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

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
31.43 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 ...
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
31.52 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 ...
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 out of 5
126 Key Rd Keene NH
31.47 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 ...
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3 out of 5
75 Railroad St Keene NH
29.7 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 ...
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

3 out of 5
30 Main Street Keene NH
29.85 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. ...
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 out of 5
80 Concord Street Peterborough NH
13.08 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 ...
Henniker Motel

Henniker Motel

2 out of 5
61 Craney Pond Rd Henniker NH
20.9 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 ...
Monadnock Inn

Monadnock Inn

2.5 out of 5
379 Main Street Jaffrey NH
22.11 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 ...
The Burrell House

The Burrell House

2.5 out of 5
112 Washington St Keene NH
29.68 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 ...
The Carriage Barn Inn

The Carriage Barn Inn

3 out of 5
358 Main St Keene NH
29.97 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 ...
Colby Hill Inn

Colby Hill Inn

3.5 out of 5
33 The Oaks Street Henniker NH
21.14 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 ...
Blue Bear Inn

Blue Bear Inn

4 out of 5
534 Mountain Rd Francestown NH
4.74 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 ...
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.

American Airlines
Thu, Dec 17 - Wed, Dec 30
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$490 Roundtrip, found 6 days ago
$490
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Dec 17 from Tampa Intl. to Manchester-Boston Regional, returning Wed, Dec 30, priced at $490 found 6 days ago
Southwest Airlines
Sun, Dec 20 - Sun, Dec 27
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$587 Roundtrip, found 6 days ago
$587
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sun, Dec 20 from Tampa Intl. to Manchester-Boston Regional, returning Sun, Dec 27, priced at $587 found 6 days ago
Breeze Airways
Fri, Dec 18 - Mon, Dec 28
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$611 Roundtrip, found 6 days ago
$611
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Dec 18 from Tampa Intl. to Manchester-Boston Regional, returning Mon, Dec 28, priced at $611 found 6 days ago
United
Sun, Dec 20 - Sun, Dec 27
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$1,076 Roundtrip, found 6 days ago
$1,076
Roundtrip
found 6 days ago
Select United flight, departing Sun, Dec 20 from Tampa Intl. to Manchester-Boston Regional, returning Sun, Dec 27, priced at $1,076 found 6 days ago