Holiday Homes in Bennington

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Bennington holiday homes

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
Aidan K.
The price is €227
includes taxes & fees
22 Jun - 23 Jun
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 €178
includes taxes & fees
7 Jun - 8 Jun
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, (26 reviews)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
United States
Chris M.
The price is €701
includes taxes & fees
8 Jun - 9 Jun
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
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 €750
includes taxes & fees
9 Jun - 10 Jun
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, (38 reviews)
"Our family had a wonderful time staying in this home."
United States
Meghan C.
The price is €570
includes taxes & fees
4 Jun - 5 Jun
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
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)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is €738
includes taxes & fees
4 Jun - 5 Jun
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
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 €308
includes taxes & fees
9 Jun - 10 Jun
3BR Family Home in Manchester, VT -Near Downtown, Outlets & Ski Resorts
Private kitchen

1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is €701
includes taxes & fees
16 Jun - 17 Jun
1812 House, 2 Stays, 1 home
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 €1,229
includes taxes & fees
8 Jun - 9 Jun
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
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 €284
includes taxes & fees
5 Jun - 6 Jun
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
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 €271
includes taxes & fees
22 Jun - 23 Jun
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
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)
"Couldn’t have picked a better place! Warm and comfy and sooo close to okemo "
United States
Erica B.
The price is €284
includes taxes & fees
4 Jun - 5 Jun
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Smart TV, fireplace, video games, books

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (41 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is €458
includes taxes & fees
7 Jun - 8 Jun
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Exterior

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
shushan
9.6 out of 10, Exceptional, (23 reviews)
"Lovely location, well appointed, dog friendly."
United States
Anonymous traveller
The price is €302
includes taxes & fees
4 Jun - 5 Jun
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Exterior

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"the hosts were great very helpful and pleasant"
United States
Ron L.
The price is €351
includes taxes & fees
4 Jun - 5 Jun
The Greylock Cabin
Exterior

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "
United States
Chi L.
The price is €666
includes taxes & fees
4 Jun - 5 Jun
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Smart TV, fireplace, books

5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (4 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
5BR Berkshire Home Mins To The Mountain
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)
"The hosts were very responsive, accommodating, and our family had a wonderful stay! "
United States
caroline m.
The price is €366
includes taxes & fees
4 Jun - 5 Jun
Modern Mount Snow Gnarvana - Balcony, Loft, Pets, Hiking
Exterior

Runamuk Farm Camp Tiny House near Cambridge, New York

Runamuk Farm Camp Tiny House near Cambridge, New York
Cambridge
The price is €120
includes taxes & fees
7 Jun - 8 Jun
Runamuk Farm Camp Tiny House near Cambridge, New York
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.
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Top Bennington Hotel Reviews

Bennington Motor Inn

Bennington Motor Inn

4/10 Poor
"Rooms were clean and staff was helpful, however, atmosphere felt like Section 8 housing. Smoking was done right outside my room and I was watched constantly by people from their rooms. There were no cars in the parking lot, but many arguments there during daylight hours. Not a comfortable place overall."
Brian 2-night trip
Posted 10 hours ago
Bennington Motor Inn

Find out more about Bennington

Bennington Holiday Homes information

Number of reviews
3
Accommodation
241 Holiday Homes
Lowest Price
Highest Price