Old Bennington Holiday Rentals

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Holiday Rentals in Old Bennington

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

Spacious apartment in beautiful, historic Arlington VT

10.0 out of 10, Exceptional, (51)
"Great place—though it’s a basement, it’s nearly perfect. We’d definitely stay here again"
The price is AU$336
includes taxes & fees
2 Oct - 3 Oct
Spacious apartment in beautiful, historic Arlington VT

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (8)
"Lovely property. Well kept house, nicely decorated. Very much enjoyed our stay."
Contemporary Berkshire Home with Views of Taconic Golf Course

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

10.0 out of 10, Exceptional, (7)
"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.

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

9.4 out of 10, Exceptional, (82)
"This unique hideaway was great for our family. The open layout might not work for everyone, but suited us just fine! We were only here a couple nights but enjoyed the location and using the hot tub! "
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

Beautiful Lodging at Mount Snow with Hot Tub on Deck

9.4 out of 10, Exceptional, (42)
"Real Vermont feel. Pretty and nice quiet neighborhood!"
Beautiful Lodging at Mount Snow with Hot Tub on Deck

Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq

10.0 out of 10, Exceptional, (5)
"My friends and I had an awesome weekend staying here. The house itself was gorgeous - the view was great, interior design and feel were cozy and beautiful, and we had a lot of space. The showers were a favorite among the group. We did several hikes and swam at a swimming hole, all on the property. It was also within driving distance of other awesome hikes too (waterfalls, etc.). The hosts had a lot of helpful information and suggestions about the area and things to do. We will definitely be...
Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq

Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

10.0 out of 10, Exceptional, (84)
"A beautiful cabin in the woods. Very clean and a perfect stay."
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

10.0 out of 10, Exceptional, (224)
"Great house, fantastically well equipped (kayaks, bikes etc). Excellent, very responsive host. View out over the lake is amazing. Really enjoyed our stay. "
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Lake life at Woodford Cottage

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

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

10.0 out of 10, Exceptional, (228)
"Beautiful property. Very relaxing, secluded. "
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow

10.0 out of 10, Exceptional, (134)
"This was our second time renting this property for a quick ski trip. The property is spacious, and well appointed. It really offers everything you need for a relaxing ski vacation. Love the game room and the space."
Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow

Waterfalls-View-Pond. Secluded Vermont Log Cabin at Mount Snow. EV Outlet

10.0 out of 10, Exceptional, (81)
"Perfectly clean and welcoming cabin. Comfy beds, great location. Would definitely return. "
Waterfalls-View-Pond. Secluded Vermont Log Cabin at Mount Snow. EV Outlet

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

9.8 out of 10, Exceptional, (46)
"Great space in house. Great that each room had its own bathroom "
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Room for the whole family 8 minutes to Manchester

10.0 out of 10, Exceptional, (7)
"Very priceable and great house with 5 bedrooms - each rooms are big and clean! Love it! Will come back again for next ski plan"
Room for the whole family 8 minutes to Manchester

The Myrtle House Heated Pool-Hot Tub, Tennis court, Firepit, Sauna, Gym, Hot Tub

The Myrtle House Heated Pool-Hot Tub, Tennis court, Firepit, Sauna, Gym, Hot Tub

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

9.0 out of 10, Wonderful, (46)
"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!

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

9.8 out of 10, Exceptional, (177)
"I would recommend this place. It was very enjoyable. Stay love the area and the staff at the swimming pool were very nice."
Seasons On Mount Snow - Ski-in/Ski-out

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

8.6 out of 10, Excellent, (31)
"The apartment was in a great location to get to the ski lifts. "
The price is AU$425
includes taxes & fees
30 Sept - 1 Oct
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

The Greylock Cabin - True Cabin in the woods on 30 acres. Pet-Friendly

10.0 out of 10, Exceptional, (3)
"Wonderful view, peaceful quiet area, cosy cabin."
The price is AU$705
includes taxes & fees
6 Oct - 7 Oct
The Greylock Cabin - True Cabin in the woods on 30 acres. Pet-Friendly
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

Find out more about Old Bennington

Find out more about Old Bennington

Everything you need to know about Old 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 Old 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 Old Bennington holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Old Bennington holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Old 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Old 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 Old Bennington holiday rentals we have selected for you start as low as AU$336 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Old Bennington rentals

At Expedia, we put the best Old 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 Old 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 Old 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 Old 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 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?

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. : This holiday home rental outside of Old 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.

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. Other places in town to visit include Old First Congregational Church and Bennington Battle Monument.

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.