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Old Bennington Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Old Bennington vacation rentals

A two-story house with a porch, surrounded by trees and snow.

1. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 reviews)
"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.
The price is AED 680
AED 1,438 total
includes taxes & fees
2 Oct - 3 Oct
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A red house with a porch, surrounded by a grassy yard and trees.

2. 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
The price is AED 642
AED 1,655 total
includes taxes & fees
2 Oct - 3 Oct
Two Brooks Lodge
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

3. 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, (115 reviews)
"This is the third time we’ve stayed at this lovely home and it’s always a treat! Very clean, with a Well stocked kitchen, comfy beds and huge back yard plus a fenced in portion, your dog will love-close to Bennington and walking trails with lots to do. A home away from home! "
United States
Anita T.
The price is AED 691
AED 1,452 total
includes taxes & fees
3 Oct - 4 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A two-story blue house with a porch, surrounded by a garden with orange flowers.

4. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (35 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
The price is AED 314
AED 599 total
includes taxes & fees
4 Oct - 5 Oct
Getaway Near Mass MoCA, Great Hiking, Scenic Views
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

5. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (9 reviews)
"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 AED 426
AED 749 total
includes taxes & fees
8 Oct - 9 Oct
Cozy Home in Pownal VT
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

6. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (12 reviews)
"We had a great stay here. Clean, well-equipped, great location. Hope to come back again!"
United States
Tricia
The price is AED 477
AED 1,062 total
includes taxes & fees
25 Oct - 26 Oct
Downtown | Waterfront | Walk to Shops
A bedroom with a bed, bedside tables, a window, and a radiator.

7. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
The price is AED 619
AED 1,652 total
includes taxes & fees
6 Oct - 7 Oct
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

8. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is AED 226
AED 1,156 total
includes taxes & fees
26 Oct - 27 Oct
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
"Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping." ...Lina -- "the fire pit and creek are like a private oasis in the backyard." ... Nachama -- ( no firewood fees )

9. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (21 reviews)
"Great place with easy access to town and even better access to a nice spot to hangout by the creek. I will definitely stay here again."
United States
Thomas
The price is AED 533
AED 1,158 total
includes taxes & fees
6 Oct - 7 Oct
2-Bdr Apt In Town, By the Water
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

10. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (19 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is AED 477
AED 1,041 total
includes taxes & fees
4 Oct - 5 Oct
New Studio In Town, By the Water
A wicker sofa with a floral cushion, a wicker table with magazines, and a standing fan in a room with large windows and wooden floors.

11. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
8.0 out of 10, Very good, (2 reviews)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
A living room with a wooden floor, a central rug, a sofa, a coffee table, and a door with a 'GUEST' sign.

12. Peaceful Cottage Retreat

Peaceful Cottage Retreat
cambridge
9.8 out of 10, Exceptional, (49 reviews)
"Nice cozy little home Was well welcomed and host very communicative"
United States
Caleb N.
The price is AED 459
AED 693 total
includes taxes & fees
4 Oct - 5 Oct
Peaceful Cottage Retreat
A picnic table in a natural setting with a view of a hilly landscape.

13. Runamuk Farm Camp Tiny House near Cambridge, New York

Runamuk Farm Camp Tiny House near Cambridge, New York
Cambridge
10.0 out of 10, Exceptional, (4 reviews)
"Phenomenal site, with stunning views. Highly recommend!"
United States
Jess M.
Runamuk Farm Camp Tiny House near Cambridge, New York
A cabin with a large window, surrounded by trees, and a hammock in front.

14. Romantic New York Getaway near the Adirondacks

Romantic New York Getaway near the Adirondacks
Cambridge
The price is AED 440
AED 521 total
includes taxes & fees
7 Oct - 8 Oct
Romantic New York Getaway near the Adirondacks
A spacious living area with a brown leather sofa, a wooden coffee table, and wicker chairs. A staircase leads to an upper level.

15. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.4 out of 10, Exceptional, (28 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is AED 484
AED 1,742 total
includes taxes & fees
27 Oct - 28 Oct
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

16. 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, (24 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
The price is AED 658
AED 1,285 total
includes taxes & fees
4 Oct - 5 Oct
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

17. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is AED 1,116
AED 2,273 total
includes taxes & fees
7 Oct - 8 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A spacious indoor area with multiple wooden tables and green chairs, large windows offering a view of a snowy mountain, and a stone fireplace with a fire.

18. Modern Mount Snow Gnarvana - Steps to Carinthia

Modern Mount Snow Gnarvana - Steps to Carinthia
Dover
10.0 out of 10, Exceptional, (26 reviews)
"Perfect for our getaway, convenient for getting to the slopes and a beautiful area to visit"
United States
Lynn B.
The price is AED 678
AED 1,820 total
includes taxes & fees
5 Oct - 6 Oct
Modern Mount Snow Gnarvana - Steps to Carinthia
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

19. 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, (21 reviews)
"Beautiful home and property with quick access to a clubhouse with a gym, indoor and outdoor pools, and hot tub. Great for our family trip (including two kids) and lots of games/entertainment for the kids. The house had everything we needed (including kitchenware needed for cooking and preparing food)."
United States
Natalie
The price is AED 720
AED 2,102 total
includes taxes & fees
6 Oct - 7 Oct
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
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

Inn At Mount Snow

Inn At Mount Snow

10/10 Excellent
"We absolutely enjoyed the property. Our room had a fireplace. The bed was very comfortable. There was a pool table and games to play. One of the best places we have stayed at!"
James 1-night trip
Posted 2 hours ago
Inn At Mount Snow

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?

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews: This vacation home rental outside of Old Bennington is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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. In the larger area, you’ll find Bennington Battle Monument and Old First Congregational Church.

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.