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25 Oct - 26 Oct
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Top Trending Hotels Near Chesterwood

Business centre
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (108)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is Rp5.137.821
Rp6.215.423 total
includes taxes & fees
9 Nov - 10 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8 out of 10, Excellent, (678)
"This motel was easy access right off the highway, super clean, and the staff was great. We would definitely stay here again. Breakfast options were good as well. "
United States
Tina
The price is Rp1.693.404
Rp1.891.533 total
includes taxes & fees
13 Nov - 14 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.4 out of 10, Exceptional, (746)
"The property is very nice and the staff was extremely friendly and helpful."
United States
Greg
The price is Rp2.374.086
Rp2.651.854 total
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
Monument Mountain Motel
Monument Mountain Motel
2.5 star property
9.0 out of 10, Wonderful, (776)
"Very convenient and we were happy that the little restaurant we'd chosen for dinner was right across the street (we drove anyway, as it's a busy street)."
United States
Elizabeth
Monument Mountain Motel
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1005)
"Great Indian restaurant in the hotel!"
United States
Chris
The price is Rp1.763.963
Rp1.970.347 total
includes taxes & fees
3 Nov - 4 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
The Little Lion
The Little Lion
3.0 star property
8.6 out of 10, Excellent, (539)
"A quiet, comfortable, chic place to stay across from Monument Mountain. "
United States
Mary Lou
The price is Rp2.141.658
Rp2.392.232 total
includes taxes & fees
2 Nov - 3 Nov
The Little Lion
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.0 out of 10, Wonderful, (768)
"Lovely spot, great accommodations, friendly staff, and great location."
United States
Joanne
The price is Rp2.141.658
Rp2.623.996 total
includes taxes & fees
3 Nov - 4 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Front of property
Chambery Inn
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (370)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Lobby
Quality Inn
Quality Inn
2.5 star property
8.4 out of 10, Very good, (1000)
"Staff was very helpful - easy location - clean rooms!"
United States
Karen
The price is Rp1.538.175
Rp1.718.141 total
includes taxes & fees
16 Nov - 17 Nov
Quality Inn
In-room safe, desk, free cots/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
7.6 out of 10, Good, (555)
"Excellent location, friendly service, clean, comfortable room."
United States
Beth
The price is Rp1.245.150
Rp1.390.916 total
includes taxes & fees
27 Oct - 28 Oct
Travelodge by Wyndham Great Barrington Berkshires
Exterior
Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge
2.0 star property
6.8 out of 10, (1001)
"good average place to stay."
United States
Terry
The price is Rp1.008.073
Rp1.105.856 total
includes taxes & fees
4 Nov - 5 Nov
Pleasant Valley Motel West Stockbridge
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds
Brook Farm Inn
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (161)
"Inn was gorgeous and staff exceptional!"
United States
Joyce
Brook Farm Inn
Standard Room, 1 King Bed | Desk, iron/ironing board, free cots/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
2.0 star property
6.4 out of 10, (643)
"Stayed one night just because we had been driving for 10 hours but nice place for the price. "
United States
patricia
The price is Rp1.018.201
Rp1.137.331 total
includes taxes & fees
18 Nov - 19 Nov
Econo Lodge Lee - Great Barrington
Premium Apartment | Private kitchen | Microwave, electric kettle
East Rock Inn
East Rock Inn
2.0 star property
9.4 out of 10, Exceptional, (35)
"Quiet and peaceful location set off the road, with woodsy area in the back. Very close to Main Street shops and restaurants. "
United States
Amanda
The price is Rp2.373.655
Rp2.651.373 total
includes taxes & fees
16 Nov - 17 Nov
East Rock Inn
Property amenity
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (582)
"new property, modern and centrally located in the Berkshires. Located very close to Lenox, giving you many dining options "
United States
Francisco
The price is Rp2.108.454
Rp2.355.143 total
includes taxes & fees
23 Nov - 24 Nov
Courtyard by Marriott Lenox Berkshires
Exterior
Element Lenox Berkshires
Element Lenox Berkshires
3.0 star property
9.4 out of 10, Exceptional, (6)
"New hotel very nice"
United States
joel
The price is Rp2.241.270
Rp2.503.498 total
includes taxes & fees
2 Nov - 3 Nov
Element Lenox Berkshires
Exterior
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, (1004)
"Very clean, nice amenities , great location!!"
United States
Erin
The price is Rp1.846.142
Rp2.062.140 total
includes taxes & fees
9 Nov - 10 Nov
Hampton Inn & Suites Berkshires-Lenox
Seasonal outdoor pool
Sunset Inn
Sunset Inn
2.0 star property
7.6 out of 10, Good, (408)
"That can be reserved at any time"
United States
Felicita
The price is Rp1.494.180
Rp1.669.000 total
includes taxes & fees
4 Nov - 5 Nov
Sunset Inn
Lobby
Quality Inn
Quality Inn
2.5 star property
8.4 out of 10, Very good, (1002)
"Clean room, nice location "
United States
Devron
The price is Rp1.397.058
Rp1.560.513 total
includes taxes & fees
9 Nov - 10 Nov
Quality Inn
Exterior
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1019)
"Good breakfast King rooms are the best facing the mountains Recently remodeled "
United States
Susan M
The price is Rp1.964.716
Rp2.194.587 total
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham
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.
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Top Chesterwood Hotel Reviews

Hotels near other Chesterwood attractions

Norman Rockwell Museum

4.7/5 (252 reviews)
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

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

Frequently asked questions

What's the area like around Chesterwood?
Chesterwood is located in a scenic area of South Lee known for its beautiful lakeside setting and hiking. If you're looking for a convenient place to stay, take a look at the 10 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 (0.6 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 10 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.