Hotels near Chesterwood

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Top 10 Hotels Near Chesterwood

Exterior
The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, (1004)
"Great visit to The Black Swan Inn. Perfectly located central to activities in the Berkshires. Fantastic customer service and very clean."
The price is S$153
includes taxes & fees
9 May - 10 May
The Black Swan Lee - Lenox, Ascend Hotel Collection
Outdoor pool, pool loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (872)
"Quaint, quiet and peaceful."
The price is S$209
includes taxes & fees
6 May - 7 May
The Red Lion Inn
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 S$150
includes taxes & fees
5 May - 6 May
Life House Berkshires
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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 S$224
includes taxes & fees
5 May - 6 May
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
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
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 S$230
includes taxes & fees
9 May - 10 May
Courtyard by Marriott Lenox Berkshires
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 S$214
includes taxes & fees
5 May - 6 May
Lakehouse Inn
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 S$244
includes taxes & fees
27 May - 28 May
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Porch
The Cornell Inn, Lenox
3.0 star property
8.6 out of 10, Excellent, (1000)
"Great breakfast. "
The price is S$194
includes taxes & fees
5 May - 6 May
The Cornell Inn, Lenox
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 S$101
includes taxes & fees
7 May - 8 May
Monument Mountain Motel
Seasonal outdoor pool
Apple Tree Inn
3.0 star property
8.2 out of 10, Very good, (212)
"Love it!!!"
The price is S$210
includes taxes & fees
9 May - 10 May
Apple Tree Inn
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 S$121
includes taxes & fees
5 May - 6 May
Quality Inn
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 S$220
includes taxes & fees
29 May - 30 May
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is S$362
includes taxes & fees
10 May - 11 May
Chambery 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 S$283
includes taxes & fees
20 May - 21 May
Blackberry River Inn
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 S$104
includes taxes & fees
7 May - 8 May
Travelodge by Wyndham Great Barrington Berkshires
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 S$166
includes taxes & fees
5 May - 6 May
The Briarcliff Motel
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
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 S$195
includes taxes & fees
4 May - 5 May
Shaker Mill Inn
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 S$94
includes taxes & fees
19 May - 20 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
9,270
Accommodation
695 hotels
Lowest Price
S$94
Highest Price
S$362

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.

Recent Reviews in Chesterwood
Expedia verified reviews

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