Londonderry Vacation Rentals

Compare 9 vacation rentals.
USA > Vermont > Londonderry

Make Londonderry your next getaway

Once a quaint, picturesque town to pass through, Londonderry has blossomed into a beloved vacation destination. With its stunning landscapes, rich history, and an array of attractions, this Vermont gem is perfect for family vacations and romantic getaways alike. Many of our Londonderry vacation rentals offer a cozy, bed-and-breakfast feel, located conveniently near the heart of town, just a short distance from all the activities and sights.

Explore Londonderry house rentals, condo rentals, and more

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House rentals

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Condo rentals

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Popular amenities for Londonderry vacation rentals

Popular
Dog-friendly Hot tub Internet
Sherwood Escape
3 Bedroom | 2 Bath | Sleeps 8 (4 Adults Max)

Sherwood Escape - Londonderry, VT

$212 avg / night
4.59 (49)
Justin Lake Lodge
8 Bedroom | 4 Bath | Sleeps 15

Justin Lake Lodge - Londonderry, VT

$1,099 avg / night
4.52 (25)
Sherwood Forest
3 Bedroom | 1.5 Bath | Sleeps 6

Sherwood Forest - Londonderry, VT

$185 avg / night
4.0 (8)
Haven on the Hill
5 Bedroom | 3.5 Bath | Sleeps 8

Haven on the Hill - Londonderry, VT

$485 avg / night
4.91 (11)
Cozy Cabin in the Woods
4 Bedroom | 3 Bath | Sleeps 8

Cozy Cabin in the Woods - Londonderry, VT

$316 avg / night
3.0 (3)

View 4 more homes

Recent Londonderry guest reviews

My family loved the layout and loved the size. The only downside was the cleanliness for some drawers in the kitchen but that was resolved quickly when I reached out to Vacasa.
Audrey H. | Oct 2024
This property was amazing. Very clean and very well stocked with the basics. The yard is super fun and has a swing set and lots of room to run around. The game room was a family favorite and we also spent a lot of time out on the deck! The lake, a short beautiful walk down a wooded path makes this home a must visit. Totally private and serene. Would absolutely stay again.
KEVIN M. | Sep 2024
The place was lovely and spacious. My old college friends and I came to raft the west river and this was the perfect spot to relax after a day on the river. A few minor issues with appliances/minor maintenance that I’m sure will be addressed but nothing that caused any real problems. Thank you again!
Patrick B. | Sep 2024
Londonderry vacation rental FAQ

Yes, 40 of our Londonderry homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 187 of our Londonderry vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Londonderry vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Londonderry team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Londonderry, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

Where is Londonderry, VT?

Nestled in the Green Mountains of southern Vermont, Londonderry provides a peaceful escape from the hustle and bustle of everyday life. It’s about 30 miles from Brattleboro and 100 miles from Albany, NY. While Londonderry offers a serene, secluded atmosphere, its proximity to major cities makes it an accessible retreat for travelers seeking both relaxation and adventure.

Things to Do in Londonderry

History enthusiasts will love exploring Londonderry's historical sites, such as the Londonderry Historical Society and the West River Railroad Museum. These attractions offer a glimpse into the town's rich past and the stories of its early settlers. Our Londonderry cabin rentals, from charming cottages to historic homes filled with antiques, reflect the town's unique architectural heritage.

Outdoor lovers will find plenty of activities in Londonderry. Hit the slopes at Magic Mountain Ski Resort, enjoy a hike through Lowell Lake State Park, or explore the beautiful trails of the Green Mountain National Forest. For those who prefer a more leisurely pace, a round of golf at the Stratton Mountain Golf Course or a stroll through the Farmers Market are excellent options.

After a day of adventure, unwind at one of Londonderry's dining spots. Enjoy a delicious meal at the New American Grill or sample local brews at the Londonderry Inn & Tavern. Whether you're seeking outdoor adventures, historical exploration, or simply a relaxing getaway, Londonderry has something for everyone.