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Stockbridge Hotels from S$102

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23 Aug - 24 Aug
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29 Aug - 31 Aug
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Top 10 trending Stockbridge hotels

Our top choices for Stockbridge hotels

The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"Loved our visit"
The price is S$334
includes taxes & fees
7 Sept - 8 Sept
The Red Lion Inn
Tanglewood Suites
1 bedroom, premium bedding, iron/ironing board, free WiFi

Tanglewood Suites

2.5 star property
7.2 out of 10, Good, (19)
"The owner did not honor our confirmed Expedia reservation, so we had to find a hotel at the last minute. She made up various excuses and was very rude."
The price is S$345
includes taxes & fees
24 Aug - 25 Aug
Tanglewood Suites
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is S$480
includes taxes & fees
8 Sept - 9 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1003)
"Wonderful place to stay"
The price is S$179
includes taxes & fees
21 Sept - 22 Sept
The Yankee, Trademark Collection by Wyndham
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is S$181
includes taxes & fees
4 Sept - 5 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (527)
"Great place , love it, will return"
The price is S$216
includes taxes & fees
7 Sept - 8 Sept
The Constance by the Lenox Collection
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (692)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise "
The price is S$230
includes taxes & fees
4 Sept - 5 Sept
Berkshires Untold
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (767)
"Close to our target event a plus"
The price is S$102
includes taxes & fees
7 Sept - 8 Sept
FairBridge Inn Express
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cots/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (22)
"Really enjoyed my stay here, definitely need a car to get around"
The price is S$193
includes taxes & fees
4 Sept - 5 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Travelodge by Wyndham Great Barrington Berkshires
In-room safe, desk, free cots/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.4 out of 10, Good, (544)
"Excellent location, friendly service, clean, comfortable room."
The price is S$107
includes taxes & fees
1 Sept - 2 Sept
Travelodge by Wyndham Great Barrington Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (703)
"Pleasant stay"
The price is S$150
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (863)
"Consistently a clean room with welcoming staff."
The price is S$156
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1000)
"Very clean rooms and excellent staff."
The price is S$152
includes taxes & fees
4 Sept - 5 Sept
Best Western Plus Berkshire Hills Inn & Suites
Berkshire Travel Lodge
Outdoor pool

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (436)
"Property is close to Tanglewood Musical Venues. Parking is easy. The rooms are impeccably clean and the office manger was curteous."
The price is S$97
includes taxes & fees
14 Sept - 15 Sept
Berkshire Travel Lodge
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (586)
"Amazing place to stay. Can’t wait to go again. "
Berkshire Mountain Lodge
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is S$233
includes taxes & fees
4 Sept - 5 Sept
The Cornell Inn, Lenox & The Berkshires
Holiday Inn Express Hotel & Suites Great Barrington by IHG
1 bedroom, premium bedding, pillow-top beds, in-room safe

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (651)
"Very Good; Clean, Quiet Motel, Area has many dining options."
The price is S$185
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (758)
"Quite and good location to around towns"
The price is S$228
includes taxes & fees
23 Sept - 24 Sept
Hotel On North
Berkshire Valley Inn
Exterior

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (558)
"Very clean and very nice staff. Breakfast was great"
The price is S$238
includes taxes & fees
4 Sept - 5 Sept
Berkshire Valley Inn
Chatham Travel Lodge
Exterior

Chatham Travel Lodge

2.5 star property
7.8 out of 10, Good, (195)
"Chatham Travel lodge was well situated for our trip further north. The area is beautiful. The town of Chatham is close by with restaurants and shopping. The guests in the room above us were noisy for a while, but not after 10 pm. The lodge is old, but the room was clean and perfect for a one night stopover."
The price is S$166
includes taxes & fees
25 Aug - 26 Aug
Chatham Travel Lodge
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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Learn more about Stockbridge

Norman Rockwell's Museum showcases the artist's iconic paintings of small-town American life in his former studio. Stroll down Main Street's historic district before hiking Monument Mountain for views that inspired Nathaniel Hawthorne's literary works.

See all hotels in Stockbridge

Top Stockbridge Hotel Reviews

The Constance by the Lenox Collection

The Constance by the Lenox Collection

10/10 Excellent
"The staff on duty were very professional and pleasant. The young man on duty on Thursday afternoon and evening was very attentive and capably answered my question about the Shakespeare theater. My room was very clean and modern. The slight problem with the bed footboard did not effect my comfort or the function of the bed."
Donald 1-night trip
Posted 16 hours ago
The Constance by the Lenox Collection

Frequently asked questions

Where is the best place for a stay in Stockbridge?

The Red Lion Inn is a favourite with Expedia customers. This hotel offers 3 restaurants and an outdoor pool. Another top choice for your trip based on traveller reviews is Tanglewood Suites. See all available top hotels, or vacation rentals in Stockbridge.

If I need to cancel my hotel reservation in Stockbridge, will I receive a refund?

Yes, the majority of hotel reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you have a reservation that's non-refundable, you might be able to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Stockbridge.

What's the best dog-friendly hotel in Stockbridge?

The Red Lion Inn is a top hotel for people travelling with their pets, and offers 3 restaurants and an outdoor pool for its human guests. See more pet-friendly hotel accommodations in Stockbridge.

What's the best high-end place to stay in Stockbridge?

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood is a luxury B&B with a seasonal outdoor pool and a terrace, and it's a popular choice for Expedia travellers looking for an elegant place to stay. Find more luxury hotels in Stockbridge.

What's the best hotel in Stockbridge to learn about local history?

Based on our travel expertise, The Red Lion Inn is a top historic hotel bookable on our site and it features free WiFi. Also, notable landmarks to visit include Naumkeag Museum, Frelinghuysen Morris House and Studio and Mission House.

What are some accommodation options with pools in Stockbridge?

The Red Lion Inn: Features 3 restaurants, an outdoor pool and spa services. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood and Vacation Village in the Berkshires are two additional hotels that feature an on-site pool. View all hotels with pools in Stockbridge.

What is staying in Stockbridge like?

Visitors to Stockbridge will definitely enjoy the bars. Tourists can also enjoy the city's gardens, museums and architecture. In Stockbridge, there are 50 hotels and other accommodation options to choose from. Find out more about Stockbridge.

What should I do while I'm visiting Stockbridge?

Cultural venues include Norman Rockwell Museum, Frelinghuysen Morris House and Studio and Mission House. Landmarks like Naumkeag Museum, National Shrine of the Divine Mercy and Stockbridge Bowl might be worth a visit. The picturesque setting of Berkshire Botanical Garden and Housatonic River exemplify the area's natural beauty. Take a look at what more there is to see and do in Expedia's Stockbridge guide.

What's the weather like in Stockbridge?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.