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

Bennington Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Bennington vacation rentals

Interior

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.
$241 nightly
The price is $270
Sep 15 - Sep 16
Total with taxes and fees
Peaceful getaway at birds of a feather
Exterior

2. 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
$392 nightly
The price is $416
Sep 13 - Sep 14
Total with taxes and fees
Two Brooks Lodge
Dining

3. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (7 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 13 - Sep 14
Total with taxes and fees
Cozy Home in Pownal VT
Exterior

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.
$307 nightly
The price is $328
Sep 21 - Sep 22
Total with taxes and fees
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Outdoor spa tub

5. 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
$311 nightly
The price is $351
Sep 6 - Sep 7
Total with taxes and fees
Long Trail House at Stratton Mountain Resort
Interior

6. 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
$227 nightly
The price is $256
Sep 7 - Sep 8
Total with taxes and fees
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Exterior

7. 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
$198 nightly
The price is $223
Sep 4 - Sep 5
Total with taxes and fees
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Property grounds

8. Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (64 reviews)
"Excellent place, fantastic hosts, highly recommend."
United States
Mike K.
$225 nightly
The price is $252
Sep 6 - Sep 7
Total with taxes and fees
Spacious apartment in beautiful, historic Arlington VT
Living area

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.
$278 nightly
The price is $314
Sep 7 - Sep 8
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Children's area

10. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (19 reviews)
"This is an amazing location. The home is exceptionally clean and well equipped. The pool was amazing and so was our experience. We were centrally located to everything we wanted to do. I would highly recommend this home and Management company to anyone visiting the Bromley area. Exceptional."
United States
Jaime
$300 nightly
The price is $339
Sep 6 - Sep 7
Total with taxes and fees
Cozy Bromley Retreat
Private kitchen

11. 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, (33 reviews)
"Great space, great location!"
United States
Jason S.
$351 nightly
The price is $396
Sep 7 - Sep 8
Total with taxes and fees
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Living area

12. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (3 reviews)
"Great location. Very clean accomodations with comfortable beds! Host was very communicative as well!"
United States
carlene p.
$432 nightly
The price is $488
Sep 16 - Sep 17
Total with taxes and fees
Long Trail House South Wing 2B2B Condo
Property grounds

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 7 - Sep 8
Total with taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Terrace/patio

14. 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.
$658 nightly
The price is $737
Sep 23 - Sep 24
Total with taxes and fees
The Birchwood Cabin - Stunning Mountain Views
Dining

15. 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.
$404 nightly
The price is $456
Sep 13 - Sep 14
Total with taxes and fees
Historic Home with Colonial Charm in Manchester
Exterior detail

16. Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (30 reviews)
"House was perfect for a guys trip for skiing. Just as expected. Would stay again. "
United States
Michael A.
$728 nightly
The price is $823
Sep 9 - Sep 10
Total with taxes and fees
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Outdoor spa tub

17. 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, (40 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
Sep 7 - Sep 8
Total with taxes and fees
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Property grounds

18. Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont

Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont
Sandgate
$265 nightly
The price is $299
Sep 8 - Sep 9
Total with taxes and fees
Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont
Private kitchen

19. 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.
$433 nightly
The price is $489
Sep 14 - Sep 15
Total with taxes and fees
Modern Mountain Retreat w/ Chef’s Kitchen
Living area

20. Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Winhall
10.0 out of 10, Exceptional, (14 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
$737 nightly
The price is $833
Sep 21 - Sep 22
Total with taxes and fees
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bennington Hotel Reviews

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

10/10 Excellent
"Our stay was pleasant and quiet. We loved the balcony off the room, where we could sit outdoors as weather permitted. The property is close to the Bennington Museum and to downtown Bennington. Both were easy walking distance, though it was raining so we drove. We appreciated the large, clean room and quiet atmosphere. We recommend this property to anyone visiting Bennington, Vermont"
Lee 2-night trip
Posted 15 hours 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 $328 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?

5 Bdrm Lakehouse, sleeps 18, private dock, hot tub, 15 minutes to Mount Snow: You might want to consider this vacation home rental near Bennington, which 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 5 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.

How many vacation rentals will I find in Bennington?

With 15 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, Prospect Mountain Cross-Country Ski Center and Woodford State Park 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.