Title: The Best Hotels Closest to Chesterwood in South Lee for 2026 | Expedia.com

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

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## Check prices for these dates

Tonight

[Feb 16 - Feb 17](https://www.expedia.com/Hotel-Search?regionId=6091841&startDate=2026-02-16&endDate=2026-02-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 17 - Feb 18](https://www.expedia.com/Hotel-Search?regionId=6091841&startDate=2026-02-17&endDate=2026-02-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=6091841&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=6091841&startDate=2026-02-27&endDate=2026-03-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Recommended

Price (low to high)

Distance

Star rating

## Our top choices for Chesterwood hotels

![Suite, Private Bathroom (RedBird Suite) | View from room](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ceeb05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/2e09a8f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, Private Bathroom (Parlour Suite) | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/d4b17f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/w3000h1988x0y3-ae06d912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

0.4 mi from Chesterwood

9.2/10

Wonderful

(110 reviews)

"Great breakfast, friendly helpful staff, pretty yard, good location "

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

Deborah

$335 nightly

$374 total

Mar 2 - Mar 3

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/4e4268ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/3e2d816d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/94cb14a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Red Lion Inn

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

2.1 mi from Chesterwood

8.8/10

Excellent

(1,000 reviews)

"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."

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

Gary

$183 nightly

$205 total

Mar 18 - Mar 19

Total with taxes and fees

[](https://www.expedia.com/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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 (Clark - Pets Allowed) | 1 bedroom](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/04b1723e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Suite, Private Bathroom (Honeymoon - Pets Allowed) | 1 bedroom](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/7ac0f2b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment, Private Bathroom (Greylock - No Pets) | 1 bedroom](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

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

3.6 mi from Chesterwood

9.6/10

Exceptional

(446 reviews)

"Had everything we needed. Very thoughtful touches. "

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

Mark

$102 nightly

$112 total

Mar 1 - Mar 2

Total with taxes and fees

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

![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/9ac40a95.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/dcdd836c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

5 mi from Chesterwood

8.8/10

Excellent

(733 reviews)

"Great property, very accommodating. "

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

Shanice

$107 nightly

$120 total

Feb 22 - Feb 23

Total with taxes and fees

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

![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Villa, 3 Bedrooms | Iron/ironing board, free cribs/infant beds, WiFi, bed sheets](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/24f01653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/226579d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/ed360a9d.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.com/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)

4.1 mi from Chesterwood

9.0/10

Wonderful

(838 reviews)

"Great overnights stay, wish I was here longer "

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

Thomas

$130 nightly

$145 total

Feb 22 - Feb 23

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/279dc540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/ef9bad04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/6fb451ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 Queen Bed, Mobility Accessible | Desk, laptop workspace, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/9c5d1ec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Little Lion

[](https://www.expedia.com/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information)

3.2 mi from Chesterwood

8.6/10

Excellent

(553 reviews)

"Great friendly staff"

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

Pablo

$110 nightly

$123 total

Feb 17 - Feb 18

Total with taxes and fees

[](https://www.expedia.com/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information)

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

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

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/1c5bd04f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/15c993a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

5.3 mi from Chesterwood

9.4/10

Exceptional

(767 reviews)

"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."

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

Dinh

$151 nightly

$169 total

Feb 22 - Feb 23

Total with taxes and fees

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

![Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/220f6cfe.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)

![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/a1ad800b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Monument Mountain Motel

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

5.4 mi from Chesterwood

9.0/10

Wonderful

(822 reviews)

"The room was clean, and the staff was friendly and helpful. "

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

Damien

$67 nightly

$74 total

Feb 22 - Feb 23

Total with taxes and fees

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

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

![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/00c971b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/e459ce18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

5.3 mi from Chesterwood

9.0/10

Wonderful

(1,000 reviews)

"Clean room, nice staff , decent breakfast. Overall a good stay . "

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

Anindita

$98 nightly

$109 total

Mar 9 - Mar 10

Total with taxes and fees

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

![Room #10 Queen's Cottage | Living room | Flat-screen TV](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/e69747b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Room #1 - Collins, 1 Queen Bed, Fireplace, not pet friendly | Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/ae0cb55d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/4f8b66e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Devonfield Inn B&B

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

4.7 mi from Chesterwood

10/10

Exceptional

(135 reviews)

"The inn has an excellent location and amenities."

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

Christopher

$279 nightly

$312 total

Feb 24 - Feb 25

Total with taxes and fees

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

![Standard Room, 1 King Bed, Non Smoking | Desk, iron/ironing board, cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/c24971a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/47150b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Lee - Lenox South

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

5.7 mi from Chesterwood

8.4/10

Very Good

(1,003 reviews)

"Safe, clean rooms, decent breakfast "

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

Neil

$86 nightly

$96 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Lee-Hotels-Quality-Inn.h459706.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 | In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/723a5f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom, Non Smoking | In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/a393dfb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/e351f473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Travelodge by Wyndham Great Barrington Berkshires

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

3.8 mi from Chesterwood

7.6/10

Good

(569 reviews)

"Excellent location!!"

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

Abdul Samad

$75 nightly

$84 total

Feb 22 - Feb 23

Total with taxes and fees

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

![Deluxe Suite | Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/e112ee1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fire Spa Suite | Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/de897732.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)

### Chambery Inn

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

5.4 mi from Chesterwood

9.6/10

Exceptional

(375 reviews)

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

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

Sophia

$190 nightly

$212 total

Feb 17 - Feb 18

Total with taxes and fees

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

![Lobby lounge](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/251da7fc.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)

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

![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/06dae0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Element Lenox Berkshires

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

7.8 mi from Chesterwood

9.8/10

Exceptional

(18 reviews)

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

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

Mary

$139 nightly

$155 total

Mar 1 - Mar 2

Total with taxes and fees

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

![Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/75dbf9d4.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)

![Garden](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/b642a3ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/51ca9ed5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### East Rock Inn

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

6.3 mi from Chesterwood

9.6/10

Exceptional

(37 reviews)

"The room was clean and comfortable wi will back next year:) "

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

Nadya

$131 nightly

$147 total

Mar 6 - Mar 7

Total with taxes and fees

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

![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)

![Dining](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/58d2b953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Library](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/9ee8409f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Loft, Private Bathroom (Skylight Loft) | Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/a856ec31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Brook Farm Inn

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

5.7 mi from Chesterwood

9.4/10

Exceptional

(164 reviews)

"Everything was perfect - location and accommodation."

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

Christopher

$154 nightly

$175 total

Feb 18 - Feb 19

Total with taxes and fees

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

![Property amenity](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/27ce1034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/5e996a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/a63e9470.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)

### Courtyard by Marriott Lenox Berkshires

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

7.5 mi from Chesterwood

9.2/10

Wonderful

(601 reviews)

"Our stay was great! "

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

Gianna

$126 nightly

$141 total

Mar 15 - Mar 16

Total with taxes and fees

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

![In-room dining](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/ca66a901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 Queen Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/ec5f4855.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/017819f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/f0e5252a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Econo Lodge Lee - Great Barrington

[](https://www.expedia.com/Lee-Hotels-Econo-Lodge-Lee-Great-Barrington.h913013.Hotel-Information)

4.6 mi from Chesterwood

6.4/10

(658 reviews)

"The room was clean and the service adequate"

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

David

$64 nightly

$71 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Lee-Hotels-Econo-Lodge-Lee-Great-Barrington.h913013.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/f0d9797c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/047ef967.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/48ee1fed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/28728ba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Whitlock

[](https://www.expedia.com/Lenox-Hotels-The-Whitlock.h66244754.Hotel-Information)

6.1 mi from Chesterwood

8.6/10

Excellent

(288 reviews)

"Super cute place and walking distance to a bunch of great shops and food! "

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

Gina

$119 nightly

$133 total

Feb 18 - Feb 19

Total with taxes and fees

[](https://www.expedia.com/Lenox-Hotels-The-Whitlock.h66244754.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/c5994ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/w488h380x9y0-567859b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/4037455f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, individually decorated, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/225b50c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 33 Main

[](https://www.expedia.com/Lenox-Hotels-33-Main.h20033760.Hotel-Information)

6.1 mi from Chesterwood

10/10

Exceptional

(74 reviews)

"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."

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

James

$406 nightly

$454 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/Lenox-Hotels-33-Main.h20033760.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.com/Hotel-Search?startDate=2026-03-02&endDate=2026-03-03&regionId=6091841&adults=2&sort=RECOMMENDED&openPlayBack=true)

## Compare popular hotels close to Chesterwood

| Property                                                                                                                                                                                                                                                                  | Star rating       | Guest rating              | Breakfast included | Pool | Spa | Pet friendly | WiFi included |  |
| ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | ----------------- | ------------------------- | ------------------ | ---- | --- | ------------ | ------------- |  |
| ![Suite, Private Bathroom (RedBird Suite) \| View from room](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ceeb05.jpg?impolicy=fcrop&w=900&h=675&p=1&q=medium)The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood | 4.5 star property | 9.2Wonderful110 reviews   | View               |      |     |              |               |  |
| ![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130.jpg?impolicy=fcrop&w=900&h=675&p=1&q=medium)The Red Lion Inn                                                                                                                   | 3.5 star property | 8.8Excellent1,000 reviews | View               |      |     |              |               |  |
| ![Garden](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57.jpg?impolicy=fcrop&w=900&h=675&p=1&q=medium)Shaker Mill Inn                                                                                                                      | 2.5 star property | 9.6Exceptional446 reviews | View               |      |     |              |               |  |
| ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=900&h=675&p=1&q=medium)Holiday Inn Express Hotel & Suites Great Barrington by IHG                                                                            | 2.5 star property | 8.8Excellent733 reviews   | View               |      |     |              |               |  |
| ![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27.jpg?impolicy=fcrop&w=900&h=675&p=1&q=medium)Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG                                               | 3.5 star property | 9.0Wonderful838 reviews   | View               |      |     |              |               |  |

## Top Chesterwood Hotel Reviews

![The Little Lion](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/6fb451ef_y.jpg)

### The Little Lion

10/10 Excellent

"Great friendly staff"

[](https://expedia.com/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information)

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

### The Red Lion Inn

10/10 Excellent

"Great stay. The only thing I would say - and I’ve been staying at the hotel since the 80s - it might be time for a few updates here and there. It runs the risk of going from rustic charm to grandma’s house in the not tooooo distant future. "

[](https://expedia.com/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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

"This is a really lovely, well-kept house. The layout is wonderful, offering plenty of space for everyone to spread out, while also having ample room for spending time all together. There is so much attention to detail (like delicious treats for us on the dining table!), well-stocked kitchen and bathrooms, and plenty of comfortable seating. The host was so nice and extremely responsive each time I reached out. We loved this house and would definitely stay again!"

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

![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://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

"Great overnights stay, wish I was here longer "

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

![Walk into town, soak up sun on enclosed porch & steps away from nature trails!](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/1993f238_y.jpg)

### Walk into town, soak up sun on enclosed porch & steps away from nature trails!

10/10 Excellent

"This is one of the most welcoming homes I have ever booked! The host Julie has gone above and beyond to make sure her guests are comfortable and happy in her home! I will definitely book here again!"

[](https://expedia.com/Stockbridge-Hotels-Walk-Into-Town.h77128037.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

"Great property and very responsive host"

[](https://expedia.com/Housatonic-Hotels-Woodland-Zen-By-AvantStay-Modern-Design-Patio.h105019545.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

"We had a great time at the Taggart River House! Views and light were unbelievable and it was so nice to be there with extended family and have everyone have their own lovely spaces with bathrooms. A quick walk into town made the days even richer. Would 100% stay again! Also well stocked for kids with a high chair, crib, etc. only missing one stair gate which would have made it perfect, but we put furniture in front of those stairs and that was a great solution too. "

[](https://expedia.com/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

"Great stay!"

[](https://expedia.com/Stockbridge-Hotels-A-Grand-Estate-In-Historic-Stockbridge.h33960335.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

"Fully equipped. Pet friendly"

[](https://expedia.com/Stockbridge-Hotels-Stockbridge-Home.h87633659.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.com/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.com/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.com/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.com/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.com/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.com/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.com/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.com/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.com/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 2.0 miles from Chesterwood. Rated an impressive 10 by travelers, this modern retreat accommodates up to 10 travelers, 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.com/West-Stockbridge-hotels-Vacation-in-a--Berkshire-Farmhouse.h33973032.Hotel-information)
> 
>   
> Located 2.9 miles 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 travelers.
> 
>   
> [The Inn at Stockbridge](https://www.expedia.com/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information)
> 
>   
> The Inn at Stockbridge is a 4-star gem just 4.1 miles from Chesterwood, rated 9.8 by travelers. 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.com/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.com/Stockbridge-hotels-Taggart-Treehouse:-Modern-Luxury-Meets-Nature:-Stunning-river-views,-sleeps-10.h92100621.Hotel-information)
> 
>   
> Taggart Treehouse: Modern Luxury Meets Nature is only 2.0 miles from Chesterwood and enjoys a perfect 10 travelers' 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 travelers. 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.com/West-Stockbridge-hotels-Vacation-in-a--Berkshire-Farmhouse.h33973032.Hotel-information)
> 
>   
> Vacation in a Berkshire Farmhouse is a fantastic option just 2.9 miles from Chesterwood, an impressive travelers' 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.com/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 4.7 miles 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 vacation.

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

> [Vacation in a Berkshire Farmhouse](https://expedia.com/West-Stockbridge-hotels-Vacation-in-a--Berkshire-Farmhouse.h33973032.Hotel-information)
> 
>   
> Located just 2.9 miles from Chesterwood, this charming farmhouse is rated an impressive 9.8 by travelers. 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.com/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 travelers. 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.com/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)
> 
>   
> This 3.5-star resort is situated 4.7 miles 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.com/Stockbridge-hotels-Taggart-Treehouse:-Modern-Luxury-Meets-Nature:-Stunning-river-views,-sleeps-10.h92100621.Hotel-information)
> 
>   
> Taggart Treehouse is a spacious retreat just 2.0 miles from Chesterwood, rated an impressive 10 by travelers. 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.com/West-Stockbridge-hotels-Vacation-in-a--Berkshire-Farmhouse.h33973032.Hotel-information)
> 
>   
> Just 2.9 miles 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.com/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information)
> 
>   
> Located 4.9 miles 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 travelers. 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.com/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information)
> 
>   
> The Inn at Stockbridge, just 4.1 miles 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 center, ensuring a comfortable and energizing stay.
> 
>   
> [The Red Lion Inn](https://expedia.com/Stockbridge-hotels-The-Red-Lion-Inn.h5780784.Hotel-information)
> 
>   
> Located only 2.3 miles 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.com/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)
> 
>   
> Situated just 4.7 miles 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.com/West-Stockbridge-hotels-Vacation-in-a--Berkshire-Farmhouse.h33973032.Hotel-information)
> 
>   
> Just 2.9 miles 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 travelers with pets alike.
> 
>   
> [The Inn at Stockbridge](https://www.expedia.com/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information)
> 
>   
> The Inn at Stockbridge, located 4.1 miles 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.com/Lee-Hotels-Econo-Lodge-Lee-Great-Barrington.h913013.Hotel-Information)
> 
>   
> Econo Lodge Lee - Great Barrington is just 5.0 miles from Chesterwood and offers a cozy stay for travelers 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 travelers 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?

> *\*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.*

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- [Norman Rockwell Museum ](https://www.expedia.com/Norman-Rockwell-Museum-Stockbridge.d6091839.Vacation-Attraction)
- [Visit Stockbridge ](https://www.expedia.com/Stockbridge.dx162575)
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- [Mission House ](https://www.expedia.com/Mission-House-Stockbridge.d553248621560941222.Vacation-Attraction)
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- [Visit West Stockbridge ](https://www.expedia.com/West-Stockbridge.dx173346)

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