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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Stockbridge bed & breakfast

Exterior
Mountain Valley Retreat

Mountain Valley Retreat

2.5 star property
Killington
9.6 out of 10, Exceptional, (189)
"Absolutely lovely stay!"
United States
Elizabeth
The price is AED 441
AED 498 total
includes taxes & fees
11 Dec - 12 Dec
Mountain Valley Retreat
Front of property
The Jackson

The Jackson

4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (256)
"Very cute inn, the restaurant was a plus. Had a great dinner there and def will come back. "
United States
Jaunita
The Jackson
Front of property
Snowed Inn

Snowed Inn

3.5 star property
Killington
9.8 out of 10, Exceptional, (372)
"The inn truly stands out for it's naturally beautifully decorated all bright wooden interior. Their recent breakfast area expansion is wonderfully bright and cheery, as are the hosts. Thank you and we are looking forward to seeing you again!"
United States
Bradford
The price is AED 690
AED 835 total
includes taxes & fees
10 Dec - 11 Dec
Snowed Inn
Front of property
The Vermont Inn

The Vermont Inn

3.0 star property
Rutland
9.2 out of 10, Wonderful, (415)
"Our room was clean and the bed was very comfortable. The Inn is for sale... which could explain the needed updates. I wish I could buy it! 🤗 We would stay here again. "
United States
Jodie
The price is AED 843
AED 919 total
includes taxes & fees
11 Dec - 12 Dec
The Vermont Inn
Front of property
Stay At Jimmy's

Stay At Jimmy's

3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
The price is AED 915
AED 1,006 total
includes taxes & fees
10 Dec - 11 Dec
Stay At Jimmy's
Economy Room | Individually decorated, individually furnished, free WiFi, bed sheets
The Vesper

The Vesper

3.0 star property
Woodstock
9.2 out of 10, Wonderful, (46)
"Cute B&B, great location! Easy walk to coffee house and downtown area. We really enjoyed our stay!"
United States
Roger
The price is AED 592
AED 651 total
includes taxes & fees
10 Dec - 11 Dec
The Vesper
Exterior
The Lilac Inn

The Lilac Inn

3.5 star property
Brandon
9.6 out of 10, Exceptional, (213)
"Clean, quaint and lovely! Great service and located in a cozy little town. "
United States
Jessica
The price is AED 816
AED 897 total
includes taxes & fees
10 Dec - 11 Dec
The Lilac Inn
Outdoor pool
Echo Lake Inn

Echo Lake Inn

2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
"Old fashioned inn with wonderful hosts."
United States
James
The price is AED 996
AED 1,085 total
includes taxes & fees
17 Dec - 18 Dec
Echo Lake Inn
Front of property - evening/night
Woodbridge Inn

Woodbridge Inn

3.0 star property
Woodstock
9.6 out of 10, Exceptional, (67)
"Staff was very friendly and welcoming "
United States
Michael
The price is AED 1,634
AED 1,798 total
includes taxes & fees
11 Dec - 12 Dec
Woodbridge Inn
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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Top Stockbridge Hotel Reviews

Mountain Sports Inn

Mountain Sports Inn

10/10 Excellent
"Everything was superb . Staff is very friendly and breakfast is fabulous ."
Bradford 2-night trip
Posted 2 days ago
Mountain Sports Inn

Frequently asked questions

Searching for B&Bs in Stockbridge?
If you're looking for something a little quirkier than your standard hotel, a bed and breakfast could be a great option for your getaway. When you want to explore some attractions in town, Green Mountain National Forest and Les Newell Wildlife Management Area are worth a stop.
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: The Jackson: 11 rooms. 15.7 mi (25.2 km) from the heart of Stockbridge. Enjoy the designer toiletries and library. The Vermont Inn: 16 rooms. 11.2 mi (18 km) from the downtown core. Enjoy the 24-hour fitness center and sauna. The Vesper: 9 rooms. Situated 16.2 mi (26 km) from the heart of Stockbridge. Snowed Inn: 19 rooms. 9.8 mi (15.8 km) from the heart of downtown. Enjoy the hot tubs and unique décor. Stay At Jimmy's: 3 rooms. Located 16.3 mi (26.3 km) from the core of Stockbridge. Enjoy the jetted tubs and private yard.
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?
When you want to check out some attractions in town, you might consider a visit to Green Mountain National Forest and Les Newell Wildlife Management Area. You might check out Belcher Library if you have time 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.