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

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  • Upfront pricing

    We are not like the others - we include taxes and fees

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
$140 nightly
The price is $154
Oct 25 - Oct 26
Total with taxes and fees
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
$176 nightly
The price is $194
Nov 5 - Nov 6
Total with taxes and fees
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, (9 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
$212 nightly
The price is $233
Nov 1 - Nov 2
Total with taxes and fees
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
$165 nightly
The price is $182
Nov 9 - Nov 10
Total with taxes and fees
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
$175 nightly
The price is $193
Oct 20 - Oct 21
Total with taxes and fees
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.
$159 nightly
The price is $175
Nov 9 - Nov 10
Total with taxes and fees
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
$206 nightly
The price is $226
Nov 17 - Nov 18
Total with taxes and fees
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
$299 nightly
The price is $329
Oct 29 - Oct 30
Total with taxes and fees
Stay At Jimmy's
A row of cabins with a snow-covered ground and trees in the background.

9. 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.
$159 nightly
The price is $175
Oct 27 - Oct 28
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
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
8.0 out of 10, Very good, (1 review)
"Old but nice and clean."
United States
James
$159 nightly
The price is $175
Nov 9 - Nov 10
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
A house with a red roof, a porch with white railings, and a blue door.

11. 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
$550 nightly
The price is $605
Oct 20 - Oct 21
Total with taxes and fees
Woodbridge Inn
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)
$159 nightly
The price is $175
Nov 16 - Nov 17
Total with taxes and fees
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
$119 nightly
The price is $131
Nov 16 - Nov 17
Total with taxes and fees
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
$159 nightly
The price is $175
Nov 9 - Nov 10
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
A row of cabins with a snow-covered ground and trees in the background.

15. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$159 nightly
The price is $175
Nov 9 - Nov 10
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
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
$159 nightly
The price is $175
Oct 27 - Oct 28
Total with taxes and fees
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
$159 nightly
The price is $175
Nov 9 - Nov 10
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

18. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$148 nightly
The price is $164
Oct 20 - Oct 21
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
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
$159 nightly
The price is $175
Oct 27 - Oct 28
Total with taxes and fees
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
$159 nightly
The price is $175
Oct 27 - Oct 28
Total with taxes and fees
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

Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"Wonderful place! Very helpful staff"
Blair 2-night trip
Posted 4 hours ago
Mountain Meadows Lodge

Find out more about Stockbridge

Stockbridge B&B information

Number of reviews
666
Accommodation
32 B&B
Lowest Price
$131
Highest Price
$605

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Stockbridge?
Prices for B&Bs in Stockbridge often vary, but you can find a great deal from $131 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Stockbridge B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Stockbridge?
The best time to book a B&B in Stockbridge is during the vibrant summer season from June to August. This period attracts visitors eager to immerse themselves in the cultural richness and natural beauty of the Berkshires. With warm temperatures generally ranging from the mid-60s to mid-80s Fahrenheit, summer is ideal for outdoor activities such as hiking and exploring the picturesque gardens and art museums that Stockbridge is known for.

July stands out as the most popular month for travelers, when the town buzzes with energy from various festivals, outdoor concerts, and art events. The lush, green landscape and lively community atmosphere create memorable experiences for those looking to enjoy both relaxation and adventure.

For travelers seeking a more budget-friendly option, consider October. This month offers a stunning display of fall foliage, transforming the region into a colorful tapestry of reds, oranges, and yellows. The cooler temperatures (typically ranging from the mid-40s to mid-60s Fahrenheit) make it a comfortable time for scenic drives and leisurely strolls through the charming town.
What is the difference between a Stockbridge Bed and Breakfast and a hotel?
Every Stockbridge B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Stockbridge B&Bs.

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