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Compare 889 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Signature Room, King plus Twin Bed,  Private Bathroom, Porch, Accessible,  RM-10 | Premium bedding, individually decorated, individually furnished
The Four Chimneys Inn
4.0 star property
9.4 out of 10, Exceptional, (257)
"We quite liked this hotel as it was charming and well thought out in many ways. We especially loved the dinner we had the first night. Our room had a fireplace and we loved that feature because it was a bit chillier than we expected. The only thing we would have wished for was a mini fridge in the room, but that’s not a huge deal breaker for us to return someday. It Is a nice walkable area and an easy to navigate town. Sadly, Bennington Pottery store isn’t open to the public anymore, but the...
The price is $257
$281 total
includes taxes & fees
May 22 - May 23
The Four Chimneys Inn
Seasonal outdoor pool, pool umbrellas, sun loungers
Paradise Inn
2.5 star property
8.2 out of 10, Very Good, (1001)
"We were late coming in and the owner was accommodating! It was quiet and clean -- not new and modern, but great for the price!"
The price is $206
$225 total
includes taxes & fees
Jun 21 - Jun 22
Paradise Inn
Front of property
The Autumn Inn
2.0 star property
7.8 out of 10, Good, (501)
"Independent motel, somewhat dated but clean with updated bathroom. Gentleman who assisted me was lovely. Short visit to Bennington to visit an elderly family member. Convenient, although I wish I could find better coffee close by. I launched early morning on low grade."
The price is $89
$97 total
includes taxes & fees
May 22 - May 23
The Autumn Inn
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Exterior
Hampton Inn Bennington
2.5 star property
8.6 out of 10, Excellent, (871)
"Serviceable. Clean, consistent with other Hampton inn properties. Friendly, responsive staff."
The price is $161
$175 total
includes taxes & fees
Jun 9 - Jun 10
Hampton Inn Bennington
In-room safe, blackout drapes, iron/ironing board
Best Western Bennington
2.5 star property
7.8 out of 10, Good, (705)
"Converted motel but nicely done"
The price is $119
$130 total
includes taxes & fees
May 29 - May 30
Best Western Bennington
Property amenity
Harwood Hill Motel
2.0 star property
9.4 out of 10, Exceptional, (433)
"Staff was awesome, super friendly and hospitable. My room was fresh and clean and the views were great. 10 out of 10 all around ."
The price is $140
$153 total
includes taxes & fees
May 22 - May 23
Harwood Hill Motel
2 Bedroom Unit | Individually decorated, iron/ironing board, cribs/infant beds, free WiFi
Bennington Motor Inn
2.0 star property
7.6 out of 10, Good, (410)
"Great stay at Bennington Motor Inn! "
The price is $121
$132 total
includes taxes & fees
May 27 - May 28
Bennington Motor Inn
Reception
South Shire
4.0 star property
9.4 out of 10, Exceptional, (58)
"Piano player was great"
The price is $186
$203 total
includes taxes & fees
May 30 - May 31
South Shire
Desk, iron/ironing board, cribs/infant beds, rollaway beds
West Road Motel
2.0 star property
5.0 out of 10, (123)
"The only decent thing was that it was clean. Broken doors, broken remote, broken lamp, was frightening pulling in with people that seemed to be just hanging out. Maybe they lived there in a room. All kinds of what appeared to be junk all around run down buildings. "
West Road Motel
View from property
Starlight Inn
2.0 star property
6.6 out of 10, (179)
"Friendly. Nice and quiet with amenities I needed."
The price is $85
$93 total
includes taxes & fees
May 22 - May 23
Starlight Inn
Porch
Eddington House Inn
3.0 star property
9.4 out of 10, Exceptional, (63)
"Enjoyed meeting Mark at breakfast and learning about his life! Great guy..."
The price is $213
$233 total
includes taxes & fees
Jun 11 - Jun 12
Eddington House Inn
Porch
Maple Shade Bed & Breakfast
3.0 star property
9.8 out of 10, Exceptional, (85)
"Super clean, friendly owners, great breakfast, rooms beautifully appointed in a country home style. Loved it!"
The price is $204
$220 total
includes taxes & fees
Jun 10 - Jun 11
Maple Shade Bed & Breakfast
Exterior
Studio style farm stay
8.8 out of 10, Excellent, (26)
"Beds were uncomfortable."
Studio style farm stay
Exterior
The Farmhouse at Saratoga - H2
10.0 out of 10, Exceptional, (4)
"Clean, well appointed one bedroom. Very comfortable bed and furniture. Nicely decorated. Thanks!"
The Farmhouse at Saratoga - H2
Golf
Cozy 1 Bedroom farm stay cottage
7.0 out of 10, Good, (6)
"We traveled with our little dog and this property accepts pets and that worked out well. Having a full kitchen helped save on going out to eat."
Cozy 1 Bedroom farm stay cottage
Boating
Arlington's West Mountain Inn
3.0 star property
8.4 out of 10, Very Good, (151)
"staff was very courteous and helpful"
Arlington's West Mountain Inn
Outdoor pool
Best Western Bennington - Deluxe King Bed #1
9.6 out of 10, Exceptional, (4)
"Nice place"
The price is $149
$185 total
includes taxes & fees
May 28 - May 29
Best Western Bennington - Deluxe King Bed #1
Exterior
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
10.0 out of 10, Exceptional, (6)
"Needed to break up our drive home from the Adirondacks where we watched the solar eclipse. This was a peaceful cute cabin that was perfect. Only thing slightly negative was that there was no doors to the bedrooms."
The price is $199
$313 total
includes taxes & fees
May 22 - May 23
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Fridge, microwave, oven, stovetop
Escape to Serenity: Cozy 3 bedroom apartment
The price is $108
$391 total
includes taxes & fees
Jun 11 - Jun 12
Escape to Serenity: Cozy 3 bedroom apartment
Dining
Sowilo Retreat All-Inclusive Cedar House
10.0 out of 10, Exceptional, (2)
The price is $199
$506 total
includes taxes & fees
May 26 - May 27
Sowilo Retreat All-Inclusive Cedar House
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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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Old Bennington Travel Info

Number of reviews
3,730
Accommodation
889 hotels
Highest price
$257
Lowest price
$69

Frequently asked questions

Where is the best place for a stay in Old Bennington?

Based on our traveler data, The Four Chimneys Inn is one of the top choices for your stay. This B&B offers free breakfast and free parking. Two other options for your trip to the area are Hotel Downstreet and Mountaineer Inn. See all available top hotels, or vacation rentals in Old Bennington.

What are some of the best vacation home rentals in Old Bennington?

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW! : You might want to consider this vacation rental near Old Bennington, which offers an indoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 12 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a pool table so you can immerse yourself in your vacation. See all vacation rentals in Old Bennington.

If I need to cancel my hotel reservation in Old Bennington, will I receive a refund?

Yes! You'll find that most hotel reservations are refundable provided that you cancel before the hotel’s cancellation deadline, which is usually within 24-48 hours of your arrival date. If your reservation is non-refundable, you might still have the option to cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Old Bennington.

Where can I learn more about changing or cancelling my trip to Old Bennington?

To access more information about picking new dates or cancelling your trip to Old Bennington, click here.

What are some hotels with pools in Old Bennington?

Hampton Inn Bennington: Provides a sauna, a pool, and free breakfast. The Lodge at Mount Snow and Big Bears Lodge are a couple of other choices that offer an onsite pool. View all hotels with pools in Old Bennington.

What is the best spa hotel in Old Bennington?

The Four Chimneys Inn is a highly recommended spa hotel with a bar. Treat yourself to a massage at the on-site spa. See all spa hotels in Old Bennington.

How is it to stay in Old Bennington?

Visitors are sure to enjoy all that Old Bennington has to offer. In Old Bennington, there are 2 hotels and other accommodations to choose from. Find out more about Old Bennington.

What should I see while I'm in Old Bennington?

Landmarks like Bennington Battle Monument and Old First Congregational Church might be worth a visit. Additionally, you might want to add Bennington Museum to your itinerary. Check out what more to see and do in Expedia's Old Bennington guide.

What's the weather like in Old Bennington?

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 Old Bennington are January, April, March, and February, with each month seeing an average of 11 inches of snowfall.

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