Search for Cheap Deals on
Hotels in Bennington

Choose from 781 Bennington Hotel Deals

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! (1,001 reviews)
All excellent

Reviewed on Mar 22, 2026

Hotel Vervana, Trademark Collection by Wyndham
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! (87 reviews)
Cozy and Comfortable Room and Friendly Service. I am definitely reserving a room here again sometime soon! Awesome family owned business! Highly Recommend to anyone looking for a place to stay while traveling!

Reviewed on Mar 12, 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. ...
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! (962 reviews)
The young man checking me in was pleasant. However, pulling up, it looked seedy, but hey let's check it out. Pulled around to our outside door and went in without luggage to check it out. Walked down to a room 109, opened the door, walked in and turned around 5 minutes later. Zero chance I could ...

Reviewed on Mar 23, 2026

Best Western Bennington
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! (588 reviews)
It was a nice small hotel/motel

Reviewed on Mar 9, 2026

Harwood Hill Motel
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 Norman Rockwell Exhibition and Robert Frost Stone ...
6.8/10 (226 reviews)
Yes

Reviewed on Feb 23, 2026

Starlight Inn
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 ...
9.4/10 Exceptional! (281 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
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! (124 reviews)
Charming B&B style hotel in beautiful Bennington, VT.

Reviewed on Feb 27, 2026

South Shire
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. ...
7.6/10 Good! (637 reviews)
Really run down establishment with sketchy lookin guests

Reviewed on Oct 28, 2025

The Autumn Inn
Bennington Motor Inn

Bennington Motor Inn

2 out of 5
143 West Main Street Bennington VT
  • 10 min drive from Prospect Mountain Cross-Country Ski Center
Stay at this motel in Bennington. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Hemmings Motor News Car Lover's Convenience Store ...
Bennington Motor Inn
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 and air conditioning. Popular attractions Hemmings Motor News Car Lover's Convenience ...
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!
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St Manchester Center VT
  • 50 min drive from Prospect Mountain Cross-Country Ski Center
Book a stay at this business-friendly hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
9.6/10 Exceptional! (1,008 reviews)
Every employee was incredibly friendly, even if only passing us in the foyer or hallways. Stacy, the operations manager, was especially engaging, knowledgeable and helpful as we were deciding what to do for dinner and what events and venues were worth visiting. We took all of her suggestions and ...

Reviewed on Mar 24, 2026

Hampton Inn and Suites Manchester
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.

Find cheap hotels in Bennington

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Bennington hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Bennington.

Choosing the right hotel in Vermont has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Bennington’s 781 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $111. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Bennington hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Bennington. No matter your reason for visiting Bennington, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Bennington hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Bennington for as low as $111.

How many hotels are there in Bennington?

With over 781 hotels in Bennington, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $111.

How to find cheap car rentals in Bennington?

Finding a cheap car rental deal in Bennington is as easy as scoring cheap hotels in Bennington. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.