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  • Upfront pricing

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

Check prices for these dates

Next weekend
Feb 13 - Feb 15
In two weeks
Feb 20 - Feb 22
In one month
Mar 6 - Mar 8
In two months
Apr 3 - Apr 5

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, (195 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
$110 nightly
The price is $124
Feb 8 - Feb 9
Total with taxes and fees
Mountain Valley Retreat
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (264 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
$199 nightly
The price is $219
Feb 9 - Feb 10
Total with taxes and fees
The Jackson
Front of property

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (418 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
$229 nightly
The price is $250
Mar 1 - Mar 2
Total with taxes and fees
The Vermont Inn
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (55 reviews)
"Charming bed and breakfast"
United States
Nicholas
$179 nightly
The price is $197
Feb 19 - Feb 20
Total with taxes and fees
The Vesper
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
$226 nightly
The price is $249
Mar 10 - Mar 11
Total with taxes and fees
Deer Brook Inn
Front of property

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (382 reviews)
"Wonderful stay"
United States
Gregory
$314 nightly
The price is $345
Feb 9 - Feb 10
Total with taxes and fees
Snowed Inn
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (47 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
$299 nightly
The price is $329
Feb 9 - Feb 10
Total with taxes and fees
Stay At Jimmy's
Aerial view

The Lilac Inn

The Lilac Inn
3.5 star property
Brandon
9.6 out of 10, Exceptional, (213 reviews)
"Clean, quaint and lovely! Great service and located in a cozy little town. "
United States
Jessica
$229 nightly
The price is $252
Feb 9 - Feb 10
Total with taxes and fees
The Lilac Inn
Exterior

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (99 reviews)
"No lake-view. Friendly staff, excellent breakfast."
United States
Wendy
$280 nightly
The price is $306
Mar 2 - Mar 3
Total with taxes and fees
Echo Lake 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

North Star Lodge and Resort

North Star Lodge and Resort

10/10 Excellent
"Staff was helpful and room was clean"
Gerry 2-night trip
Posted 3 days ago
North Star Lodge and Resort

Find out more about Stockbridge

Stockbridge B&B information

Number of reviews
1,635
Accommodation
16 B&B
Lowest Price
$124
Highest Price
$345

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 $124 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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