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Search Vacation Homes in Old Bennington

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Dec 19 - Dec 21
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Jan 9 - Jan 11
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Our top choices for Old Bennington vacation homes

Fridge, microwave, oven, stovetop
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

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Bennington
8.6 out of 10, Excellent, (34)
"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.
$256 nightly
The price is $272
Dec 14 - Dec 15
Total with taxes and fees
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Exterior detail
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!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
9.8 out of 10, Exceptional, (99)
"Quiet and relaxing property "
United States
Michelle S.
$280 nightly
The price is $311
Dec 14 - Dec 15
Total with taxes and fees
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
TV
Florida Mountain Log Cabin

Florida Mountain Log Cabin

Florida Mountain Log Cabin
2.0 star property
Florida
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
$316 nightly
The price is $339
Dec 22 - Dec 23
Total with taxes and fees
Florida Mountain Log Cabin
Terrace/patio
Mountain Dream Escape

Mountain Dream Escape

Mountain Dream Escape
2.0 star property
Sandgate
10.0 out of 10, Exceptional, (1)
"Beautiful location and home! The apartment was beautifully decorated and so cozy. The hot tub was a great place for stargazing! It was wonderful for our anniversary weekend but would also be great for a longer stay.Great communication with hosts and they were super helpful when we had a minor issue with check in."
United States
Morgan C.
$440 nightly
The price is $493
Dec 15 - Dec 16
Total with taxes and fees
Mountain Dream Escape
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

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
shushan
9.6 out of 10, Exceptional, (20)
"Lovely home. Very pet friendly. "
United States
Kimberly D.
$333 nightly
The price is $370
Dec 14 - Dec 15
Total with taxes and fees
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Property grounds
Amanita Dome. All-inclusive food and drinks.

Amanita Dome. All-inclusive food and drinks.

Amanita Dome. All-inclusive food and drinks.
2.0 star property
Cambridge
$441 nightly
The price is $455
Dec 15 - Dec 16
Total with taxes and fees
Amanita Dome. All-inclusive food and drinks.
Exterior
North Getaway Cottage

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (24)
"The cottage was the perfect accommodations for our overnight stay in town for a funeral. Thank you Claudia. "
United States
Mary Alice H.
$427 nightly
The price is $477
Dec 14 - Dec 15
Total with taxes and fees
North Getaway Cottage
House, 4 Bedrooms | Exterior
Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Bear Pass - Mountain View 4 Bedroom Home by RedAwning
3.0 star property
Arlington
8.0 out of 10, Very Good, (1)
"Cozy cottage. Very clean and everything you need is there. Nice kitchen and fireplace. Lots of room and 3 bathrooms as well. Reasonably close to the ski mountains. "
United States
Manish
$583 nightly
The price is $641
Dec 20 - Dec 21
Total with taxes and fees
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Fridge, microwave, oven, stovetop
The Greylock Cabin

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (4)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveler
$344 nightly
The price is $370
Dec 15 - Dec 16
Total with taxes and fees
The Greylock Cabin
Smart TV, fireplace, table tennis
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.

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Dover
10.0 out of 10, Exceptional, (5)
"We enjoyed our stay."
United States
Anonymous traveler
$557 nightly
The price is $630
Dec 15 - Dec 16
Total with taxes and fees
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Smart TV, fireplace, video games, offices
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (17)
"Great place!"
United States
Jack & Heather G.
$583 nightly
The price is $623
Dec 17 - Dec 18
Total with taxes and fees
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Exterior
Bear Pass - Mountain View by RedAwning

Bear Pass - Mountain View by RedAwning

Bear Pass - Mountain View by RedAwning
Sunderland
9.6 out of 10, Exceptional, (5)
"We loved our stay at Bear Pass! The kitchen was more than adequately stocked. The hous was great for our extended family and our 3 dogs"
United States
Megan G.
$599 nightly
The price is $671
Dec 14 - Dec 15
Total with taxes and fees
Bear Pass - Mountain View by RedAwning
Outdoor spa tub
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun

Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun

Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun
Wilmington
10.0 out of 10, Exceptional, (52)
"We were a group of 11 and we had a great weekend. Comfortable to stay and plenty to do!"
United States
Olivia R.
$664 nightly
The price is $750
Dec 15 - Dec 16
Total with taxes and fees
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun
Panoramic House | Private kitchen
Two Brooks Lodge

Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3)
"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
$240 nightly
The price is $250
Dec 14 - Dec 15
Total with taxes and fees
Two Brooks Lodge
TV, fireplace
Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow

Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow

Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow
2.0 star property
Dover
9.0 out of 10, Wonderful, (2)
"Weekend stay.Clean, comfortable, well equipped. Was as advertised.I would stay there again"
United States
Noah K.
$640 nightly
The price is $706
Jan 13 - Jan 14, 2026
Total with taxes and fees
Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow
Interior
Modern Mount Snow Gnarvana - Walk to Lodge & Lifts, Balcony, Loft

Modern Mount Snow Gnarvana - Walk to Lodge & Lifts, Balcony, Loft

Modern Mount Snow Gnarvana - Walk to Lodge & Lifts, Balcony, Loft
Dover
10.0 out of 10, Exceptional, (20)
"Super nice place (very clean and modern) in a quiet area."
United States
Pete N.
$509 nightly
The price is $575
Dec 15 - Dec 16
Total with taxes and fees
Modern Mount Snow Gnarvana - Walk to Lodge & Lifts, Balcony, Loft
Outdoor pool, a heated pool
SKI-IN MOUNT SNOW, FREE SHUTTLE, POOL, FIREPLACE, BEARS CROSSING, PICKLEBALL CT

SKI-IN MOUNT SNOW, FREE SHUTTLE, POOL, FIREPLACE, BEARS CROSSING, PICKLEBALL CT

SKI-IN MOUNT SNOW, FREE SHUTTLE, POOL, FIREPLACE, BEARS CROSSING, PICKLEBALL CT
Dover
10.0 out of 10, Exceptional, (12)
"Cozy place!"
United States
Preeti Y.
$632 nightly
The price is $714
Dec 14 - Dec 15
Total with taxes and fees
SKI-IN MOUNT SNOW, FREE SHUTTLE, POOL, FIREPLACE, BEARS CROSSING, PICKLEBALL CT
Fridge, microwave, oven, stovetop
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (8)
"Nice in all respects,"
United States
Ken
$1,230 nightly
The price is $1,389
Dec 14 - Dec 15
Total with taxes and fees
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Property grounds
Enjoy a dash of luxury & whimsy only 5 min from Mt. Snow!

Enjoy a dash of luxury & whimsy only 5 min from Mt. Snow!

Enjoy a dash of luxury & whimsy only 5 min from Mt. Snow!
Dover
10.0 out of 10, Exceptional, (38)
"Everything about the Lemondrop Lodge was first class. From check in to check out, communication with the owner was quick and responsive. If you’re on the fence at all comparing this property to another, don’t hesitate to book the lemondrop lodge. You won’t be disappointed. "
United States
David M.
$671 nightly
The price is $758
Dec 14 - Dec 15
Total with taxes and fees
Enjoy a dash of luxury & whimsy only 5 min from Mt. Snow!
Microwave, oven, stovetop, dishwasher
Completely Updated 3 bdrm Home- Minutes from Mt. Snow and the Hermitage Club

Completely Updated 3 bdrm Home- Minutes from Mt. Snow and the Hermitage Club

Completely Updated 3 bdrm Home- Minutes from Mt. Snow and the Hermitage Club
Wilmington
$924 nightly
The price is $1,044
Dec 15 - Dec 16
Total with taxes and fees
Completely Updated 3 bdrm Home- Minutes from Mt. Snow and the Hermitage Club
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 Old Bennington Hotel Reviews

Knotty Pine

Knotty Pine

10/10 Excellent
"Yes"
Clark 3-night trip
Posted 4 days ago
Knotty Pine

Find out more about Old Bennington

Old Bennington Vacation Homes information

Number of reviews
330
Accommodation
323 Vacation Homes
Lowest Price
$250
Highest Price
$1,389

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