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1862 Seasons on Main Bed and Breakfast
4.5 out of 5
47 Main Street, Stockbridge, MA
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0.99 km from city centre
5/5Exceptional! (19 reviews)
The best B & B we have ever stayed in!

"We have done B&B's for many years, but this experience beats them all. From the communication ahead of time by the lovely innkeeper Amanda, every detail was tended to. Small things like reading glasses in the dining room, umbrellas for loan at every door, use of the kitchen including silverware, ..."…"

Reviewed on Aug. 21, 2017

1862 Seasons on Main Bed and Breakfast
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
Free cancellationReserve now, pay when you stay
The price is CA $129 per night from Mar 17 to Mar 18
9.29 km from city centre
4.5/5Wonderful! (416 reviews)

"Perfect little get away. Clean with options for the kids with the pool and arcade"…"

Reviewed on Jan. 25, 2021

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Stockbridge Country Inn
4.5 out of 5
26 Glendale Road, RR 183, Stockbridge, MA
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2.28 km from city centre
4.6/5Wonderful! (62 reviews)
Foliage weekend, great location

"Stay was nice at a beautiful time of year for the area. Inn did a thorough job with Covid precautions and cleanliness. Breakfast included with room was also good. Did have issue with Wifi in the room we were staying, which was a bit frustrating"…"

Reviewed on Oct. 27, 2020

Stockbridge Country Inn
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Cozy Stockbridge Home - Walk To Golf Course!
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1.24 km from city centre
4.8/5Exceptional! (12 reviews)
Another amazing stay!

"This was the third time our family has stayed at this lovely house. It's the perfect 'home away from home' for us. We look forward to coming back next year!"…"

Reviewed on Jan. 29, 2020

Cozy Stockbridge Home - Walk To Golf Course!
"Too Good" With 11 Private Acres. Contact us for Monthly Specials!
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1.29 km from city centre
4.9/5Exceptional! (29 reviews)
Beautiful stay in the Berkshires!

"The communication with the owner, Teva, was exceptional and appreciated as we had plenty of questions. I was initially concerned about the road noise we would hear when being outside, but between the kids playing and enjoying our music on the Sonos speaker it was no issue at all. Indoors, we could ..."…"

Reviewed on Nov. 11, 2020

"Too Good" With 11 Private Acres. Contact us for Monthly Specials!
General Williams Estate House Lenox/stockbridge
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2.64 km from city centre
4.8/5Exceptional! (50 reviews)
Travel through Time

"What an amazing house! Secret stairs, lots of space and wide open fun! The kids loved going into every nook and cranny and there was plenty of room for the adults to have some adult time! We loved it and will definitely be back!"…"

Reviewed on Feb. 2, 2021

General Williams Estate House Lenox/stockbridge
Modern New England Farmhouse on Prospect Hill
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1.01 km from city centre
5/5Exceptional! (2 reviews)
Clean, well equipped kitchen, easy to use all aspects operationally

"Homeowner was very responsive to any minor issues or wuestions"…"

Reviewed on Oct. 10, 2020

Modern New England Farmhouse on Prospect Hill
Completely Renovated Historic Home in the Heart of the Berkshires
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2.32 km from city centre
5/5Exceptional! (11 reviews)
Loved this home!

"We really enjoyed our too short stay. The home had all the amenities and comfort needed for a wonderful weekend. We will definitely be back!"…"

Reviewed on Jan. 22, 2020

Completely Renovated Historic Home in the Heart of the Berkshires
One block from Main St Stockbridge
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0.8 km from city centre
One block from Main St Stockbridge
A Grand Estate in Historic Stockbridge
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0.69 km from city centre
4.9/5Exceptional! (38 reviews)
Wonderful home and spectacular host.

"So easy to deal with host and property was awesome."…"

Reviewed on Jan. 23, 2021

A Grand Estate in Historic Stockbridge
The Inn at Stockbridge
4 out of 5
30 East Street, Stockbridge, MA
The price is CA $353 per night from Apr 1 to Apr 2
2.41 km from city centre
4.8/5Exceptional! (80 reviews)

"Everything from arrival to departure was fabulous."…"

Reviewed on Sep. 21, 2020

The Inn at Stockbridge
New! Cozy Berkshires Cabin - Walk to Beach & Lake!
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3.5 km from city centre
4/5Very Good! (2 reviews)
Very cozy getaway

"Perfect getaway. Easy access to lake. 10-15 min by car to nice easy/intermediate grade hikes."…"

Reviewed on Sep. 5, 2020

New! Cozy Berkshires Cabin - Walk to Beach & Lake!
Artist's Cottage on the Lake Mahkeenac
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4.2 km from city centre
5/5Exceptional! (1 review)
Wonderful Dream Vacation

"The cottage is just perfect! We had the most wonderful stay! We can not wait to book it again."…"

Reviewed on Jul. 20, 2020

Artist's Cottage on the Lake Mahkeenac
Courtyard by Marriott Lenox Berkshires
3 out of 5
70 Pittsfield Rd, Lenox, MA
Free cancellationReserve now, pay when you stay
The price is CA $124 per night from Mar 14 to Mar 15
10.59 km from city centre
4.6/5Exceptional! (259 reviews)

"I will definitely come back next time I'm in the area"…"

Reviewed on Feb. 27, 2021

Courtyard by Marriott Lenox Berkshires
Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Free cancellationReserve now, pay when you stay
The price is CA $122 per night from Mar 5 to Mar 6
16.21 km from city centre
4.2/5Very Good! (694 reviews)

"We stayed for one night in a suite with a king and two double beds. The room was clean, spacious and quiet. The front desk staff was friendly and helpful. For the price is was great. We would stay again."…"

Reviewed on Feb. 28, 2021

Best Western Plus Berkshire Hills Inn & Suites
Yankee Inn
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Free cancellationReserve now, pay when you stay
The price is CA $121 per night from Mar 18 to Mar 19
11.79 km from city centre
4.1/5Very Good! (907 reviews)

"Simple, clean and quiet hours 10pm-7am I’d stay again"…"

Reviewed on Feb. 22, 2021

Yankee Inn
Conroy's B&B
3.5 out of 5
11 East Street (Route 7), Stockbridge, MA
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2.35 km from city centre
4.2/5Excellent! (22 reviews)

"We were informed that the bathroom would be shared; it was unfortunate that there was no private bathroom option."…"

Reviewed on Oct. 6, 2019

Conroy's B&B
Tanglewood Suites
2.5 out of 5
MA-102, Stockbridge, MA
The price is CA $126 per night from Mar 23 to Mar 24
0.24 km from city centre
4/5Very Good! (5 reviews)

"We had difficulty finding the place. However after phoning Carol, she not only directed us to the location she drove us to the festivities and recommended things to do. The room was clean and comfortable. The only thing missing was no coffee setup."…"

Reviewed on Dec. 10, 2019

Tanglewood Suites
Hampton Inn & Suites Berkshires Lenox
2.5 out of 5
445 Pittsfield Rd, Lenox, MA
Free cancellationReserve now, pay when you stay
The price is CA $123 per night from Mar 2 to Mar 3
13.18 km from city centre
4.6/5Wonderful! (659 reviews)

"The staff was very nice, the room was large. I was just disappointed in my booking site told me that refrigerator and microwave was in every room, I confirmed this when I called. We arrived at 3:30 pm , check in starts at 3, our room was not ready so they switched us to another room. However there ..."…"

Reviewed on Feb. 21, 2021

Hampton Inn & Suites Berkshires Lenox
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Free cancellationReserve now, pay when you stay
The price is CA $204 per night from Mar 3 to Mar 4
0.85 km from city centre
4.3/5Excellent! (427 reviews)

"Hotel is historic landmark. Beautiful antique best location. Each floor full of artifacts like a museum. Room kind of outdated- furniture, floor carpet re way too old. Especially compare to new bathroom. Bathroom robes re nice surprise. Heat was a little too noisy. Still nice place for Christmas ..."…"

Reviewed on Dec. 20, 2020

The Red Lion Inn
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Stockbridge Hotel Guide

You will find yourself spoiled for choice when it comes to finding quality hotels in Stockbridge. On Expedia's up-to-the-minute booking pages you can browse 37 accommodation choices within a 0.1-kilometre (0.06-mile) radius of Stockbridge's heart.

Why not book a room close to the heart of Stockbridge? The The Cottage B&B and The Red Lion Inn are conveniently located 1 kilometre (0.6 miles) of the city's downtown.

The Rookwood Inn is located 8 kilometres (5 miles) from the main part of Stockbridge. Alternatively, the Gateways Inn & Restaurant is 8 kilometres (5 miles) away. Some other accommodation options are the Hampton Terrace Inn and the Cranwell Spa and Golf Resort.

50 kilometres (30 miles) to the north of Stockbridge is Williamstown, where you can find Williams College and Williams College Museum of Art. The The Orchards Hotel and House On Main Street are a few of the great hotel and apartment options in Williamstown. Alternatively, you could consider staying at Lee, 6 kilometres (4 miles) to the east of Stockbridge, where you can pick from the Federal House Inn and Black Swan Inn, an Ascend Collection Hotel. Should you choose to stay in Lee, set aside some time to visit the Lee Prime Outlets and Tyringham Cobble.

Why not spend an afternoon cheering along with The Berkshires sports enthusiasts at a local match. You'll find Times Union Center 55 kilometres (33 miles) to the northwest of Stockbridge. Those sports fans wishing to find a room or apartment nearby can make a choice from the Hilton Albany or the TownePlace Suites by Marriott Albany Downtown/Medical Center.

Albany International Airport is a logical airport for flying in and out of Stockbridge. It is 65 kilometres (40 miles) drive away. If you would like to stay nearby, try the Residence Inn by Marriott Albany Airport or The Desmond Hotel Albany.

Frequently asked questions

Where is the best place for a stay in Stockbridge?
The Inn at Stockbridge is a favorite with Expedia customers. This 4-star B&B offers free breakfast and an outdoor pool. Another top choice for your stay based on traveler reviews is The Red Lion Inn.
If I need to cancel my hotel reservation in Stockbridge, will I receive a refund?
Yes! You’ll find that most hotel room reservations are fully refundable as long as you cancel prior to the hotel’s cancellation deadline, which is often 24 or 48 hours before check in. If you have a non-refundable reservation, you might be able to cancel it and get a refund within a 24-hour period of your booking. Enter your dates, click on “Search”, then filter by “free cancellation” to get the best deals available in Stockbridge.
What's the best budget-friendly hotel in Stockbridge?
Based on reviews, The Red Lion Inn is a popular 3.5-star hotel for our travelers looking for an economical choice, and features free WiFi and an outdoor pool.
What's the best accommodation for a romantic vacation to Stockbridge?
1862 Seasons on Main Bed and Breakfast is a favorite 4.5-star B&B for couples, and features premium bedding and a restaurant. Other good choices for a stay with your sweetheart include Stockbridge Country Inn and The Inn at Stockbridge.
What's the best pet-friendly accommodation in Stockbridge?
The Inn at Stockbridge is a top dog-friendly B&B, and offers an outdoor pool and a fitness center for its human guests.
What are some hotels with pools in Stockbridge?
Conroy’s B&B is a popular 3.5-star B&B featuring an outdoor pool, free buffet breakfast, and free WiFi. Other choices that feature an onsite pool include The Inn at Stockbridge and Stockbridge Country Inn.
What is the best spa hotel in Stockbridge?
Conroy’s B&B is a top spa hotel featuring an outdoor pool and an outdoor tennis court. Why not spend some time relaxing in the spa tub? Another popular spa hotel in Stockbridge is 1862 Seasons on Main Bed and Breakfast.
What is staying in Stockbridge like?
Visitors to Stockbridge are sure to enjoy the bars. Tourists can also enjoy the city’s gardens, museums, and architecture. Top sights around the area include Jiminy Peak Mountain Resort, Tanglewood Music Center, and Ski Butternut. In Stockbridge, there are 36 hotels and other accommodations to choose from.
What should I see while I'm in Stockbridge?
Cultural venues include Norman Rockwell Museum, Mission House, and Berkshire Theatre Festival. The picturesque setting of Beartown State Forest and Naumkeag exemplify the area’s natural beauty. Additionally, you’ll find Jiminy Peak Mountain Resort and Tanglewood Music Center in the area.
What's the weather like in Stockbridge?
The hottest months are usually July and August with an average temp of 64°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Stockbridge are December, February, January, and March, with each month seeing an average of 9 inches of snowfall.

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