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Old Bennington Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Old Bennington vacation rentals

A two-story house with a porch, surrounded by trees and snow.

1. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 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.
$284 nightly
The price is $302
Nov 11 - Nov 12
Total with taxes and fees
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

2. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (13 reviews)
"Absolutely wonderful place to stay. Quiet, clean, comfortable and close to a lot of things while feeling secluded. Owner communicated quickly and entry was easy. Loved every minute of our stay."
United States
Jeri R.
$174 nightly
The price is $195
Nov 8 - Nov 9
Total with taxes and fees
Cozy Home in Pownal VT
A covered porch with wooden beams, a pool, and chairs.

3. West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub

West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub
Bennington
$245 nightly
The price is $274
Nov 7 - Nov 8
Total with taxes and fees
West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

4. 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, (118 reviews)
"enjoyed our week at this property"
United States
cory p.
$337 nightly
The price is $374
Nov 7 - Nov 8
Total with taxes and fees
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

5. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay! Very clean and comfortable."
United States
Dana W.
$460 nightly
The price is $519
Nov 9 - Nov 10
Total with taxes and fees
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A wicker sofa with a floral cushion, a wicker table with magazines, and a standing fan in a room with large windows and wooden floors.

6. 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
8.0 out of 10, Very good, (2 reviews)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
$241 nightly
The price is $269
Nov 9 - Nov 10
Total with taxes and fees
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
A large, white building with a covered porch and stone foundation.

7. East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub

East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
Bennington
$245 nightly
The price is $274
Nov 7 - Nov 8
Total with taxes and fees
East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
A living room with a wooden floor, a central rug, a sofa, a coffee table, and a door with a 'GUEST' sign.

8. Peaceful Cottage Retreat

Peaceful Cottage Retreat
cambridge
9.8 out of 10, Exceptional, (50 reviews)
"Nice cozy little home Was well welcomed and host very communicative"
United States
Caleb N.
$156 nightly
The price is $173
Nov 8 - Nov 9
Total with taxes and fees
Peaceful Cottage Retreat
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

9. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (21 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
$248 nightly
The price is $279
Nov 15 - Nov 16
Total with taxes and fees
New Studio In Town, By the Water
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

10. 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.
$277 nightly
The price is $314
Nov 9 - Nov 10
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

11. Seasons ski-in/ski-out condo with balcony and wood-burning fireplace

Seasons ski-in/ski-out condo with balcony and wood-burning fireplace
Dover
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
$316 nightly
The price is $357
Nov 7 - Nov 8
Total with taxes and fees
Seasons ski-in/ski-out condo with balcony and wood-burning fireplace
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

12. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (13 reviews)
"Great location, very clean, included washer dryer, picnic area by river, large parking space."
United States
Douglas
$269 nightly
The price is $303
Nov 8 - Nov 9
Total with taxes and fees
Downtown | Waterfront | Walk to Shops
"Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping." ...Lina -- "the fire pit and creek are like a private oasis in the backyard." ... Nachama -- ( no firewood fees )

13. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (22 reviews)
"Great place with easy access to town and even better access to a nice spot to hangout by the creek. I will definitely stay here again."
United States
Thomas
$272 nightly
The price is $306
Nov 8 - Nov 9
Total with taxes and fees
2-Bdr Apt In Town, By the Water
A calm lake with a wooden boat on the shore.

14. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
$248 nightly
The price is $280
Nov 12 - Nov 13
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A snow-covered landscape with a cabin surrounded by trees.

15. Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown
Pownal
10.0 out of 10, Exceptional, (41 reviews)
"We enjoyed our stay! The home was clean, well-stocked, and very comfortable. I loved the serenity of the location. We took walks on trails through the forest and enjoyed the peace and quiet."
United States
Claudette R.
$528 nightly
The price is $591
Nov 11 - Nov 12
Total with taxes and fees
Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

16. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
$508 nightly
The price is $543
Nov 22 - Nov 23
Total with taxes and fees
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Property grounds

17. Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (66 reviews)
"Excellent place, fantastic hosts, highly recommend."
United States
Mike K.
$231 nightly
The price is $258
Nov 8 - Nov 9
Total with taxes and fees
Spacious apartment in beautiful, historic Arlington VT
A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

18. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (19 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
$239 nightly
The price is $267
Nov 7 - Nov 8
Total with taxes and fees
Penthouse Apartment on Park Street
A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

19. 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, (27 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
$329 nightly
The price is $365
Nov 7 - Nov 8
Total with taxes and fees
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A kitchen with white cabinets, a wooden dining table, and pendant lights.

20. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
$432 nightly
The price is $483
Nov 9 - Nov 10
Total with taxes and fees
A roomy remodeled retreat close to MassMoCA
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

A large, two-story house with a covered porch and multiple chimneys.
The Four Chimneys Inn

The Four Chimneys Inn

The Four Chimneys Inn
Bennington

10/10 Excellent

Conveniently located. Breakfast was delicious. Extremely clean and nicely decorated.
United States
Randall
Reviewed September 19, 2024
The Four Chimneys Inn

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 $173 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?

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews: This vacation home rental outside of Old Bennington is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.