Holiday Homes in Bennington

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 June - 21 June
In four months
17 July - 19 July

Our top choices for Bennington holiday 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, (56 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is AU$375
includes taxes & fees
21 Apr - 22 Apr
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, (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 AU$1,232
includes taxes & fees
25 Mar - 26 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 AU$271
includes taxes & fees
25 Mar - 26 Mar
Cozy Home in Pownal VT
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 AU$798
includes taxes & fees
25 Mar - 26 Mar
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 AU$1,252
includes taxes & fees
6 Apr - 7 Apr
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
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 AU$1,064
includes taxes & fees
2 Apr - 3 Apr
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
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 AU$918
includes taxes & fees
6 Apr - 7 Apr
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
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 AU$602
includes taxes & fees
30 Mar - 31 Mar
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 AU$1,026
includes taxes & fees
14 Apr - 15 Apr
1812 House, 2 Stays, 1 home
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
Two Brooks Lodge
Interior

7200 sf Villa & Barn on 4 Acre Manchester Estate

7200 sf Villa & Barn on 4 Acre Manchester Estate
Manchester
9.4 out of 10, Exceptional, (13 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 AU$2,556
includes taxes & fees
24 Mar - 25 Mar
7200 sf Villa & Barn on 4 Acre Manchester Estate
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, (52 reviews)
"Had a great time."
United States
Neetesh B.
The price is AU$3,014
includes taxes & fees
30 Mar - 31 Mar
6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT
Exterior

Lakefront 9BR Retreat - Hot Tub + Game room + Sleeps 15

Lakefront 9BR Retreat - Hot Tub + Game room + Sleeps 15
Peru
The price is AU$4,268
includes taxes & fees
31 Mar - 1 Apr
Lakefront 9BR Retreat - Hot Tub + Game room + Sleeps 15
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 AU$442
includes taxes & fees
24 Mar - 25 Mar
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
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 AU$539
includes taxes & fees
4 Apr - 5 Apr
Killington Retreat | Deck-Fire Pit-Mountain Views!
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 AU$438
includes taxes & fees
24 Mar - 25 Mar
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, (15 reviews)
"We enjoyed our stay."
United States
Anonymous traveller
The price is AU$801
includes taxes & fees
1 Apr - 2 Apr
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
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 AU$590
includes taxes & fees
25 Mar - 26 Mar
Chester Farmhouse Ski Retreat near Slopes
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
7.0 out of 10, Good, (2 reviews)
"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 AU$694
includes taxes & fees
24 Mar - 25 Mar
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Exterior

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (24 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is AU$623
includes taxes & fees
24 Mar - 25 Mar
North Getaway Cottage
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

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Nice and clean hotel. A restaurant on the property, "Lost Marble Brewing Company", was convenient from the hotel. "
Etsuko 3-night trip
Posted 2 hours ago
Hampton Inn and Suites Manchester

Find out more about Bennington

Bennington Holiday Homes information

Number of reviews
339
Accommodation
238 Holiday Homes
Lowest Price
AU$271
Highest Price
AU$3,014