Old Bennington Vacation Rentals

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Browse Select Old Bennington Vacation Homes

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (5)
Contemporary Berkshire Home with Views of Taconic Golf Course

Peaceful Stay at Birds of a Feather Farm & Spa

9.6 out of 10, Exceptional, (20)
"Wonderful get away for the week in VT. Place was clean and beautiful, host was very helpful, and views were gorgeous! "
The price is CA $161
CA $370 total
includes taxes & fees
Aug 24 - Aug 25
Peaceful Stay at Birds of a Feather Farm & Spa

Mountain Sanctuary Dome Rustic Solitude 5BR

9.8 out of 10, Exceptional, (6)
"We had an awesome stay at Nate’s place! The stone architecture and wood oven fireplace gave a truly unique experience, and the house was very spacious. The fully equipped kitchen made for anxenjoyable cooking experience. Nate was also flexible and responsive. Definitely recommend this for your weekend getaway home!"
Mountain Sanctuary Dome Rustic Solitude 5BR

Room for the whole family 8 minutes to Manchester

10.0 out of 10, Exceptional, (5)
"Very priceable and great house with 5 bedrooms - each rooms are big and clean! Love it! Will come back again for next ski plan"
Room for the whole family 8 minutes to Manchester

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

10.0 out of 10, Exceptional, (223)
"Beautiful property. Very relaxing, secluded. "
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

10.0 out of 10, Exceptional, (46)
"We enjoyed our stay at the tiny home!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

The S T A C K HAUS on golf course/10 mins to Lake Witingham <br>

9.8 out of 10, Exceptional, (6)
The S T A C K HAUS on golf course/10 mins to Lake Witingham <br>

Art House! Spacious Getaway By Mass Moca

10.0 out of 10, Exceptional, (11)
"We had a great girls weekend e joying local trails, MassMOCA, local restaurants and this very clean, spacious house! Location is walkable to the museum and down town and we enjoyed a soak in the tub after a day of hiking in local conservation areas! "
Art House! Spacious Getaway By Mass Moca

My Abode: Heated Pool - Hot Tub, Tennis court, Firepit, Sauna, Gym, Hot Tub

My Abode: Heated Pool - Hot Tub, Tennis court, Firepit, Sauna, Gym, Hot Tub

Spyglass village- Golf & Ski

10.0 out of 10, Exceptional, (3)
"Great location, close to Mount Snow, ideal for skiing. Property is newly renovated, very functional and well appointed. We really enjoyed our stay."
Spyglass village- Golf & Ski

'Luna Stella' - West Dover Home 1 Mi to Mt Snow!

9.8 out of 10, Exceptional, (64)
"Great property. Enjoyed our stay."
'Luna Stella' - West Dover Home 1 Mi to Mt Snow!

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

9.0 out of 10, Wonderful, (44)
"We enjoyed our stay at the Blue House. Its size and location cannot be beat when it comes to group trips. We will be back!"
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

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

8.6 out of 10, Excellent, (31)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is CA $157
CA $399 total
includes taxes & fees
Aug 11 - Aug 12
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

9.6 out of 10, Exceptional, (8)
"The house was clean, nicely decorated, comfortable and all the amenities we needed! "
Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

9.8 out of 10, Exceptional, (93)
"This VRBO was stocked to the brim with everything you would need. It was on the boarder of three different states , nestled on five acres of private property. It was the perfect private weekend getaway . Highly recommend for any family looking for a ski trip. The host responded to anything we needed immediately. We will definitely be back, 5 out of 5."
The price is CA $259
CA $545 total
includes taxes & fees
Aug 18 - Aug 19
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+

6.0 out of 10, (1)
"Inside property was great - house was very fun and spacious and clean . HOWEVER..the driveway clearly hadn’t been plowed for a long time when we got there and so once we pulled in our cars were stuck. We were trapped at the house for 3 days. The plow driver came to plow the neighbor and told us he hadn’t been paid by the owners so hadn’t been plowing for some time The owners finally arranged for a different plow to come but not being able to leave for 3 days really affected our ability to...
Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+

Charming Berkshires Retreat – Minutes to Williamstown

6.0 out of 10, (2)
"This was the perfect little spot for our family to stop and stay on our way to dropping our daughter at camp and enjoy Williamstown. Our hike at the Clark Institute was a highlight along with the proximity to downtown’s great restaurants.We were talking about how gorgeous it must be in the fall… when it must be even more scenic and amazing."
Charming Berkshires Retreat – Minutes to Williamstown

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

10.0 out of 10, Exceptional, (5)
"Great house for skiing, within 5 minutes of Mt Snow and the shuttle seems very convenient. The house was great for 8 of us with plenty of room. "
The price is CA $613
CA $1,192 total
includes taxes & fees
Aug 11 - Aug 12
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Outdoor Enthusiasts Paradise in Beautiful Vermont!

10.0 out of 10, Exceptional, (15)
"Perfect rental for a great ski weekend with family."
Outdoor Enthusiasts Paradise in Beautiful Vermont!

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

10.0 out of 10, Exceptional, (13)
"Husband and i stayed for an overnight get-away. Perfect for relaxing, great views from porch. Great for a couple or small family"
The price is CA $246
CA $442 total
includes taxes & fees
Aug 11 - Aug 12
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
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