Old Bennington Holidays

  • Plan, book, travel with confidence
    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Old Bennington

The Four Chimneys Inn
The Four Chimneys Inn
4 out of 5
21 West Road, Bennington, VT
The price is S$365 per night from 2 Dec to 3 Dec
S$365
includes taxes & fees
2 Dec - 3 Dec
9.6/10 Exceptional! (214 reviews)
Home away from home!
"What a charming B&B . So warming and inviting.Staff made you feel at home and were all so kind and friendly.Oh and the food was delicious,"

Reviewed on 23 Oct,2024

The Four Chimneys 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 S$194 per night from 2 Dec to 3 Dec
S$194
includes taxes & fees
2 Dec - 3 Dec
8.6/10 Excellent! (999 reviews)
"Great location, wonderful staff, fun pool and cool art. Would definitely stay again!"

Reviewed on 15 Nov,2024

Hotel Downstreet
Mountaineer Inn
Mountaineer Inn
2 out of 5
270 Handle Rd, West Dover, VT
9/10 Wonderful! (349 reviews)
"Nice quiet getaway about 30 min from Stratton. We went off season to see the leaves in October so a lot of stores and restaurants were closed, but what is open nearby is delicious. The place is a standard motel, room was clean, coffee maker in the dining area, several lounge spaces, pool table, and ..."

Reviewed on 29 Oct,2024

Get rates
Mountaineer Inn
See all 874 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.

Frequently asked questions

How much does an Old Bennington holiday package cost?
Starting from a low , a holiday 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 holiday 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 Centre 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 holiday?
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 holiday rentals such as beachside villas and city apartments. The list is almost endless!
Can I choose my airline with an Old Bennington Expedia holiday 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 holiday 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 holiday 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.

What to do in Old Bennington

Vermont RT 100: Self-Guided Driving Audio Tour

Vermont RT 100: Self-Guided Driving Audio Tour

S$20
Per adult
Vermont RT 100: Self-Guided Driving Audio Tour
See all activities in Old Bennington

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.