Deals on vacations and trips to Bennington

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Bennington flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Wildcat Inn & Tavern

Wildcat Inn & Tavern

3 out of 5
Price was $565, price is now $465 per person
$465
per person
Oct 16 - Oct 18
found 5 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Manchester (MHT)
Ski-in/ski-out access and a restaurant are featured at this smoke-free inn. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A terrace, a garden, and a picnic area are also on offer.
Tiny Home Topline

Tiny Home Topline

2 out of 5
Save 100% on your flight
Price was $4,178, price is now $3,208 per person
$3,208
per person
Oct 2 - Oct 5
found 20 hours ago
Roundtrip non-stop flight included
Savannah (SAV) to Manchester (MHT)
This apartment featured laundry facilities and a virtual front desk. Take advantage of the free self parking.
The Aurora Inn & Cottages

The Aurora Inn & Cottages

2 out of 5
Price was $715, price is now $553 per person
$553
per person
Oct 16 - Oct 18
found 5 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Manchester (MHT)
This guesthouse features a seasonal outdoor pool and a sauna. Guests will appreciate free perks like free self parking and WiFi in public areas. A communal living room, barbecue grills, and a virtual front desk are also on offer.
Cranmore Mountain Lodge Bed & Breakfast

Cranmore Mountain Lodge Bed & Breakfast

3 out of 5
Kearsarge
Price was $829, price is now $647 per person
$647
per person
Oct 16 - Oct 18
found 5 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Manchester (MHT)
A restaurant and a seasonal outdoor pool are featured at this bed & breakfast. Enjoy the hot tub and free perks like full breakfast and free self parking. Free WiFi in public areas, a terrace, and a garden are also on offer.
The Village of Loon Mountain Fixed Rooms

The Village of Loon Mountain Fixed Rooms

2 out of 5
Price was $1,521, price is now $1,211 per person
$1,211
per person
Oct 2 - Oct 5
found 20 hours ago
Roundtrip non-stop flight included
Savannah (SAV) to Manchester (MHT)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this aparthotel. A terrace and a picnic area are also provided.

Top Bennington hotels 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
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $124 total per night
$124 total
Sep 1 - Sep 2
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $162 total per night
$162 total
Aug 23 - Aug 24
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

3 out of 5
30 Main Street Keene NH
$180 nightly
The price is $195 total per night
$195 total
Aug 30 - Aug 31
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Breakfast included
Parking included
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3 out of 5
75 Railroad St Keene NH
Free Cancellation
Reserve now, pay when you stay
$180 nightly
The price is $195 total per night
$195 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 out of 5
126 Key Rd Keene NH
Free Cancellation
Reserve now, pay when you stay
$150 nightly
The price is $163 total per night
$163 total
Sep 1 - Sep 2
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Colby Hill Inn

Colby Hill Inn

3.5 out of 5
33 The Oaks Street Henniker NH
$222 nightly
The price is $241 total per night
$241 total
Aug 23 - Aug 24
Total with taxes and fees
Ski-in/ski-out access and an outdoor pool are featured at this smoke-free inn. Enjoy the seasonal outdoor pool and free perks like full breakfast and free self parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a terrace.
Pool
Breakfast included
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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.

Frequently asked questions

How much are vacation packages to Bennington?
With vacation packages on offer for just $465, there's no need to empty your piggy bank for your getaway to Bennington. Travelocity can help. Bundle experiences, flights and hotels into a convenient package and land excellent discounts. The more you book, the bigger the savings.
Where can I get the best vacation package deals for Bennington?
You'll discover a fantastic range of Bennington package deals on Travelocity. With 400 air carriers and 1,000,000 properties across the globe, crafting the ultimate getaway will be simple.
Why should I purchase my Bennington vacation bundle via Travelocity?
We have destinations for every type of traveler, exceptional service and 24/7 customer support. And to top it off, we'll match any cheaper price you find with our Price Match Guarantee.
Will I save money on my Bennington car rental if I combine it with hotels and flights?
You most certainly can — bundle your flight, hotel and car into a Bennington vacation package and you can save a handsome sum. With so much to see and do in and around Bennington, having your own wheels will make exploring a breeze. Once you're in the driver's seat, crank up the tunes and make your way to Fenway Park, a must-see attraction roughly 60 mi from Bennington.
Which airport is best for Bennington?
Manchester-Boston Regional Airport (MHT) is where many tourists land. You'll find it situated 25 mi east from the heart of Bennington. You can also check out the deals to Lebanon Municipal Airport (LEB), which is 50 mi away from central Bennington.
Where should I stay when visiting Bennington?
The COZY CONDO ACROSS THE STREET FROM CROTCHED MOUTIAN SKI&RIDE is the number one choice of many visitors. Book as soon as possible to avoid missing out.

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