Bennington County Holiday Rentals

    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

Top Holiday Rentals Destinations in Bennington County

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (221)
"Cabin was beautiful! Love the little stream outside. Very close to restaurants, shopping, and hiking trails. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

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

9.8 out of 10, Exceptional, (23)
"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!

8.0 out of 10, Very good, (1)
8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

9.4 out of 10, Exceptional, (81)
"Nice place, just what we were looking for to stay the weekend. "
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

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 AU$1,166
includes taxes & fees
11 Aug - 12 Aug
The Mountain Escape!

Breaktime - Quiet and Private on dead end street

10.0 out of 10, Exceptional, (29)
"I like the location close to mountain walking trails and fine dining options. "
Breaktime - Quiet and Private on dead end street

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 AU$1,076
includes taxes & fees
11 Aug - 12 Aug
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

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

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

9.0 out of 10, Wonderful, (29)
"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

Renovated Ski-In/Ski-Out Peru Condo at Bromley Mtn

9.6 out of 10, Exceptional, (38)
"Great stay, super easy access to the slopes. Place was great with helpful and communicable hosts. Will stay again! "
Renovated Ski-In/Ski-Out Peru Condo at Bromley Mtn

Studio style farm stay

8.8 out of 10, Excellent, (30)
"Quaint room with lots of artistic charm. Convenient location. Well worth it."
Studio style farm stay

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

Bright & cheery condo with seasonal pool access

8.2 out of 10, Very good, (39)
"Perfect for adults and kids looking to ski. Easy access. Clean and easy rental"
Bright & cheery condo with seasonal pool access

Green Mountain Getaway

2.0 star property
9.8 out of 10, Exceptional, (11)
"Great Location -- place was spotless and very accommodating"
The price is AU$590
includes taxes & fees
16 July - 17 July
Green Mountain Getaway

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!

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

Spacious apartment in beautiful, historic Arlington VT

10.0 out of 10, Exceptional, (43)
"Wow this was more than I expected. It was a great way to experience my first Vrbo. Property was conveniently located and easy to find. We had a very lovely stay. "
The price is AU$334
includes taxes & fees
13 July - 14 July
Spacious apartment in beautiful, historic Arlington VT

Vermont house in stunning private country setting and 360 degree panoramic views

10.0 out of 10, Exceptional, (12)
"Fantastic place to get away from it all. Romantic and serene with everything you need to enjoy the stunning area. We will absolutely come back "
Vermont house in stunning private country setting and 360 degree panoramic views

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

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.
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