A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.

Bennington Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Bennington vacation rentals

A room with wooden walls, a window with a view of the sky and greenery, a hanging macrame wall decoration, and a vase with flowers on the windowsill.

1. Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (38 reviews)
"Laurie was an amazing host, with an amazing property! What an adorable home with an adorable view."
United States
Michaela J.
Peaceful getaway at birds of a feather
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, (9 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.
$172 nightly
The price is $193
Sep 27 - Sep 28
Total with taxes and fees
Cozy Home in Pownal VT
A red house with a porch, surrounded by a grassy yard and trees.

3. 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
$403 nightly
The price is $428
Sep 29 - Sep 30
Total with taxes and fees
Two Brooks Lodge
A two-story house with a porch, surrounded by trees and snow.

4. 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.
$320 nightly
The price is $342
Sep 29 - Sep 30
Total with taxes and fees
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
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
$395 nightly
The price is $446
Sep 28 - Sep 29
Total with taxes and fees
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

6. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
$199 nightly
The price is $224
Sep 25 - Sep 26
Total with taxes and fees
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

7. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
$218 nightly
The price is $246
Sep 27 - Sep 28
Total with taxes and fees
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

8. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Stratton Mountain
10.0 out of 10, Exceptional, (34 reviews)
"Great space, great location!"
United States
Jason S.
$388 nightly
The price is $438
Sep 27 - Sep 28
Total with taxes and fees
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

9. Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very good, (36 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
$267 nightly
The price is $301
Sep 27 - Sep 28
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

10. Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (83 reviews)
"Nice place and great location!!!"
United States
William
$371 nightly
The price is $419
Oct 1 - Oct 2
Total with taxes and fees
Long Trail House at Stratton Mountain Resort

11. Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (65 reviews)
"Excellent place, fantastic hosts, highly recommend."
United States
Mike K.
$227 nightly
The price is $254
Oct 6 - Oct 7
Total with taxes and fees
Spacious apartment in beautiful, historic Arlington VT
A living room with a television, sofa, and coffee table.

12. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (5 reviews)
$432 nightly
The price is $488
Oct 4 - Oct 5
Total with taxes and fees
Long Trail House South Wing 2B2B Condo
A multi-story building with a stone facade, a central courtyard with a hot tub, and a stone pathway.

13. Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
8.0 out of 10, Very good, (1 review)
$359 nightly
The price is $405
Sep 25 - Sep 26
Total with taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

14. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.4 out of 10, Exceptional, (41 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
$591 nightly
The price is $663
Oct 19 - Oct 20
Total with taxes and fees
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A playground with slides and climbing structures surrounded by trees.

15. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (20 reviews)
"Nice place "
United States
Janja L.
$333 nightly
The price is $376
Sep 30 - Oct 1
Total with taxes and fees
Cozy Bromley Retreat
A dining room with a wooden table, four chairs, a vase with flowers, and a view of greenery outside.

16. Historic Home with Colonial Charm in Manchester

Historic Home with Colonial Charm in Manchester
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations were absolutely amazing. We had a wonderful time. The home is beautiful. The host is very communicative."
United States
Victor G.
$367 nightly
The price is $415
Sep 29 - Sep 30
Total with taxes and fees
Historic Home with Colonial Charm in Manchester
A cabin with a triangular roof, a wooden deck, and a front porch.

17. The Vermont A-Frame Mountain Retreat

The Vermont A-Frame Mountain Retreat
Winhall
9.8 out of 10, Exceptional, (29 reviews)
"Great home, perfect weekend away at Stratton. Host was great and so was the property"
United States
Kevin M.
$573 nightly
The price is $608
Sep 30 - Oct 1
Total with taxes and fees
The Vermont A-Frame Mountain Retreat
A modern kitchen with a central island, stainless steel appliances, pendant lighting, and a view to the dining area.

18. Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
10.0 out of 10, Exceptional, (1 review)
"Communication with Caroline was top notch and speedy! Very clear instructions for accessing the property and check out. Even though this place is connected with two other rooms/units ( I think that is what it is) we never heard them and hopefully we didn't bother them either!The house was amazing inside and out. The location was exceptional!Thank you for a beautiful stay!"
United States
Eva G.
$409 nightly
The price is $462
Sep 29 - Sep 30
Total with taxes and fees
Modern Mountain Retreat w/ Chef’s Kitchen
A spacious kitchen with a large island, a stone fireplace, and wooden beams.

19. Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley

Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley
Winhall
10.0 out of 10, Exceptional, (13 reviews)
"House was great for our family ski trip! "
United States
Brooke S.
$621 nightly
The price is $702
Oct 1 - Oct 2
Total with taxes and fees
Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley

20. The Birchwood Cabin - Stunning Mountain Views

The Birchwood Cabin - Stunning Mountain Views
Sunderland
10.0 out of 10, Exceptional, (4 reviews)
"Excellent host very responsive. Beautiful cozy cabin with all the amenities you need. Highly recommend! "
United States
Robert V.
$652 nightly
The price is $730
Oct 21 - Oct 22
Total with taxes and fees
The Birchwood Cabin - Stunning Mountain Views
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 Bennington Hotel Reviews

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

10/10 Excellent
"I travel for work and had the opportunity to stay at this property for 2 months. This is a great lodge in a lovely part of the country. The friendly staff will go out of their way to accomodate guests if at all possible. This is a modernized lodge type property in a picturesque setting. There are room options that include a sauna in the room. There is also a flash heater type of water heater that provides almost instant and endless hot water on demand. The breakfast offerings include the personal waffle iron kit and all you can eat of it. I never had even the slightest issue with cleanliness and the staff strives to make your stay enjoyable. I don’t know how this property rates with others, but I give it a solid 5 out of 5 stars."
Jason 2-night trip
Posted 2 days ago
Hotel Vervana, Trademark Collection by Wyndham

Find out more about Bennington

Everything you need to know about 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 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 Bennington vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Bennington vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in 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 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 $224 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 Bennington rentals

At Expedia, we put the best 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 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 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 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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Bennington?

Yes, we have vacation rentals in Bennington close to Bennington Center for the Arts, or you can select a more remote option if you'd like a relaxing place to stay. Tourists who visit Bennington speak highly of the ski slopes and array of shops. While you're in the area, you can also enjoy the majestic mountain landscape and museums.

What are some of the best vacation rentals in Bennington?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: Visitors like this Bennington vacation home rental. It is located on a lake and has a fireplace, a balcony, 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 games.

How many vacation rentals will I find in Bennington?

With 16 Expedia vacation rentals, you're sure to find just the right place for your Bennington stay.

What’s there to see and do in Bennington?

Enjoy the outdoors at Green Mountain National Forest and Harmon Hill, or simply take in cultural attractions like Bennington Museum and Robert Frost Stone House Museum. While here, Bennington Center for the Arts and Prospect Mountain Cross-Country Ski Center are other places worth a visit.

What’s a vacation rental in Bennington like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Bennington. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a family trip.