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Old Bennington Vacation Rentals

Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Old Bennington vacation rentals

Living area

Green Mountain Getaway

Green Mountain Getaway
Bennington
9.6 out of 10, Exceptional, (19 reviews)
"Very clean property. The location was very convenient to the Main Street of Bennington. Easy check in process. Would definitely stay here again! "
United States
Meredith Y.
$378 nightly
The price is $404
Jul 22 - Jul 23
Total with taxes and fees
Green Mountain Getaway
Coffee/tea maker, fridge, microwave, oven

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
9.8 out of 10, Exceptional, (107 reviews)
"This is the third time we’ve stayed at this lovely home and it’s always a treat! Very clean, with a Well stocked kitchen, comfy beds and huge back yard plus a fenced in portion, your dog will love-close to Bennington and walking trails with lots to do. A home away from home! "
United States
Anita T.
$341 nightly
The price is $379
Jul 27 - Jul 28
Total with taxes and fees
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Terrace/patio

Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (36 reviews)
"Great place"
United States
Aidan K.
$235 nightly
The price is $263
Jul 28 - Jul 29
Total with taxes and fees
Peaceful getaway at birds of a feather
Exterior

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Bennington
8.6 out of 10, Excellent, (35 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
$293 nightly
The price is $312
Jul 22 - Jul 23
Total with taxes and fees
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Exterior

Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
$380 nightly
The price is $403
Jul 22 - Jul 23
Total with taxes and fees
Two Brooks Lodge
Exterior

Perfect for a peaceful get away in clean fresh Vermont air!

Perfect for a peaceful get away in clean fresh Vermont air!
Woodford
10.0 out of 10, Exceptional, (84 reviews)
"We had the most wonderful stay! The house and the property were beautiful, the amentities were excellent, and Linda Jane was an incredibly generous and accommodating host. We visit Bennington every year for Thanksgiving with family and we hope to rent with Linda Jane again in the future."
United States
Karissa A.
$340 nightly
The price is $381
Jul 22 - Jul 23
Total with taxes and fees
Perfect for a peaceful get away in clean fresh Vermont air!
Fireplace, books, video library

Mountain Sanctuary Dome Rustic Solitude 5BR

Mountain Sanctuary Dome Rustic Solitude 5BR
Pownal
9.8 out of 10, Exceptional, (11 reviews)
"The facilities were as described; everything that was needed was easily accessible. When we couldn't find something, Nate was on hand to give us the guidance we needed."
United States
Cyndi L.
$534 nightly
The price is $599
Jul 30 - Jul 31
Total with taxes and fees
Mountain Sanctuary Dome Rustic Solitude 5BR
Dining

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (4 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
$184 nightly
The price is $206
Jul 30 - Jul 31
Total with taxes and fees
Cozy Home in Pownal VT
Outdoor dining

New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (15 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
$240 nightly
The price is $270
Jul 22 - Jul 23
Total with taxes and fees
New Studio In Town, By the Water
Outdoor dining

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (8 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
$252 nightly
The price is $283
Jul 22 - Jul 23
Total with taxes and fees
Downtown | Waterfront | Walk to Shops
Outdoor dining

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (14 reviews)
"Location was very good-close to campus. Host was responsive. Accommodations were just right"
United States
Dan R.
$263 nightly
The price is $296
Jul 22 - Jul 23
Total with taxes and fees
2-Bdr Apt In Town, By the Water
Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
$279 nightly
The price is $316
Jul 22 - Jul 23
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Property grounds

Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (64 reviews)
"This home was spacious, super clean, and in a great location. "
United States
Des C.
$226 nightly
The price is $253
Jul 22 - Jul 23
Total with taxes and fees
Spacious apartment in beautiful, historic Arlington VT
Exterior

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
shushan
9.6 out of 10, Exceptional, (23 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
$315 nightly
The price is $350
Jul 22 - Jul 23
Total with taxes and fees
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Dining

Sowilo Retreat All-Inclusive Maple House

Sowilo Retreat All-Inclusive Maple House
Cambridge
10.0 out of 10, Exceptional, (1 review)
$630 nightly
The price is $671
Jul 22 - Jul 23
Total with taxes and fees
Sowilo Retreat All-Inclusive Maple House
Interior

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
$178 nightly
The price is $199
Jul 22 - Jul 23
Total with taxes and fees
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Smart TV, fireplace, Netflix, streaming services

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.6 out of 10, Exceptional, (27 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
$405 nightly
The price is $457
Jul 22 - Jul 23
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Exterior

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful cabin in a beautiful location. Host is amazing, very responsive. "
United States
Anonymous traveler
$406 nightly
The price is $439
Aug 17 - Aug 18
Total with taxes and fees
The Greylock Cabin
Dining

Sowilo Pine House. All-inclusive food and drinks.

Sowilo Pine House. All-inclusive food and drinks.
Cambridge
10.0 out of 10, Exceptional, (4 reviews)
"BEAUTIFUL HOME GREAT VIEWS, CLEAN, SPACIOUS, AND A VERY HELPFUL PROPERTY MANAGER. CLOSE TO OUR WEDDING DESTINATION. HAD A WONDERFUL TIME. WOULD HIGHLY RECOMMEND THIS PROPERTY."
United States
diane
$630 nightly
The price is $671
Jul 27 - Jul 28
Total with taxes and fees
Sowilo Pine House. All-inclusive food and drinks.
Dining

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (19 reviews)
"Great place!"
United States
Jack & Heather G.
$553 nightly
The price is $589
Jul 29 - Jul 30
Total with taxes and fees
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
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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Top Old Bennington Hotel Reviews

Cozy Corner Motel

Cozy Corner Motel

10/10 Excellent
"I only stayed one night at the Cozy Rest but it was a great night. The beds were very comfortable, the room was clean and cozy. The rooms are not large but there is a nice little balcony and sitting area outside each room that I spent some time working on my computer that evening before bed. The breakfast did not have a lot of options but the fruit was fresh and the hard boiled eggs were still warm. I will definitly stay here again when I am in the area."
Harry 1-night trip
Posted 2 hours ago
Cozy Corner Motel

Find out more about Old Bennington

Everything you need to know about Old Bennington vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Old Bennington vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Old Bennington vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Old Bennington vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Old Bennington. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Old Bennington in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $206 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Old Bennington rentals

At Expedia, we put the best Old Bennington vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Old Bennington rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Old Bennington vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Old Bennington. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Old Bennington?

Yes, you can find vacation rentals near the most popular points of interest in Old Bennington, or you can choose a more remote option if you're looking for relaxation.

What are some of the best vacation home rentals in Old Bennington?

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!: This vacation home rental outside of Old Bennington is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

What’s there to see and do in Old Bennington?

Explore the area and cultural attractions such as Bennington Museum, or visit a family-friendly sight such as Sugar Shack. In the larger area, you’ll find Bennington Battle Monument and Old First Congregational Church.

What’s a vacation rental in Old Bennington like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Old Bennington. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for family trips or small group gatherings.