Book a hotel near Chesterwood, South Lee
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
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
$414 nightly
The price is $462 total per night
$462 total
Nov 30 - Dec 1
Total with 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
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
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Kitchen
Pet friendly
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
1.57 mi from Chesterwood
This farm stay features a garden, laundry facilities, and barbecue grills.
Free WiFi
Air conditioning
Spacious & Modern Berkshires Getaway
1.61 mi from Chesterwood
A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
Tanglewood Suites
MA-102, Stockbridge, MA
1.62 mi from Chesterwood
$219 nightly
The price is $219 total per night
$219 total
Dec 1 - Dec 2
Total with 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
Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay
1.65 mi from Chesterwood
This vacation home features a garden, laundry facilities, and concierge services. Barbecue grills are provided for your convenience.
Kitchen
Washer
Stockbridge Retreat w/ Pool & Hot Tub!
1.66 mi from Chesterwood
An outdoor pool, free self parking, and barbecue grills are featured at this cottage. WiFi in public areas is free. A garden is also provided.
Pool
Kitchen
The Red Lion Inn
30 Main Street, Stockbridge, MA
Free Cancellation
Reserve now, pay when you stay
2.06 mi from Chesterwood
$182 nightly
The price is $204 total per night
$204 total
Dec 15 - Dec 16
Total with 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
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 | 745 hotels |
|---|---|
Lowest Price | $204 |
Highest Price | $462 |
Popular hotels | The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, Classic Stockbridge Cottage, The Red Lion Inn, Tranquil 3 BR Stockbridge House w/ Private Deck!, Secluded Family Home in Serene Stockbridge Woods, Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions, Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10, 1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge, Tanglewood Suites, Spacious & Modern Berkshires Getaway, Stockbridge Retreat w/ Pool & Hot Tub!, Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay |
Recent Chesterwood hotel reviews by fellow wanderers
The Red Lion Inn
5 out of 5
Posted 9 days ago
Travelocity Verified Review
"I love the ambience - historic and comfortable and excellent food. "
A verified traveler stayed at The Red Lion Inn
Explore More Ways to Travel with Travelocity
- Lenox Hotels
- Hotels near Lake Mansfield Park
- B&B in Housatonic
- Cabins in Housatonic
- Cottages in Housatonic
- Housatonic Hotels
- Inns in Housatonic
- Rv Parks in Housatonic
- Hotels near Animagic Museum of Animation
- Hotels near Ski Butternut
- Hotels near Mahaiwe Performing Arts Center
- Hotels near Berkshire Mountain Country Store
- Richmond Hotels
- Hotels near Shakespeare and Company
- Hotels near Wyndhurst Golf & Club
- Hotels near Tanglewood Music Center
- Hotels near Ventfort Hall Mansion and Gilded Age Museum
- B&B in West Stockbridge
- Cabins in West Stockbridge
- Cottages in West Stockbridge
- Extended Stay Hotels in West Stockbridge
- Hotels with Hot Tubs in West Stockbridge
- Pet Friendly Hotels in West Stockbridge
- West Stockbridge Hotels
- Inns in West Stockbridge
- Vacation Homes in West Stockbridge
- Villas in West Stockbridge
- Hotels near Frelinghuysen Morris House and Studio
- Hotels near National Shrine of the Divine Mercy
- Great Barrington Hotels
- Hotels near Naumkeag Museum
- Hotels near Lee Premium Outlets
- Apartments in South Lee
- Extended Stay Hotels in South Lee
- Hotels with Pools in South Lee
- Romantic Getaways & Hotels in South Lee
- South Lee Hotels
- Vacation Homes in South Lee
- Villas in South Lee
- Apartments in Alford
- B&B in Alford
- Cabins in Alford
- Condos in Alford
- Cottages in Alford
- Extended Stay Hotels in Alford
- Alford Hotels
- Rv Parks in Alford
- Resorts in Alford
- Hotels near Greenock Country Club
- Hotels near The Mount
- Hotels near Wood's Pond
- Hotels near Tyringham Cobble
- Lee Hotels
- 4 Star Hotels in Stockbridge
- Farmstay in Stockbridge
- Apartments in Stockbridge
- B&B in Stockbridge
- Cabins in Stockbridge
- Condo Resorts in Stockbridge
- Extended Stay Hotels in Stockbridge
- Guest Houses in Stockbridge
- Beach Resorts & in Stockbridge
- Boutique Hotels in Stockbridge
- Convention Center Hotels in Stockbridge
- Kid Friendly Hotels in Stockbridge
- Fishing Resorts & in Stockbridge
- Golf Resorts & in Stockbridge
- Historic Hotels in Stockbridge
- Hotels with Pools in Stockbridge
- Hotels with Balconies in Stockbridge
- Hotels with Hot Tubs in Stockbridge
- Independent Hotels in Stockbridge
- Luxury Hotels in Stockbridge
- Pet Friendly Hotels in Stockbridge
- Romantic Getaways & Hotels in Stockbridge
- Stockbridge Hotels
- Lodges in Stockbridge
- Motels in Stockbridge
- Vacation Homes in Stockbridge
- Rv Parks in Stockbridge
- Hotels near Berkshire Botanical Garden
- Hotels near Kennedy Park
- Hotels near Norman Rockwell Museum
- Hotels near Housatonic River Walk
- Flights to South Lee
- Flights to Stockbridge
- Flights from Austin to Stockbridge
- Flights from Los Angeles to Stockbridge
- Flights from Phoenix to Stockbridge
- Flights from Vancouver to Stockbridge
- Flights from Reno to Stockbridge
- Flights from Birmingham to Stockbridge
- Flights from Jacksonville to Stockbridge