Stockbridge Hotel & Accommodation Deals 2026 from NZ$130 - Fully Refundable Options

Our top choices for Stockbridge hotels

The Red Lion Inn

Stockbridge

molly

includes taxes & fees

31 May - 1 June

Suite, Private Bathroom (RedBird Suite) | View from room

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

Stockbridge

Deborah

includes taxes & fees

8 June - 9 June

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Melinda

includes taxes & fees

27 May - 28 May

Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

The Yankee Inn

Lenox

Peter

includes taxes & fees

25 May - 26 May

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Helen

includes taxes & fees

28 May - 29 May

Quality Inn Lee - Lenox South

Lee

Edith

includes taxes & fees

25 May - 26 May

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

Helena

includes taxes & fees

3 June - 4 June

Blackberry River Inn

Norfolk

Archna

includes taxes & fees

26 May - 27 May

In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Lenox

robert

includes taxes & fees

25 May - 26 May

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Laraib

includes taxes & fees

3 June - 4 June

Berkshires Untold

Lenox

Aditya

includes taxes & fees

2 June - 3 June

Berkshire Mountain Lodge

Pittsfield

Daniel

includes taxes & fees

24 May - 25 May

Hampton Inn & Suites Berkshires-Lenox

Lenox

Linda

includes taxes & fees

28 May - 29 May

Shaker Mill Inn

West Stockbridge

Mervin

includes taxes & fees

25 May - 26 May

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Pittsfield

Kathleen

includes taxes & fees

27 May - 28 May

Quality Inn Great Barrington

Great Barrington

Braynd

includes taxes & fees

26 May - 27 May

Vacation Village in the Berkshires

Williamstown

John

includes taxes & fees

25 May - 26 May

Hilton Garden Inn Lenox Pittsfield

Pittsfield

Donna

includes taxes & fees

28 May - 29 May

Little Cat Lodge

Copake Falls

John

includes taxes & fees

26 May - 27 May

Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Pittsfield

Jennifer

includes taxes & fees

28 May - 29 May

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Stay near popular Stockbridge attractions

Norman Rockwell Museum

4.7/5 (347 reviews)

This gallery houses the world's largest collection of Norman Rockwell's iconic American illustrations. Explore his relocated studio on the scenic Berkshire estate for insight into his creative process.

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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

Vivid autumn foliage reflected in a calm lake surrounded by a dense forest under a clear blue sky in Stockbridge, Massachusetts

Top Stockbridge Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Nice staff, nice room and facilities. Having stayed there several times happily and will be back again in June. Thanks."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"The Cornell Inn completely won us over from the moment we walked in. The staff are genuinely warm and welcoming — the kind of friendly that feels real, not scripted — and they go out of their way to make you feel at home. We arrived after hours and the check-in process couldn't have been smoother — they left clear, easy-to-follow instructions that made the whole thing stress-free. Breakfast is a nice touch — solid and satisfying. The pastries pair nicely with your morning coffee and are a pleasant way to start the day. The rooms themselves are clean, comfortable, and well-appointed. Everything felt well-maintained and thoughtfully put together — no complaints whatsoever. And it's worth calling out that the Cornell Inn is proudly LGBTQIA+ friendly. It's a welcoming space for everyone, and that inclusivity is genuinely felt throughout the property, not just a line on a website. Highly recommend. This place has the hospitality, the atmosphere, and the little details that make any stay memorable."

Hotel On North

10/10 Excellent

"We had no expectations- so finding an impeccable hotel was a delight. We had no anticipation of beautiful bucolic views and quiet nature - so their absence didn’t matter. Had read the food was good - so that it was great was a surprise. The room size - if i had arithmetic skill and spatial awareness would have been obvious - but I don’t- so that the room was Yuge (sic) was great. Pro Tips: book a room not on street side - and above the 2nd floor. Noise level was too high there. Oh, one last thing: great art"

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

10/10 Excellent

"Beautiful resort, excellent amenities. Wished checkout was a little bit later but overall a great stay and looking forward to returning. Had a fun time in the game room and the pools were lovely!"

More cheap accommodation in Stockbridge

Monument Mountain Motel

247 Stockbridge Rd Great Barrington MA

NZ$130

31 May - 1 June

includes taxes & fees

9/10 Wonderful! (856 reviews)

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?

Spacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay: This highly rated holiday home rental in Stockbridge offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. 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, Frelinghuysen Morris House and Studio and Mission House. 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 Berkshire Mountain Lodge 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.

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Our top choices for Stockbridge hotels

The Red Lion Inn

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

Best Western Plus Berkshire Hills Inn & Suites

The Yankee Inn

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Quality Inn Lee - Lenox South

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Blackberry River Inn

Howard Johnson by Wyndham Lenox

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshires Untold

Berkshire Mountain Lodge

Hampton Inn & Suites Berkshires-Lenox

Shaker Mill Inn

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Quality Inn Great Barrington

Vacation Village in the Berkshires

Hilton Garden Inn Lenox Pittsfield

Little Cat Lodge

Berkshire Inn

Stay near popular Stockbridge attractions

Norman Rockwell Museum

Learn more about Stockbridge

Top Stockbridge Hotel Reviews

Vacation Village in the Berkshires

More cheap accommodation in Stockbridge

Monument Mountain Motel

Frequently asked questions

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