Hotels near Chesterwood

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4 Nov - 5 Nov
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5 Nov - 6 Nov
This weekend
7 Nov - 9 Nov
Next weekend
14 Nov - 16 Nov

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Top 10 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, (109)
"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 S$489
includes taxes & fees
18 Nov - 19 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Outdoor pool, pool loungers
The Red Lion Inn
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1028)
"Food was great!"
United States
Emily
The price is S$260
includes taxes & fees
13 Nov - 14 Nov
The Red Lion Inn
Garden
Shaker Mill Inn
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (433)
"Nice place, easy check in"
United States
Robert
The price is S$143
includes taxes & fees
12 Nov - 13 Nov
Shaker Mill Inn
Individually decorated, individually furnished, desk, laptop workspace
Granville House
Granville House
3.0 star property
10.0 out of 10, Exceptional, (86)
"Wonderful! Will stay again!"
Canada
Rebecca
The price is S$327
includes taxes & fees
16 Nov - 17 Nov
Granville House
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, (775)
"Lovely spot, great accommodations, friendly staff, and great location."
United States
Joanne
The price is S$188
includes taxes & fees
12 Nov - 13 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior
The Inn at Stockbridge
The Inn at Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (98)
"A first class little inn"
United States
Philip
The price is S$419
includes taxes & fees
9 Nov - 10 Nov
The Inn at Stockbridge
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, (749)
"We had a nice stay at the Fairfield Inn in Great Barrington. It’s conveniently located not far from downtown and just a short drive to Stockbridge. The front desk staff was welcoming, the room spacious and clean, and plenty of breakfast items to choose from. Definitely recommend!"
United States
Denise
The price is S$208
includes taxes & fees
9 Nov - 10 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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, (688)
"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 S$155
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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, (782)
"This was an older property, but room was nice and bathroom was updated. "
United States
Martha
Monument Mountain Motel
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, (543)
"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 S$187
includes taxes & fees
5 Nov - 6 Nov
The Little Lion
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, (1007)
"We had a lakeside room which was wonderful!"
United States
Nancy
The price is S$159
includes taxes & fees
10 Nov - 11 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Front of property – evening/night
Devonfield Inn B&B
Devonfield Inn B&B
4.0 star property
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
9.6 out of 10, Exceptional, (372)
"We LOVED our mini getaway at the Chambery Inn. The room was gorgeous, spacious, and very comfortable. The fireplace couldn't have been easier to operate. The jetted tubs were divine with plenty of hot water the towel warmer was a nice bonus. The room was fully stocked with glassware and a corkscrew which was appreciated. We look forward to coming back"
United States
Samuel
Chambery 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, (556)
"Excellent location, friendly service, clean, comfortable room."
United States
Beth
The price is S$109
includes taxes & fees
5 Nov - 6 Nov
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 S$83
includes taxes & fees
12 Nov - 13 Nov
Pleasant Valley Motel West Stockbridge
Lobby
Quality Inn
Quality Inn
2.5 star property
8.4 out of 10, Very good, (1010)
"Fine lodging for short term business stay"
United States
Lawrence
The price is S$135
includes taxes & fees
23 Nov - 24 Nov
Quality Inn
Private kitchen
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 S$192
includes taxes & fees
17 Nov - 18 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, (585)
"Fabulous place"
United States
Mary
The price is S$185
includes taxes & fees
23 Nov - 24 Nov
Courtyard by Marriott Lenox Berkshires
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, (644)
"Staff friendly, room was quiet, large and comfortable. "
United States
Barbara
The price is S$85
includes taxes & fees
18 Nov - 19 Nov
Econo Lodge Lee - Great Barrington
Front of property
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1003)
"Honestly I just enjoyed being able to relax Play some games in the cute pub and the breakfast was yummy and stuff was inviting and so helpful "
United States
Sandra
The price is S$238
includes taxes & fees
6 Nov - 7 Nov
The Cornell Inn, Lenox & The 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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Hotels close to Chesterwood with free breakfast

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
  • Breakfast included
9.2 out of 10, Wonderful, (109)
The price is S$489
includes taxes & fees
18 Nov - 19 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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Top guest rated hotels close to Chesterwood

Outdoor pool, pool loungers
The Red Lion Inn
The Red Lion Inn
3.5 star property
    8.8 out of 10, Excellent, (1028)
    The price is S$260
    includes taxes & fees
    13 Nov - 14 Nov
    The Red Lion Inn
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    Top Chesterwood Hotel Reviews

    The Red Lion Inn

    The Red Lion Inn

    10/10 Excellent
    "Room was clean and comfortable. Antique furnishings throughout the hotel, all spotlessly clean but period correct for the past. Staff were all helpful and professional."
    Harold 2-night trip
    Posted 4 days ago
    The Red Lion Inn

    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.
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    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.