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  • Upfront pricing

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

Check prices for these dates

Next weekend
May 1 - May 3
In two weeks
May 8 - May 10
In one month
May 22 - May 24
In two months
Jun 19 - Jun 21

Our top choices for Stockbridge bed & breakfast

Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.4 out of 10, Exceptional, (59 reviews)
"Uniqueness of rooms, breakfast options and walking distance to so many great spots!"
United States
Emily
$156 nightly
The price is $172
Apr 23 - Apr 24
Total with taxes and fees
The Vesper
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (278 reviews)
"Easy Check-In; Lovely Room; Great Location & Atmosphere. The staff was very friendly,"
United States
Michael
$169 nightly
The price is $186
May 19 - May 20
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
$246 nightly
The price is $270
May 14 - May 15
Total with taxes and fees
Deer Brook Inn
Exterior detail

Sleep Woodstock Mobility Impaired Accessible Suite

Sleep Woodstock Mobility Impaired Accessible Suite
Woodstock
$114 nightly
The price is $125
Apr 23 - Apr 24
Total with taxes and fees
Sleep Woodstock Mobility Impaired Accessible Suite
Exterior

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$114 nightly
The price is $125
Apr 23 - Apr 24
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
$119 nightly
The price is $131
Apr 26 - Apr 27
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
Exterior

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$119 nightly
The price is $131
Apr 23 - Apr 24
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
$114 nightly
The price is $125
Apr 26 - Apr 27
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
Exterior

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$114 nightly
The price is $125
Apr 26 - Apr 27
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
Exterior

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$114 nightly
The price is $125
Apr 26 - Apr 27
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
$119 nightly
The price is $131
Apr 23 - Apr 24
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
Exterior

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$119 nightly
The price is $131
Apr 23 - Apr 24
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
Exterior

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$119 nightly
The price is $131
Apr 26 - Apr 27
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
Exterior

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$119 nightly
The price is $131
Apr 26 - Apr 27
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
$114 nightly
The price is $125
Apr 30 - May 1
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
Front of property

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (394 reviews)
"Wonderful stay"
United States
Gregory
$245 nightly
The price is $270
Apr 23 - Apr 24
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, (428 reviews)
"Amazing place to stay all around! Beautiful inn, friendly staff, incredibly clean, great breakfast.....will absolutely return!"
United States
Dana
$205 nightly
The price is $223
May 3 - May 4
Total with taxes and fees
The Vermont Inn
Exterior

Inn at Neshobe River

Inn at Neshobe River
3.0 star property
Brandon
9.4 out of 10, Exceptional, (16 reviews)
"Great little BAnd B just outside town. Shares property with a brewery and also offers a small food menu for dinner Fantastic view of the golf course 5 th hole Great hospitality and crazy good breakfast "
United States
Keith
$175 nightly
The price is $193
May 15 - May 16
Total with taxes and fees
Inn at Neshobe River
Exterior

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
$219 nightly
The price is $241
Apr 27 - Apr 28
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.
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Top Stockbridge Hotel Reviews

On The River Inn

On The River Inn

8/10 Good
"Clean room, friendly staff, family-friendly. "
Suwei 1-night trip
Posted 7 hours ago
On The River Inn

Find out more about Stockbridge

Stockbridge B&B information

Number of reviews
1,176
Accommodation
34 B&B
Lowest Price
$125
Highest Price
$270

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 $125 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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