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Compare 11 B&B in Bennington with updated reviews, rates, and availability.

South Shire
Front of property

South Shire

4.0 star property
9.2 out of 10, Wonderful, (75)
"Rather unique We liked the piano player "
The price is AED 617
AED 810 total
includes taxes & fees
24 Nov - 25 Nov
South Shire
The Inn at Manchester
Exterior

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (218)
"Great place. Excellent hosts. Great location. Very well kept. "
The price is AED 569
AED 626 total
includes taxes & fees
24 Nov - 25 Nov
The Inn at Manchester
The Ira Allen House
Exterior

The Ira Allen House

3.5 star property
9.8 out of 10, Exceptional, (178)
"Always enjoyable visit. Kevin and Mike are very friendly and the breakfast is always delicious!"
The price is AED 643
AED 701 total
includes taxes & fees
24 Nov - 25 Nov
The Ira Allen House
Bromley View Inn
Restaurant

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (322)
"Very nice stay. Cozy and comfortable."
Bromley View Inn
Hill Farm Inn
Front of property

Hill Farm Inn

4.0 star property
9.6 out of 10, Exceptional, (165)
"Its exactly what you think of when you think of a Vermont Inn. "
The price is AED 951
AED 1,863 total
includes taxes & fees
24 Nov - 25 Nov
Hill Farm Inn
The Four Chimneys Inn
Exterior

The Four Chimneys Inn

4.0 star property
9.4 out of 10, Exceptional, (272)
"What a charming B&B . So warming and inviting.Staff made you feel at home and were all so kind and friendly.Oh and the food was delicious,"
The price is AED 915
AED 997 total
includes taxes & fees
24 Nov - 25 Nov
The Four Chimneys Inn
The Inn at Ormsby Hill
Terrace/patio

The Inn at Ormsby Hill

3.5 star property
9.8 out of 10, Exceptional, (113)
"What a beautiful B&B! The staff was super kind and friendly. Loved my room and how it was so nicely decorated. Cozy and comfortable. Breakfast was great and town was just a 5 minute drive away. So glad my last minute decision to visit Vermont turned out so perfect. ❤️"
The price is AED 1,061
AED 1,167 total
includes taxes & fees
24 Nov - 25 Nov
The Inn at Ormsby Hill
North Shire Lodge
Front of property

North Shire Lodge

3.0 star property
9.4 out of 10, Exceptional, (146)
"Beautiful view from the room!"
The price is AED 650
AED 716 total
includes taxes & fees
24 Nov - 25 Nov
North Shire Lodge
Arlington's West Mountain Inn
Front of property

Arlington's West Mountain Inn

3.0 star property
8.4 out of 10, Very Good, (154)
"A most wonderful place to stay! Breakfasts and dinners are heavenly and the Inn is very friendly and welcoming."
Arlington's West Mountain Inn
Victorian mansion's Jim-Dandy Suite
Bedroom

Victorian mansion's Jim-Dandy Suite

10.0 out of 10, Exceptional, (5)
"It was such a relief to enter a space that honors a time gone by. The attention to detail—perfect touches—from the sheets and pillows tot he fresh flowers at the breakfast table added to the hospitality and warmth we felt immediately walking into the inn. There is NOTHING like staying at a place where the owner is present and attending to guests//thank you, Jim for a lovely respite from the circus."
Victorian mansion's Jim-Dandy Suite
Victorian mansions Coach Room with Breakfast
Coach Bedroom

Victorian mansions Coach Room with Breakfast

Victorian mansions Coach Room with Breakfast
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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Other property types in Bennington

Perfect for Leaf Peeping w/Bar Room, Hot Tub
Bar Room

Perfect for Leaf Peeping w/Bar Room, Hot Tub

10.0 out of 10, Exceptional, (11)
"Wonderful experience, extremely communicative and helpful management, and just a beautiful building to stay in. We wanted for nothing. Thank you!"
Perfect for Leaf Peeping w/Bar Room, Hot Tub
Great Place to get away and have clean fresh air surround you!
Book now for a magical & peaceful fall stay before its too late!

Great Place to get away and have clean fresh air surround you!

9.8 out of 10, Exceptional, (131)
"This was one of our favorite family trips ever! So fun using the paddle boat and seeing the misty mornings and starry nights in the lake."
Great Place to get away and have clean fresh air surround you!
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
Nighttime view

Two Brooks Lodge, Beautiful Waterfront Vermont Retreat

8.8 out of 10, Excellent, (27)
"In town for a long weekend and loved the location. The owner was prompt and very helpful as we made a mistake in booking. FYI, The pictures are great but it’s a bit more rustic than they make it seem. Still, it was great to sit outside and hear the brooks flowing. Very quiet street! Housecleaning was a bit lacking though as there were some huge cobwebs in the corners. That was fine for us as we spend our time in a barn anyway. "
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
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 Bennington?
If you’re looking for something a little different than the traditional hotel experience, a bed and breakfast could be a great option for your getaway. While you’re enjoying your trip to Bennington, Green Mountain National Forest and Woodford State Park are perfect spots to get in some fresh air and greenery.
Are you thinking about B&Bs over traditional hotel rooms?
B&Bs all have a unique charm. Whether it’s a cozy reading space or a sunlit breakfast nook, the small details are what make bed and breakfasts the perfect escape.
What are the top B&Bs in Bennington?
Below are some well-liked B&Bs in the area: The Four Chimneys Inn: 11 rooms. 0.2 mi (0.3 km) from the heart of Bennington. Enjoy the free full breakfast and unique décor. Big Bears Lodge: 24 rooms. 17.5 mi (28.2 km) from the downtown core. Enjoy the free cooked breakfast and outdoor pool. The Nutmeg: 14 rooms. Situated 16.7 mi (26.9 km) from the heart of Bennington. Enjoy the free cooked breakfast and outdoor pool.
How many Bed & Breakfasts will I be able to find in Bennington?
Expedia offers 10 BnBs in Bennington so you’ll have lots of options for your stay.
When is the best time to book my B&B in Bennington?
When you’re planning your escape to Bennington, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Bennington are January, March, February, and December, with each month seeing an average of 8 inches of snowfall.
What is there to do in Bennington?
If you’re looking for some things to do on your trip, travelers enjoy Bennington for its skiing and hiking. If you’re looking for some activities to entertain you on your trip, consider visiting Harmon Hill and Prospect Mountain Nordic Ski Center. You might put Bennington Museum and Bennington Battle Monument on your list if you want to see more of the area.
How can I get to and around Bennington?
Mapping out your trip in and around Bennington is easy with these transportation options. Fly into Albany Intl. Airport (ALB), which is located 31.7 mi (51 km) away from the city center. You can also search for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 31.9 mi (51.4 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.