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B&B in Stockbridge

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (233)
"Excellent Vintage style B&B. "
$292 nightly
The price is $322
Oct 26 - Oct 27
Total with taxes and fees
The Jackson

The Vesper

3.0 star property
9.2 out of 10, Wonderful, (32)
"The location is fabulous bc you can walk everywhere once you arrive. Beds were comfortable and great options at breakfast(the oats and fresh strawberries were my favorite)"
$212 nightly
The price is $234
Oct 26 - Oct 27
Total with taxes and fees
The Vesper

The Lilac Inn

3.5 star property
9.6 out of 10, Exceptional, (206)
"I love staying at the Lilac Inn when visiting family in the area. "
$218 nightly
The price is $240
Oct 8 - Oct 9
Total with taxes and fees
The Lilac Inn

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (360)
"Beautiful place to stay! 10/10 would recommend. You're going to love it!"
$316 nightly
The price is $347
Oct 7 - Oct 8
Total with taxes and fees
Snowed Inn

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (63)
"Elizabeth and Richard are amazing people and welcomed us into their home. The property is beautifully maintained and Elizabeth's cooking is top notch. "
The Buckmaster Inn

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (183)
"Absolutely lovely stay!"
$120 nightly
The price is $136
Oct 21 - Oct 22
Total with taxes and fees
Mountain Valley Retreat

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (42)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
$299 nightly
The price is $329
Oct 26 - Oct 27
Total with taxes and fees
Stay At Jimmy's

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (66)
"Staff was very friendly and welcoming "
$464 nightly
The price is $511
Sep 28 - Sep 29
Total with taxes and fees
Woodbridge Inn

The Vermont Inn

3.0 star property
9.2 out of 10, Wonderful, (408)
"Great location & affordable lodging. "
$275 nightly
The price is $300
Sep 29 - Sep 30
Total with taxes and fees
The Vermont Inn

Chipman Inn

Chipman Inn

Inn at Neshobe River

3.0 star property
9.4 out of 10, Exceptional, (15)
"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 "
Inn at Neshobe River

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (97)
"Charming place, the food was great, rooms clean, and service was excellent"
Echo Lake Inn

The Woodstocker B&B

4.0 star property
10.0 out of 10, Exceptional, (51)
"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! "
The Woodstocker B&B

Deer Brook Inn

4.0 star property
10.0 out of 10, Exceptional, (21)
"One of the best experiences I have ever had! The staff were kind, attentive, and just plain wonderful! I can't wait to return as soon as possible! This place is BEAUTIFUL inside and out! (Not to mention that the breakfast was to die for). Don't think twice- you need to stay at the Deer Brook Inn!"
Deer Brook Inn

Inn at Water's Edge

3.0 star property
Inn at Water's Edge

All guest rooms in Chipman Inn- Your classic B&B in Vermont

All guest rooms in Chipman Inn- Your classic B&B in Vermont
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

Find out more about Stockbridge

Find out more about Stockbridge

Stockbridge B&B information

Number of reviews
1,659
Accommodation
15 B&B
Lowest Price
$136
Highest Price
$511

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 $136 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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