A snowy ski slope with skiers, a cabin, and a mountain range in the background.

Find a Bed and Breakfast in Stockbridge from CA $189

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Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13

Our top choices for Stockbridge bed & breakfast

A large, stone and wood lodge with a sign reading 'The Snowed Inn,' surrounded by snow-covered trees and a snow-covered driveway.

1. Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (423 reviews)
"A+ stay, everything was great about our stay here"
United States
Melissa
The price is CA $180
CA $217 total
includes taxes & fees
Oct 25 - Oct 26
Snowed Inn
A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.

2. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (331 reviews)
"Amazing stay and great restaurant!"
United States
Ava
The price is CA $174
CA $192 total
includes taxes & fees
Nov 5 - Nov 6
The Jackson
A cozy living room with a fireplace, wicker chairs, and a coffee table with snacks.

3. Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (8 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
The price is CA $329
CA $362 total
includes taxes & fees
Nov 1 - Nov 2
Deer Brook Inn
A living room with a grey sectional sofa, a potted plant, and a radiator.

4. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (81 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
The price is CA $233
CA $257 total
includes taxes & fees
Nov 9 - Nov 10
The Vesper
A two-story house with a porch, surrounded by trees.

5. Inn at Neshobe River

Inn at Neshobe River
3.0 star property
Brandon
9.8 out of 10, Exceptional, (26 reviews)
"Cozy inn with great innkeepers and outstanding breakfast. Loved our room and our conversations with the innkeepers."
United States
John
The price is CA $247
CA $272 total
includes taxes & fees
Oct 20 - Oct 21
Inn at Neshobe River
A row of cabins with a snow-covered ground and trees in the background.

6. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
10.0 out of 10, Exceptional, (1 review)
"Our stay at this property was a pleasant surprise. Room was spotless and provided everything we needed. Bed was super comfortable and the location was perfect. There is a bit of road noise during the day but none at all at night. Would highly recommend this property."
United States
Mark & Joan S.
The price is CA $147
CA $248 total
includes taxes & fees
Nov 9 - Nov 10
Sleep Woodstock - Dog Friendly King Suite
A large, two-story house with a central courtyard, surrounded by a well-maintained lawn and trees.

7. The Lilac Inn

The Lilac Inn
3.5 star property
Brandon
9.6 out of 10, Exceptional, (224 reviews)
"Great breakfast….friendly staff…spotless room"
United States
Judith M
The price is CA $287
CA $316 total
includes taxes & fees
Nov 8 - Nov 9
The Lilac Inn
A modern fitness center with exercise equipment, mirrors, and a reception area.

8. Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (54 reviews)
"My husband kept saying that the room was a model for providing everything a traveler might need. Lovely stay."
United States
Jeanne
The price is CA $423
CA $465 total
includes taxes & fees
Oct 29 - Oct 30
Stay At Jimmy's
A house with a red roof, a porch with white railings, and a blue door.

9. Woodbridge Inn

Woodbridge Inn
3.0 star property
Woodstock
9.6 out of 10, Exceptional, (70 reviews)
"We loved our stay here. Everyone was so nice. The beds were incredibly comfortable. We arrived in the late afternoon in time for happy hour. We sat outside near the fire pit and watched the sunset behind the mountains. It’s a little outside of Woodstock but very convenient."
United States
Michelle
The price is CA $700
CA $770 total
includes taxes & fees
Oct 20 - Oct 21
Woodbridge Inn
A row of cabins with a snow-covered ground and trees in the background.

10. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
10.0 out of 10, Exceptional, (1 review)
"Considering the place was hit by a TORNADO the week prior to our visit, the accommodations were great, and the owner/host was in remarkably good spirits despite hassles with insurance."
United States
David M.
The price is CA $147
CA $248 total
includes taxes & fees
Oct 27 - Oct 28
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

11. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
8.0 out of 10, Very good, (1 review)
"Old but nice and clean."
United States
James
The price is CA $147
CA $248 total
includes taxes & fees
Nov 9 - Nov 10
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

12. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
8.0 out of 10, Very good, (1 review)
The price is CA $147
CA $248 total
includes taxes & fees
Nov 16 - Nov 17
Sleep Woodstock - Dog Friendly King Suite
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen area in the background.

13. Sleep Woodstock Mobility Impaired Accessible Suite

Sleep Woodstock Mobility Impaired Accessible Suite
Woodstock
The price is CA $114
CA $189 total
includes taxes & fees
Nov 16 - Nov 17
Sleep Woodstock Mobility Impaired Accessible Suite
A row of cabins with a snow-covered ground and trees in the background.

14. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is CA $147
CA $248 total
includes taxes & fees
Nov 9 - Nov 10
Sleep Woodstock - 2 Double Beds - Dog Friendly
A row of cabins with a snow-covered ground and trees in the background.

15. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is CA $147
CA $248 total
includes taxes & fees
Oct 27 - Oct 28
Sleep Woodstock - 2 Double Beds - Dog Friendly
A row of cabins with a snow-covered ground and trees in the background.

16. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is CA $133
CA $233 total
includes taxes & fees
Oct 20 - Oct 21
Sleep Woodstock - 2 Double Beds - Dog Friendly
A row of cabins with a snow-covered ground and trees in the background.

17. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is CA $147
CA $248 total
includes taxes & fees
Nov 9 - Nov 10
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

18. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is CA $147
CA $248 total
includes taxes & fees
Nov 9 - Nov 10
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

19. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is CA $147
CA $248 total
includes taxes & fees
Oct 27 - Oct 28
Sleep Woodstock - 2 Double Beds - Dog Friendly
A row of cabins with a snow-covered ground and trees in the background.

20. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is CA $147
CA $248 total
includes taxes & fees
Oct 27 - Oct 28
Sleep Woodstock - 2 Double Beds - Dog Friendly
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

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"Excellent"
Mingjiang 1-night trip
Posted 2 hours ago
My Place Hotel-Randolph VT

Find out more about Stockbridge

Stockbridge B&B information

Number of reviews
665
Accommodation
32 B&B
Lowest Price
CA $189
Highest Price
CA $770

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. Snowed Inn: 19 rooms. 9.8 mi (15.8 km) from the downtown core. Enjoy the hot tubs and unique décor. The Vesper: 9 rooms. Situated 16.2 mi (26 km) from the heart of Stockbridge. Deer Brook Inn: 5 rooms. 15 mi (24.2 km) from the heart of downtown.The Lilac Inn: 9 rooms. Located 16.4 mi (26.4 km) from the core of Stockbridge. Enjoy the free cooked breakfast and unique décor.
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.

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