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Old Bennington Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Old Bennington holiday rentals

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

1. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (10 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 HK$911
HK$1,609 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Home in Pownal VT
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

2. 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, (116 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 HK$1,476
HK$3,102 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A two-story house with a porch, surrounded by trees and snow.

3. 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 HK$1,256
HK$2,817 total
includes taxes & fees
13 Oct - 14 Oct
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
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
9.8 out of 10, Exceptional, (36 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 HK$565
HK$1,160 total
includes taxes & fees
14 Oct - 15 Oct
Getaway Near Mass MoCA, Great Hiking, Scenic Views
A bedroom with a bed, bedside tables, a window, and a radiator.

5. 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 HK$1,458
HK$3,701 total
includes taxes & fees
26 Oct - 27 Oct
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
"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. 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 HK$981
HK$2,171 total
includes taxes & fees
26 Oct - 27 Oct
New Studio 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)

7. 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 HK$965
HK$2,189 total
includes taxes & fees
4 Nov - 5 Nov
Downtown | Waterfront | Walk to Shops
A living room with a wooden floor, a central rug, a sofa, a coffee table, and a door with a 'GUEST' sign.

8. Peaceful Cottage Retreat

Peaceful Cottage Retreat
cambridge
9.8 out of 10, Exceptional, (50 reviews)
"Nice cozy little home Was well welcomed and host very communicative"
United States
Caleb N.
The price is HK$981
HK$1,490 total
includes taxes & fees
18 Oct - 19 Oct
Peaceful Cottage Retreat
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.

9. 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.
The price is HK$1,257
HK$2,255 total
includes taxes & fees
14 Oct - 15 Oct
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
"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 )

10. 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 HK$1,059
HK$2,375 total
includes taxes & fees
19 Oct - 20 Oct
2-Bdr Apt In Town, By the Water
Terrace/patio

11. Romantic New York Getaway near the Adirondacks

Romantic New York Getaway near the Adirondacks
Cambridge
The price is HK$939
HK$1,114 total
includes taxes & fees
13 Oct - 14 Oct
Romantic New York Getaway near the Adirondacks
Property grounds

12. 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.
The price is HK$984
HK$1,158 total
includes taxes & fees
13 Oct - 14 Oct
Runamuk Farm Camp Tiny House near Cambridge, New York
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

13. 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 HK$483
HK$2,399 total
includes taxes & fees
27 Oct - 28 Oct
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

14. Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
The price is HK$824
HK$2,830 total
includes taxes & fees
13 Oct - 14 Oct
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
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, (29 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is HK$1,000
HK$3,666 total
includes taxes & fees
20 Oct - 21 Oct
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A calm lake with a wooden boat on the shore.

16. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
The price is HK$785
HK$2,403 total
includes taxes & fees
1 Nov - 2 Nov
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Property grounds

17. Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (65 reviews)
"Excellent place, fantastic hosts, highly recommend."
United States
Mike K.
The price is HK$1,519
HK$2,131 total
includes taxes & fees
13 Oct - 14 Oct
Spacious apartment in beautiful, historic Arlington VT
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

18. 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.
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

19. 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 HK$1,406
HK$2,745 total
includes taxes & fees
13 Oct - 14 Oct
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A kitchen with white cabinets, a wooden dining table, and pendant lights.

20. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is HK$1,797
HK$3,804 total
includes taxes & fees
13 Oct - 14 Oct
A roomy remodeled retreat close to MassMoCA
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
"It was amazing other than no staff being on site. Breakfast was very slim, no many choices at all."
Grace 1-night trip
Posted 1 hour ago
Inn At Mount Snow

Find out more about Old Bennington

Search for holiday rentals in Old Bennington on Expedia! You can easily find your home rentals, villas, holiday apartments in Old Bennington using one of the methods below:

  • View our selection of featured holiday rentals in Old Bennington
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Look no further and take a look at our great range of rental properties in Old Bennington!

Frequently asked questions

Can I find a holiday rental in Old Bennington?

Yes, there are holiday rentals close to the most popular sights in Old Bennington, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Old Bennington has to offer?

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews: This holiday home rental outside of Old Bennington is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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

Explore the area and cultural attractions such as Bennington Museum, or visit one of the family-friendly sights such as Sugar Shack. In the wider area, you’ll find Bennington Battle Monument and Old First Congregational Church.

What’s a holiday rental in Old Bennington like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Old Bennington. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for families.