Holiday Rentals 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

Our top choices for Bennington County holiday rentals

Exterior
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Holiday Home in Jamaica

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
9.6 out of 10, Exceptional, (22)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
United States
Chris M.
The price is €1,153
includes taxes & fees
19 Jan - 20 Jan 2026
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Exterior
Perfect Reunion House! Fire. Ski. Pool. Dogs!

Holiday Home in Manchester

Perfect Reunion House! Fire. Ski. Pool. Dogs!
9.8 out of 10, Exceptional, (24)
"The property and house are very well kept. The house was extremely clean and the hosts were very pleasant and helpful. "
United States
Charles R.
Perfect Reunion House! Fire. Ski. Pool. Dogs!
Interior
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

Holiday Home in Manchester

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
10.0 out of 10, Exceptional, (72)
"We had a lovely stay."
United States
Jennifer M.
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
Smart TV, fireplace
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Holiday Home in Sunderland

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
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
Exterior
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Holiday Home in Dorset

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
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
Outdoor spa tub
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Holiday Home in Winhall

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
9.6 out of 10, Exceptional, (31)
"It was exactly what we wanted. Fireplace , hot tub, and ample sleeping arrangements "
United States
Craig F.
The price is €1,058
includes taxes & fees
21 Dec - 22 Dec
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
TV, fireplace, books, stereo
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Cottage in Winhall

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (243)
"If I could give the Honeymoon Cottage 11 out of 10 stars, I would!Everything was lovely- it was just fantastic. We loved the cottage itself, the location, everything. It was cozy and comfortable. We will 100% be booking another stay. "
United States
Susan R.
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
TV, fireplace, books, music library
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Holiday Home in Winhall

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
10.0 out of 10, Exceptional, (8)
"Great location, large space for family, good amenities, love the fireplace and coffee set up."
United States
Eitan S.
The price is €922
includes taxes & fees
21 Dec - 22 Dec
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Dining
2 Free Nights* , Hot Tub,Sauna,Stratton Shuttle,

Holiday Home in Stratton Mountain

2 Free Nights* , Hot Tub,Sauna,Stratton Shuttle,
10.0 out of 10, Exceptional, (56)
"We were very happy with this stay. The house is clean, comfortable, and spacious, as advertised. The hot tub was clean and worked perfectly. The property owner is a very responsive. I would definitely stay here again. "
United States
Steve B.
2 Free Nights* , Hot Tub,Sauna,Stratton Shuttle,
Interior
Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside

Apartment in Dorset

Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside
10.0 out of 10, Exceptional, (16)
"Amazing property and place to stay. So warm and cozy. Definitely off the grid feeling but not far from great Vermont towns. Will stay again. Place was perfect "
United States
vincent v.
Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside
Property grounds
Green Mountain Manor - Ski and Summer Chalet

Chalet in Winhall

Green Mountain Manor - Ski and Summer Chalet
9.8 out of 10, Exceptional, (7)
"Beautiful property less than 5 minutes from Stratton!! Very private and secluded"
United States
Jay T.
Green Mountain Manor - Ski and Summer Chalet
Fridge, microwave, oven, stovetop
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!

Chalet in Winhall

Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!
10.0 out of 10, Exceptional, (13)
"This property is great, plenty of space for the whole family. We enjoyed the hot tub after many days of mountain biking at Stratton and riding the alpine slide at Bromley. I like this area as it offers plenty of options for activities and food both at Stratton Village or In Manchester. I plan to stay at this property in the future."
United States
Gary A.
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!
Exterior
Sleep 34 in huge VT Mansion! 15 bedrms/12 bath: Xmas, Ski, weddings, family reunions, Yoga, corporate, Dogs loved

Holiday Home in Manchester

Sleep 34 in huge VT Mansion! 15 bedrms/12 bath: Xmas, Ski, weddings, family reunions, Yoga, corporate, Dogs loved
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
Terrace/patio
Peaceful Stay at Birds of a Feather Farm & Spa

Holiday Home in Shaftsbury

Peaceful Stay at Birds of a Feather Farm & Spa
9.8 out of 10, Exceptional, (29)
"Laurie was very friendly and easy to work with, the onsite spa offerings were fantastic as well! Really enjoyed her home and would stay there again. "
United States
Mike B.
Peaceful Stay at Birds of a Feather Farm & Spa
Property grounds
Room for the whole family 8 minutes to Manchester

Holiday Home in Sunderland

Room for the whole family 8 minutes to Manchester
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
Exterior
Luxury Condo*Hot Tub*Pool*Fireplace*Walk to Lifts*Near Golf Course & Fitness Ctr

Condo in Stratton Mountain 0.3 miles from resort

Luxury Condo*Hot Tub*Pool*Fireplace*Walk to Lifts*Near Golf Course & Fitness Ctr
10.0 out of 10, Exceptional, (34)
"The condo is absolutely beautiful and stocked with everything you need. David the host was extremely easy to work with and very accommodating. He went above and beyond to enhance our stay with a lovely welcome basket. I would highly recommend staying here and look forward to booking again"
United States
Virginia D.
Luxury Condo*Hot Tub*Pool*Fireplace*Walk to Lifts*Near Golf Course & Fitness Ctr
Exterior
Sleep 20, 6BR/6BA home on #1 TripAdvisor resort - ski, pool, dogs

Holiday Home in Manchester

Sleep 20, 6BR/6BA home on #1 TripAdvisor resort - ski, pool, dogs
9.8 out of 10, Exceptional, (17)
"Spacious house and beautiful grounds."
United States
Anonymous traveller
Sleep 20, 6BR/6BA home on #1 TripAdvisor resort - ski, pool, dogs
Property grounds
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

Cottage in Woodford

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
8.8 out of 10, Excellent, (3)
"Perfect cottage on the water!! Enjoyed kayaking and pedal boat with family. Beautiful greenery! Very quick respond."
United States
Elzbieta M.
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
Property grounds
Home with a spring-fed pond and mountain view.

Cottage in Manchester

Home with a spring-fed pond and mountain view.
10.0 out of 10, Exceptional, (122)
"Jeremy was a great host! Checkin was easy, he was very responsive to any questions we had.Kitchen is fully stocked and his farm fresh eggs were delicious! "
United States
Lisa R.
Home with a spring-fed pond and mountain view.
Fridge, microwave, oven, stovetop
Mountain-view condo w/ pool & hot tubs

Condo in Stratton

Mountain-view condo w/ pool & hot tubs
10.0 out of 10, Exceptional, (8)
"Absolutely amazing place! Condo is very big and spacious, located within walking distance to the mountain. "
United States
Agata
Mountain-view condo w/ pool & hot tubs
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
"Room was spotless. Staff was friendly."
Kathleen 2-night trip
Posted 4 days ago
Hampton Inn and Suites Manchester

Find out more about Bennington County

Holiday Homes in Bennington County

Search for holiday homes in Bennington County on Expedia.ie! You can easily find your home rentals, villas, holiday apartments in Bennington County using one of the methods below: 

  • View our selection of featured holiday homes in Bennington County
  • Use the map to find apartments and other holiday rentals in the Bennington County neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday homes in Bennington County while they last

Look no further and take a look at our great range of rental properties in Bennington County!