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
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Bennington vacation rentals

Outdoor spa tub

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
The price is AED 1,108
AED 1,378 total
includes taxes & fees
28 Jun - 29 Jun
Long Trail House at Stratton Mountain Resort
Cottage (1 Bedroom) | Interior

< 6 Mi to Arlington: 'whimsical Stone Abode!'

< 6 Mi to Arlington: 'whimsical Stone Abode!'
3.0 star property
Arlington
10.0 out of 10, Exceptional, (1 review)
"We came into town for a few days to visit friends. This was a perfect place. The home was clean and very inviting! Quiet location. Fully stocked kitchen with all the appliances and cooking ware you may need. You will not regret staying here. We loved the photo album of how the home was built! "
United States
Dale
The price is AED 823
AED 1,264 total
includes taxes & fees
29 Jun - 30 Jun
< 6 Mi to Arlington: 'whimsical Stone Abode!'
Children's area

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.6 out of 10, Exceptional, (12 reviews)
"The best stay ever!!! Very clean, great location, super cozy, all the amenities you would need. 5/5 stars, we will be coming back :)"
United States
Carolina I.
Cozy Bromley Retreat
Terrace/patio

Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (33 reviews)
"Great place"
United States
Aidan K.
The price is AED 364
AED 909 total
includes taxes & fees
30 Jun - 1 Jul
Peaceful getaway at birds of a feather
Property grounds

Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (63 reviews)
"This home was spacious, super clean, and in a great location. "
United States
Des C.
The price is AED 628
AED 897 total
includes taxes & fees
29 Jun - 30 Jun
Spacious apartment in beautiful, historic Arlington VT
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, (83 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.
The price is AED 628
AED 1,415 total
includes taxes & fees
30 Jun - 1 Jul
Perfect for a peaceful get away in clean fresh Vermont air!
Fridge, microwave, oven, stovetop

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, (31 reviews)
"Great space, great location!"
United States
Jason S.
The price is AED 493
AED 1,341 total
includes taxes & fees
28 Jun - 29 Jun
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
House, 4 Bedrooms | View from property

Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Bear Pass - Mountain View 4 Bedroom Home by RedAwning
3.0 star property
Arlington
8.0 out of 10, Very Good, (1 review)
"Cozy cottage. Very clean and everything you need is there. Nice kitchen and fireplace. Lots of room and 3 bathrooms as well. Reasonably close to the ski mountains. "
United States
Manish
The price is AED 1,222
AED 2,991 total
includes taxes & fees
5 Jul - 6 Jul
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Living area

Green Mountain Getaway

Green Mountain Getaway
Bennington
9.6 out of 10, Exceptional, (18 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.
The price is AED 757
AED 1,504 total
includes taxes & fees
29 Jun - 30 Jun
Green Mountain Getaway
Exterior detail

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, (29 reviews)
"EXCELLENT location managed by an amazing host who was very communicative and helpful!Hottub was perfect, plenty of sleeping and activities available at the house and in the immediate area (local food was AWESOME)."
United States
s w.
The price is AED 907
AED 3,436 total
includes taxes & fees
28 Jun - 29 Jun
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Outdoor spa tub

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, (39 reviews)
"Our family had a wonderful time staying in this home."
United States
Meghan C.
The price is AED 725
AED 2,435 total
includes taxes & fees
28 Jun - 29 Jun
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Terrace/patio

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.
The price is AED 1,662
AED 3,359 total
includes taxes & fees
8 Jul - 9 Jul
The Birchwood Cabin - Stunning Mountain Views
Smart TV, fireplace

New! Vermont Getaway! Stratton - close to skiing!

New! Vermont Getaway! Stratton - close to skiing!
Winhall
10.0 out of 10, Exceptional, (1 review)
"The place was perfect for us! Easy stay. Very clean and the wood burning fireplace was great. Would def recommend!"
United States
Carolyn K.
The price is AED 918
AED 1,693 total
includes taxes & fees
28 Jun - 29 Jun
New! Vermont Getaway! Stratton - close to skiing!
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
The price is AED 399
AED 1,390 total
includes taxes & fees
29 Jun - 30 Jun
Two Brooks Lodge
Smart TV

Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
The price is AED 595
AED 1,473 total
includes taxes & fees
28 Jun - 29 Jun
Long Trail House South Wing 2B2B Condo
Property grounds

3 Levels w/ Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit, ACs

3 Levels w/ Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit, ACs
Winhall
9.6 out of 10, Exceptional, (23 reviews)
"Very beautiful home with plenty of room for a big group! Easy drive to Stratton. Would definitely stay again!"
United States
Sarah S.
The price is AED 1,349
AED 3,110 total
includes taxes & fees
2 Jul - 3 Jul
3 Levels w/ Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit, ACs
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.
The price is AED 422
AED 1,117 total
includes taxes & fees
29 Jun - 30 Jun
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Dining

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.
The price is AED 577
AED 1,685 total
includes taxes & fees
30 Jun - 1 Jul
Historic Home with Colonial Charm in Manchester
TV, fireplace, books, music library

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, (12 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is AED 1,414
AED 3,366 total
includes taxes & fees
9 Jul - 10 Jul
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Dining

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (3 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.
The price is AED 474
AED 810 total
includes taxes & fees
28 Jul - 29 Jul
Cozy Home in Pownal VT
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
"Great room great staff. Love staying at Hotel Vervana"
Damian 2-night trip
Posted 1 day ago
Hotel Vervana, Trademark Collection by Wyndham

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?

Riverfront 2-bedroom house with tons of light, AC, deck & patio. Pet Friendly: Visitors like this Bennington vacation home rental. It is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of books.

How many vacation rentals will I find in Bennington?

With 14 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 Harmen Hills Trail, or simply take in cultural attractions like Bennington Museum and Robert Frost Stone House Museum. While here, Hemmings Motor News Car Lover's Convenience Store & Vehicle Display and Bennington Center for the Arts 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.