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Choose from 785 Bennington Hotel Deals

Knotty Pine

Knotty Pine

2.5 out of 5
130 Northside Dr Bennington VT
  • 11 min drive from Prospect Mountain Cross-Country Ski Center
Stay at this motel in Bennington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bennington Battle Monument and Bennington Museum are ...
8.6/10 Excellent! (55 reviews)
Great property and a great value!

Reviewed on Jan 13, 2026

Knotty Pine
Hampton Inn Bennington

Hampton Inn Bennington

2.5 out of 5
51 Hannaford Square Bennington VT
  • 13 min drive from Prospect Mountain Cross-Country Ski Center
Book a stay at this business-friendly hotel in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (1,000 reviews)
Good Beautiful stay

Reviewed on Jan 10, 2026

Hampton Inn Bennington
Best Western Bennington

Best Western Bennington

2.5 out of 5
220 Northside Drive Bennington VT
  • 12 min drive from Prospect Mountain Cross-Country Ski Center
Stay at this hotel in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
7.6/10 Good! (949 reviews)
Location and amenities basic, which is all we needed.

Reviewed on Jan 12, 2026

Best Western Bennington
Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
141 West Main Street Bennington VT
  • 10 min drive from Prospect Mountain Cross-Country Ski Center
Book a stay at this ski hotel in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
8.2/10 Very Good! (999 reviews)
Staff were great and very accommodating. Room is very nice and spacious. Great hotel

Reviewed on Jan 11, 2026

Hotel Vervana, Trademark Collection by Wyndham
South Shire

South Shire

4 out of 5
124 Elm St Bennington VT
  • 10 min drive from Prospect Mountain Cross-Country Ski Center
Stay at this inn in Bennington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (121 reviews)
A+ service, room we stayed in was perfect size with king bed. had an issue with heater first night but Inn Keeper was great to deal with and provided alternative heat source on first evening plus they have working fireplace (bonus++). We stayed 3 nights and just enjoyed ourselves during our visit. ...

Reviewed on Jan 5, 2026

South Shire
Harwood Hill Motel

Harwood Hill Motel

2 out of 5
864 Harwood Hill Road Bennington VT
  • 13 min drive from Prospect Mountain Cross-Country Ski Center
Stay at this motel in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9.4/10 Exceptional! (581 reviews)
Clean room & courteous staff.

Reviewed on Jan 12, 2026

Harwood Hill Motel
The Four Chimneys Inn

The Four Chimneys Inn

4 out of 5
21 West Road Bennington VT
  • 11 min drive from Prospect Mountain Cross-Country Ski Center
Book a stay at this golf B&B in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.6/10 Exceptional! (223 reviews)
This is a quintessential Vermont inn in beautiful historic Bennington. The inn was lovingly cared for by the owner who was very attentive to his guests. We will stay again.

Reviewed on Jan 12, 2026

The Four Chimneys Inn
The Autumn Inn

The Autumn Inn

2 out of 5
924 East Main Street Bennington VT
  • 8 min drive from Prospect Mountain Cross-Country Ski Center
Stay at this motel in Bennington. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.4/10 Good! (637 reviews)
Nice staff, but dated condition

Reviewed on Oct 19, 2025

The Autumn Inn
Starlight Inn

Starlight Inn

2 out of 5
357 Us Route 7 S Bennington VT
  • 10 min drive from Prospect Mountain Cross-Country Ski Center
Stay at this hotel in Bennington. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Robert Frost Stone House Museum and Norman Rockwell ...
6.6/10 (222 reviews)
Convenient. Close to shops and restaurants. Prperry was a bit run down but charming in its way. Staff was very friendly.

Reviewed on Oct 3, 2025

Starlight Inn
Breathtaking Mtn Views: Stylish Rustic Retreat!

Breathtaking Mtn Views: Stylish Rustic Retreat!

3 out of 5
Bennington VT
  • 14 min drive from Prospect Mountain Cross-Country Ski Center
Stay at this cottage in Bennington. Enjoy free parking, an in-room coffeemaker, and air conditioning. Popular attractions Bennington Center for the Arts and ...
Breathtaking Mtn Views: Stylish Rustic Retreat!
Bennington Gem w/ Smart TV Near Historic District!

Bennington Gem w/ Smart TV Near Historic District!

3 out of 5
Bennington VT
  • 10 min drive from Prospect Mountain Cross-Country Ski Center
Book a stay at this business-friendly cottage in Bennington. Enjoy free parking. Popular attractions Hemmings Motor News Car Lover's Convenience Store & Vehicle ...
8/10 Very Good! (2 reviews)
Two things can improved: 1). The bathroom needs to be renovated. It has a dirty look. 2). The security alarm was beeping irritatingly all the first night. This prevented us from getting anywhere near a good night sleep. I did not find the owner very responsive. He said someone would be there by 4 ...

Reviewed on Oct 21, 2025

Bennington Gem w/ Smart TV Near Historic District!
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
  • 49 min drive from Prospect Mountain Cross-Country Ski Center
Book a stay at this golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (825 reviews)
Staff, cleanliness, ambience, restaurant, all perfect! We can’t wait to return!

Reviewed on Jan 4, 2026

Kimpton Taconic Hotel by IHG
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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