Silk Road covered bridge with trees showing fall colors near Paper Mill Village, Vermont.

Bennington Vacation Rentals

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Our top choices for Bennington vacation rentals

< 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 ¥31,407
¥55,066 total
includes taxes & fees
Jun 24 - Jun 25
< 6 Mi to Arlington: 'whimsical Stone Abode!'

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.
The price is ¥14,531
¥51,761 total
includes taxes & fees
Jun 17 - Jun 18
Cozy Bromley Retreat

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 ¥15,864
¥39,842 total
includes taxes & fees
Jun 23 - Jun 24
Peaceful getaway at birds of a feather

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (2 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 ¥18,604
¥33,040 total
includes taxes & fees
Jun 29 - Jun 30
Cozy Home in Pownal VT

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 ¥50,891
¥63,258 total
includes taxes & fees
Jun 17 - Jun 18
Long Trail House at Stratton Mountain Resort

Stratton Mtn Studio | Renovated | Walk to Lifts

Stratton Mtn Studio | Renovated | Walk to Lifts
Stratton Mountain
10.0 out of 10, Exceptional, (31 reviews)
"Great space, great location!"
United States
Jason S.
The price is ¥23,876
¥61,564 total
includes taxes & fees
Jun 21 - Jun 22
Stratton Mtn Studio | Renovated | Walk to Lifts

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 ¥27,401
¥38,586 total
includes taxes & fees
Jun 17 - Jun 18
Spacious apartment in beautiful, historic Arlington VT

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 ¥17,300
¥63,753 total
includes taxes & fees
Jun 17 - Jun 18
Historic Home with Colonial Charm in Manchester

Tranquil Brookside Retreat with Hot Tub & Firepit

Tranquil Brookside Retreat with Hot Tub & Firepit
Peru
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful place. Comfortable and well furnished. "
United States
Michael B.
The price is ¥36,553
¥108,094 total
includes taxes & fees
Jun 17 - Jun 18
Tranquil Brookside Retreat with Hot Tub & Firepit

Luxury Condo*Hot Tub*Pool*Fireplace*Walk to Lifts*Near Golf Course & Fitness Ctr

Luxury Condo*Hot Tub*Pool*Fireplace*Walk to Lifts*Near Golf Course & Fitness Ctr
Stratton Mountain 0.3 miles from resort
10.0 out of 10, Exceptional, (42 reviews)
"Great location and amenities. Condo was well equipped with everything needed for an excellent stay."
United States
Brooke S.
The price is ¥35,910
¥72,265 total
includes taxes & fees
Jun 17 - Jun 18
Luxury Condo*Hot Tub*Pool*Fireplace*Walk to Lifts*Near Golf Course & Fitness Ctr

Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
The price is ¥44,910
¥98,576 total
includes taxes & fees
Jul 7 - Jul 8
Modern Mountain Retreat w/ Chef’s Kitchen

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 ¥33,026
¥65,629 total
includes taxes & fees
Jun 23 - Jun 24
Green Mountain Getaway

3BR Family Home in Manchester, VT -Near Downtown, Outlets & Ski Resorts

3BR Family Home in Manchester, VT -Near Downtown, Outlets & Ski Resorts
Richville
The price is ¥50,187
¥69,387 total
includes taxes & fees
Jun 22 - Jun 23
3BR Family Home in Manchester, VT -Near Downtown, Outlets & Ski Resorts

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Jamaica
9.6 out of 10, Exceptional, (26 reviews)
"We enjoyed our stay at a great ski house that was in a good location to the mountain. Accommodations were comfortable for 6 adults and 4 kids and the shuffleboard, foosball and pool tables were a hit. "
United States
Jonathan H.
The price is ¥23,984
¥129,277 total
includes taxes & fees
Jun 17 - Jun 18
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
The price is ¥25,959
¥64,461 total
includes taxes & fees
Jun 17 - Jun 18
Long Trail House South Wing 2B2B Condo

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 ¥23,984
¥131,451 total
includes taxes & fees
Jun 17 - Jun 18
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

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, (38 reviews)
"Our family had a wonderful time staying in this home."
United States
Meghan C.
The price is ¥31,623
¥106,242 total
includes taxes & fees
Jun 24 - Jun 25
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

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 ¥44,152
¥111,937 total
includes taxes & fees
Jun 29 - Jun 30
The Birchwood Cabin - Stunning Mountain Views

Bear Pass - Mountain View by RedAwning

Bear Pass - Mountain View by RedAwning
Sunderland
9.4 out of 10, Exceptional, (8 reviews)
"The rooms were very clean a"
United States
kevin
The price is ¥45,628
¥116,984 total
includes taxes & fees
Jun 21 - Jun 22
Bear Pass - Mountain View by RedAwning

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 ¥40,060
¥73,331 total
includes taxes & fees
Jun 18 - Jun 19
New! Vermont Getaway! Stratton - close to skiing!
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

Find out more about Bennington

Search for holiday rentals in Bennington on Expedia! You can easily find your home rentals, villas, holiday apartments in Bennington using one of the methods below:

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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, Old First Congregational Church 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.