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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.

Historical building . Bed was comfortable
8.0
Scored 8.0
Very Good
Rated very good
282 reviews
Price from$187per night
Stockbridge Country Inn, hotel in Stockbridge

Located 0.9 mi from Norman Rockwell and 0.6 mi from Chesterwood Museums at Stockbridge, Stockbridge Country Inn is nestled on 4 private acres of Berkshire landscape.

Location is excellent for all the Berkshire activities.Great sense of history staying in an old but updated house. Great breakfast Lovely host with lots of maps and info on area and activities.
9.4
Scored 9.4
Wonderful
Rated wonderful
15 reviews
Price from$458.85per night
The Cottage, hotel in Stockbridge

Located 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.

The room was very VERY spacious with a full wall of windows to enjoy the private view outside. It was one of the coziest places that we stayed in on our trip. The area was beautiful and the "cottages" surrounding were amazing. OH the Hostess was very helpful with local activities and SO fun!
7.0
Scored 7.0
Good
Rated good
64 reviews
Price from$259per night
The Black Swan Lee - Lenox, Ascend Hotel Collection, hotel in Stockbridge

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

Quiet, lovely lake view, close to town.
8.4
Scored 8.4
Very Good
Rated very good
599 reviews
Price from$90.91per night
Quality Inn, hotel in Stockbridge

Quality Inn has accommodations in Lee. The property is around 6 miles from Tanglewood, 6.2 miles from Tanglewood Musical Center and 7.6 miles from Norman Rockwell Museum.

Nice area , gas station and stores near by.
8.2
Scored 8.2
Very Good
Rated very good
474 reviews
Price from$84.15per night
Holiday Inn Express Great Barrington, an IHG Hotel, hotel in Stockbridge

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.

I’ve always preferred staying at any Holiday Express because of its cleanliness and the free breakfast
8.2
Scored 8.2
Very Good
Rated very good
301 reviews
Price from$157.52per night
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 a 5-minute drive away.

Great location, nice breakfast
9.4
Scored 9.4
Wonderful
Rated wonderful
8 reviews
Price from$306.90per night
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires, hotel in Stockbridge

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

Clean, location, free breakfast and welcoming staff
8.8
Scored 8.8
Excellent
Rated excellent
211 reviews
Price from$188per night
The Cornell Inn, hotel in Stockbridge

Located on four acres, this bed and breakfast features traditional exteriors and stunning, updated designer rooms and bathrooms which are all equipped with cable TV, high-speed internet, and coffee...

The colorful and interesting design style/decor/colors. The absolutely lovely, kind and welcoming staff. The comfy bed. The very cool bar!! Welcome drinks!!
9.3
Scored 9.3
Wonderful
Rated wonderful
419 reviews
Price from$145per night
Pilgrim Inn, hotel in Stockbridge

Located 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.

Love the location of this property. We got snowed in and even then we had everything we needed just a few steps away - the supermarket, breakfast and lunch spot, and Starbucks. It’s also in a central location for exploring all of the Berkshires
6.7
Scored 6.7
Pleasant
Rated pleasant
628 reviews
Price from$89per night
See all hotels in and around Stockbridge
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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 of America
  • 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 of America
  • 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 of America
  • 10
    Scored 10

    Stockbridge is best in the summer because there’s not a lot...

    Stockbridge is best in the summer because there’s not a lot to do inside unless you go to other towns an hour or so away. There’s Lenix for shopping but I’ve been several times and that’s not Stockbridge. Only a few shops still left in the town itself.
    Anita
    United States of America

Explore guest reviews of hotels in Stockbridge

  • From $284.12 per night
    7.0
    Scored 7.0
    Good
    Rated good
     · 64 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 of America
  • 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 of America
  • 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 of America
  • 9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 26 reviews
    The room was beautiful and the common areas were very warm and inviting. The happy hour was a nice touch and a great way to meet the other guests. The breakfast was fantastic and the coffee was exceptional! Great location, close to many of the sights I came to Stockbridge to see. Jeff and his staff were also wonderful.
    Sandra
    United States of America
  • 9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 26 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 of America
  • 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 of America
  • 9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 26 reviews
    Loved having a pet friendly place near my sister that was comfortable and exceeded my expectations in terms of cleaniness. Breakfast was delivered to the room. Food was fabulous, especially the homemade granola!
    Michelle
    United States of America
  • From $284.12 per night
    7.0
    Scored 7.0
    Good
    Rated good
     · 64 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
  • From $206.64 per night
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 282 reviews
    We were upgraded to the suite, which was very nice! The Red Lion Inn is a really special place. Met some very nice people on the porch. The Berkshires are a wonderful place.
    C
    Coleen
    United States of America
  • From $206.64 per night
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 282 reviews
    It was a beautiful old Hotel which reminded me of a bygone era. It needs some work but on the whole, it was a wonderful place to stay. We would stay there again.
    Louise
    United States of America
  • From $284.12 per night
    7.0
    Scored 7.0
    Good
    Rated good
     · 64 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 of America
  • 9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 26 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 of America
  • From $206.64 per night
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 282 reviews
    Fantastic historic hotel. Perfect holiday. nice atmosphere. The restaurant- honestly- is not the “burner”. Will definitely come back.
    Axel
    Germany
  • From $284.12 per night
    7.0
    Scored 7.0
    Good
    Rated good
     · 64 reviews
    Great location. Easy to get to Stockbridge, Lenox and other towns in the Berkshires.
    William
    United States of America
  • From $206.64 per night
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 282 reviews
    Dinner was great. Beautiful old historic hotel. Great porch
    Penny
    United States of America

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