Bennington Vacations from $344

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Your Bennington Vacation

With a vacation package to Bennington, say goodbye to endless planning and hello to an effortless adventure. Every detail of your escape has been taken care of before departing, so you can enjoy each moment experiencing this interesting city. Every trip to Bennington needs a well-designed itinerary. Fill yours with big-name attractions like Crotched Mountain Ski and Ride Area, Peterborough Players and Greenfield State Park. Stop dreaming and start traveling. Check out the multitude of options on Expedia today and put your Bennington vacation plans into action!

The Latest Bennington vacation packages

Price found within the past 48 hours. Click for updated prices.
Moultonborough Inn

Moultonborough Inn

3 out of 5
Price was $460, price is now $344 per person
$344
per person
Oct 16 - Oct 20
found 17 hours ago
Roundtrip flight included
Tampa (TPA) to Manchester (MHT)
9/10 Wonderful! (173 reviews)
Beds were great, everything is new. Kitchenette is convenient. Convenience store right next door. I messaged that stairs are a problem and they called and emailed that we would be on the first floor. Not much room in the bathroom, only sink is part of kitchenette, but there is counter space for toiletries there.

Reviewed on Aug 11, 2025

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 out of 5
Save 100% on your flight
Price was $869, price is now $610 per person
$610
per person
Nov 1 - Nov 8
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Manchester (MHT)
9/10 Wonderful! (138 reviews)
2 night stay there was comfortable and convenient. Enjoyed the 2 days there. We didn't get to use the pool and gym room but we were given all the information about them. Would stay again .

Reviewed on Aug 25, 2025

A Hotel Inn Sunapee

A Hotel Inn Sunapee

3 out of 5
Price was $746, price is now $552 per person
$552
per person
Nov 1 - Nov 8
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Manchester (MHT)
8.8/10 Excellent! (739 reviews)
Very clean, comfortable bed. Great ambience!

Reviewed on Aug 13, 2025

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

2.5 out of 5
Price was $725, price is now $608 per person
$608
per person
Nov 1 - Nov 8
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Manchester (MHT)
9.4/10 Exceptional! (1,000 reviews)
Great place with staff who care.

Reviewed on Aug 25, 2025

Super 8 by Wyndham Tilton/Lake Winnipesaukee

Super 8 by Wyndham Tilton/Lake Winnipesaukee

2 out of 5
Price was $663, price is now $566 per person
$566
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Manchester (MHT)
7.4/10 Good! (1,001 reviews)
Get what ypu pay for

Reviewed on Aug 11, 2025

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Bennington Hotel Deals

Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $136 total per night from Sep 3 to Sep 4
$136 total
Sep 3 - Sep 4
Total with taxes and fees
8.4/10 Very Good! (882 reviews)
"Great experience but our only issue was that the sink was outside of the bathroom in the sleeping area other than that I would definitely recommend this hotel and stay again. The hotel was spotless and the breakfast was very good for what we paid for the room, 9 out of 10 just because of the wash ..."

Reviewed on Aug 23, 2025

Keene Elm City Hotel, Ascend Hotel Collection
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $170 total per night from Aug 31 to Sep 1
$170 total
Aug 31 - Sep 1
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
"Clean, comfortable room, great breakfast & friendly staff."

Reviewed on Aug 17, 2025

Best Western Plus Keene Hotel
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 out of 5
80 Concord Street, Peterborough, NH
$130 nightly
The price is $141 total per night from Aug 31 to Sep 1
$141 total
Aug 31 - Sep 1
Total with taxes and fees
9.2/10 Wonderful! (416 reviews)
"Highly recommend PEARL restaurant nearby! Always comfortable accommodations."

Reviewed on Aug 13, 2025

Riverhouse by Weekender (Formerly Jack Daniels Inn)
See all 304 properties in Bennington
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.

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Frequently asked questions

How much does a Bennington vacation package cost?
You can grab a vacation package to this top destination from $344 on Expedia. But how much your vacation to Bennington costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Bennington?
You can generally find lower prices and better availability in October, November and December. Browse our cheap Bennington vacation packages and you could land some great off-season discounts.
How many days is enough for Bennington?
Typically, a handful of days is enough to explore the top sights during your Bennington vacation. But if you want to have time to unwind or take day trips, think about extending your itinerary.
How to find the best Bennington package deals?
Use Expedia's filters to help you find some tempting Bennington package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Bennington package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Bennington vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component separately. And you'll still get the freedom to create a tailored Bennington vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Bennington?
If you're planning a spontaneous Bennington trip, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score amazing deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Bennington vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Bennington vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.

Explore a world of travel with Expedia

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.