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Search Vacation Homes in Old Bennington

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Our top choices for Old Bennington vacation homes

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

Vacation Home in Bennington

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
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.
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Fridge, microwave, oven, stovetop
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Vacation Home in Hoosick Falls

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
9.8 out of 10, Exceptional, (99)
"Quiet and relaxing property "
United States
Michelle S.
$278 nightly
The price is $309
Dec 16 - Dec 17
Total with taxes and fees
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
TV
Florida Mountain Log Cabin

Vacation Home in Florida

Florida Mountain Log Cabin
2.0 star property
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

Vacation Home in Sandgate

Mountain Dream Escape
2.0 star property
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.
Mountain Dream Escape
Exterior
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

Vacation Home in shushan

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
9.6 out of 10, Exceptional, (20)
"Lovely home. Very pet friendly. "
United States
Kimberly D.
$337 nightly
The price is $374
Dec 16 - Dec 17
Total with taxes and fees
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
House, 4 Bedrooms | View from property
Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Vacation Home in Arlington

Bear Pass - Mountain View 4 Bedroom Home by RedAwning
3.0 star property
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
$586 nightly
The price is $644
Dec 16 - Dec 17
Total with taxes and fees
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Interior
Bear Pass - Mountain View by RedAwning

Vacation Home in Sunderland

Bear Pass - Mountain View by RedAwning
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 16 - Dec 17
Total with taxes and fees
Bear Pass - Mountain View by RedAwning
Exterior
The Greylock Cabin

Vacation Home in Florida

The Greylock Cabin
10.0 out of 10, Exceptional, (4)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveler
$341 nightly
The price is $367
Dec 16 - Dec 17
Total with taxes and fees
The Greylock Cabin
Property grounds
Amanita Dome. All-inclusive food and drinks.

Vacation Home in Cambridge

Amanita Dome. All-inclusive food and drinks.
2.0 star property
$446 nightly
The price is $461
Dec 16 - Dec 17
Total with taxes and fees
Amanita Dome. All-inclusive food and drinks.
Interior
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Vacation Home in Dover

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
10.0 out of 10, Exceptional, (5)
"We enjoyed our stay."
United States
Anonymous traveler
$557 nightly
The price is $630
Dec 16 - Dec 17
Total with taxes and fees
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Dining
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

Vacation Home in Wilmington

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
10.0 out of 10, Exceptional, (17)
"Great place!"
United States
Jack & Heather G.
$651 nightly
The price is $700
Jan 12 - Jan 13, 2026
Total with taxes and fees
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Exterior
Two Brooks Lodge

Vacation Home in Bennington

Two Brooks Lodge
3.0 star property
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
Two Brooks Lodge
Smart TV, fireplace, video games, DVD player
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun

Vacation Home in Wilmington

Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun
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 16 - Dec 17
Total with taxes and fees
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun
Smart TV, fireplace, DVD player, table tennis
SKI-IN MOUNT SNOW, FREE SHUTTLE, POOL, FIREPLACE, BEARS CROSSING, PICKLEBALL CT

Vacation Home in Dover

SKI-IN MOUNT SNOW, FREE SHUTTLE, POOL, FIREPLACE, BEARS CROSSING, PICKLEBALL CT
10.0 out of 10, Exceptional, (12)
"Cozy place!"
United States
Preeti Y.
$632 nightly
The price is $714
Dec 16 - Dec 17
Total with taxes and fees
SKI-IN MOUNT SNOW, FREE SHUTTLE, POOL, FIREPLACE, BEARS CROSSING, PICKLEBALL CT
TV, fireplace
Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow

Vacation Home in Dover

Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow
2.0 star property
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.
$650 nightly
The price is $717
Jan 13 - Jan 14, 2026
Total with taxes and fees
Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow
Fridge, microwave, oven, stovetop
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Vacation Home in Dover

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
10.0 out of 10, Exceptional, (8)
"Nice in all respects,"
United States
Ken
$1,193 nightly
The price is $1,348
Dec 16 - Dec 17
Total with taxes and fees
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dining
Modern Mount Snow Gnarvana - Walk to Lodge & Lifts, Balcony, Loft

Vacation Home in Dover

Modern Mount Snow Gnarvana - Walk to Lodge & Lifts, Balcony, Loft
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 16 - Dec 17
Total with taxes and fees
Modern Mount Snow Gnarvana - Walk to Lodge & Lifts, Balcony, Loft
Smart TV, fireplace, video games, DVD player
Enjoy a dash of luxury & whimsy only 5 min from Mt. Snow!

Vacation Home in Dover

Enjoy a dash of luxury & whimsy only 5 min from Mt. Snow!
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.
$488 nightly
The price is $551
Dec 16 - Dec 17
Total with taxes and fees
Enjoy a dash of luxury & whimsy only 5 min from Mt. Snow!
TV, fireplace
Completely Updated 3 bdrm Home- Minutes from Mt. Snow and the Hermitage Club

Vacation Home in Wilmington

Completely Updated 3 bdrm Home- Minutes from Mt. Snow and the Hermitage Club
$942 nightly
The price is $1,064
Dec 18 - Dec 19
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

Valley Craft Ales

Valley Craft Ales

10/10 Excellent
"Very easy check in process. They let us know due to it being a pub, it would be loud, but it was very quiet and easy to sleep! The pub area was lovely and had a huge chimney fire for everyone to enjoy and keep warm. The room was clean and well kept! Great experience! "
Karen 1-night trip
Posted 3 days ago
Valley Craft Ales

Find out more about Old Bennington

Old Bennington Vacation Homes information

Number of reviews
306
Accommodation
330 Vacation Homes
Lowest Price
$309
Highest Price
$1,348

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