Photo by William Keller

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Our top choices for Stockbridge hotels

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
Stockbridge
9.2 out of 10, Wonderful, (110)
Luxurious B&B featuring a seasonal outdoor pool and beautiful terrace surrounded by nature. Enjoy complimentary breakfast before hiking nearby trails or kayaking. Just minutes from Tanglewood Music Centre with free WiFi and parking for seamless exploration.

"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$801
includes taxes & fees
18 Jan - 19 Jan
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1003)
"Old time charm and hot tub under the stars"
United States
Lori
The price is NZ$346
includes taxes & fees
4 Jan - 5 Jan
The Red Lion Inn

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (89)
Embrace the natural charm at this New Ashford motel offering a refreshing seasonal outdoor pool. Free WiFi and parking make exploration easy, with Jiminy Peak Mountain Resort and Brodie Mountain just a short drive away. Enjoy the garden and terrace areas.

"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
The price is NZ$209
includes taxes & fees
4 Jan - 5 Jan
The Springs Motel

Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (214)
Peaceful countryside motel offers daily housekeeping, free WiFi, and complimentary parking. Explore nearby attractions like The Mac-Haydn Theatre or Shaker Museum, with convenient access to Hudson Station and airport.

"Room is clean but bed uncomfortable"
United States
Vivian
The price is NZ$225
includes taxes & fees
4 Jan - 5 Jan
Chatham Travel Lodge

The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (123)
Stay at this inviting Hillsdale motel near Catamount Aerial Adventure Park. Enjoy premium bedding after a day of skiing and snowboarding in the area. Convenient amenities include free WiFi and parking.

"So peaceful and beautiful. Very clean ! "
United States
Asanda
The Brooks Motel

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (66)
Relax at this inviting lodge near Catamount Ski Area featuring a seasonal outdoor pool and restaurant. After adventures, unwind in the sauna or garden, or sip drinks at the bar while enjoying free breakfast, WiFi, and parking.

"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. "
United States
kim
Little Cat Lodge

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
South Lee
9.0 out of 10, Wonderful, (814)
Nestled in the Berkshires, this family-friendly resort features 2 outdoor and 2 indoor swimming pools. Enjoy refreshments at the pool bar or coffee shop while staying near cultural attractions like Tanglewood Music Centre and Berkshire Theatre Festival.

"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is NZ$238
includes taxes & fees
5 Jan - 6 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (92)
Discover this charming B&B in Housatonic offering complimentary full breakfast, WiFi, and parking. Conveniently located near Monument Mountain and its reservation, this business-friendly getaway provides a perfect base for exploring local attractions.

"Absolutely magical at Christmas time! It was only for a quick overnight but felt like time stood still while we were there. The service was impeccable and Terry and Terri were a delight! I look forward to returning. "
United States
Jennifer
The price is NZ$385
includes taxes & fees
11 Jan - 12 Jan
Granville House

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (802)
Set in Pittsfield near Guido's Marketplace and Herman Melville's Arrowhead, this lodge offers an indoor pool and spa pool for relaxation. Enjoy free WiFi and parking while staying in clean rooms. The helpful staff ensures a pleasant mountain getaway.

"great stall and friendly pet friendly place"
United States
bonnie
The price is NZ$230
includes taxes & fees
1 Feb - 2 Feb
Berkshire Mountain Lodge

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (653)
Set in Lee, this motel offers fun mini golf on the property and free continental breakfast each morning. Just a short drive from Greenock Country Club and shopping at Lee Premium Outlets, guests appreciate the attentive staff and convenient free parking.

"The room was clean and the service adequate"
United States
David
The price is NZ$143
includes taxes & fees
31 Jan - 1 Feb
Econo Lodge Lee - Great Barrington

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1003)
Experience tranquility at this welcoming hotel, just 15 minutes from Tanglewood Music Centre. Guests praise the quiet atmosphere, helpful staff, and complimentary continental breakfast. Conveniently located near Lee Library and local restaurants with easy access to shopping.

"Safe, clean rooms, decent breakfast "
United States
Neil
The price is NZ$159
includes taxes & fees
1 Feb - 2 Feb
Quality Inn Lee - Lenox South

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (194)
Discover tranquility at this countryside lodge featuring the North Star restaurant serving American cuisine for dinner. Enjoy free WiFi and parking while exploring nearby Undermountain Golf Course and Copake Town Park. Rooms offer rainfall showerheads for extra comfort.

"Nice room and reasonable prices! Will recommend."
United States
Jianyang
The price is NZ$272
includes taxes & fees
5 Jan - 6 Jan
the Alander

Pilgrim Inn

Pilgrim Inn
2.5 star property
Lee
5.8 out of 10, (332)
Experience countryside tranquility at this golf-adjacent hotel in Lee, where free WiFi and parking enhance your stay. Explore nearby Lee Library and Animagic Museum, or embrace seasonal activities like cross-country skiing and snowboarding.

"Was horrible. Unsafe and scarey"
United States
Sharon
The price is NZ$85
includes taxes & fees
3 Feb - 4 Feb
Pilgrim Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
Located in Lee, this inviting B&B offers kayaking adventures and a terrace with lakefront views. Wake up to a full breakfast each morning before exploring nearby attractions like The Mount and Wyndhurst Golf & Club. Helpful staff ensure a memorable stay.

"A charming inn in the center of the Berkshires."
United States
Danny
The price is NZ$352
includes taxes & fees
18 Jan - 19 Jan
Lakehouse Inn

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2199)
"I great place to stay!!"
United Kingdom
Maricel
The price is NZ$220
includes taxes & fees
4 Jan - 5 Jan
Vacation Village in the Berkshires

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
Set in Lee, this B&B offers serene escapes with an outdoor pool and rejuvenating massages. Explore nearby National Shrine of Divine Mercy while enjoying free breakfast, WiFi, and parking. The 24-hour fitness centre and garden create a peaceful country getaway.

"Well-run and elegant property. "
United States
Steven
The price is NZ$486
includes taxes & fees
4 Jan - 5 Jan
The Inn at Stockbridge

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
This peaceful motel offers a seasonal outdoor pool and clean rooms just 15 minutes from Tanglewood Music Centre. Close to Colonial Theatre and Berkshire Museum, with free WiFi and parking. Guests praise the helpful staff and quiet, relaxing atmosphere.

"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is NZ$158
includes taxes & fees
20 Jan - 21 Jan
Berkshire Inn

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is NZ$808
includes taxes & fees
4 Jan - 5 Jan
Inn at Kenmore Hall

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (811)
Peaceful accommodation in a safe location make this motel a smart choice for travellers. Free perks include WiFi and self parking, while the 24-hour front desk ensures assistance anytime. Nearby attractions and skiing opportunities add adventure to your restful stay.

"Room spotless and staff helpful."
United States
William
The price is NZ$155
includes taxes & fees
17 Jan - 18 Jan
FairBridge Inn Express

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411)
Discover this charming motel in Lee with free WiFi and parking. The helpful staff ensures a welcoming stay while the seasonal outdoor pool provides refreshment. Nearby attractions include Lee Library and Tanglewood Music Centre, with hiking trails waiting for exploration.

"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is NZ$174
includes taxes & fees
4 Jan - 5 Jan
Sunset Inn
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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Stay near popular Stockbridge attractions

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.

Linwood House at the Norman Rockwell Museum Stockbridge Massachusetts USA.

Significant collection of the artist's original work & memorabilia on display in his hometown.
Photo by William Keller
Open Photo by William Keller

Top Stockbridge Hotel Reviews

More cheap accommodation in Stockbridge

Frequently asked questions

Where is the best place for a stay in Stockbridge?
The Red Lion Inn is one of the top choices for your stay based on our traveller data. This hotel offers 3 restaurants and an outdoor pool. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood is another good choice for your stay. See all available top hotels, or vacation rentals in Stockbridge.
What are some of the best holiday rentals that Stockbridge has to offer?
Peace and quiet on the lake: This holiday home rental outside of Stockbridge is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind. See all 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, Mission House and Berkshire Theatre Festival. See more options for historical stays in Stockbridge.
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 45 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, Mission House and Berkshire Theatre Festival. 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.

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