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Bennington Vacation Rentals

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Our top choices for Bennington vacation rentals

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 CA $423
CA $526 total
includes taxes & fees
Jul 2 - Jul 3
Long Trail House at Stratton Mountain Resort

< 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 CA $279
CA $489 total
includes taxes & fees
Jun 29 - Jun 30
< 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 CA $129
CA $466 total
includes taxes & fees
Jun 28 - Jun 29
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 CA $141
CA $354 total
includes taxes & fees
Jun 30 - Jul 1
Peaceful getaway at birds of a feather

Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (63 reviews)
"This apartment is absolutely beautiful and spacious. It was immaculately clean and provided everything we needed. Communication from Kate was great. We would absolutely stay here again if we are ever in the area. "
United States
Lisa S.
The price is CA $243
CA $343 total
includes taxes & fees
Jul 7 - Jul 8
Spacious apartment in beautiful, historic Arlington VT

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 CA $270
CA $582 total
includes taxes & fees
Jul 21 - Jul 22
Perfect for a peaceful get away in clean fresh Vermont air!

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 CA $191
CA $517 total
includes taxes & fees
Jun 28 - Jun 29
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

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
Bear Pass - Mountain View 4 Bedroom Home by RedAwning

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 CA $292
CA $581 total
includes taxes & fees
Jun 29 - Jun 30
Green Mountain Getaway

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 CA $351
CA $1,324 total
includes taxes & fees
Jun 28 - Jun 29
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, (39 reviews)
"Our family had a wonderful time staying in this home."
United States
Meghan C.
The price is CA $280
CA $930 total
includes taxes & fees
Jul 7 - Jul 8
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 CA $532
CA $1,154 total
includes taxes & fees
Jul 7 - Jul 8
The Birchwood Cabin - Stunning Mountain Views

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 CA $355
CA $656 total
includes taxes & fees
Jun 27 - Jun 28
New! Vermont Getaway! Stratton - close to skiing!

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 CA $173
CA $558 total
includes taxes & fees
Jun 29 - Jun 30
Two Brooks Lodge

Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
The price is CA $231
CA $568 total
includes taxes & fees
Jun 28 - Jun 29
Long Trail House South Wing 2B2B Condo

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 CA $523
CA $1,199 total
includes taxes & fees
Jul 2 - Jul 3
3 Levels w/ Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit, ACs

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 CA $190
CA $467 total
includes taxes & fees
Jul 1 - Jul 2
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

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 CA $222
CA $654 total
includes taxes & fees
Jun 30 - Jul 1
Historic Home with Colonial Charm in Manchester

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 CA $546
CA $1,301 total
includes taxes & fees
Jul 9 - Jul 10
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

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 CA $165
CA $293 total
includes taxes & fees
Jun 30 - Jul 1
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

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Bennington vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Bennington vacation rentals we have selected for you start as low as CA $467 per night. Entering your travel dates in the search wizard 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?

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.