Barrington.dx110336)
- [Lake Mansfield Park ](https://www.expedia.ca/Lake-Mansfield-Park-Great-Barrington.d553248621560926695.Vacation-Attraction)
- [National Shrine of the Divine Mercy ](https://www.expedia.ca/National-Shrine-Of-The-Divine-Mercy-Stockbridge.d553248621532665250.Vacation-Attraction)
- [Naumkeag Museum ](https://www.expedia.ca/Naumkeag-Museum-Stockbridge.d6091843.Vacation-Attraction)
- [Norman Rockwell Museum ](https://www.expedia.ca/Norman-Rockwell-Museum-Stockbridge.d6091839.Vacation-Attraction)
- [Visit South Lee ](https://www.expedia.ca/South-Lee.dx183343)
- [Visit Stockbridge ](https://www.expedia.ca/Stockbridge.dx162575)
- [Ventfort Hall Mansion and Gilded Age Museum ](https://www.expedia.ca/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Vacation-Attraction)

- [Avis Rental Cars in Lenox ](https://www.expedia.ca/Avis-Car-Rentals-In-Lenox.d8587-c41.Car-Rental-Guide-Suppliers)
- [Avis Rental Cars in Stockbridge ](https://www.expedia.ca/Avis-Car-Rentals-In-Stockbridge.d162575-c41.Car-Rental-Guide-Suppliers)
- [Car rental Lee ](https://www.expedia.ca/Car-Rentals-In-Lee.d8572.Car-Rental-Guide)
- [Car rental Lenox ](https://www.expedia.ca/Car-Rentals-In-Lenox.d8587.Car-Rental-Guide)
- [Car rental Stockbridge ](https://www.expedia.ca/Car-Rentals-In-Stockbridge.d162575.Car-Rental-Guide)