Book Exclusive Bennington County Vacation Packages
Bennington County flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
Price was CAÂ $1,037, price is now CAÂ $788 per person
CAÂ $788
per person
Sep 26 - Oct 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Berkshire Mountain Lodge
Price was CAÂ $1,242, price is now CAÂ $920 per person
CAÂ $920
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Hideaway Inn Lenox
Price was CAÂ $1,722, price is now CAÂ $1,358 per person
CAÂ $1,358
per person
Sep 26 - Oct 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this family-friendly guesthouse in Lenox. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Tanglewood Music Center and Lenox Library are located nearby.
The Porches Inn at Mass MoCA
Price was CAÂ $1,423, price is now CAÂ $1,201 per person
CAÂ $1,201
per person
Sep 26 - Oct 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bracewell Park and Massachusetts Museum of Contemporary Art are located nearby.
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Price was CAÂ $1,347, price is now CAÂ $1,137 per person
CAÂ $1,137
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Top Bennington County hotels deals
Hotel Vervana, Trademark Collection by Wyndham
141 West Main Street Bennington VT
Free cancellation
Reserve now, pay when you stay
The price is CAÂ $136 per night
CAÂ $136
CAÂ $148 total
Sep 8 - Sep 9
includes taxes & fees
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 reviews. Popular attractions Hemmings Motor News Car Lover's Convenience Store & Vehicle Display and Bennington Museum are located nearby.
Pool
Breakfast included
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
Free cancellation
The price is CAÂ $301 per night
CAÂ $301
CAÂ $389 total
Sep 9 - Sep 10
includes taxes & fees
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. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Pool
Pet-friendly
The Equinox Golf Resort & Spa
3567 Main Street Route 7A Manchester VT
Free cancellation
Reserve now, pay when you stay
The price is CAÂ $213 per night
CAÂ $213
CAÂ $310 total
Sep 7 - Sep 8
includes taxes & fees
Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Pool
Hot tub
The Palmer House Resort, an Ascend Collection Hotel
5383 Main St Manchester Center VT
Free cancellation
The price is CAÂ $139 per night
CAÂ $139
CAÂ $176 total
Sep 13 - Sep 14
includes taxes & fees
Book a stay at this golf hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lye Brook Falls and Dana L. Thompson Memorial Park are located nearby.
Pool
Hot tub
Hampton Inn and Suites Manchester
4519 Main St Manchester Center VT
Free cancellation
Reserve now, pay when you stay
The price is CAÂ $213 per night
CAÂ $213
CAÂ $235 total
Aug 31 - Sep 1
includes taxes & fees
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 helpful staff in our reviews. Popular attractions Manchester Designer Outlets and American Museum of Fly Fishing are located nearby.
Pool
Hot tub
Brittany Motel
1056 Main Street/Historic Route 7A Manchester Center VT
Free cancellation
Reserve now, pay when you stay
The price is CAÂ $118 per night
CAÂ $118
CAÂ $130 total
Aug 31 - Sep 1
includes taxes & fees
Stay at this motel in Manchester Center. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hildene and Mount Equinox are located nearby.
Pet-friendly
Parking included
Don't see what you're looking for?
See all available properties in Bennington County
View all propertiesLowest 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.
Stay near popular Bennington County attractions
Photos of local treasures
Browse Bennington County vacation photos for more inspiration
