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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Bennington holiday homes

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, (31 reviews)
"Great place!!"
United States
Margaret D.
The price is £182
includes taxes & fees
22 Feb - 23 Feb
Peaceful Stay at Birds of a Feather Farm & Spa
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
7.6 out of 10, Good, (54 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is £273
includes taxes & fees
22 Feb - 23 Feb
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
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, (23 reviews)
"Absolutely a wonderful place to vacation. The house is comfortable and warming. The hosts went above and beyond to make our stay great and responded to our questions promptly. We will definitely rent again. "
United States
Lee Anna C.
The price is £661
includes taxes & fees
17 Mar - 18 Mar
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Dining

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (1 review)
"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 £141
includes taxes & fees
25 Feb - 26 Feb
Cozy Home in Pownal VT
Exterior detail

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

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.8 out of 10, Exceptional, (27 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 £661
includes taxes & fees
17 Mar - 18 Mar
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 £553
includes taxes & fees
17 Mar - 18 Mar
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Private kitchen

1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is £606
includes taxes & fees
10 Mar - 11 Mar
1812 House, 2 Stays, 1 home
Interior

7200 sf Villa & Barn on 4 Acre Manchester Estate

7200 sf Villa & Barn on 4 Acre Manchester Estate
Manchester
9.2 out of 10, Wonderful, (12 reviews)
"Check in and communication were super great and easy. The property is absolutely stunning. House is plenty big for group of 10. The house itself is lovely but needs a little tlc in places. Overall a wonderful stay. "
United States
Alex H.
The price is £1,298
includes taxes & fees
16 Feb - 17 Feb
7200 sf Villa & Barn on 4 Acre Manchester Estate
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, (9 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 £1,030
includes taxes & fees
17 Feb - 18 Feb
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
The price is £410
includes taxes & fees
10 Mar - 11 Mar
Cozy 3 Bedroom Condo in the Heart of Manchester VT
Exterior

6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT

6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT
Manchester Center
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time."
United States
Neetesh B.
The price is £1,657
includes taxes & fees
3 Mar - 4 Mar
6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT
Exterior

95° Winter Pool, Hot Tub, Sauna, VIP Parking, Shuttle, EV Charging & more!

95° Winter Pool, Hot Tub, Sauna, VIP Parking, Shuttle, EV Charging & more!
Winhall
10.0 out of 10, Exceptional, (17 reviews)
"Great Property!!"
United States
David L.
The price is £4,172
includes taxes & fees
19 Feb - 20 Feb
95° Winter Pool, Hot Tub, Sauna, VIP Parking, Shuttle, EV Charging & more!
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, (102 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 £229
includes taxes & fees
16 Feb - 17 Feb
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
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 £250
includes taxes & fees
16 Feb - 17 Feb
Florida Mountain Log Cabin
Interior

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Dover
9.8 out of 10, Exceptional, (10 reviews)
"We enjoyed our stay."
United States
Anonymous traveller
The price is £381
includes taxes & fees
23 Feb - 24 Feb
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
TV, stereo

Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.0 out of 10, Wonderful, (4 reviews)
"This place is a perfect rustic getaway with easy convenience to town. The host was great. Spacious and super relaxing with nice view out back. "
United States
Thaddeus T.
The price is £307
includes taxes & fees
22 Feb - 23 Feb
Killington Retreat | Deck-Fire Pit-Mountain Views!
Fridge, oven, stovetop, dishwasher

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Londonderry
8.0 out of 10, Very good, (1 review)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
The price is £360
includes taxes & fees
16 Mar - 17 Mar
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Dining

Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near 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 £313
includes taxes & fees
2 Mar - 3 Mar
Chester Farmhouse Ski Retreat near Slopes
Outdoor dining

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is £357
includes taxes & fees
16 Feb - 17 Feb
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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 £455
includes taxes & fees
10 Mar - 11 Mar
14mi to Mt. Snow! Arcade, Private Suite, King Bed!
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

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"excellent "
Jacob 1-night trip
Posted 11 days ago
The Palmer House Resort, an Ascend Collection Hotel

Find out more about Bennington

Bennington Holiday Homes information

Number of reviews
391
Accommodation
238 Holiday Homes
Lowest Price
£182
Highest Price
£4,172