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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

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, (57 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is AED 312
AED 963 total
includes taxes & fees
27 Apr - 28 Apr
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Exterior

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

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Bennington
8.6 out of 10, Excellent, (35 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is AED 397
AED 1,027 total
includes taxes & fees
7 Apr - 8 Apr
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Terrace/patio

Peaceful Stay at Birds of a Feather Farm & Spa

Peaceful Stay at Birds of a Feather Farm & Spa
Shaftsbury
9.8 out of 10, Exceptional, (32 reviews)
"Great place!!"
United States
Margaret D.
The price is AED 331
AED 860 total
includes taxes & fees
12 Apr - 13 Apr
Peaceful Stay at Birds of a Feather Farm & Spa
Dining

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 379
AED 692 total
includes taxes & fees
6 Apr - 7 Apr
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)
"I stayed here for a few days in October with friends. We had some initial confusion with the door locks, but the hosts were able to resolve it quickly.Great location, tons of sleeping and living space, and the hot tub was a welcome addition. We had a great time and would recommend this spot."
United States
Jonathan E.
The price is AED 804
AED 3,291 total
includes taxes & fees
6 Apr - 7 Apr
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
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
6 Apr - 7 Apr
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, (28 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 804
AED 3,337 total
includes taxes & fees
8 Apr - 9 Apr
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, (36 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
26 Apr - 27 Apr
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)
"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.
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Private kitchen

1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is AED 1,065
AED 2,797 total
includes taxes & fees
21 Apr - 22 Apr
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 1,137
AED 1,567 total
includes taxes & fees
12 Apr - 13 Apr
3BR Family Home in Manchester, VT -Near Downtown, Outlets & Ski Resorts
Interior

Idyllic Village Estate: Luxury Villa Historic Barn

Idyllic Village Estate: Luxury Villa Historic Barn
Manchester
9.4 out of 10, Exceptional, (13 reviews)
"It was a fantastic stay! The house is beautiful with stunning views in every direction. It is well-appointed and very comfortable. It has special amenities like a hot tub and party barn. Communication with the host was easy; he responded almost immediately and was quite pleasant. He gave us lots of useful information and even honored a couple of unique requests. This is a super special property. "
United States
Elizabeth C.
The price is AED 2,975
AED 6,687 total
includes taxes & fees
8 Apr - 9 Apr
Idyllic Village Estate: Luxury Villa Historic Barn
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 411
AED 907 total
includes taxes & fees
7 Apr - 8 Apr
Two Brooks Lodge
Fridge, microwave, oven, stovetop

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
6 Apr - 7 Apr
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
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, (103 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
6 Apr - 7 Apr
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 393
AED 1,433 total
includes taxes & fees
6 Apr - 7 Apr
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)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is AED 413
AED 1,114 total
includes taxes & fees
6 Apr - 7 Apr
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
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 675
AED 1,249 total
includes taxes & fees
6 Apr - 7 Apr
Florida Mountain Log Cabin
Exterior

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

14mi to Mt. Snow! Arcade, Private Suite, King Bed!
Whitingham
10.0 out of 10, Exceptional, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is AED 731
AED 1,868 total
includes taxes & fees
6 Apr - 7 Apr
14mi to Mt. Snow! Arcade, Private Suite, King Bed!
Dining

Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.6 out of 10, Exceptional, (18 reviews)
"House was in a perfect location. The town was adorable. "
United States
Michelle A.
The price is AED 727
AED 1,510 total
includes taxes & fees
6 Apr - 7 Apr
Charming Chester Farmhouse near Near VT Slopes
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

Best Western Bennington

Best Western Bennington

6/10 Okay
"There was a connecting room between the 2 rooms that didnt lock,it just had one of those door stop things. There was large gap between the door and the frame of the door. Not a very secure feeling while you're trying to sleep. Otherwise it was clean "
Penny S 1-night trip
Posted 6 days ago
Best Western Bennington