Book Stockbridge Bed & Breakfast

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

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

Check prices for these dates

Next weekend
Apr 10 - Apr 12
In two weeks
Apr 17 - Apr 19
In one month
May 1 - May 3
In two months
May 29 - May 31

Our top choices for Stockbridge bed & breakfast

Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (57 reviews)
"Uniqueness of rooms, breakfast options and walking distance to so many great spots!"
United States
Emily
$128 nightly
The price is $141
Apr 7 - Apr 8
Total with taxes and fees
The Vesper
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
$340 nightly
The price is $374
Apr 3 - Apr 4
Total with taxes and fees
The Woodstocker B&B
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (276 reviews)
"Easy Check-In; Lovely Room; Great Location & Atmosphere. The staff was very friendly,"
United States
Michael
$263 nightly
The price is $289
Apr 1 - Apr 2
Total with taxes and fees
The Jackson
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (1 review)
"The property manager greeted us when we walked in and she was extremely friendly and kind. The inn was charming and had a homey feel, and the rooms were very clean and well maintained with awesome amenities."
United States
Sara
$227 nightly
The price is $250
Apr 2 - Apr 3
Total with taxes and fees
Deer Brook Inn
Exterior detail

Sleep Woodstock Mobility Impaired Accessible Suite

Sleep Woodstock Mobility Impaired Accessible Suite
Woodstock
$119 nightly
The price is $130
Mar 31 - Apr 1
Total with taxes and fees
Sleep Woodstock Mobility Impaired Accessible Suite
Game room

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$109 nightly
The price is $120
Mar 31 - Apr 1
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
Exterior

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$114 nightly
The price is $126
Mar 31 - Apr 1
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
Private kitchen

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$114 nightly
The price is $126
Mar 31 - Apr 1
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
Dining

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$114 nightly
The price is $126
Mar 31 - Apr 1
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
Private kitchen

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$109 nightly
The price is $120
Apr 2 - Apr 3
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
Room

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$109 nightly
The price is $120
Apr 1 - Apr 2
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
Private kitchen

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$109 nightly
The price is $120
Apr 2 - Apr 3
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
Living area

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$114 nightly
The price is $126
Apr 1 - Apr 2
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
Dining

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$114 nightly
The price is $126
Apr 1 - Apr 2
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
Exterior

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$109 nightly
The price is $120
Apr 7 - Apr 8
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
Room

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$114 nightly
The price is $126
Apr 5 - Apr 6
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
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
$210 nightly
The price is $229
Apr 6 - Apr 7
Total with taxes and fees
Echo Lake Inn
Front of property

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (392 reviews)
"Wonderful stay"
United States
Gregory
$172 nightly
The price is $189
Apr 15 - Apr 16
Total with taxes and fees
Snowed Inn
Front of property

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (426 reviews)
"Greeted with cookies and a cozy living room with games and cute decorations. Nice, clean room with a comfortable bed. Breakfast was great (fresh berries, make your own waffles, muffins, etc). Breakfast is at 8 so you may not make first tracks in the slopes"
United States
Piruz
$229 nightly
The price is $250
Apr 8 - Apr 9
Total with taxes and fees
The Vermont Inn
Aerial view

The Lilac Inn

The Lilac Inn
3.5 star property
Brandon
9.6 out of 10, Exceptional, (216 reviews)
"Great breakfast….friendly staff…spotless room"
United States
Judith M
$215 nightly
The price is $237
Apr 6 - Apr 7
Total with taxes and fees
The Lilac 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Stockbridge Hotel Reviews

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

4/10 Poor
"they save a lot"
Yauheni 2-night trip
Posted 13 hours ago
Days Inn by Wyndham Rutland/Killington Area

Find out more about Stockbridge

Stockbridge B&B information

Number of reviews
1,203
Accommodation
16 B&B
Lowest Price
$141
Highest Price
$374

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 $141 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.

Explore a world of travel with Expedia