Book a hotel near Chesterwood, South Lee
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Top hotels close to Chesterwood

Classic Stockbridge Cottage
0.26 mi from Chesterwood
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183, Stockbridge, MA
0.4 mi from Chesterwood
$468 nightly
The price is $523 total per night
$523 total
Jul 28 - Jul 29
Total includes taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a lobby fireplace are also on offer.
Pool
Breakfast included

Tranquil 3 BR Stockbridge House w/ Private Deck!
0.85 mi from Chesterwood
This vacation home features laundry facilities.
Kitchen
Washer

Tranquil 3 BR Stockbridge House w/ Private Deck!
0.85 mi from Chesterwood
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Kitchen
Pet friendly

Secluded Family Home in Serene Stockbridge Woods
1.11 mi from Chesterwood
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer

Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions
1.45 mi from Chesterwood
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
1.54 mi from Chesterwood
A garden is available at this cottage.
Kitchen
Pet friendly

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
1.54 mi from Chesterwood
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Kitchen
Pet friendly

8 Mi to Tanglewood & Butternut Ski: Spacious Home!
1.59 mi from Chesterwood
A gym is featured at this vacation home, along with laundry facilities and barbecue grills.
Kitchen
Washer

Tanglewood Suites
MA-102, Stockbridge, MA
1.62 mi from Chesterwood
$269 nightly
The price is $269 total per night
$269 total
Jul 27 - Jul 28
Total includes taxes and fees
A steam room, free self parking, and barbecue grills are featured at this bed & breakfast. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.
Breakfast included
Parking included

The Red Lion Inn
30 Main Street, Stockbridge, MA
2.06 mi from Chesterwood
$236 nightly
The price is $264 total per night
$264 total
Aug 12 - Aug 13
Total includes taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Pool
Spa

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Free Cancellation
Reserve now, pay when you stay
4.09 mi from Chesterwood
$151 nightly
The price is $169 total per night
$169 total
Jul 30 - Jul 31
Total includes taxes and fees
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.
Pool
Air conditioning
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.
Chesterwood hotels essential information
Accommodation | 755 hotels |
---|---|
Lowest Price | $169 |
Highest Price | $523 |
Popular hotels | The Red Lion Inn, Classic Stockbridge Cottage, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, Tranquil 3 BR Stockbridge House w/ Private Deck!, Tranquil 3 BR Stockbridge House w/ Private Deck!, Secluded Family Home in Serene Stockbridge Woods, Tanglewood Suites, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions, 1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge, 1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge, 8 Mi to Tanglewood & Butternut Ski: Spacious Home! |
Recent Chesterwood hotel reviews by fellow wanderers

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
5 out of 5
Posted 1 day ago
Travelocity Verified Review
"Loved the property, room was clean and had everything you needed!! We had an upgrade that was wonderful!! Only downfall was the outside little deck! No privacy all out In the open, side by side and facing the other units with a walkway in front of it!! Was looking forward to sitting out side but ended up not using it at all.
"
A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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