Search B&B in Stockbridge

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 15 B&B in Stockbridge with updated reviews, rates, and availability.

The Jackson
Fireplace

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (212)
"The innkeeper, Lea, was excellent! She helped with our check in process. It went seamlessly. And she helped us when we had an issue with our TV. She was also extremely helpful with our breakfast and checkout! I would give her 5 stars! And the home was beautiful!!!"
The price is AED 820
AED 902 total
includes taxes & fees
27 Apr - 28 Apr
The Jackson
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (346)
"Fantastic and friendly "
The price is AED 628
AED 760 total
includes taxes & fees
22 May - 23 May
Snowed Inn
The Vesper
Economy Room | Individually decorated, individually furnished, free WiFi, bed sheets

The Vesper

3.0 star property
9.8 out of 10, Exceptional, (17)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
The price is AED 386
AED 424 total
includes taxes & fees
28 Apr - 29 Apr
The Vesper
Mountain Valley Retreat
Exterior

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (172)
"Very pleasant couple "
The price is AED 404
AED 457 total
includes taxes & fees
27 Apr - 28 Apr
Mountain Valley Retreat
The Lilac Inn
Exterior

The Lilac Inn

3.5 star property
9.6 out of 10, Exceptional, (186)
"This was a delightful stay and breakfast was wonderful. We will definitely return. "
The price is AED 774
AED 851 total
includes taxes & fees
26 Apr - 27 Apr
The Lilac Inn
The Vermont Inn
Front of property

The Vermont Inn

3.0 star property
9.2 out of 10, Wonderful, (401)
"Awesome spot. "
The Vermont Inn
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (29)
"Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return."
The price is AED 731
AED 804 total
includes taxes & fees
27 Apr - 28 Apr
Stay At Jimmy's
Echo Lake Inn
Exterior

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (96)
"Old fashioned inn with wonderful hosts."
The price is AED 737
AED 803 total
includes taxes & fees
26 May - 27 May
Echo Lake Inn
The Buckmaster Inn
Exterior

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (60)
"I had a great stay at the Buckmaster Inn for ski weekend at Okemo. The house is beautiful with many classic colonial touches throughout. Best of all, Richard and Elizabeth are gracious hosts who go above and beyond to make their guests comfortable. It snowed the last night of my stay and Richard got up extra early to clear the driveway and my car! I will be back whenever I can visit. "
The Buckmaster Inn
Woodbridge Inn
Front of property - evening/night

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"Darling -- Wonderful location, hosts and great breakfast -- We will be back during ski season. Thank you. "
Woodbridge Inn
The Woodstocker B&B
Front of property

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
Whimsical Vermont Farmhouse – Cozy, Inspiring & Close to Nature
Terrace/patio

Whimsical Vermont Farmhouse – Cozy, Inspiring & Close to Nature

The price is AED 647
AED 1,042 total
includes taxes & fees
26 Apr - 27 Apr
Whimsical Vermont Farmhouse – Cozy, Inspiring & Close to Nature
The Upper Suites at Chipman Inn- 5 min to Middlebury College's Rikert Outdoor Center
Terrace/patio

The Upper Suites at Chipman Inn- 5 min to Middlebury College's Rikert Outdoor Center

The price is AED 4,408
AED 5,290 total
includes taxes & fees
27 Apr - 28 Apr
The Upper Suites at Chipman Inn- 5 min to Middlebury College's Rikert Outdoor Center
Inn at Neshobe River
Exterior

Inn at Neshobe River

3.0 star property
9.0 out of 10, Wonderful, (10)
"Owners were so nice, bed was great, linens and towels were wonderful. House is very old and only drawback (which is original to the house and should not be changed!) is the bar/latch style door handles. The Violet Room has its private bathroom across the hall landing, but if you get up in the night as we do, you do make a lot of noise rattling those handles! Walls are thin.But that didn't disturb us, since the other patrons on our visit were very quiet and considerate. If you are looking for...
Inn at Neshobe River
Inn at Water's Edge
Bar (on property)

Inn at Water's Edge

3.0 star property
Inn at Water's Edge
Deer Brook Inn
Terrace/patio

Deer Brook Inn

4.0 star property
10.0 out of 10, Exceptional, (21)
"The Inn was so lovely and charming and exceeded our expectations! The hospitality offered by the Inn Keeper and his team was truly remarkable and we felt welcome and spoiled throughout our stay. The property itself is stunning and the attention to detail is five star in our book!!! We will definitely be back! Plan your stay!! You won’t be disappointed!!"
Deer Brook 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.
Don't see what you're looking for?
See all available properties in Stockbridge
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Stockbridge

Cozy Loft for two with Hot Tub & Mtn Views
Exterior

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (236)
"My wife and I stayed in "The Little Loft" for a ski trip to Sugarbush. The cabin it small for sure but offers everything you will need from a standpoint of short term livability. We used that hot tub daily / nightly after skiing all day, had a great meal we grilled out and had a few nice bonfires as well. If you do not want to have to drive 30 minutes for dinner or shop for your food and cook it, then you may find it a small inconvenience but for us we intentionally wanted to be in a quiet cabin...
Cozy Loft for two with Hot Tub & Mtn Views
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
TV, fireplace, DVD player, books

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (489)
"The cabin had everything we needed, was comfortable, and quiet. It was clean and the beds were comfortable. We had a nice getaway to celebrate a milestone birthday. Jeff couldn't have been nicer and provided ample information about the area and where to eat, etc. Would highly recommend staying at the cabin if you're looking for a quiet escape from your regular life...even if you already live in rural new england as we do. "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
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.

Frequently asked questions

Searching for B&Bs in Stockbridge?
If you’re looking for something a little quirkier than your standard hotel, a bed and breakfast could be a great option for your getaway. If your ideal vacation to Stockbridge includes spending lots of time outside, Green Mountain National Forest is a good spot to enjoy the scenery.
Why would you choose a B&B over a traditional hotel room?
With attentive service, opportunities to socialize with other guests, and tasty breakfasts, B&Bs offer a one-of-a-kind setting.
What are the best B&Bs in Stockbridge?
Below are some B&Bs in the surrounding area: The Jackson: 11 rooms. 15.7 mi (25.2 km) from the heart of Stockbridge. Enjoy the designer toiletries and library. The Vesper: 9 rooms. 16.2 mi (26 km) from the downtown core. Snowed Inn: 19 rooms. Situated 9.8 mi (15.8 km) from the heart of Stockbridge. Enjoy the hot tubs and unique décor. Mountain Valley Retreat: 2 rooms. 7.2 mi (11.5 km) from the heart of downtown. Enjoy the free full breakfast and private yard. Stay At Jimmy’s: 3 rooms. Located 16.3 mi (26.3 km) from the core of Stockbridge. Enjoy the jetted tubs and private yard.
What's the best time of year to stay at a B&B in Stockbridge?
When you’re dreaming of a stay in Stockbridge, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Stockbridge are March, January, December, and February, with each month seeing an average of 22 inches of snowfall.
What is there to do in Stockbridge?
When you want to check out some attractions in town, you might consider a visit to Green Mountain National Forest and Les Newell Wildlife Management Area. You might check out Belcher Library if you have time to see more of the area.
How can I get to and around Stockbridge?
Mapping out your trip in and around Stockbridge is easy with these transportation options. Fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is located 20.1 mi (32.4 km) away from the city center. You can also search for flights into Lebanon, NH (LEB-Lebanon Municipal), which is 24.8 mi (39.9 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.