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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.

Great location and wonderful history. Hot tub was an unexpected bonus and felt wonderful after a nine hour drive. The bar was fun and the barkeeper was superb!
8.0
Scored 8.0
Very Good
Rated very good
282 reviews
Price from$119per 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
63 reviews
Price from$259per 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
210 reviews
Price from$188per 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
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
300 reviews
Price from$157.52per 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.

Reasonably priced place that accepts dogs all while providing an exceptional view!!! We enjoy the stay at the Black Swan with staff eager to meet the needs of all customers. The room is a good size, the deck was clean and semi-private, and the view was priceless!
8.3
Scored 8.3
Very Good
Rated very good
597 reviews
Price from$90.78per night
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.

Bar and pool
8.4
Scored 8.4
Very Good
Rated very good
438 reviews
Price from$129per night
Quality Inn, hotel in Stockbridge

Quality Inn has accommodations in Lee. This 2-star inn offers free WiFi. The property is non-smoking throughout and is located 3.5 miles from Cranwell Spa & Golf Club.

Clean and quiet
8.2
Scored 8.2
Very Good
Rated very good
479 reviews
Price from$84.15per 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
627 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

Explore guest reviews of hotels in Stockbridge

  • From $284.12 per night
    7.0
    Scored 7.0
    Good
    Rated good
     · 63 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
    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 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
  • From $284.12 per night
    7.0
    Scored 7.0
    Good
    Rated good
     · 63 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 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
     · 63 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 $284.12 per night
    7.0
    Scored 7.0
    Good
    Rated good
     · 63 reviews
    If you are looking for a peaceful quiet place a short drive from major attractions, including Stockbridge museums, botanical garden, and downtown, this is a lovely choice for you.
    Barbara
    United States of America
  • From $284.12 per night
    7.0
    Scored 7.0
    Good
    Rated good
     · 63 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
  • From $211.11 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 $211.11 per night
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 282 reviews
    so cute and historic well situated in Berkshires great location in Stockbridge nice pool and hot tub fabulous bathroom and shower
    Jared
    United States of America
  • From $211.11 per night
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 282 reviews
    the friendliest, kind, staff, clean, unique style, location is the best!!! loved it all!!
    Maria
    United States of America
  • From $211.11 per night
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 282 reviews
    Quaint New England interesting hotel.
    Maryann
    United States of America

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