Bennington Vacations from $464

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Your Bennington Vacation

Our vacation packages to Bennington allow you to create your own adventure. Tailor your getaway to your interests and needs and make every moment count in this interesting city. Every trip to Bennington needs a well-planned itinerary. Fill yours with famous sights like Bennington College, Hemmings Motor News Car Lovers Convenience Store & Vehicle Display and Bennington Battle Monument. Don't put off visiting this city any longer. The ultimate Bennington vacation is only a few clicks away with Expedia.

The Latest Bennington vacation packages

Price found within the past 48 hours. Click for updated prices.
South Shire

South Shire

4 out of 5
Price was $576, price is now $464 per person
$464
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9/10 Wonderful! (116 reviews)
Very cool rooms. Al different and many with fireplaces. Friendly staff

Reviewed on Oct 31, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was $826, price is now $549 per person
$549
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
7.4/10 Good! (567 reviews)
We feel that the resort fee to access the pool and hot tub as well as the other services covered are over priced. We stay at resorts and hotels all over the US and you are the ONlY place that charges for this.

Reviewed on Nov 21, 2025

Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Price was $881, price is now $589 per person
$589
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9.2/10 Wonderful! (218 reviews)
Everything was great

Reviewed on Nov 24, 2025

Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was $896, price is now $668 per person
$668
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9.4/10 Exceptional! (531 reviews)
Staff were awesome . The owners are the greatest people . Their son went above and beyond for us. Our view and room was unbelievable. The boathouse is so inviting, great opportunity to meet people, and food outstanding. John the bartender is the best!!! Highly recommend this place !!!

Reviewed on Nov 23, 2025

Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Save 100% on your flight
Price was $817, price is now $641 per person
$641
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
8.8/10 Excellent! (600 reviews)
Great location Everything updated Pleasant greeting in lobby

Reviewed on Nov 25, 2025

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Discover the most popular places to visit in Bennington

Bennington Battle Monument showing landscape views

Bennington Battle Monument

4.5/5(71 reviews)

Learn about the local history of Old Bennington when you spend time at Bennington Battle Monument. In the area, take in the art scene and mountain views.

Bennington Battle Monument
2017

Old First Congregational Church

5/5(4 reviews)

Find out about the history of Old Bennington with a stop at Old First Congregational Church. In the area, take in the art scene and mountain views.

Old First Congregational Church

Prospect Mountain Cross-Country Ski Center

4.5/5(11 reviews)

Hit the slopes in Woodford with a visit to Prospect Mountain Cross-Country Ski Center. In the area, take in the festivals and mountain views.

Prospect Mountain Cross-Country Ski Center

What to do in Bennington

Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 Self Guided Driving Audio Tour

$17
per traveler
Vermont RT 100 Self Guided Driving Audio Tour
See all activities in Bennington

Bennington Hotel Deals

Knotty Pine

Knotty Pine

2.5 out of 5
130 Northside Dr Bennington VT
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $120 total per night from Dec 2 to Dec 3
$120 total
Dec 2 - Dec 3
Total with taxes and fees
9/10 Wonderful! (26 reviews)
Yes

Reviewed on Nov 28, 2025

Knotty Pine
Hampton Inn Bennington

Hampton Inn Bennington

2.5 out of 5
51 Hannaford Square Bennington VT
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $151 total per night from Dec 7 to Dec 8
$151 total
Dec 7 - Dec 8
Total with taxes and fees
8.6/10 Excellent! (1,006 reviews)
Yes everything is great

Reviewed on Nov 27, 2025

Hampton Inn Bennington
Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
141 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $114 total per night from Dec 9 to Dec 10
$114 total
Dec 9 - Dec 10
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
Great place for the price! Clean and comfortable.

Reviewed on Nov 11, 2025

Hotel Vervana, Trademark Collection by Wyndham
See all 777 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.

Find the Best Bennington Vacation Packages

Bennington Essential Information

Language
English
Currency
U.S dollars
Population
9,100
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Lake Shaftsbury State Park, Prospect Mountain Cross-Country Ski Center and Woodford State Park

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Frequently asked questions

How much does a Bennington vacation package cost?
Offering excellent value package deals from $464 on Expedia, you'll be thrilled with how little a vacation to Bennington costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Bennington?
You can typically find lower prices and greater availability in September, October and November. Take a look at our cheap Bennington vacation packages and you could score some great off-season discounts.
How many days is enough for Bennington?
We recommend booking a Bennington vacation for at least 2 days. This will give you plenty of time to tick off key attractions including Robert Frost Stone House Museum and Southern Vermont College, as well as explore neighborhoods like Old Bennington and South Shaftsbury. You might even be able to slot in a day trip beyond Bennington.
Is it worth booking a vacation package to Bennington?
It's no wonder a Bennington vacation is on the must-do list of many travelers. Leading attractions like Bennington Battle Monument are just the start of what you can explore here.
How to find the best Bennington package deals?
Finding a cheap Bennington package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can tailor your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most affordable Bennington package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Bennington vacation as a package?
You can enjoy significant savings on your Bennington getaway by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Bennington?
Score amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Bennington adventure.
How to plan a trip to Bennington?

  1. Choose when to get away: Check your calendar and pack your bags. Your favorite season and the available activities will also help you decide when to vacation in Bennington.
  2. Set your budget: Consider costs such as transportation, flights and meals when calculating how much to save for your trip to Bennington. Then, pick a hotel that matches your budget, whether that's a wallet-friendly option or a swankier retreat.
  3. Discover Bennington using Expedia's trip planning tool: Gain insights into the most popular attractions and best stays for your trip to Bennington. You can also save your favorite places, collaborate with your group and organize all your plans in one place.
  4. Decide how long to go for: Now that you're more familiar with Bennington, you can figure out the ideal length of your break. Put together a draft plan and allocate enough time to get through everything on your must-do list.
  5. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a customized Bennington vacation package.
  6. Book any activities or day trips: Now to the fun part — locking in everything you want to do and see. Browse some of the top things to do in Bennington and book your tickets in advance to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Bennington vacation packages?
Secure your dream escape to Bennington with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait until your next paycheck — we've joined forces with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to budget for your trip and snag great deals before they disappear.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.