Old Bennington Trip
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₹100,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Old Bennington
The Four Chimneys Inn
21 West Road Bennington VT
The price is ₹20,742 per night from 14 May to 15 May
₹20,742
₹22,608 total
14 May - 15 May
includes taxes & fees
9.4/10 Exceptional! (283 reviews)
Peaceful and whimsical stay in a historic inn. The breakfast was delicious (served with the best local maple syrup) and location was a 5 minute drive to the downtown area.
Reviewed on 19 Apr 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
The price is ₹13,747 per night from 17 May to 18 May
₹13,747
₹15,356 total
17 May - 18 May
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
Super clean, great coffee spread for breakfast. I really enjoyed my stay.
Reviewed on 9 May 2026
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is ₹28,909 per night from 28 May to 29 May
₹28,909
₹32,292 total
28 May - 29 May
includes taxes & fees
9.6/10 Exceptional! (625 reviews)
Staff was very helpful. Rooms were great. Unbeatable location for Williamstown (especially if you’re in town for an athletic event at Williams). Really solid breakfast with friendly and attentive wait staff. Only minor complaint is that the WiFi is not great. Other than that it was a perfect ...
Reviewed on 10 May 2026
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.
Popular places to visit
Bennington Battle Monument
Learn about the local history of Old Bennington with a stop at Bennington Battle Monument. In the area, take in the art scene and mountain views.
Prospect Mountain Nordic Ski Center
Hit the slopes in Woodford with a visit to Prospect Mountain Nordic Ski Center. Discover the area's mountain views and cafes.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
