Top Hotels Near Chesterwood in South Lee from NZ$110

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28 Oct - 29 Oct
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31 Oct - 2 Nov
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Accommodation 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 NZ$648
includes taxes & fees
11 Nov - 12 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, (1022)
"Picture perfect Inn"
United States
jeff
The price is NZ$351
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
Garden
Shaker Mill Inn
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (432)
"Very casual and easy check in and out; lovely and substantial breakfast"
United States
Jamie
The price is NZ$205
includes taxes & fees
4 Nov - 5 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)
"Outstanding all around!"
United States
Jonathan
The price is NZ$435
includes taxes & fees
3 Nov - 4 Nov
Granville House
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, (681)
"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 NZ$198
includes taxes & fees
13 Nov - 14 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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, (771)
"We enjoyed our stay and will definitely be back."
United States
Howard
The price is NZ$236
includes taxes & fees
30 Oct - 31 Oct
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires 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, (747)
"The property is very nice and the staff was extremely friendly and helpful."
United States
Greg
The price is NZ$277
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Exterior
The Inn at Stockbridge
The Inn at Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
United States
Steven
The price is NZ$704
includes taxes & fees
3 Nov - 4 Nov
The Inn at Stockbridge
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, (1000)
"Great Indian restaurant in the hotel!"
United States
Chris
The price is NZ$206
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, (541)
"A quiet, comfortable, chic place to stay across from Monument Mountain. "
United States
Mary Lou
The price is NZ$240
includes taxes & fees
2 Nov - 3 Nov
The Little Lion
Room, 1 Queen Bed, Non Smoking
Monument Mountain Motel
Monument Mountain Motel
2.5 star property
9.0 out of 10, Wonderful, (780)
"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
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, (371)
"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, (1004)
"Staff was very helpful - easy location - clean rooms!"
United States
Karen
The price is NZ$179
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, (556)
"The staff were very friendly and accommodating "
United States
Tom
The price is NZ$145
includes taxes & fees
29 Oct - 30 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 NZ$110
includes taxes & fees
2 Nov - 3 Nov
Pleasant Valley Motel West Stockbridge
Premium Apartment | 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 NZ$258
includes taxes & fees
11 Nov - 12 Nov
East Rock Inn
Standard Room, 1 King Bed
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
2.0 star property
6.4 out of 10, (643)
"Staff friendly, room was quiet, large and comfortable. "
United States
Barbara
The price is NZ$119
includes taxes & fees
11 Nov - 12 Nov
Econo Lodge Lee - Great Barrington
Property amenity
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (583)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is NZ$246
includes taxes & fees
23 Nov - 24 Nov
Courtyard by Marriott Lenox Berkshires
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, (1000)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is NZ$315
includes taxes & fees
29 Oct - 30 Oct
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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Top Chesterwood Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This is a historical hotel and indeed the history is fabulous, everything appears like it did in 1773. Trouble is the rooms are also like this and the beds felt like they were 200 years old - so very uncomfortable. All part of the experience. Our room faced the street and I was surprised how much traffic noise kept me up until late at night, next time I will request a room facing inward. Not enough staff at the bar and dining during peak weekends, took forever just to get a cup of hot chocolate for the kids. But, very quaint, beautiful, that Main Street is just classic. "
Jane 2-night trip
Posted 7 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.
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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.

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