Stockbridge Hotels

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Stockbridge - Exterior
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$203+
| Excellent - 9 reviews
Air-conditioned
Internet
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Kitchenette
 
 
 
 
In 1862, Seasons on Main B&B was built as a Greek revival era home. This elegant, restored boutique inn is located in Norman Rockwell’s village, made famous by his painting Main Street at Christmas and is listed on the National Register of Historic Places. This lovely 14 room inn is just 5 minutes to Tanglewood, Laurel Hill Walking Trails & Tower, Ice Glen a...
Overall Rating - Excellent - 9 reviews
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1862 Seasons on Main B and B
$184+
| Good - 19 reviews
Air-conditioned
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Turn of the century Dutch Colonial Inn nestled in the heart of the Berkshire Hills. Skiing only 2 miles away! Cozy 13 Guest Rooms with private bath.Hot tub on the deck. Some rooms have fireplaces or relax by the fireplace in the living room. Beautiful decks and porches surround the building and overlook the view. In summer enjoy our backyard swimming pool...
Overall Rating - Good - 19 reviews
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Thornewood Inn
$115+
| Excellent - 274 reviews
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When you stay at The Red Lion Inn in Stockbridge, you'll be in the historical district and convenient to Naumkeag and Norman Rockwell Museum. This historic hotel is within the vicinity of Chesterwood and Prime Outlets Lee. Make yourself at home in one of the 125 air-conditioned rooms featuring refrigerators and DVD players. Complimentary wireless Internet ac...
Overall Rating - Excellent - 274 reviews
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Excellent 10.0
Sep 1 2014 Posted by Steve

Very much what I would expect of a New England country inn. Comfortable, relaxing.

Cell service in the entire area is extremely poor.

Excellent 10.0
Aug 28 2014 Posted by Verified Hotel Guest

It would have been lovely if it had been centrally air-conditioned instead of using noisy room a/c's, but I know that would have been impossible. I wanted a distinguished old hotel and that is exactly what I got.

The Red Lion Inn
$195+
| Excellent - 39 reviews
Air-conditioned
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Fairy-tale Victorian B&B in the heart of the Berkshires. Modern amenities in antique-filled rooms. Healthy gourmet breakfast. For romance, relaxation & families. NY Magazine's best rated!
Overall Rating - Excellent - 39 reviews
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Rookwood Inn
$222+
| Excellent - 32 reviews
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Elegant country Lenox inn offering beautiful guestrooms featuring luxury linens, private baths and free WiFi. Enjoy a full gourmet breakfast each morning. Pet friendly rooms available
Overall Rating - Excellent - 32 reviews
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Birchwood Inn
$218+
| Good - 1 reviews
Air-conditioned
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Located in Lenox, Cranwell Resort Spa & Golf Club is close to Shakespeare and Company and Tanglewood. This golf resort is within the vicinity of Prime Outlets Lee and Naumkeag. Stay in one of 114 guestrooms featuring flat-screen televisions. Complimentary wireless Internet access keeps you connected, and cable programming is available for your entertainment...
Overall Rating - Good - 1 reviews
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Good 7.0
Aug 25 2014 Posted by Anonymous

Spectacular location at one of the grandest "cottages" remaining in the Berkshires. A 5 minute drive to downtown Lenox. Delicious brunch. The bathroom in our room was newly renovated and luxurious. Good service.

The main building of Cranwell is breathtaking, and the prices are what you would expect to stay in such a historic and beautiful place. However, our room was in an adjacent building, circa 1963. It was pretty nice, but definitely more like what I would expect for $300 rather than $500. Perhaps on their website they make it more clear that you aren't staying in the main house, but booking through Kayak I was surprised to get less than I thought I'd paid for. I found the walls to be pretty thin in the building we stayed in (Founders).

Cranwell Resort Spa & Golf Club
$240+
| Excellent - 38 reviews
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Enjoy peaceful charm and elegance in a 1906 Georgian style mansion secluded on 12 acres in Stockbridge, a town described by Norman Rockwell as the "best of America, best of New England." Choose from one of fifteen well appointed, individually decorated guest rooms and suites, many with whirlpools and gas fireplaces. A delicious homemade breakfast and wine...
Overall Rating - Excellent - 38 reviews
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The Inn at Stockbridge
$222+
| Excellent - 7 reviews
Air-conditioned
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Built in the 1920's by a New York surgeon for use as a summer estate, Applegate is set amid towering pines and manicured lawns. Rose gardens, perennial beds, and mature apple trees covering the nearly six acres of the property. A circular drive leads to the two-story pillared Georgian colonial where, inside, you will find Applegate tastefully decorated wit...
Overall Rating - Excellent - 7 reviews
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Applegate Inn
$446+
| Excellent - 17 reviews
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Overall Rating - Excellent - 17 reviews
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Garden Gables Inn
$50+
| Good - 173 reviews
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Overall Rating - Good - 173 reviews
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Excellent 10.0
Aug 1 2014 Posted by April

It had everything I was needing: Great shower & bathroom, T.V., Small refrigerator & Microwave, Working AC, & Adequate beds.

Beds could have been a little softer. But they worked and were not horrible.

I loved the friendly staff and they even let me print out my boarding pass for my return flight up at their office, which I had not done prior to the night before. This was greatly appreciated.
Okay 6.0
Oct 14 2013 Posted by Verified Hotel Guest

Liked price and location.

No dislikes

Wagon Wheel was exactly as advertised. Friendly owner, nice location. Certainly not the Ritz but clean and simple. Stayed with my young family - all were satisfied with the stay. Would surely stay there again
Wagon Wheel Inn
$1006+
| Excellent - 20 reviews
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A late-19th century mansion perched on a grand, green knoll in Massachusetts’ beautiful Berkshire Hills, Wheatleigh blends the ornate grandeur of a 16th-century Florentine palazzo with every modern comfort you’d expect, including fine French dining, lush landscaped grounds, antique furnishings (check out the Tiffany stained glass) and a gallery-load of conte...
Overall Rating - Excellent - 20 reviews
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Wheatleigh
$123+
| Good - 110 reviews
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The Holiday Inn Express Hotel & Suites Great Barrington is situated in the heart of the beautiful Southern Berkshire Mountains. We are in close proximity to many boutique shops, several ski areas, a host of cultural activities, including Tanglewood, Shakespeare and Company, Barrington Stage Company, and The Berkshire Opera Company to name a few. Every room i...
Overall Rating - Good - 110 reviews
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Excellent 9.0
Jul 20 2013 Posted by Jessica

The staff was very friendly and our room was very clean.

The hot tub had a few random bugs floating in it, but nothing too gross.

Excellent 10.0
May 27 2013 Posted by Ellen

Accommodations were fine. Bed and pillows...excellent. Bathroom immaculate.

Coffee in room...terrible.

I believe the charge for the room was a bit excessive probably due to it being Memorial Weekend/Graduation time. Other local inns were even more. Discouraging for seniors on a budget. Otherwise, fine.
Holiday Inn Express & Suites Great Barrington - Lenox Area
$150+
| Excellent - 68 reviews
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With a stay at Federal House Inn in Lee, you'll be close to Naumkeag and Prime Outlets Lee. This bed & breakfast is within the vicinity of Norman Rockwell Museum and Chesterwood. Make yourself at home in one of the 9 air-conditioned rooms featuring fireplaces. Complimentary wireless Internet access keeps you connected, and cable programming is available for...
Overall Rating - Excellent - 68 reviews
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Federal House Inn
$146+
| Excellent - 1 reviews
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When you stay at Whistler's Inn Bed & Breakfast in Lenox, you'll be in the mountains and convenient to Shakespeare and Company and Tanglewood. This bed & breakfast is within the vicinity of Arrowhead Museum and Prime Outlets Lee. Make yourself at home in one of the 14 air-conditioned guestrooms. Make use of convenient amenities, which include wedding service...
Overall Rating - Excellent - 1 reviews
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Excellent 10.0
Jul 24 2014 Posted by Anonymous

Beautiful home, beautiful people, beautiful surroundings, beautiful food.

Overhead fan in room didn't work if overhead light was turned off.

Whistler's Inn Bed & Breakfast
$141+
| no reviews
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The Summer White House is just a mile from Tanglewood, in the very heart of historic Lenox. Our guest rooms are lavishly decorated in traditional style and each features air conditioning and private bath.With many of the area's finest restaurants and specialty shops within walking distance from our property, your visit to the Berkshires will be comfortable a...
Overall Rating - Poor - 0 reviews
The Summer White House Inn
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