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Stockbridge – 3 hotels and places to stay
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The Red Lion Inn, hotel in Stockbridge

Nestled in the heart of central Stockbridge, Massachusetts, this historic hotel offers luxurious accommodations, friendly service and gourmet on-site dining options.

The room was small but comfortable. Breakfast was excellent in the very nice dining room. The old-fashioned atmosphere of the Inn is a welcome change from Marriott, etc.
8.0
Scored 8.0
Very good
Rated very good
285 reviews
Price fromTHB 5,692.33per night
Check availability
The Cottage, hotel in Stockbridge

Situated on two acres of hills and forest, this Stockbridge B&B offers free Wi-Fi, free breakfast and stunning views of the surrounding Berkshire mountains.

Beautiful location and the owner was very welcoming and chatty. She also provided helpful advice on where to hike and where to eat, which was excellent given we only had one full day there. The bed was comfortable and the size of the unit was generous.
7.0
Scored 7.0
Good
Rated good
59 reviews
Price fromTHB 10,416.66per night
Check availability
Stockbridge Country Inn, hotel in Stockbridge

Located 1.5 km from Norman Rockwell and 1 km from Chesterwood Museums at Stockbridge, Stockbridge Country Inn is nestled on 4 private acres of Berkshire landscape.

Very friendly owner and lovely country inn.
9.4
Scored 9.4
Superb
Rated superb
15 reviews
Price fromTHB 18,820.36per night
Check availability
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires, hotel in Stockbridge

The 100 percent non-smoking Fairfield Inn and Suites by Marriott is located in the heart of the Berkshires.

The hotel was perfect. Staff was fantastic. Location was great.
8.8
Scored 8.8
Fabulous
Rated fabulous
204 reviews
Price fromTHB 7,698.98per night
Check availability
Hampton Terrace Inn, hotel in Stockbridge

Swim in the outdoor pool or take advantage of the on-site tennis courts at this Massachusetts bed and breakfast. Tanglewood Musical Center is 5 minutes’ drive away.

9.2
Scored 9.2
Superb
Rated superb
9 reviews
Price fromTHB 11,749.13per night
Check availability
Holiday Inn Express Great Barrington, an IHG Hotel, hotel in Stockbridge

Located in the Southern Berkshire Mountains, this hotel boasts an indoor pool and hot tub, as well as a daily continental breakfast. The Catamount Ski Area is 11 miles away.

Very good breakfast and gym
8.2
Scored 8.2
Very good
Rated very good
296 reviews
Price fromTHB 5,534.66per night
Check availability
The Black Swan Lee - Lenox, Ascend Hotel Collection, hotel in Stockbridge

The Black Swan Lee - Lenox, Ascend Hotel Collection is conveniently located in the foothills of the Berkshire Mountains.

staff !!! Michelle
8.3
Scored 8.3
Very good
Rated very good
587 reviews
Price fromTHB 4,490.39per night
Check availability
Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires an IHG Hotel, hotel in Stockbridge

All rooms feature a flat-screen TV with satellite channels and a private bathroom. Free WiFi is available.

I liked the pool, the rooms, the jacuzzi tub, and-at least at the time of year when I stayed-the price.
8.4
Scored 8.4
Very good
Rated very good
441 reviews
Price fromTHB 5,761.95per night
Check availability
Quality Inn, hotel in Stockbridge

Quality Inn is located in Lee, 10 km from Tanglewood and 10 km from Tanglewood Musical Center. This 2-star inn offers free WiFi.

Location and cleanliness
8.2
Scored 8.2
Very good
Rated very good
484 reviews
Price fromTHB 3,446.11per night
Check availability
Pilgrim Inn, hotel in Stockbridge

Situated in Lee, between the beautiful Beartown and October Mountain State Forests, Pilgrim Inn is a 20-minute drive from Pitsfield. It features a swimming pool and cozy rooms with free Wi-Fi.

We upgraded to a newly decorated room as the first one was a little old and musty. Great room, lots of space and fridge and microwave really useful. Comfy beds and good location with easy walking access to food. Self check in was fine. Rooms could be cleaned as regularly as you wanted, clean towels requested etc. On site caretaker lady was very welcoming.
6.7
Scored 6.7
Pleasant
Rated pleasant
627 reviews
Price fromTHB 3,644.73per night
Check availability
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What guests said about Stockbridge:

  • 6.0
    Scored 6.0

    Charming town and area, but I visited in February when there...

    Charming town and area, but I visited in February when there was not much to do. I wasn't impressed with any of the restaurants either. It was easy to drive around but there was more traffic than what I would have expected.
    Daniel
    United States
  • 10
    Scored 10

    There is so much to see and do in the area.

    There is so much to see and do in the area. We visited Naemkeg, Joseph Choate’s “Berkshire Cottage”. Very nice tour and in the evening they had a jazz band in the garden and an art exhibit offering wine and snacks. Today we’ll visit the Botanical Gardens and Edith Wharton’s “Berkshire Cottage”. We probably won’t have time for the Norman Rockwell Museum which we’d love to see as well.
    Pam
    United States
  • 8.0
    Scored 8.0

    The location to Tanglewood is good.

    The location to Tanglewood is good. A little further than I remember. Stockbridge is a safe and inviting town. Many stores within walking distance, however, we were not in town long enough to really shop. We enjoyed the Botanical Garden very much.
    Linda
    United States

Explore guest reviews of hotels in Stockbridge

  • The Cottage

    The Cottage

    Stockbridge
    From THB 10,416.66 per night
    7.0
    Scored 7.0
    Good
    Rated good
     · 59 reviews
    We liked the closeness to the Naumkeag garden where we attended the Winter lights ~ also close to downtown Stockbridge. We liked that one of the tvs worked fine.. no need to stream or know how to use streaming.. just turn it on and watch :) The owner called to give us directions and was easy to communicate with. The two bedroom space is large.
    S
    United States
  • Holmes Suite PRIME Downtown Stockbridge

    Holmes Suite PRIME Downtown Stockbridge

    Stockbridge
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 2 reviews
    Holmes is a spacious suite for 2-3 people right in the middle of Stockbridge. It has a well stocked kitchen, and groceries, restaurants, and coffee shops are all a short walk away. There's also outdoor space. Many attractions are nearby, Tanglewood, The Mount (Edith Wharton's house) and areas for hiking and outdoor activities.
    Andrea
    United States
  • Berkshires Cabin Rental - Walk to Stockbridge Bowl

    Berkshires Cabin Rental - Walk to Stockbridge Bowl

    Stockbridge
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 7 reviews
    Had a conversation with owner about keys, and she answered other questions. We loved the home and the location (we were exploring Stockbridge this trip). Loved the picnic table outside and the lovely little beach across the street. We didn't use the TV or kayak or fireplace. Hot water was plentiful and good water pressure.
    Tim the traveler
    United States
  • The Inn at Stockbridge

    The Inn at Stockbridge

    Stockbridge
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 25 reviews
    Convenient location. Close to Lenox, Tanglewood, Edith Wharton’s beautiful home and the Norman Rockwell Museum, some easy hikes. Delicious breakfast - loved the scones! Room was lovely, clean and comfortable! Owners are helpful and responsive. Inn and grounds are very charming!
    L
    Linda
    United States
  • The Red Lion Inn

    The Red Lion Inn

    Stockbridge
    From THB 9,787.53 per night
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 285 reviews
    Offered twin beds in large room. The decor was fun and interesting, including lots of antiques all over the hotel. The staff was super helpful. The bar in the basement was great and the wide porches with chairs were a nice touch. The staff was courteous and personable.
    Kathryn
    United States
  • The Inn at Stockbridge

    The Inn at Stockbridge

    Stockbridge
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 25 reviews
    Garden apartment. Breakfast. Serene setting. Jeff responded immediately to texts. Jeff graciously accommodated us when we arrived 90 min early to check in. The library and comfortable anterooms. Proximity to Stockbridge, Tanglewood. Friendliness of other guests.
    P
    Peter
    United States
  • The Cottage

    The Cottage

    Stockbridge
    From THB 10,416.66 per night
    7.0
    Scored 7.0
    Good
    Rated good
     · 59 reviews
    Great location, right next to two local attractions and minutes from downtown Stockbridge. The host was very friendly, and eager to please. The queen bed was comfortable. The bathroom was large and had a steam shower, though we did not try that out.
    Dilworth
    United States
  • Berkshires Cabin Rental - Walk to Stockbridge Bowl

    Berkshires Cabin Rental - Walk to Stockbridge Bowl

    Stockbridge
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 7 reviews
    Such a beautiful location, with a glimpse of Stockbridge Bowl through the trees, and Town Beach merely steps away. Well equipped for cooking and comfort, and close to most of the Berkshires' best attractions. The kayaks were so much fun!
    CHRISTOPHER
    United States
  • The Red Lion Inn

    The Red Lion Inn

    Stockbridge
    From THB 9,787.53 per night
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 285 reviews
    We have always loved the red Lion and it's funkiness, and treasure the fact that the Inn has not been overly modernized. And of course the porch and pet friendliness are big plusses, not to mention being in the middle of Stockbridge.
    David
    United States
  • The Cottage

    The Cottage

    Stockbridge
    From THB 10,416.66 per night
    7.0
    Scored 7.0
    Good
    Rated good
     · 59 reviews
    We loved the location of the property. It is ideally located within walking distance of Stockbridge. The house is in a beautiful setting surrounded by treas. Having a spacious separate suite was very special.
    Deirdre
    Ireland
  • The Cottage

    The Cottage

    Stockbridge
    From THB 10,416.66 per night
    7.0
    Scored 7.0
    Good
    Rated good
     · 59 reviews
    Location is excellent. Close to town and events. Also enjoyed the spacious accommodations and pet friendly offerings. Private entrance as well.
    Scott
    United States
  • The Inn at Stockbridge

    The Inn at Stockbridge

    Stockbridge
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 25 reviews
    Beautiful iconic New England Inn! Near local attractions we wanted to visit. Near fine dining. Breakfast was wonderful! The room was excellent.
    Robert
    United States
  • The Red Lion Inn

    The Red Lion Inn

    Stockbridge
    From THB 9,787.53 per night
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 285 reviews
    Fantastic historic hotel. Perfect holiday. nice atmosphere. The restaurant- honestly- is not the “burner”. Will definitely come back.
    Axel
    Germany
  • The Cottage

    The Cottage

    Stockbridge
    From THB 10,416.66 per night
    7.0
    Scored 7.0
    Good
    Rated good
     · 59 reviews
    Great location. Easy to get to Stockbridge, Lenox and other towns in the Berkshires.
    William
    United States
  • The Red Lion Inn

    The Red Lion Inn

    Stockbridge
    From THB 9,787.53 per night
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 285 reviews
    we enjoy the hotel and staff
    A
    Anonymous
    United States

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