Hotels near Chesterwood

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Top Trending Hotels Near Chesterwood

Business center
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
0.6 km from Chesterwood
9.2 out of 10, Wonderful, (110)
"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 P22,554
P27,284 total
includes taxes & fees
Dec 1 - Dec 2
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
1 bedroom, premium bedding, iron/ironing board, free WiFi
Tanglewood Suites

Tanglewood Suites

2.5 star property
2.6 km from Chesterwood
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
United States
Elizabeth
The price is P12,933
P12,933 total
includes taxes & fees
Dec 1 - Dec 2
Tanglewood Suites
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
3.3 km from Chesterwood
8.8 out of 10, Excellent, (1001)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is P8,799
P12,467 total
includes taxes & fees
Dec 15 - Dec 16
The Red Lion Inn
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (435)
"Nice place, easy check in"
United States
Robert
The price is P6,437
P7,061 total
includes taxes & fees
Nov 18 - Nov 19
Shaker Mill Inn
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
5.2 km from Chesterwood
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
United States
Steven
The price is P14,811
P17,372 total
includes taxes & fees
Nov 20 - Nov 21
The Inn at Stockbridge
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8 km from Chesterwood
8.8 out of 10, Excellent, (695)
"Solid location, great room, good breakfast. Fair Price. Been 3 different times and look forward to returning again "
United States
Jamie
The price is P6,319
P7,058 total
includes taxes & fees
Nov 24 - Nov 25
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
8.6 km from Chesterwood
9.4 out of 10, Exceptional, (754)
"Clean room, very courteous staff "
United States
Thomas
The price is P8,445
P9,433 total
includes taxes & fees
Nov 23 - Nov 24
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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
6.6 km from Chesterwood
9.0 out of 10, Wonderful, (783)
"Place was great!"
United States
Benjamin
The price is P7,530
P9,235 total
includes taxes & fees
Nov 20 - Nov 21
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
8.6 km from Chesterwood
9.0 out of 10, Wonderful, (1002)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is P6,475
P7,233 total
includes taxes & fees
Dec 8 - Dec 9
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (790)
"Clean and quiet. "
United States
Daniel
Monument Mountain Motel
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
The Little Lion

The Little Lion

3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (544)
"The check-in was easy and the room was ready and clean. It was nice having our dogs with us. "
United States
Maria
The price is P7,618
P8,509 total
includes taxes & fees
Nov 18 - Nov 19
The Little Lion
Front of property - evening/night
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (133)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Front of property
Chambery Inn

Chambery Inn

3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (372)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
6.2 km from Chesterwood
7.6 out of 10, Good, (559)
"The staff were very friendly and accommodating "
United States
Tom
The price is P4,429
P4,948 total
includes taxes & fees
Nov 18 - Nov 19
Travelodge by Wyndham Great Barrington Berkshires
Lobby
Quality Inn

Quality Inn

2.5 star property
9.2 km from Chesterwood
8.4 out of 10, Very Good, (1001)
"Clean room and good breakfast "
United States
Kelly
The price is P5,471
P6,112 total
includes taxes & fees
Nov 30 - Dec 1
Quality Inn
1 bedroom, premium bedding, iron/ironing board, rollaway beds
Brook Farm Inn

Brook Farm Inn

3.5 star property
9.1 km from Chesterwood
9.4 out of 10, Exceptional, (162)
"Comfortable, quiet, convenient location, very friendly staff. "
United States
Susan
Brook Farm Inn
Desk, iron/ironing board, free cribs/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

2.0 star property
7.4 km from Chesterwood
6.4 out of 10, (647)
"Great place. , good staff "
United States
ketul
The price is P3,464
P3,869 total
includes taxes & fees
Dec 1 - Dec 2
Econo Lodge Lee - Great Barrington
Private kitchen
East Rock Inn

East Rock Inn

2.0 star property
10.1 km from Chesterwood
9.4 out of 10, Exceptional, (36)
"We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again."
United States
Laura
The price is P8,094
P9,041 total
includes taxes & fees
Dec 15 - Dec 16
East Rock Inn
Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

4.0 star property
9.8 km from Chesterwood
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is P28,287
P31,597 total
includes taxes & fees
Nov 23 - Nov 24
33 Main
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
12.1 km from Chesterwood
9.2 out of 10, Wonderful, (586)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is P6,968
P7,784 total
includes taxes & fees
Dec 14 - Dec 15
Courtyard by Marriott Lenox Berkshires
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 guest rated hotels close to Chesterwood

Business center
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, (110)
    The price is P22,554
    P27,284 total
    includes taxes & fees
    Dec 1 - Dec 2
    The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
    See more properties

    Top Chesterwood Hotel Reviews

    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

    10/10 Excellent
    "Place was great!"
    Benjamin 4-night trip
    Posted 12 days ago
    Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

    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

    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, check out the 10 hotels and other accommodations you'll find within a mile.
    What's the best hotel 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 traveler 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 are there close to Chesterwood?
    Expedia has 10 hotels and other accommodations within a mile from Chesterwood.
    If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund?
    Yes, the majority of room reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to review 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.