Bennington Holiday Rentals

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Holiday Rentals in Bennington

Lake life at Woodford Cottage

9.6 out of 10, Exceptional, (15)
"Perfect getaway for a family ski trip."
Lake life at Woodford Cottage

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

Mountain Sanctuary Dome Rustic Solitude 5BR

9.6 out of 10, Exceptional, (9)
"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

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

8.6 out of 10, Excellent, (34)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is NZ$540
includes taxes & fees
2 Oct - 3 Oct
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Bennington Gem w/ Smart TV Near Historic District!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We liked staying at the place as it had good amenities (washer, dryer, dishwasher, fridge with a freezer, fan, inflatable bed, wifi, cable, free parking spots. etc) and a lot of space. Where there is no central AC, it had a window unit which worked well - we had a comfortable stay in mid-July."
Bennington Gem w/ Smart TV Near Historic District!

VT at its best! Near hiking trails, museums & colleges.

10.0 out of 10, Exceptional, (1)
"The property was even more beautiful than the detailed photos depicted. It is secluded and private and yet, only a short drive to downtown.The interior finishes were homey and classy at the same time.Courtney is a fantastic host, who communicated thoroughly and responded promptly.If you’re looking for a quiet get away, you will love this property. "
VT at its best! Near hiking trails, museums & colleges.

Green Mountain Getaway

2.0 star property
9.8 out of 10, Exceptional, (15)
"Great Location -- place was spotless and very accommodating"
The price is NZ$643
includes taxes & fees
30 Oct - 31 Oct
Green Mountain Getaway

Meme's High Mountain Lake House

10.0 out of 10, Exceptional, (9)
"We loved this spot! From chilling by the water in the great yard and deck to explore nearby hiking spots, we couldn’t have asked for more! Jessica was very communicative as well. "
Meme's High Mountain Lake House

Perfect for a peaceful get away in clean fresh Vermont air!

10.0 out of 10, Exceptional, (76)
"Loved the place and the stay. The pictures don’t do it justice. Its was everything we hoped for and more."
Perfect for a peaceful get away in clean fresh Vermont air!

Charming 2-bedroom apartment in superb Bennington with WiFi

9.6 out of 10, Exceptional, (4)
"The pictures don’t do the listing justice, much bigger than the puctures suggest. The location is great with minutes away from Main St. (bars restaurants). Robin is also a great host! Really enjoyed our stay look forward to booking again next winter "
Charming 2-bedroom apartment in superb Bennington with WiFi

Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

10.0 out of 10, Exceptional, (4)
"The apartment was even better than the pictures. The beds were very comfortable and the location was excellent for walking around. There is no other place anyone should stay in Bennington besides this place."
Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

Breathtaking Mtn Views: Stylish Rustic Retreat!

3.0 star property
Breathtaking Mtn Views: Stylish Rustic Retreat!

Charming 3-bedroom cabin in Woodford private with mountain and pond view

Charming 3-bedroom cabin in Woodford private with mountain and pond view

Modern Woodford Estate, Lake, Mountain, VAST entrance

Modern Woodford Estate, Lake, Mountain, VAST entrance

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is NZ$622
includes taxes & fees
9 Oct - 10 Oct
Long Trail House at Stratton Mountain Resort

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (24)
"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "
The price is NZ$1,086
includes taxes & fees
2 Oct - 3 Oct
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Studio style farm stay

8.8 out of 10, Excellent, (33)
"Quaint room with lots of artistic charm. Convenient location. Well worth it."
Studio style farm stay

Long Trail House Studio at Stratton Mountain Resort

10.0 out of 10, Exceptional, (64)
"Incredible stay in the perfect location! Walking distance to everything at Stratton and amenities that are perfect after a long ski day. Highly recommend and would stay again!"
Long Trail House Studio at Stratton Mountain Resort

Stratton 1 Bedroom Long Trail Condo, Walk to Village and Lifts

9.6 out of 10, Exceptional, (54)
"Great, clean condo right near the village. It was a really nice place to stay and a good for a family of 4."
Stratton 1 Bedroom Long Trail Condo, Walk to Village and Lifts

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (234)
"Extremely cozy. Would highly recommend staying here."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
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 Bennington Hotel Reviews

Find out more about Bennington

Find out more about Bennington

Everything you need to know about 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 Bennington holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Bennington holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Bennington holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in 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 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 Bennington holiday rentals we have selected for you start as low as NZ$540 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Bennington rentals

At Expedia, we put the best 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 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 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 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 a holiday rental in Bennington?

Yes, there are holiday rentals close to the most popular sights in Bennington, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Bennington speak highly of the ski slopes and array of shops. While you're in the area, you can also enjoy the majestic mountain landscape and museums.

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

Your Vermont Mountain Haven Pet Friendly home with Hot tub!: This holiday home rental outside of Bennington is located in the mountains, and has a fireplace, a garden 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. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals will I find in Bennington?

With 15 Expedia holiday rentals, you're guaranteed to find just the right place for your Bennington stay.

What’s there to see and do in Bennington?

Enjoy the outdoors at Green Mountain National Forest and Harmen Hills Trail, or simply take in cultural attractions like Bennington Museum and Robert Frost Stone House Museum. While here, Old First Congregational Church and Bennington Battle Monument are other places worth a visit.

What’s a holiday rental in Bennington like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Bennington. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a family getaway.