Top Hotels Near Chesterwood in South Lee from NZ$178
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Our top choices for Chesterwood hotels
10.0 out of 10, Exceptional, (89)
10/10
Exceptional
(89)
"Outstanding all around!"
"Outstanding all around!"
Jonathan
The price is NZ$386
NZ$386
includes taxes & fees
4 Jan - 5 Jan 2026
10.0 out of 10, Exceptional, (134)
10/10
Exceptional
(134)
"The inn has an excellent location and amenities."
"The inn has an excellent location and amenities."Christopher
9.8 out of 10, Exceptional, (99)
9.8/10
Exceptional
(99)
"Well-run and elegant property. "
"Well-run and elegant property. "Steven
The price is NZ$509
NZ$509
includes taxes & fees
4 Jan - 5 Jan 2026
10.0 out of 10, Exceptional, (74)
10/10
Exceptional
(74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."James
The price is NZ$665
NZ$665
includes taxes & fees
18 Jan - 19 Jan 2026
9.6 out of 10, Exceptional, (437)
9.6/10
Exceptional
(437)
"Nice place, easy check in"
"Nice place, easy check in"Robert
The price is NZ$208
NZ$208
includes taxes & fees
21 Dec - 22 Dec
9.8 out of 10, Exceptional, (13)
9.8/10
Exceptional
(13)
"New hotel very nice"
"New hotel very nice"joel
The price is NZ$261
NZ$261
includes taxes & fees
4 Jan - 5 Jan 2026
9.6 out of 10, Exceptional, (373)
9.6/10
Exceptional
(373)
"Amazing customer service! Location was very good to explore the area."
"Amazing customer service! Location was very good to explore the area."Sophia
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires2.5 star property
8.6 km from Chesterwood
9.4 out of 10, Exceptional, (758)
9.4/10
Exceptional
(758)
"Clean room, very courteous staff "
"Clean room, very courteous staff "Thomas
The price is NZ$261
NZ$261
includes taxes & fees
4 Jan - 5 Jan 2026
9.4 out of 10, Exceptional, (164)
9.4/10
Exceptional
(164)
"Everything was perfect - location and accommodation."
"Everything was perfect - location and accommodation."Christopher
9.6 out of 10, Exceptional, (15)
9.6/10
Exceptional
(15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay....
"
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay....
"Laura
The price is NZ$455
NZ$455
includes taxes & fees
4 Jan - 5 Jan 2026
10.0 out of 10, Exceptional, (27)
10/10
Exceptional
(27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "Margaret
The price is NZ$1,091
NZ$1,091
includes taxes & fees
19 Dec - 20 Dec
9.4 out of 10, Exceptional, (36)
9.4/10
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."
"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."Laura
The price is NZ$231
NZ$231
includes taxes & fees
4 Jan - 5 Jan 2026
9.8 out of 10, Exceptional, (39)
9.8/10
Exceptional
(39)
"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "
"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "Allison
The price is NZ$313
NZ$313
includes taxes & fees
21 Dec - 22 Dec
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 IHG3.5 star property
6.6 km from Chesterwood
9.0 out of 10, Wonderful, (804)
9.0/10
Wonderful
(804)
"Convenient location, very roomy, well equipped kitchen.
"
"Convenient location, very roomy, well equipped kitchen.
"Carolyn
The price is NZ$281
NZ$281
includes taxes & fees
4 Jan - 5 Jan 2026
9.0 out of 10, Wonderful, (805)
9.0/10
Wonderful
(805)
"Yes it was clean & staff was very polite. "
"Yes it was clean & staff was very polite. "Barbara L.
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel3.0 star property
8.6 km from Chesterwood
9.0 out of 10, Wonderful, (1000)
9.0/10
Wonderful
(1000)
"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!"
"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!"Elisabeth
The price is NZ$194
NZ$194
includes taxes & fees
8 Jan - 9 Jan 2026
8.8 out of 10, Excellent, (1004)
8.8/10
Excellent
(1004)
"Old time charm and hot tub under the stars"
"Old time charm and hot tub under the stars"Lori
The price is NZ$345
NZ$345
includes taxes & fees
14 Jan - 15 Jan 2026
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires3.0 star property
12.1 km from Chesterwood
9.2 out of 10, Wonderful, (590)
9.2/10
Wonderful
(590)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "Mingming
The price is NZ$261
NZ$261
includes taxes & fees
21 Dec - 22 Dec
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham2.5 star property
14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1004)
9.2/10
Wonderful
(1004)
"Friendly staff, very clean room and super comfy bed"
"Friendly staff, very clean room and super comfy bed"Linda
The price is NZ$178
NZ$178
includes taxes & fees
1 Jan - 2 Jan 2026
9.4 out of 10, Exceptional, (66)
9.4/10
Exceptional
(66)
"Good sized room with a comfortable bed. Friendly staff and breakfast was nice. The area was rather odd. Far too expensive for what I got but prices were really high the night I stayed. "
"Good sized room with a comfortable bed. Friendly staff and breakfast was nice. The area was rather odd. Far too expensive for what I got but prices were really high the night I stayed. "kim
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.
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.
Top Chesterwood Hotel Reviews
The Red Lion Inn
10/10 Excellent
"We had a very nice experience staying at the Red Lion Inn. Our room was upgraded when checking in which was a nice surprise. The hotel was beautifully decorated for the season. We loved the cozy feel of the fireplace in the lobby especially on such a cold day. "
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
10/10 Excellent
"Spacious house with large, well designed kitchen Excellent location Responsive host "
Stockbridge Home, Come Experience The Berkshires!
10/10 Excellent
"Our stay at the Stockbridge Home was fabulous! Lovely home! Clean, well stocked kitchen and beautiful comfortable bedrooms. The bathrooms were spotless and spacious. We loved the private backyard in the quiet neighborhood. We were able to walk into town on safe walkways. Short drive to hiking trails. We would highly recommend this home for your visit to the Berkshires! Thank you Lucas and Drew! Excellent hosts. "
Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay
10/10 Excellent
"Clean "
Lofted Hideaway on Pixley Hill
10/10 Excellent
"The house was clean and cozy but large enough for a big family. We brought our dog and there were no problems doing so. The hosts responded to all of our inquiries very quickly. The house was on a hill so kids and dogs would need outside supervision. The kids rooms indoors were wonderful! The deck was the perfect place to read and unwind. "
Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions
10/10 Excellent
"Lovely home, great location. The grounds, outdoor dining setup, etc. were all terrific."
Hotels near other Chesterwood attractions
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 Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10.
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.