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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 29 - May 31
In two weeks
Jun 5 - Jun 7
In one month
Jun 19 - Jun 21
In two months
Jul 17 - Jul 19

Our top choices for Stockbridge bed & breakfast

Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (281 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
$149 nightly
The price is $164
May 24 - May 25
Total with taxes and fees
The Jackson
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.4 out of 10, Exceptional, (61 reviews)
"This was the cutest little bed and breakfast. The staff was lovely, the check-in was easy, and we had a great time in Woodstock! "
United States
Melissa
$175 nightly
The price is $193
May 21 - May 22
Total with taxes and fees
The Vesper
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
$228 nightly
The price is $251
Jun 17 - Jun 18
Total with taxes and fees
Deer Brook Inn
Exterior

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$114 nightly
The price is $125
Jun 3 - Jun 4
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
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
$208 nightly
The price is $227
May 26 - May 27
Total with taxes and fees
Echo Lake Inn
Front of property

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (429 reviews)
"Clean room | Hot tub | Pet-friendly "
United States
Shanshan
$205 nightly
The price is $223
May 21 - May 22
Total with taxes and fees
The Vermont Inn
Lobby sitting area

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (394 reviews)
"Wonderful stay"
United States
Gregory
$127 nightly
The price is $140
Jun 4 - Jun 5
Total with taxes and fees
Snowed 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 22 - May 23
Total with taxes and fees
Inn at Neshobe River
Exterior

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$117 nightly
The price is $129
May 27 - May 28
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
Property grounds

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$119 nightly
The price is $131
Jun 2 - Jun 3
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
Microwave, coffee/tea maker, ice maker

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$126 nightly
The price is $139
Jun 1 - Jun 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
$117 nightly
The price is $129
May 27 - May 28
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
Property grounds

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$119 nightly
The price is $131
Jun 1 - Jun 2
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
$125 nightly
The price is $138
Jun 3 - Jun 4
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
Property grounds

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$126 nightly
The price is $139
May 27 - May 28
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
Iron/ironing board, travel crib, WiFi, bed sheets

Sleep Woodstock Mobility Impaired Accessible Suite

Sleep Woodstock Mobility Impaired Accessible Suite
Woodstock
$125 nightly
The price is $137
Jun 3 - Jun 4
Total with taxes and fees
Sleep Woodstock Mobility Impaired Accessible Suite
Exterior

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$121 nightly
The price is $134
Jun 9 - Jun 10
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
Jun 3 - Jun 4
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
Jun 8 - Jun 9
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
Exterior

The Lilac Inn

The Lilac Inn
3.5 star property
Brandon
9.6 out of 10, Exceptional, (217 reviews)
"Great breakfast….friendly staff…spotless room"
United States
Judith M
$230 nightly
The price is $253
May 21 - May 22
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

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent
"Everything was good, plenty of parking .the room was clean and the heater worked great.staff staff was very helpful. "
Mike 1-night trip
Posted 15 hours ago
Days Inn by Wyndham Rutland/Killington Area

Find out more about Stockbridge

Stockbridge B&B information

Number of reviews
1,182
Accommodation
34 B&B
Lowest Price
$125
Highest Price
$253

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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