Bennington County Vacation Rentals

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Check prices for these dates

Next weekend
Jul 25 - Jul 27
In two weeks
Aug 1 - Aug 3
In one month
Aug 15 - Aug 17
In two months
Sep 12 - Sep 14

Top Cities in Bennington County

Bennington Battle Monument featuring landscape views
Vacation HomesVacation Homes

Bennington

Bennington

Featured Vacation Homes in Bennington County

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
Cozy cabin retreat with a high ceiling, central fireplace, and comfortable seating area.

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

9.6 out of 10, Exceptional, (25)
"Beautiful location and so many cozy touches throughout home!"
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!
Fully equipped kitchen with stainless steel appliances, dark cabinets, and a white tiled backsplash.

8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!

8.0 out of 10, Very good, (1)
8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!
Breaktime - Quiet and Private on dead end street
Stroll through a vibrant garden featuring a diverse selection of flowering plants and lush greenery.

Breaktime - Quiet and Private on dead end street

10.0 out of 10, Exceptional, (30)
"I like the location close to mountain walking trails and fine dining options. "
Breaktime - Quiet and Private on dead end street
Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester
Relax by the fire pit in a serene outdoor setting surrounded by lush greenery.

Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester

9.0 out of 10, Wonderful, (20)
"Property out and peaceful and quiet. View is great thanks."
Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Relax in a serene hot tub surrounded by a wooded area and a wooden deck.

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (21)
"This place was very enjoyable, it was just 3 of us so there was more than enough room. It is a very comfortable home and we enjoyed the easy trip into Manchester for some meals and a wonderful day of hiking some great nearby trails."
The price is CA $316
CA $932 total
includes taxes & fees
Aug 12 - Aug 13
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
The Mountain Escape!
Relax in a hot tub on a snow-covered deck.

The Mountain Escape!

9.8 out of 10, Exceptional, (17)
"Good spot for catching up with friends for the weekend. Hot tub was perfect and everything was comfortable."
The price is CA $152
CA $1,041 total
includes taxes & fees
Aug 11 - Aug 12
The Mountain Escape!
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Features an oven, microwave, and refrigerator, along with a large window and ceiling lights.

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

8.8 out of 10, Excellent, (30)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Cozy space with a high ceiling and exposed beams, featuring a dining area with a round table and chairs.

Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

10.0 out of 10, Exceptional, (201)
"This location is awesome. Close to town and skiing but we felt like we were secluded in the forest when sitting in the hot tub. We had a great time!"
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Cozy retreat with a high ceiling and exposed beams, featuring a ladder, picture frame, and kitchen area.

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

10.0 out of 10, Exceptional, (221)
"Beautiful property. Very relaxing, secluded. "
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Peaceful Stay at Birds of a Feather Farm & Spa
Relax in this serene space with a large window, a vase with flowers, and a macrame wall hanging.

Peaceful Stay at Birds of a Feather Farm & Spa

9.6 out of 10, Exceptional, (20)
"Wonderful get away for the week in VT. Place was clean and beautiful, host was very helpful, and views were gorgeous! "
The price is CA $148
CA $356 total
includes taxes & fees
Jul 16 - Jul 17
Peaceful Stay at Birds of a Feather Farm & Spa
Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.
Relax on the covered porch with comfortable seating and a scenic view of the surrounding mountains and trees.

Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.

9.6 out of 10, Exceptional, (15)
"Spacious house and beautiful grounds."
Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.
Luxury 4-BR Mountain Estate 10-min to Manchester
Cozy living room with a stone fireplace, American flag, and comfortable seating.

Luxury 4-BR Mountain Estate 10-min to Manchester

2.0 star property
10.0 out of 10, Exceptional, (2)
"This property is amazing: the grounds, the gardens and of course an exceptional, well equipped house. The architecture, the views and the many bedrooms and bathrooms made it so comfortable for our group of nine. The kitchen is well organized and has every convenience for cooking in."
Luxury 4-BR Mountain Estate 10-min to Manchester
Stylish Mountain Home Near Ski, Golf + Manchester!
Relax in a hot tub with multiple seating areas, surrounded by a metal frame and serene surroundings.

Stylish Mountain Home Near Ski, Golf + Manchester!

9.8 out of 10, Exceptional, (30)
"Relaxing weekend just a few miles from the ski mountain. Hot tub was great."
Stylish Mountain Home Near Ski, Golf + Manchester!
2Free Nights,Stratton Mtn,Hot Tub,Sauna,Shuttle,
Enjoy meals in the kitchen with a dining area and appliances.

2Free Nights,Stratton Mtn,Hot Tub,Sauna,Shuttle,

10.0 out of 10, Exceptional, (53)
"We had a great time and enjoyed the location!"
2Free Nights,Stratton Mtn,Hot Tub,Sauna,Shuttle,
Gather Together – Stratton Mtn Luxury & Comfort with a View
Enter through a grand entrance, leading to a spacious garage and multiple levels with a balcony offering a view of the surrounding landscape.

Gather Together – Stratton Mtn Luxury & Comfort with a View

8.0 out of 10, Very good, (5)
"Lots of Room, Clean, 5 min to the Slopes, we will stay here again!"
Gather Together – Stratton Mtn Luxury & Comfort with a View
Cozy ski home with amazing views of Stratton & Bromley Mountains.
Enjoy breathtaking views of the mountainous landscape from this balcony.

Cozy ski home with amazing views of Stratton & Bromley Mountains.

9.4 out of 10, Exceptional, (30)
"The convenient near-mountain location and living room views are hard to beat; the hot tub was a great touch as well! It was perfect for our large group over a holiday weekend."
Cozy ski home with amazing views of Stratton & Bromley Mountains.
8-bedroom vacation home just 16 minutes from Golf Club at Equinox
Enjoy communal dining at this kitchen with a long table and bench, featuring modern appliances and a window.

8-bedroom vacation home just 16 minutes from Golf Club at Equinox

9.6 out of 10, Exceptional, (15)
"Happy experience and plenty of room. Everyone enjoyed the lake and sounding places."
8-bedroom vacation home just 16 minutes from Golf Club at Equinox
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
Stroll through the beautifully maintained garden, surrounded by lush plants and a serene natural setting.

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

10.0 out of 10, Exceptional, (62)
"The barn is beautiful and much more spacious than it looks in the photos. The property the barn is on is also beautiful, a short drive from the town center, and also close to cool sites to visit like the Lincoln House and many amazing hiking trains."
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
Perfect Reunion House w/pool, tennis, fireplace & piano. Dogs welcome.
Kitchen features a clean design with light cabinetry, microwave, oven, and sink.

Perfect Reunion House w/pool, tennis, fireplace & piano. Dogs welcome.

9.8 out of 10, Exceptional, (23)
"Great location near Bromley and Stratton for skiing. Our group of 16 had plenty of room and were very comfortable. Melissa was very accommodating and responsive. Would definitely recommend this property."
Perfect Reunion House w/pool, tennis, fireplace & piano. Dogs welcome.
Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths, Fire Pit, Baths Ensuite - Shop or Ski!
Relax in a serene outdoor space with a fire pit surrounded by Adirondack chairs.

Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths, Fire Pit, Baths Ensuite - Shop or Ski!

10.0 out of 10, Exceptional, (48)
"Once again the property was amazing!! The Fall foliage made the stay even more wonderful. I look forward to our next stay!!"
Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths, Fire Pit, Baths Ensuite - Shop or Ski!
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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