Search Vacation Homes in Bennington

  • 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

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Bennington vacation homes

Interior

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
7.8 out of 10, Good, (58 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is AED 261
AED 887 total
includes taxes & fees
12 May - 13 May
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Terrace/patio

Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (32 reviews)
"Great place!!"
United States
Margaret D.
The price is AED 364
AED 901 total
includes taxes & fees
18 May - 19 May
Peaceful getaway at birds of a feather
Smart TV

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (2 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is AED 426
AED 745 total
includes taxes & fees
11 May - 12 May
Cozy Home in Pownal VT
Exterior

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

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Jamaica
9.6 out of 10, Exceptional, (25 reviews)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
United States
Chris M.
The price is AED 683
AED 3,134 total
includes taxes & fees
17 May - 18 May
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
TV, fireplace, books, music library

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Winhall
10.0 out of 10, Exceptional, (12 reviews)
"Comfortable accommodations, with responsive and helpful hosts! We had a lovely stay as a large family group for a wedding weekend in Manchester. "
United States
Colleen H.
The price is AED 661
AED 2,395 total
includes taxes & fees
11 May - 12 May
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Interior

Cozy 3 Bedroom Condo in the Heart of Manchester VT

Cozy 3 Bedroom Condo in the Heart of Manchester VT
Manchester
10.0 out of 10, Exceptional, (1 review)
"Beautiful place Very spacious and super organized we love our stay "
United States
Rafael
The price is AED 837
AED 2,050 total
includes taxes & fees
12 May - 13 May
Cozy 3 Bedroom Condo in the Heart of Manchester VT
Exterior detail

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (29 reviews)
"EXCELLENT location managed by an amazing host who was very communicative and helpful!Hottub was perfect, plenty of sleeping and activities available at the house and in the immediate area (local food was AWESOME)."
United States
s w.
The price is AED 683
AED 3,151 total
includes taxes & fees
18 May - 19 May
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.4 out of 10, Exceptional, (37 reviews)
"Our family had a wonderful time staying in this home."
United States
Meghan C.
The price is AED 725
AED 2,435 total
includes taxes & fees
11 May - 12 May
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Outdoor dining

Your perfect pet friendly, summer retreat w/ serene brook, hot tub and fire pit.

Your perfect pet friendly, summer retreat w/ serene brook, hot tub and fire pit.
Peru
10.0 out of 10, Exceptional, (5 reviews)
"Property was gorgeous and very well maintained. The owners thought of everything and were very welcome to our dog, Stewie! "
United States
Adrienne C.
The price is AED 942
AED 2,610 total
includes taxes & fees
11 May - 12 May
Your perfect pet friendly, summer retreat w/ serene brook, hot tub and fire pit.
Exterior

Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
The price is AED 437
AED 1,432 total
includes taxes & fees
11 May - 12 May
Two Brooks Lodge
Private kitchen

1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is AED 993
AED 2,703 total
includes taxes & fees
12 May - 13 May
1812 House, 2 Stays, 1 home
Microwave, oven, stovetop, dishwasher

3BR Family Home in Manchester, VT -Near Downtown, Outlets & Ski Resorts

3BR Family Home in Manchester, VT -Near Downtown, Outlets & Ski Resorts
Richville
The price is AED 992
AED 1,395 total
includes taxes & fees
21 May - 22 May
3BR Family Home in Manchester, VT -Near Downtown, Outlets & Ski Resorts
Exterior

Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.

Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
Stratton
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful stay! The location was extremely convenient to the mountain, and the house was clean, comfortable and spacious. We loved all of the seating in the living room, the large fireplace, and cozy hot tub."
United States
Steve M.
The price is AED 1,795
AED 5,046 total
includes taxes & fees
12 May - 13 May
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
Fridge, microwave, oven, stovetop

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
9.8 out of 10, Exceptional, (105 reviews)
"The host was very responsive and helpful. The property itself was also fantastic, with plenty of amenities and kept very clean."
United States
Jon
The price is AED 426
AED 1,134 total
includes taxes & fees
11 May - 12 May
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Interior

Stratton Woods · Secluded Vermont Cabin Retreat

Stratton Woods · Secluded Vermont Cabin Retreat
Wardsboro
9.4 out of 10, Exceptional, (3 reviews)
"Cabin was wonderful!Thank you,The Katz Family "
United States
kim k.
The price is AED 261
AED 1,276 total
includes taxes & fees
11 May - 12 May
Stratton Woods · Secluded Vermont Cabin Retreat
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"Great proximity to mountain and Ludlow downtown area."
United States
Yasmine O.
The price is AED 413
AED 1,114 total
includes taxes & fees
11 May - 12 May
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Property grounds

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (108 reviews)
"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."
United States
Hannah M.
The price is AED 413
AED 1,114 total
includes taxes & fees
11 May - 12 May
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Dining

Modern Mount Snow Gnarvana - Balcony, Loft, Pets, Hiking

Modern Mount Snow Gnarvana - Balcony, Loft, Pets, Hiking
Dover
10.0 out of 10, Exceptional, (26 reviews)
"Beautiful place. We had a blast. So close to the slopes!"
United States
Joseph B.
The price is AED 364
AED 1,420 total
includes taxes & fees
11 May - 12 May
Modern Mount Snow Gnarvana - Balcony, Loft, Pets, Hiking
TV

Florida Mountain Log Cabin

Florida Mountain Log Cabin
Florida
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is AED 752
AED 1,351 total
includes taxes & fees
11 May - 12 May
Florida Mountain Log Cabin
4 bedrooms, travel crib, internet, bed sheets

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
West Dover
10.0 out of 10, Exceptional, (5 reviews)
"The house was just as listed. Everything we needed was there for us upon arrival. The host is amazing and was happy to welcome us in their home. We would definitely come back"
United States
Louis
The price is AED 503
AED 2,001 total
includes taxes & fees
11 May - 12 May
Outdoor Adventure Hub! Family Home in West Dover
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 Hotel Reviews

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

10/10 Excellent
"This is an older hotel that has been nicely updated. It was clean and bed was firm but comfortable. A hot breakfast was newly started and the eggs were better tasting than alot of other smaller hotel buffet types . Staff was very helpful and willing to help with any needs. We would stay here again."
Deborah 2-night trip
Posted 3 days ago
Hotel Vervana, Trademark Collection by Wyndham