Bennington Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top Hotel Deals

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
31.94 km from city center
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
31.84 km from city center
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

3 out of 5
30 Main Street Keene NH
30.28 km from city center
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3 out of 5
75 Railroad St Keene NH
30.12 km from city center
Book a stay at this business-friendly hotel in Keene. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 out of 5
126 Key Rd Keene NH
31.88 km from city center
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free parking, and room service. Our guests praise the breakfast and the helpful staff ...
Colby Hill Inn

Colby Hill Inn

3.5 out of 5
33 The Oaks Street Henniker NH
21.44 km from city center
Book a stay at this ski inn in Henniker. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tucker Free Library and Contoocook River are ...
Henniker Motel

Henniker Motel

2 out of 5
61 Craney Pond Rd Henniker NH
21.07 km from city center
Stay at this motel in Henniker. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions ...
The Burrell House

The Burrell House

2.5 out of 5
112 Washington St Keene NH
30.12 km from city center
Stay at this guesthouse in Keene. Enjoy free WiFi, free parking, and a picnic area. Popular attractions CC&H Framing / Pepper Pete's Hot Shop and Central Square ...
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 out of 5
80 Concord Street Peterborough NH
12.66 km from city center
Stay at this hotel in Peterborough. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Mariposa ...
The Carriage Barn Inn

The Carriage Barn Inn

3 out of 5
358 Main St Keene NH
30.38 km from city center
Stay at this B&B in Keene. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thorne-Sagendorph Art Gallery and Redfern Arts Center are located ...
Monadnock Inn

Monadnock Inn

2.5 out of 5
379 Main Street Jaffrey NH
21.94 km from city center
Book a stay at this golf B&B in Jaffrey. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Shattuck Golf Course and Jaffrey Civic Center ...
Blue Bear Inn

Blue Bear Inn

4 out of 5
534 Mountain Rd Francestown NH
4.28 km from city center
Stay at this inn in Francestown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Crotched ...
The Birchwood Inn

The Birchwood Inn

3.5 out of 5
340 Senator Tobey Highway Temple NH
20.39 km from city center
Stay at this inn in Temple. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Solon ...
Don't see what you're looking for?
See all available properties in Bennington
View all properties
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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Wed, Sep 16 - Sat, Oct 3
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$144 Roundtrip, found 3 days ago
$144
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Sep 16 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Oct 3, priced at $144 found 3 days ago
American Airlines
Wed, Sep 16 - Sat, Oct 3
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Sep 16 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Oct 3, priced at $237 found 3 days ago
Southwest Airlines
Tue, Oct 20 - Wed, Oct 28
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$295 Roundtrip, found 2 days ago
$295
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Oct 20 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Wed, Oct 28, priced at $295 found 2 days ago
United
Tue, Oct 20 - Wed, Oct 28
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$303 Roundtrip, found 2 days ago
$303
Roundtrip
found 2 days ago
Select United flight, departing Tue, Oct 20 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Wed, Oct 28, priced at $303 found 2 days ago