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Check prices for these dates

Next weekend
13 Mar - 15 Mar
In two weeks
20 Mar - 22 Mar
In one month
3 Apr - 5 Apr
In two months
1 May - 3 May

Our top choices for Stockbridge bed & breakfast

Property grounds

Mountain Valley Retreat

Mountain Valley Retreat
2.5 star property
Killington
9.6 out of 10, Exceptional, (199 reviews)
"Superb stay all the way around! Mike and Barbara work very hard for their guests and it shows with all the room details and breakfast is 5 out of 5 stars everytime. Check in and out is very easy as well as parking even on snow covered days as the property is very well kept and cleared. Loved it and want to return!"
United States
Steven
The price is SAR 413
SAR 467 total
includes taxes & fees
8 Mar - 9 Mar
Mountain Valley Retreat
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (272 reviews)
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The Jackson
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (57 reviews)
"Charming bed and breakfast"
United States
Nicholas
The price is SAR 605
SAR 666 total
includes taxes & fees
11 Mar - 12 Mar
The Vesper
Front of property

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (425 reviews)
"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 SAR 817
SAR 890 total
includes taxes & fees
10 Mar - 11 Mar
The Vermont Inn
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
The price is SAR 842
SAR 927 total
includes taxes & fees
8 Mar - 9 Mar
Deer Brook Inn
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (48 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is SAR 1,122
SAR 1,234 total
includes taxes & fees
8 Mar - 9 Mar
Stay At Jimmy's
Aerial view

The Lilac Inn

The Lilac Inn
3.5 star property
Brandon
9.6 out of 10, Exceptional, (215 reviews)
"Such a charming inn, we loved staying there while visiting Middlebury "
United States
Caryn
The price is SAR 843
SAR 928 total
includes taxes & fees
8 Mar - 9 Mar
The Lilac Inn
Exterior

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (100 reviews)
"Food was excellent. Room was clean and cozy. Staff were all incredibly welcoming and friendly. Perfect location. Would highly recommend. "
United States
Danielle
The price is SAR 822
SAR 896 total
includes taxes & fees
1 Apr - 2 Apr
Echo Lake Inn
Front of property

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (388 reviews)
"Wonderful stay"
United States
Gregory
The price is SAR 821
SAR 994 total
includes taxes & fees
1 Apr - 2 Apr
Snowed Inn
Property entrance

The Woodstocker B&B

The Woodstocker B&B
4.0 star property
Woodstock
10.0 out of 10, Exceptional, (51 reviews)
"This food at this property is amazing!! I would come back any day, the bread and entire menu is incredible. The zagat should try their breakfast! "
United States
Kavina
The price is SAR 925
SAR 1,018 total
includes taxes & fees
3 Apr - 4 Apr
The Woodstocker B&B
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

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent
"Everything was great except the mini split sounded like a plane engine. Fortunately I was too sleepy to be annoyed."
Maxine 2-night trip
Posted 6 hours ago
Days Inn by Wyndham Rutland/Killington Area

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 Vermont Inn: 16 rooms. 11.2 mi (18 km) from the heart of Stockbridge. Enjoy the 24-hour fitness center and sauna. The Jackson: 11 rooms. 15.7 mi (25.2 km) from the downtown core. Enjoy the designer toiletries and library. Snowed Inn: 19 rooms. Situated 9.8 mi (15.8 km) from the heart of Stockbridge. Enjoy the hot tubs and unique décor. The Vesper: 9 rooms. 16.2 mi (26 km) from the heart of downtown.Mountain Valley Retreat: 2 rooms. Located 7.2 mi (11.5 km) from the core of Stockbridge. Enjoy the free full breakfast 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.