Photo by Justin Hunter

Vacation Homes in Bennington County

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Featured Vacation Homes in Bennington County

Smart TV, fireplace, video games, table football
Beautifully Remodeled VT Mountain Oasis with Stratton Views and private Hot Tub

Holiday Home in Bromley Mountain

2.0 star property
Beautifully Remodeled VT Mountain Oasis with Stratton Views and private Hot Tub
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Holiday Home in Shaftsbury

10.0 out of 10, Exceptional, (231)
"The cabin was easy to find and the property is gorgeous ! Clean and quiet, it was the perfect place for a weekend away! "
United States
Erin C.
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Outdoor spa tub
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Holiday Home in Winhall

9.6 out of 10, Exceptional, (30)
"It was exactly what we wanted. Fireplace , hot tub, and ample sleeping arrangements "
United States
Craig F.
The price is HK$1,598
HK$5,037 total
includes taxes & fees
9 Dec - 10 Dec
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Dining
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

Holiday Home in Manchester Center

10.0 out of 10, Exceptional, (207)
"This is a fabulous and incredibly special home on the most beautiful property. Extremely convenient to Manchester and Jeff is a perfect host."
United States
sari a.
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Outdoor spa tub
UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets

Holiday Home in Sunderland

4.0 star property
10.0 out of 10, Exceptional, (22)
"Incredible property that is very kid friendly. Great views and accommodations to house, lots of toys and books for the kids. "
United States
David John D.
UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets
Exterior
Miner Cottage-Historic Antique Home just steps from the Equinox Resort

Holiday Home in Manchester

10.0 out of 10, Exceptional, (25)
"GREAT TIME ! GREAT HOUSE"
United States
JOHN B.
Miner Cottage-Historic Antique Home just steps from the Equinox Resort
Fridge, microwave, oven, stovetop
Stratton; 4 min! Shuttle, King Beds, Hot Tub, 2 FP

Holiday Home in Jamaica

Stratton; 4 min! Shuttle, King Beds, Hot Tub, 2 FP
Interior
Sleep 34 in huge VT Mansion! 15 bedrms/12 bath: Xmas, Ski, weddings, family reunions, Yoga, corporate, Dogs loved

Holiday Home in Manchester

10.0 out of 10, Exceptional, (58)
"Great place for a big group. Kids loved exploring and parents loved the space."
United States
John L.
Sleep 34 in huge VT Mansion! 15 bedrms/12 bath: Xmas, Ski, weddings, family reunions, Yoga, corporate, Dogs loved
Outdoor spa tub
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Holiday Home in Jamaica

9.6 out of 10, Exceptional, (21)
"House was perfect and just what we were looking for! Very clean, great hot tub, loved the fire pit!Cassie was incredibly helpful with local recommendations and going above and beyond!Highly recommend!"
United States
Neal T.
The price is HK$1,716
HK$6,205 total
includes taxes & fees
9 Dec - 10 Dec
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Fridge, microwave, oven, stovetop
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Holiday Home in Sunderland

10.0 out of 10, Exceptional, (127)
"Lovely home with beautiful view! Excellent host. We had a wonderful stay. "
United States
Julia P.
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Interior
Peaceful Stay at Birds of a Feather Farm & Spa

Holiday Home in Shaftsbury

9.8 out of 10, Exceptional, (28)
"Beautiful location and very cozy place to stay. Thank you!"
United States
Kristin G.
Peaceful Stay at Birds of a Feather Farm & Spa
Terrace/patio
Room for the whole family 8 minutes to Manchester

Holiday Home in Sunderland

10.0 out of 10, Exceptional, (13)
"Clean and comfortable. Beautiful gardens and Mountain View "
United States
Beverly S.
Room for the whole family 8 minutes to Manchester
Property grounds
Unexpected Style in a Cosy, Convenient In-Town Apartment

Holiday Home in Manchester Center

9.8 out of 10, Exceptional, (82)
"Listing was very accurate-quiet cozy upstairs apartment. Location was excellent-easy to walk into town."
United States
Felice R.
Unexpected Style in a Cosy, Convenient In-Town Apartment
Terrace/patio
Sleep 20, 6BR/6BA home on #1 TripAdvisor resort - ski, pool, dogs

Holiday Home in Manchester

9.8 out of 10, Exceptional, (17)
"Stayed here for a weekend with a family of 19. Everyone had a great time! Great onsite amenities and nearby places to explore. Loved that each room had a private bath as we had multiple families, some with little kids. I wish the kitchen area was bigger as we spent most of the time there, especially in the mornings making breakfast. Host was very responsive and accommodating!"
United States
Annu K.
Sleep 20, 6BR/6BA home on #1 TripAdvisor resort - ski, pool, dogs
Property grounds
Welcome to Laurel Hill in Beautiful Manchester VT 5 Bedrooms Sleeps 10 EVCharger

Holiday Home in Manchester

10.0 out of 10, Exceptional, (58)
"The house is super comfortable, clean and spacious. The beds are very comfortable and kitchen was well stocked. The back deck with fire pit and lounge area created the perfect space for unwinding at night. Check-in process and instructions and communications with the host seamless. "
United States
Linda M.
Welcome to Laurel Hill in Beautiful Manchester VT 5 Bedrooms Sleeps 10 EVCharger
4 bedrooms, free WiFi, bed sheets
Family Friendly Stratton Home for All Seasons, 7 min to ski mountain

Holiday Home in Winhall

10.0 out of 10, Exceptional, (5)
"This house was perfect for a big group of friends skiing at Stratton! Super spacious and clean and filled with lots of fun games for after skiing. Less than 10 minute drive to the mountain. Definitely would recommend to any group of 10-16 people of all ages!"
United States
Maddie D.
Family Friendly Stratton Home for All Seasons, 7 min to ski mountain
Exterior
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Holiday Home in Dorset

10.0 out of 10, Exceptional, (184)
"Lovely spot next to the creek, quiet and relaxing with top of the line amenities and located close to many things to do and see. Hope to get back here again someday, it was fantastic."
United States
chris f.
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Exterior
Mountain views. Ski Bromley, Stratton. Minutes to restaurants, Equinox, Ekwanok.

Holiday Home in Manchester

10.0 out of 10, Exceptional, (74)
"This is a lovely home, nicely furnished with comfy beds, thick bath towels, spacious kitchen/dining area, and pleasant outdoor space. Check in was super easy. Property is conveniently located. Would definitely stay here again. "
United States
Phyllis P.
Mountain views. Ski Bromley, Stratton. Minutes to restaurants, Equinox, Ekwanok.
Interior
Enjoy each season's weather in historic Manchester. Plenty to do year round!!

Holiday Home in Manchester

10.0 out of 10, Exceptional, (67)
"Enjoyed out stay in Manchester. House was very comfortable and in a great location close to town and outlets"
United States
Alice's F.
Enjoy each season's weather in historic Manchester. Plenty to do year round!!
Exterior
Gather Together – Stratton Mtn Luxury & Comfort with a View

Holiday Home in Winhall

8.0 out of 10, Very good, (5)
"Lots of Room, Clean, 5 min to the Slopes, we will stay here again!"
United States
Kevin N.
Gather Together – Stratton Mtn Luxury & Comfort with a View
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bennington County Hotel Reviews

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"The entire property is spotless. Don’t think I’ve ever a cleaner hotel. Staff was very friendly and accommodating. Definitely a keeper!"
Joel 2-night trip
Posted 2 days ago
Hampton Inn and Suites Manchester

Find out more about Bennington County

Bennington County Vacation Homes information

Number of reviews
1,149
Accommodation
215 Vacation Homes
Lowest Price
HK$5,037
Highest Price
HK$6,205