Top 5 hotels in Stockbridge, United States

July 9, 2022 Tonie Szymanski

Discover the best hotels in Stockbridge, Massachusetts including The Red Lion Inn, Stockbridge Country Inn, The Cottage B&B, Conroy's B&B, The Red Lion Inn.
Things to do in Stockbridge

1. The Red Lion Inn

30 Main St, Stockbridge, MA 01262-9701
Excellent
46%
Good
29%
Satisfactory
14%
Poor
8%
Terrible
4%
Overall Ratings

4 based on 1461 reviews

The Red Lion Inn

Welcoming guests with genuine New England hospitality for over two centuries. Antique-filled rooms, suites, & guesthouses. Contemporary regional cuisine, 3 restaurants, elegant & casual indoor & outdoor dining, award-winning wine list. Heated year-round outdoor pool & hot tub, Gift Shop, WiFi. Memorable weddings & events. Small to mid-size meetings, unique spaces.

An excellent Inn

Reviewed By Tfl1

We stayed here for one night as part of a trip to visit family. We had a really lovely room in one of the outbuildings. A fantastic room and the bathroom was to die for. The bed was very comfortable and the place was very, very quiet. The service was great and the meals in the dining room were all excellent.

2. Stockbridge Country Inn

26 Glendale Rd. PO Box 525, Stockbridge, MA 01262
Excellent
81%
Good
14%
Satisfactory
4%
Poor
2%
Terrible
0%
Overall Ratings

4.5 based on 185 reviews

Stockbridge Country Inn

Closest Inn to The Norman Rockwell Museum and Chesterwood Museum, 5 minutes to Tanglewood, Central of all major Berkshire attractions, set up high on 4 private and professionally landscaped acres, in-ground swimming pool, bicycle and ski storage, full-service country breakfast, private bath en-suite, fine antiques, comfort at your service!

Like Staying with Friends

Reviewed By EmpressMW

Diane and Vernon were probably the best B and B hosts we have ever encountered in our travels. They made us feel welcomed the minute we stepped through the door. They were so helpful with information on where to go, where to eat etc. The inn was beautifully decorated and immaculately kept yet each room was so comfortable to be in. Our room was so pretty and welcoming after a day of sightseeing. The bathroom was so cute and had plenty of towels and toiletries. The breakfast was plentiful, delicious and different everyday. Diane is an excellent chef. She made sure we were well fed. It was really like staying with friends as they chatted with us everyday and were truly interested in our travels and experience. Her staff Anne and Cheryl made us feel pampered and taken care of. When it was time to leave we were sad to say good bye. We will definitely come back if just to visit our new found friends.

3. The Cottage B&B

Prospect Hill Road, Stockbridge, MA 01262
Excellent
63%
Good
15%
Satisfactory
3%
Poor
12%
Terrible
7%
Overall Ratings

4 based on 59 reviews

The Cottage B&B

The Cottage is located 3 minutes from Tanglewood and close to all Berkshire attractions. It is on two landscaped acres with beautiful mountain views. Private beach, tennis courts, ski slopes, and walking trails within minutes of your door at The Cottage. Accommodations offer space, privacy and comfortable plus specuial amenities such as steam room, movies, private patios, oputdoor grills and much more.

Unique property with a great location.

Reviewed By Ruthie m

We had a suite in a vintage mid-century modern property. The shower included a steam shower--turning the stall into a mini-steam room if you wanted to use it! The Cottage is in a great location. Carole made sure we had everything we needed. The food prep area had a fridge, microwave, toaster over, electric kettle, and real china to use. Breakfast was in our fridge when we arrived. We loved our small private patio and also used the beautiful large shared patio.

4. Conroy's B&B

11 East Street, Route 7 N. PO Box 191, Stockbridge, MA 01262
Excellent
68%
Good
23%
Satisfactory
5%
Poor
5%
Terrible
0%
Overall Ratings

4.5 based on 40 reviews

Conroy's B&B

See why so many travelers make Conroy's B&B their bed and breakfast of choice when visiting Stockbridge. Providing an ideal mix of value, comfort and convenience, it offers a romantic setting with an array of amenities designed for travelers like you. Conroy's B&B is a romantic bed and breakfast offering air conditioning in the rooms, and it is easy to stay connected during your stay as free wifi is offered to guests. Plus, guests can enjoy a pool, which has made this a popular choice among travelers visiting Stockbridge. For guests with a vehicle, free parking is available. For those interested in checking out popular landmarks while visiting Stockbridge, Conroy's B&B is located a short distance from National Shrine of the Divine Mercy (1.3 mi) and The Mission House (1.6 mi). Stockbridge has plenty of pubs. So when you’re here, be sure to check out popular spots like Lion's Den Pub and Michael's, which are serving up some great dishes. Stockbridge is also home to Norman Rockwell Museum, a popular art museum that is not too far from Conroy's B&B. We’re sure you’ll enjoy your stay at Conroy's B&B as you experience all of the things Stockbridge has to offer.

what Bed and breakfasts were meant to be

Reviewed By ADog56

We just came back from a long weekend with Joanne and her brther Jim (her husband sadly, passed away suddenly last winter), and I say, the guests were better than ever, interestng,, nay fascinating, and the breakfast conversation scintillating. No more pool (town regs), yet even nicer, more comfy Keep up the great wrok Joanne!

5. The Red Lion Inn

30 Main St, Stockbridge, MA 01262-9701
Excellent
46%
Good
29%
Satisfactory
14%
Poor
8%
Terrible
4%
Overall Ratings

4 based on 1461 reviews

The Red Lion Inn

Welcoming guests with genuine New England hospitality for over two centuries. Antique-filled rooms, suites, & guesthouses. Contemporary regional cuisine, 3 restaurants, elegant & casual indoor & outdoor dining, award-winning wine list. Heated year-round outdoor pool & hot tub, Gift Shop, WiFi. Memorable weddings & events. Small to mid-size meetings, unique spaces.

An excellent Inn

Reviewed By Tfl1

We stayed here for one night as part of a trip to visit family. We had a really lovely room in one of the outbuildings. A fantastic room and the bathroom was to die for. The bed was very comfortable and the place was very, very quiet. The service was great and the meals in the dining room were all excellent.

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