Old Bennington Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 24 - Aug 25
Tomorrow
Aug 25 - Aug 26
Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7

Vacation Rentals in Old Bennington

Park Street Penthouse Apartment
Game room

Park Street Penthouse Apartment

9.4 out of 10, Exceptional, (9)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
The price is ￥19,837
￥39,392 total
includes taxes & fees
Aug 25 - Aug 26
Park Street Penthouse Apartment
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Smart TV, fireplace, DVD player, music library

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

9.4 out of 10, Exceptional, (82)
"Nice place, just what we were looking for to stay the weekend. "
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Contemporary Berkshire Home with Views of Taconic Golf Course
Smart TV, fireplace, DVD player, books

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
Beautiful Lodging at Mount Snow with Hot Tub on Deck
Property grounds

Beautiful Lodging at Mount Snow with Hot Tub on Deck

9.4 out of 10, Exceptional, (41)
"Real Vermont feel. Pretty and nice quiet neighborhood!"
Beautiful Lodging at Mount Snow with Hot Tub on Deck
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Interior

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

10.0 out of 10, Exceptional, (6)
"Great house, great location, Great communication with Todd. Will be back for sure!!!! Thanks for everything Todd. "
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.
Terrace/patio

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.
Mountain Sanctuary Dome Rustic Solitude 5BR
Interior

Mountain Sanctuary Dome Rustic Solitude 5BR

9.8 out of 10, Exceptional, (7)
"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
Florida Mountain Log Cabin!
TV

Florida Mountain Log Cabin!

2.0 star property
10.0 out of 10, Exceptional, (3)
"Place was super clean. Beds were comfortable. Location was great."
The price is ￥27,000
￥58,360 total
includes taxes & fees
Sep 3 - Sep 4
Florida Mountain Log Cabin!
Reflections of Tranquility- Lakefront Splendor
Private kitchen

Reflections of Tranquility- Lakefront Splendor

10.0 out of 10, Exceptional, (3)
"Excellent all around! Loved the location, everything was clean and comfortable. Will definitely stay again! "
Reflections of Tranquility- Lakefront Splendor
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Exterior detail

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

9.8 out of 10, Exceptional, (93)
"We had another wonderful stay despite the weather, thank you for letting us enjoy your beautiful home"
The price is ￥23,804
￥53,824 total
includes taxes & fees
Aug 26 - Aug 27
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Seasons On Mount Snow - Ski-in/Ski-out
Indoor pool, a heated pool

Seasons On Mount Snow - Ski-in/Ski-out

9.8 out of 10, Exceptional, (171)
"Wonderful host / fantastic location "
Seasons On Mount Snow - Ski-in/Ski-out
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
Exterior

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

8.8 out of 10, Excellent, (3)
"Perfect cottage on the water!! Enjoyed kayaking and pedal boat with family. Beautiful greenery! Very quick respond."
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (6)
"Nice in all respects,"
The price is ￥65,462
￥127,274 total
includes taxes & fees
Aug 25 - Aug 26
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Exterior

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

10.0 out of 10, Exceptional, (15)
"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 ￥26,317
￥46,825 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Outdoor spa tub

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!
Mountains, pond, old barn, hiking trails- quintessential Vermont
Property grounds

Mountains, pond, old barn, hiking trails- quintessential Vermont

9.4 out of 10, Exceptional, (110)
"The accommodations for our week’s vacation were awesome. The home was beautiful, the goats and chickens enjoyed by all, and the views of the autumn foliage from the back porch were amazing. "
Mountains, pond, old barn, hiking trails- quintessential Vermont
Private Indoor Heated Pool + Hot Tub + Fire Pit + Pond, on 35 Acres - sleeps 20
Exterior

Private Indoor Heated Pool + Hot Tub + Fire Pit + Pond, on 35 Acres - sleeps 20

9.2 out of 10, Wonderful, (5)
"Amazing stay in Hoosick! The kids loved the pool and the the views from the property were stunning"
Private Indoor Heated Pool + Hot Tub + Fire Pit + Pond, on 35 Acres - sleeps 20
Studio style farm stay
Terrace/patio

Studio style farm stay

8.8 out of 10, Excellent, (31)
"Quaint room with lots of artistic charm. Convenient location. Well worth it."
Studio style farm stay
Red Country Escape with Mountain Views
Smart TV, fireplace, video games, books

Red Country Escape with Mountain Views

Red Country Escape with Mountain Views
Charming 1-bedroom condo in delightful Dover
Fridge, microwave, oven, stovetop

Charming 1-bedroom condo in delightful Dover

10.0 out of 10, Exceptional, (1)
"The place was nice. It was clean, lots of supplies were provided, and it was in a great location. The host contacted me the day before, letting me know that the wifi was out, and the technician was unavailable until the next week. I was appreciative of the heads up. Unfortunately, the TV was unusable without wifi, no option to watch local channels. Cellular (Verizon) data was non-existent throughout the majority of daytime hours. Despite this smallish issue, I would stay here again! "
The price is ￥15,723
￥29,722 total
includes taxes & fees
Sep 4 - Sep 5
Charming 1-bedroom condo in delightful Dover
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Old Bennington Hotel Reviews

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

10/10 Excellent
"Staff were wonderful. Bethany at the front desk was friendly and helpful!Very clean. Have stayed here numerous times and always have fun. It’s a good area with cute shops."
Janice 2-night trip
Posted 2 days ago
Hotel Downstreet, Ascend Hotel Collection

Frequently asked questions

Can I find a vacation rental in Old Bennington?

Yes, you can find vacation rentals near the most popular points of interest in Old Bennington, or you can choose a more remote option if you're looking for relaxation.

What are some of the best vacation home rentals in Old Bennington?

Contemporary Berkshire Home with Views of Taconic Golf Course: This vacation home rental outside of Old Bennington offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Old Bennington?

Explore the area and cultural attractions such as Bennington Museum, or visit a family-friendly sight such as Sugar Shack. Other places in town to visit include Old First Congregational Church and Bennington Battle Monument.

What’s a vacation rental in Old Bennington like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Old Bennington. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for family trips or small group gatherings.