Photo by Laury Kelly

Holiday Rentals in North Bennington

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in North Bennington

Florida Mountain Log Cabin

2.0 star property
Florida
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is €300
includes taxes & fees
1 Dec - 2 Dec
Florida Mountain Log Cabin

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

Dover
9.4 out of 10, Exceptional, (16)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is €220
includes taxes & fees
1 Dec - 2 Dec
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Private cabin: 7 mins to slopes, wood fireplace

2.0 star property
Dover
9.6 out of 10, Exceptional, (5)
"We spent the week, excellent location and the home was exactly as described in listing."
United States
Chris R.
The price is €725
includes taxes & fees
1 Dec - 2 Dec
Private cabin: 7 mins to slopes, wood fireplace

Long Trail House at Stratton Mountain Resort

3.0 star property
Stratton
8.6 out of 10, Excellent, (77)
"Nice, clean room in prime location"
United States
Kristin
The price is €423
includes taxes & fees
1 Dec - 2 Dec
Long Trail House at Stratton Mountain Resort

Cozy, welcoming, 3-bedroom cabin abutting the Green Mountain National Forest!

Woodford
10.0 out of 10, Exceptional, (1)
"This Cozy Cabin was amazing. Chris and Nicole were great hosts who were very responsive and courteous to make our trip as relaxing as we needed. They left detailed instructions on how the place operated and made sure the place was ready to go for when we arrived. If you want to get away for some peace and quiet whether it be for a day or a week, I highly recommend this spot. We would absolutely book with them again!! "
United States
Evan M.
The price is €399
includes taxes & fees
2 Dec - 3 Dec
Cozy, welcoming, 3-bedroom cabin abutting the Green Mountain National Forest!

Green Mountain Getaway

2.0 star property
Bennington
9.6 out of 10, Exceptional, (18)
"Great one night stay for a work trip. Common living space and bedrooms are very large. Very clean especially the bathroom. "
United States
Robyn H.
The price is €383
includes taxes & fees
12 Dec - 13 Dec
Green Mountain Getaway

Mountain Dream Escape

2.0 star property
Sandgate
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.
The price is €401
includes taxes & fees
8 Dec - 9 Dec
Mountain Dream Escape

New Studio In Town, By the Water

Williamstown
10.0 out of 10, Exceptional, (10)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is €228
includes taxes & fees
1 Dec - 2 Dec
New Studio In Town, By the Water

The Greylock Cabin

Florida
10.0 out of 10, Exceptional, (4)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveller
The price is €386
includes taxes & fees
8 Dec - 9 Dec
The Greylock Cabin

The Birchwood Cabin - Stunning Mountain Views

2.0 star property
Sunderland
10.0 out of 10, Exceptional, (2)
"This cabin was everything we could have asked for! Great, peaceful location with a beautiful view. Tastefully decorated and wonderful open concept for kitchen and living room set-up. We really enjoyed the game room downstairs, too. We will definitely be back soon."
United States
Shannon C.
The price is €588
includes taxes & fees
8 Dec - 9 Dec
The Birchwood Cabin - Stunning Mountain Views

Sowilo Retreat All-Inclusive Maple House

Cambridge
10.0 out of 10, Exceptional, (1)
The price is €476
includes taxes & fees
1 Dec - 2 Dec
Sowilo Retreat All-Inclusive Maple House

Amanita Dome. All-inclusive food and drinks.

2.0 star property
Cambridge
The price is €409
includes taxes & fees
2 Dec - 3 Dec
Amanita Dome. All-inclusive food and drinks.

The Allen House historic North Adams Home in the Berkshire Mountains

2.0 star property
North Adams
The price is €338
includes taxes & fees
13 Dec - 14 Dec
The Allen House historic North Adams Home in the Berkshire Mountains

Bear Pass - Mountain View 4 Bedroom Home by RedAwning

3.0 star property
Arlington
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
The price is €569
includes taxes & fees
1 Dec - 2 Dec
Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Charming 1-bedroom condo in delightful Dover

Dover
9.6 out of 10, Exceptional, (7)
"Easy to find. Good communication helped, but the sliding door was a little wonky. Additional security for single female travelers would be nice. A bedside table would be useful. All the amenities you would ever need."
United States
Tia
Charming 1-bedroom condo in delightful Dover

Bear Pass - Mountain View by RedAwning

Sunderland
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.
The price is €601
includes taxes & fees
1 Dec - 2 Dec
Bear Pass - Mountain View by RedAwning

Charming 3-bedroom condo in serene Wilmington - Your home away from home!

Wilmington
10.0 out of 10, Exceptional, (1)
"Beautiful condo that is spacious in a quiet spot"
United States
Linda
The price is €573
includes taxes & fees
1 Dec - 2 Dec
Charming 3-bedroom condo in serene Wilmington - Your home away from home!

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

Hoosick Falls
9.8 out of 10, Exceptional, (99)
"Quiet and relaxing property "
United States
Michelle S.
The price is €275
includes taxes & fees
1 Dec - 2 Dec
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

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

Dover
9.8 out of 10, Exceptional, (22)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
United States
SZU YIN C.
The price is €358
includes taxes & fees
15 Dec - 16 Dec
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres

Stratton
10.0 out of 10, Exceptional, (5)
"We had an amazing stay. It was the perfect location for 4 couples. The owners were super responsive. Amenities were great (our only kitchen recommendation is a non-glass cutting board and individual salt and pepper shakers). Would love to stay again in the summer next time! "
United States
Nicholas D.
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
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

Top North Bennington Hotel Reviews

Find out more about North Bennington

Everything you need to know about North Bennington holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the North Bennington holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect North Bennington holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

North Bennington holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in North Bennington. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A North Bennington holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of North Bennington holiday rentals we have selected for you start as low as €220 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on North Bennington rentals

At Expedia, we put the best North Bennington holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top North Bennington rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream North Bennington holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around North Bennington. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in North Bennington?

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

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

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. : This holiday home rental outside of North Bennington is located in the mountains, and has a fireplace, a patio and laundry facilities to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

How many holiday rentals are there in North Bennington?

Expedia has 3 holiday rentals for your stay in North Bennington.

What can I see and do in North Bennington?

While exploring the area, visit family-friendly sights like Sugar Shack, or get outside and enjoy nature at Green Mountain National Forest. In the wider area, you’ll find Bennington College and Park McCullough House.

What’s a holiday rental in North Bennington like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in North Bennington. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll feel right 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 concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a small group gathering.