Search Hotels Near Chesterwood, West Stockbridge

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Filter by

Popular filters
Popular filters
Price per night
Guest rating
Guest rating
Property class
Payment type
Payment type
Property type
Property type
Area
Area
Popular locations
1
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveller experience
Traveller experience

Top Trending Hotels Near Chesterwood

Exterior
The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, (1003)
"Lovely property and very polite and accommodating staff. The room was very clean and comfortable. My only respectful suggestion is that a microwave be included in the rooms."
The price is ฿3,660
฿4,088 total
includes taxes & fees
23 May - 24 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, (882)
"Stay was great"
The price is ฿5,030
฿6,426 total
includes taxes & fees
28 May - 29 May
The Red Lion Inn
Lobby
Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (240)
"Driveway entrance is on a very busy road where cars & trucks go very fast, so turning into & out of drive is tricky."
The price is ฿3,582
฿4,001 total
includes taxes & fees
21 May - 22 May
Life House Berkshires
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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, (467)
"Clean, friendly staff, plenty of indoor/outdoor activities."
The price is ฿5,030
฿5,980 total
includes taxes & fees
21 May - 22 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, (508)
"Beautiful location, property in very good condition, clean. "
The price is ฿6,115
฿6,831 total
includes taxes & fees
28 May - 29 May
Courtyard by Marriott Lenox Berkshires
Aerial view
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (152)
"The Lakehouse Inn is really cute, right on a lake with wonderful waterfront spaces. The bathroom situation is more European--toilet and shower in the bathroom, sink outside. There was no tub, not a problem for me but good to be aware of. The morning breakfast was delicious! I was greeted with a white wine sangria. It's conveniently located for roaming around Stockbridge, Great Barrington, etc. Close to the Norman Rockwell museum, Hancock Shaker Village, Edith Wharton estate. Would absolutely...
The price is ฿4,885
฿5,729 total
includes taxes & fees
19 May - 20 May
Lakehouse Inn
Reception
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.4 out of 10, Exceptional, (648)
"Staff was very friendly. Facilities were clean and comfortable. Breakfast was quite good. Convenient location. We had a terrific stay!"
The price is ฿5,500
฿6,143 total
includes taxes & fees
28 May - 29 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)
"It was a great place to stay for the night. "
The price is ฿4,414
฿5,177 total
includes taxes & fees
19 May - 20 May
The Cornell Inn, Lenox
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, (593)
"Very convenient and affordable price!!"
The price is ฿2,406
฿2,688 total
includes taxes & fees
19 May - 20 May
Monument Mountain Motel
Seasonal outdoor pool
Apple Tree Inn
3.0 star property
8.2 out of 10, Very good, (212)
"Absolutely gorgeous room. Wonderful staff, I felt like royalty. "
The price is ฿4,475
฿5,605 total
includes taxes & fees
23 May - 24 May
Apple Tree 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)
"Whenever we are in the area we have stayed and been pleased. "
The price is ฿2,898
฿3,237 total
includes taxes & fees
19 May - 20 May
Quality Inn
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, (498)
"Really enjoyed the seating outside and pool side was very relaxing. The staff was very helpful and informative. Great experience!!!"
The price is ฿4,936
฿5,513 total
includes taxes & fees
30 May - 31 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 ฿8,655
฿9,668 total
includes taxes & fees
28 May - 29 May
Chambery Inn
Library
Blackberry River Inn
3.0 star property
9.6 out of 10, Exceptional, (26)
"Cozy, comfortable, feels like you are staying at someone’s home that you love, but, lol with privacy! Breakfast is fabulous and eggs are made to order!"
The price is ฿6,567
฿7,553 total
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, (455)
"Manager was friendly and patient late at night. "
The price is ฿2,497
฿2,789 total
includes taxes & fees
19 May - 20 May
Travelodge by Wyndham Great Barrington Berkshires
Exterior
The Briarcliff Motel
3.0 star property
8.8 out of 10, Excellent, (385)
"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 ฿3,980
฿4,446 total
includes taxes & fees
21 May - 22 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, (383)
"Perfect little country inn tucked in the Berkshires, convenient to the highway but off the beaten path on a quiet rural road. Our first floor suite was spacious, inviting, comfortable, and clearly designed with care. Would definitely return next time we’re in the area. "
The price is ฿4,958
฿5,439 total
includes taxes & fees
29 May - 30 May
Shaker Mill Inn
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, (504)
"The woman at check-in was kind. We had a lovely view. Place was in a great location with a comfortable bed."
The price is ฿2,051
฿2,291 total
includes taxes & fees
19 May - 20 May
Econo Lodge Lee - Great Barrington
Don't see what you're looking for?
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
9,326
Accommodation
684 hotels
Lowest Price
฿2,051
Highest Price
฿8,655

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.

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

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
"Just like home"
A verified traveller stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Posted 3 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
The Red Lion Inn

The Red Lion Inn

5/5 Excellent
"Stay was great"
A verified traveller stayed at The Red Lion Inn
Posted 4 days ago
The Red Lion Inn