Search Hotels Near Chesterwood, West Stockbridge

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Top Trending Hotels Near Chesterwood

The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior
The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, (1004)
"Just a nice, cozy and very clean little hotel. We would stay there again if in the area."
The price is ฿3,739
฿4,176 total
includes taxes & fees
9 May - 10 May
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Red Lion Inn
Outdoor pool, pool loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (872)
"The most quaint and cozy New England Inn, with multiple dining options, two boutiques, heated swimming pool, close to all the Berkshires has to offer, everything is perfect!"
The price is ฿4,337
฿5,667 total
includes taxes & fees
6 May - 7 May
The Red Lion Inn
Life House Berkshires
Lobby
Life House Berkshires
3.5 star property
9.2 out of 10, Wonderful, (232)
"It’s the perfect place to go for a weekend or weeklong stay and be as isolated as social as you want. The towns nearby are fantastic. Will definitely be back a lot "
The price is ฿3,644
฿4,071 total
includes taxes & fees
6 May - 7 May
Life House Berkshires
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Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 star property
9.0 out of 10, Wonderful, (461)
"The room was spacious- 2 bedrooms, large living room, full kitchen, terrace, TV's in every room. It was spotless when we arrived. The stay was exceptional."
The price is ฿5,117
฿6,084 total
includes taxes & fees
6 May - 7 May
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Seven Hills Inn
Terrace/patio
Seven Hills Inn
4.0 star property
7.8 out of 10, Good, (467)
"Great breakfast, amazing property, comfortable beds! Water in shower wasn’t hot, had to take a “warm-cold” fast shower but it didn’t matter. The view, the quiet, nature and siting areas made the stay perfect. Will come again!!"
Seven Hills Inn
Courtyard by Marriott Lenox Berkshires
Indoor pool
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (507)
"Beautiful location, property in very good condition, clean. "
The price is ฿5,595
฿6,250 total
includes taxes & fees
5 May - 6 May
Courtyard by Marriott Lenox Berkshires
Lakehouse Inn
Aerial view
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (150)
"Love this Inn, all employees were friendly and knowledgeable about things to do in the area. The breakfast was delicious . I look forward to staying at the Inn again."
The price is ฿4,970
฿5,829 total
includes taxes & fees
5 May - 6 May
Lakehouse Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Reception
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.2 out of 10, Wonderful, (645)
"Employees were excellent. Very nice location to stay. Pool was nice and well kept "
The price is ฿5,927
฿6,620 total
includes taxes & fees
27 May - 28 May
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
The Cornell Inn, Lenox
Porch
The Cornell Inn, Lenox
3.0 star property
8.6 out of 10, Excellent, (1000)
"Great breakfast. "
The price is ฿4,491
฿5,267 total
includes taxes & fees
5 May - 6 May
The Cornell Inn, Lenox
Monument Mountain Motel
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
Monument Mountain Motel
2.5 star property
9.0 out of 10, Wonderful, (587)
"Easy access, very clean, nearby restaurants "
The price is ฿2,448
฿2,734 total
includes taxes & fees
6 May - 7 May
Monument Mountain Motel
Apple Tree Inn
Seasonal outdoor pool
Apple Tree Inn
3.0 star property
8.2 out of 10, Very good, (212)
"Love it!!!"
The price is ฿4,553
฿5,702 total
includes taxes & fees
9 May - 10 May
Apple Tree Inn
Quality Inn
Standard Room, 2 Queen Beds, Non Smoking | 1 bedroom, premium bedding, pillow-top beds, desk
Quality Inn
2.5 star property
8.0 out of 10, Very good, (1000)
"Generally a good stay, great value"
The price is ฿2,949
฿3,294 total
includes taxes & fees
5 May - 6 May
Quality Inn
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Standard Room | Premium bedding, pillow-top beds, in-room safe, desk
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (495)
"Really enjoyed the seating outside and pool side was very relaxing. The staff was very helpful and informative. Great experience!!!"
The price is ฿5,497
฿6,141 total
includes taxes & fees
19 May - 20 May
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Chambery Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is ฿8,842
฿9,877 total
includes taxes & fees
10 May - 11 May
Chambery Inn
Blackberry River Inn
Library
Blackberry River Inn
3.0 star property
9.6 out of 10, Exceptional, (24)
"Lucas was very accommodating and helpful. Pleasant and great place to stay. Great fresh breakfast!!"
The price is ฿6,681
฿7,684 total
includes taxes & fees
29 May - 30 May
Blackberry River Inn
Travelodge by Wyndham Great Barrington Berkshires
In-room safe, desk, free cots/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
7.6 out of 10, Good, (452)
"Right next to 2 great breakfast diner options, and close to both the ski mountains and the COVE Bowling lanes for a night time activity"
The price is ฿2,540
฿2,837 total
includes taxes & fees
5 May - 6 May
Travelodge by Wyndham Great Barrington Berkshires
The Briarcliff Motel
Exterior
The Briarcliff Motel
3.0 star property
8.8 out of 10, Excellent, (384)
"We loved this place. It's dog friendly, the place is clean and quiet. The proprietor is awesome. It's super friendly. We spent a total of 9 days here, and I'd definitely come back again. Thanks for a great stay"
The price is ฿4,049
฿4,523 total
includes taxes & fees
5 May - 6 May
The Briarcliff Motel
The Ponds at Foxhollow by Capital Vacations
Property grounds
The Ponds at Foxhollow by Capital Vacations
3.0 star property
8.6 out of 10, Excellent, (110)
"Comfortable condo accommodations. Ample size, Workable kitchen. Comfortable bed. Lovely setting. And a community facility with a pool, workout equipment, and sauna too! Small but tangible complaint: outside lighting is very bright and shines into BR window. "
The Ponds at Foxhollow by Capital Vacations
Shaker Mill Inn
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (380)
"This is a lovely place to say. Very warm and welcoming. The staff was very helpful and even brought a little doggy basket for my dog. It included a blanket, dog bowls treats and more!! Had a very very nice time. "
The price is ฿3,445
฿3,779 total
includes taxes & fees
5 May - 6 May
Shaker Mill Inn
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cots/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington
2.0 star property
6.2 out of 10, (501)
"Excellent "
The price is ฿2,296
฿2,564 total
includes taxes & fees
16 May - 17 May
Econo Lodge Lee - Great Barrington
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See all available properties in Chesterwood
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.

Chesterwood hotels information

Number of reviews
9,272
Accommodation
695 hotels
Lowest Price
฿2,296
Highest Price
฿8,842

Destinations near West Stockbridge

Image for Norman Rockwell Museum

Norman Rockwell Museum

5/5(1 review)

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

See properties
Norman Rockwell Museum

Frequently asked questions

What's the area like around Chesterwood?

Chesterwood is located in a scenic area of West Stockbridge known for its beautiful lakeside setting and hiking. If you're looking for a convenient place to stay, take a look at the 7 hotels and other accommodation options you'll find within a mile.

Where is the best place to stay close to Chesterwood?

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood is one of the top choices for your stay based on our traveller data, and this B&B offers free breakfast and free parking. It's located just a short 0.4 mi (0.7 km) from Chesterwood. Other good choices within a few miles include The Red Lion Inn and Tanglewood Suites.

How many hotels will I find near Chesterwood?

Expedia has 7 hotels and other accommodation options within a mile from Chesterwood.

If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund?

Yes! You'll find that most room reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of booking. Enter your dates, click on "Search", then you can filter by "fully refundable" to get the best options available near Chesterwood.

What can I see and do near Chesterwood?

You'll want to browse the exhibits at Norman Rockwell Museum and Mission House. Naumkeag Museum, The Mount and Berkshire Theatre Festival are monuments to see when you're exploring the area around Chesterwood. Be sure to get some family photos at Berkshire Botanical Garden, Hoffman's Pottery and Charles H. Baldwin & Sons while you're out sightseeing near Chesterwood.

Chesterwood Hotel Reviews
Expedia verified reviews

The Red Lion Inn

The Red Lion Inn

5/5 Excellent
"The most quaint and cozy New England Inn, with multiple dining options, two boutiques, heated swimming pool, close to all the Berkshires has to offer, everything is perfect!"
A verified traveller stayed at The Red Lion Inn
Posted 21 hours ago
The Red Lion Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

5/5 Excellent
"The room was spacious- 2 bedrooms, large living room, full kitchen, terrace, TV's in every room. It was spotless when we arrived. The stay was exceptional."
A verified traveller from beechurst stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Posted 7 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel