Bennington County Vacation Rentals

Compare and save

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Top Cities in Bennington County

Featured Vacation Homes in Bennington County

Our top choices for Bennington County vacation homes

Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!

9.8 out of 10, Exceptional, (18)
"Came for skiing and NYE, had a great time with a great location"
Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!

Beautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester

10.0 out of 10, Exceptional, (72)
"Great spot for a quick visit to Manchester VT."
Beautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester

Bright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown

10.0 out of 10, Exceptional, (23)
"The property was beautiful! The kids enjoyed fishing in the pond with their grandpa. The hosts were nice enough to let us have a small impromptu family cookout and were very helpful when we accidentally locked ourselves out. It was a great stay!"
Bright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (21)
"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "
The price is CA $265
CA $862 total
includes taxes & fees
Sep 8 - Sep 9
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

10.0 out of 10, Exceptional, (120)
"House was accurately described. Kitchen was well-equipped. Village of Manchester is just a short drive away. Deck and hot tub were awesome!"
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets

4.0 star property
10.0 out of 10, Exceptional, (18)
"We had a wonderful stay, the property was perfect for our family. The view was especially nice. Very quick & easy to get to Manchester and ski mountains."
UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets

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

9.8 out of 10, Exceptional, (17)
"Spacious house and beautiful grounds."
Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.

Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq

10.0 out of 10, Exceptional, (5)
Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq

Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

10.0 out of 10, Exceptional, (40)
"Great property and location for our family and friends, we’ll be back in the future!"
Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

Luxury 5-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 5-BR Mountain Estate 10-min to Manchester

Luxury Post and Beam Barn Set On 10 Acres

10.0 out of 10, Exceptional, (86)
"Amazing property and host. Would love to stay again next time in the area. "
Luxury Post and Beam Barn Set On 10 Acres

Stylish Mountain Home Near Ski, Golf + Manchester!

9.8 out of 10, Exceptional, (33)
"Relaxing weekend just a few miles from the ski mountain. Hot tub was great."
Stylish Mountain Home Near Ski, Golf + Manchester!

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.

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

9.6 out of 10, Exceptional, (17)
"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

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

10.0 out of 10, Exceptional, (227)
"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

9.8 out of 10, Exceptional, (22)
"Great little quiet and peaceful spot that was still very close to Bennington and Manchester.Neighborhood was good for walks or gravel rides."
The price is CA $161
CA $369 total
includes taxes & fees
Sep 8 - Sep 9
Peaceful Stay at Birds of a Feather Farm & Spa

Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

10.0 out of 10, Exceptional, (203)
"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

Your own Private Lake - Breathtaking Views - Gym - Sauna - Hot Tub

10.0 out of 10, Exceptional, (32)
"To celebrate my daughters college graduation I booked this property for the family and a few friends. The weather was cold and rainy the whole trip but we made the best of it. The house is massive and all the amenities inside were great!"
Your own Private Lake - Breathtaking Views - Gym - Sauna - Hot Tub

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

9.8 out of 10, Exceptional, (24)
"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.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Bennington County Hotel Reviews

Find out more about Bennington County

Find out more about Bennington County

Bennington County Vacation Homes information

Number of reviews
Accommodation
255 Vacation Homes
Lowest Price
CA $161
Highest Price
CA $265

Explore a world of travel with Expedia

Explore a world of travel with Expedia