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Compare 15 B&B in Stockbridge with updated reviews, rates, and availability.

The Vesper
Room

The Vesper

3.0 star property
9.6 out of 10, Exceptional, (11)
"Dana and her staff were so welcoming and our experience was nothing less than perfect. My husband and I travel for a living and I feel like The Vesper is a little hidden gem that we have discovered and we look forward to staying there again. Stephanie Louris Ps.. Breakfast was so delicious!!"
The price is AED 599
AED 659 total
includes taxes & fees
26 Nov - 27 Nov
The Vesper
The Jackson House Inn
Exterior

The Jackson House Inn

4.0 star property
10.0 out of 10, Exceptional, (180)
"We had a lot of fun staying at the Jackson House Inn. We loved the charm and the landscape out back. What a lovely place to stay."
The price is AED 729
AED 802 total
includes taxes & fees
28 Nov - 29 Nov
The Jackson House Inn
The Chipman Inn
Terrace/patio

The Chipman Inn

3.0 star property
9.6 out of 10, Exceptional, (138)
"This is a lovely old Inn. We found that there was not good lighting to read in our room and just one chair. As the weather was poor It would have been nice to spend time reading. Ther is a couch downstairs that we could have used. "
The Chipman Inn
The Vermont Inn
Front of property

The Vermont Inn

3.0 star property
9.2 out of 10, Wonderful, (389)
"Nice place. Rooms were nice and comfortable."
The Vermont Inn
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (309)
"The kindest and most accommodating hosts. We enjoyed their level of hospitality. The sleep was a bit interrupted throughout the night with doors constantly slamming. Overall though, we enjoyed our stay and will stay again (in a different room downstairs possibly). "
The price is AED 613
AED 742 total
includes taxes & fees
27 Nov - 28 Nov
Snowed Inn
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (21)
"Wow! Loved our visit at Stay at Jimmy's. Room was beautifully decorated and supplied with everything we needed. Location was perfect for exploring Woodstock. We had excellent communication from John and Jimmy. A bonus for us was the EV charging station across the street. "
The price is AED 915
AED 1,006 total
includes taxes & fees
26 Nov - 27 Nov
Stay At Jimmy's
The Lilac Inn
Exterior

The Lilac Inn

3.5 star property
9.6 out of 10, Exceptional, (177)
"The Lilac Inn was lovely and the Inn owner was welcoming. The 2 bed room my daughter and I shared was very nice and comfortable. The Inn was an easy walk to downtown."
The price is AED 804
AED 885 total
includes taxes & fees
1 Dec - 2 Dec
The Lilac Inn
Mountain Valley Retreat
Property grounds

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (155)
"Nestled beneath Killington this cute gem was a lovely spot not too far off Rt4, for our overnight stay. Nicely clean, artfully decorated and equipped. Staff were lovely and breakfast was delicious."
The price is AED 404
AED 457 total
includes taxes & fees
26 Nov - 27 Nov
Mountain Valley Retreat
Echo Lake Inn
Front of property

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (94)
"Old fashioned inn with wonderful hosts."
The price is AED 899
AED 980 total
includes taxes & fees
11 Dec - 12 Dec
Echo Lake Inn
The Buckmaster Inn
Property entrance

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (56)
"Elizabeth and Richard were absolutely wonderful hosts! I enjoyed every second of staying at this property. They went out of their way to be hospitable and to make all guests comfortable. The breakfast was fantastic each day and they had wonderful suggestions for the local area. I was already planning a trip back before I had even checked out. Highly recommend!!"
The Buckmaster Inn
The Woodstocker B&B
Front of property

The Woodstocker B&B

4.0 star property
10.0 out of 10, Exceptional, (50)
"This is a lovely and charming guest house / B&B, run by a very nice and friendly couple. During our stay they recommended a number of places to visit and were warm and welcoming every day. I would not hesitate to book with them again."
The Woodstocker B&B
Woodbridge Inn
Front of property - evening/night

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"Darling -- Wonderful location, hosts and great breakfast -- We will be back during ski season. Thank you. "
Woodbridge Inn
Deer Brook Inn
Property entrance

Deer Brook Inn

4.0 star property
10.0 out of 10, Exceptional, (21)
"The Inn was so lovely and charming and exceeded our expectations! The hospitality offered by the Inn Keeper and his team was truly remarkable and we felt welcome and spoiled throughout our stay. The property itself is stunning and the attention to detail is five star in our book!!! We will definitely be back! Plan your stay!! You won’t be disappointed!!"
Deer Brook Inn
Inn at Water's Edge
Front of property

Inn at Water's Edge

3.0 star property
Inn at Water's Edge
Inn at Neshobe River
Exterior

Inn at Neshobe River

3.0 star property
9.0 out of 10, Wonderful, (10)
"Owners were so nice, bed was great, linens and towels were wonderful. House is very old and only drawback (which is original to the house and should not be changed!) is the bar/latch style door handles. The Violet Room has its private bathroom across the hall landing, but if you get up in the night as we do, you do make a lot of noise rattling those handles! Walls are thin.But that didn't disturb us, since the other patrons on our visit were very quiet and considerate. If you are looking for...
Inn at Neshobe River
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Stockbridge

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
"The cabin was peaceful and everything was provided, plus some!" Stacy S

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (473)
"The cabin was amazing, the design and decor is perfect and the space is perfect. The hot tub and fire pit were so lovely in the evening, and the movie theatre was also excellent for watching TV and films. Jeff was an excellent host, super friendly and helpful and the area was lovely and quiet, very peaceful. Thanks again! "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Cozy Loft for two with Hot Tub
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (220)
"The Cozy Loft was the perfect place to get away from everyday work and left stressors. It provided us a place to rest and relax. It was also not far from towns to explore (great hiking, restaurants, antique shopping). Would highly recommend to others traveling to that area. "
Cozy Loft for two with Hot Tub
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Searching for B&Bs in Stockbridge?
If you want to find a place to stay with fewer rooms than the traditional hotel and a cozy environment, a bed and breakfast might be the perfect option for your getaway to Stockbridge.
Why would you choose a B&B over a traditional hotel room?
With attentive service, opportunities to socialize with other guests, and tasty breakfasts, B&Bs offer a one-of-a-kind setting.
What are the best B&Bs in Stockbridge?
Below are some B&Bs in the surrounding area: Snowed Inn: 19 rooms. 9.8 mi (15.8 km) from the heart of Stockbridge. Enjoy the spa tubs and unique décor. The Jackson House Inn: 11 rooms. 15.7 mi (25.2 km) from the downtown core. Enjoy the designer toiletries and library. The Lilac Inn: 9 rooms. Situated 16.4 mi (26.4 km) from the heart of Stockbridge. Enjoy the free cooked breakfast and unique décor. Mountain Valley Retreat: 2 rooms. 7.2 mi (11.5 km) from the heart of downtown. Enjoy the free full breakfast and private yard. The Vesper: 9 rooms. Located 16.2 mi (26 km) from the core of Stockbridge.
What's the best time of year to stay at a B&B in Stockbridge?
When you’re dreaming of a stay in Stockbridge, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Stockbridge are March, January, December, and February, with each month seeing an average of 22 inches of snowfall.
What is there to do in Stockbridge?
If you’re looking for some activities to entertain you on your trip, consider visiting Pico Mountain at Killington Ski Resort and Killington Resort. You might put Saskadena Six Ski Area and Marsh-Billings-Rockefeller National Historical Park on your list if you want to see more of the area.
How can I get to and around Stockbridge?
Mapping out your trip in and around Stockbridge is easy with these transportation options. Fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is located 20.1 mi (32.4 km) away from the city center. You can also search for flights into Lebanon, NH (LEB-Lebanon Municipal), which is 24.8 mi (39.9 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.