Old Bennington Vacations from $404

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Your Old Bennington Vacation

From its spectacular views to its rich history and beyond, there's lots to like about Old Bennington. Discover the delights of this exciting city with an Old Bennington vacation package that's made for you. Eager to explore? Bennington College, Bennington Battle Monument and Bennington Potters Yard are three of the most popular places to visit during a trip to Old Bennington. Whoever you're taking time off with and whatever you plan to spend, your dream Old Bennington vacation is just a few clicks away with Expedia.

The Latest Old Bennington Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Parker Inn & Suites

The Parker Inn & Suites

3.5 out of 5
Seward Place
per person
Aug 16 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Albany (ALB)
7.8/10 Good! (429 reviews)
I just needed a bed for the night, as I was in Schenectady for a wedding. I read good reviews from the past, and recent bad reviews, but stayed here anyway. The room was fine. Bed, comfortable. Microwave, and mini fridge (Slightly cold).The shower, large, but the shower head is terrible. No pressure… seems they are under renovation, and trying to make things better. AC not working, but fan provided. One man running everything, (He was very nice when he was actually there…), but Front desk often vacant. Only a cell phone number to call, and you may get no answer… No bar, breakfast, ice or coffee (yet). Still, I liked my room, and would stay here again. Less expensive than other nearby hotels. Great location, right next to Proctors Theater, restaurants, and Sunday large Farmers Market across the street.

Reviewed on Aug 26, 2022

South Shire

South Shire

4 out of 5
per person
Aug 16 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Albany (ALB)
9.4/10 Exceptional! (57 reviews)
Piano player was great

Reviewed on May 13, 2024

Paradise Inn

Paradise Inn

2.5 out of 5
per person
Aug 16 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Albany (ALB)
8.2/10 Very Good! (1,001 reviews)
We were late coming in and the owner was accommodating! It was quiet and clean -- not new and modern, but great for the price!

Reviewed on Apr 17, 2024

Hilton Albany

Hilton Albany

3.5 out of 5
Downtown Albany
per person
Aug 15 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Albany (ALB)
7/10 Good! (1,006 reviews)
The staff were very helpful and friendly!

Reviewed on Jun 2, 2024

Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
per person
Aug 15 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Albany (ALB)
7.8/10 Good! (1,009 reviews)
Not bad! Especially for the price

Reviewed on May 30, 2024

Old Bennington Essential Information

Language
English
Currency
U.S dollars
Top Sights
Prospect Mountain Cross-Country Ski Center, Woodford State Park and Prospect Mountain Nordic Ski Center

Old Bennington Hotel Deals

The Four Chimneys Inn
The Four Chimneys Inn
4 out of 5
21 West Road, Bennington, VT
The price is $269 per night from Jun 4 to Jun 5
$269
$293 total
includes taxes & fees
Jun 4 - Jun 5
9.6/10 Exceptional! (199 reviews)
"We quite liked this hotel as it was charming and well thought out in many ways. We especially loved the dinner we had the first night. Our room had a fireplace and we loved that feature because it was a bit chillier than we expected. The only thing we would have wished for was a mini fridge in the ..."

Reviewed on Apr 23, 2024

The Four Chimneys Inn
The Williams Inn
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is $275 per night from Jun 10 to Jun 11
$275
$308 total
includes taxes & fees
Jun 10 - Jun 11
9.6/10 Exceptional! (295 reviews)
"Love the Williams Inn"

Reviewed on May 3, 2024

The Williams Inn
Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is $159 per night from Jun 4 to Jun 5
$159
$178 total
includes taxes & fees
Jun 4 - Jun 5
8.4/10 Very Good! (925 reviews)
"Very comfortable room."

Reviewed on May 29, 2024

Hotel Downstreet
See all 888 properties in Old 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does an Old Bennington vacation package cost?
Starting from a low $404, a vacation package is your portal to low-priced travel. Custom build your Old Bennington getaway by choosing from our comprehensive range of hotels, flights and rental cars.
How do I get a cheap travel package to Old Bennington?
Booking a hotel and flight together with Expedia won’t just save precious time — it’ll save you cash too. An Old Bennington vacation package makes it a breeze to arrange your dream adventure. With more than 550 airlines across the world to select from, finding flights that fit your schedule won’t be a problem. In addition to that, we’ve got over 1,000,000 properties globally to pick from. Now that’s what you call choice. No matter who you are, Expedia puts the world within your reach.
Where should I stay in Old Bennington?
A trip to Old Bennington isn’t complete without visiting Bennington Battle Monument, Southern Vermont College and Bennington Center for the Arts. Stay near these attractions and make sightseeing a breeze.
What are the top hotels in Old Bennington?
The Four Chimneys Inn is one of Old Bennington’s top hotels. Check in to a room here and you’ll be able to rest easy knowing you’re in capable hands.
How far in advance should I book my Old Bennington vacation?
It depends on the air carrier, but you can usually browse through international airfares on Expedia nearly a year in advance. While it’s generally a good idea to book ahead of time, lucky customers occasionally find a cheaper ticket just weeks prior to departure dates.
What should I know before booking an Old Bennington travel package?
Booking all the parts of your trip together is a great way to save. Combine your car rentals, flights and hotels into one little package. But it’s not just hotels. Expedia has all sorts of properties, including vacation rentals such as beachside villas and city apartments. The list is almost endless!
Can I choose my airline with an Old Bennington Expedia vacation package?
Yes, you’re in charge. We have access to over 550 airlines worldwide, so you can design your Old Bennington getaway according to your budget and needs.
If I'm not able to travel, can I cancel my Old Bennington vacation package?
Yes, you can. We understand that even the best-laid plans can fail, so we’re here to help if you have to make changes to your Old Bennington vacation package. It may be possible to cancel or change your itinerary for free if you’ve booked within 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Old Bennington

Image for Bennington Battle Monument

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
Image for Old First Congregational Church

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
Image for Bennington Museum

Bennington Museum

4.5/5(11 reviews)

You can enjoy some culture when you stop by Bennington Museum in Old Bennington. Discover the area's mountain views and coffeehouses.

Bennington Museum

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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.