Vacation rentals in Londonderry

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Top-rated vacation rentals in Londonderry

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite
The exterior of a two-story contemporary home is depicted, featuring green-framed windows and a pathway lined with gravel. Adjacent grassy areas and trees create a natural setting. A blue flag flutters near the entrance, enhancing the welcoming feel of the property.
Home in Weston
4.96 out of 5 average rating, 313 reviews

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly

Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

Guest favourite
A charming treehouse is nestled in a snowy landscape, elevated on stilts with a wraparound deck. Soft white lights illuminate the exterior, while snow gently falls around it. A wooden staircase leads up to the entrance, highlighting the inviting ambiance.
Treehouse in Londonderry
4.88 out of 5 average rating, 158 reviews

Riverbed Treehouse @hot tub & a new sauna & views!

The beautiful & brand new Riverbed Treehouse with private sauna and a stunning new hot tub! Views all day long and wildly awesome sunsets!! Stratton mountain is right at your toes with a babbling brook turned raging river in the Spring! Beautiful woods & trails to explore. Stunning ridge line off the ski trails of Magic Mnt!! Close to town for quick shopping & coffee shops! Xcountry ski or snowshoe or walk our groomed trails!! FAST WiFi, nature lovers & a birdwatchers paradise!! @bentapplefarm

Top guest favourite
Tiny homes in Chester
4.99 out of 5 average rating, 106 reviews

Tiny A-Frame Rest House in Woods near Mountains

Newly built A-Frame getaway cabin built in the middle of the woods of Vermont. Unplug from it all at this special space surrounded by nature. Enjoy doing yoga and relaxing on the deck, remote working with fiber optic wifi, utilizing the fire pit to roast smores, or taking a walk around the walking paths on the property! There are also nearby hikes, swimming spots, skiing destinations, and drinking/eating spots! We are 35-40 minutes from Stratton, Mount Snow, Bromley, Okemo, and Magic Mountain!

Top guest favourite
Tiny homes in Wilmington
4.99 out of 5 average rating, 369 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Top guest favourite
An outdoor seating area features a stone pathway leading to wooden chairs arranged around a fire pit. The cabin's exterior showcases large windows and doors, framed by trees with autumn foliage, creating a welcoming ambiance.
Cabin in Londonderry
4.95 out of 5 average rating, 178 reviews

Holiday Ski Cabin in VT, Hot Tub, Fire Pit, Charm

We can’t wait to host you at Deerwood Hill in Londonderry VT! Featured on Levi Kelly's Cabin Tours! 🌲 Deerwood Hill is a private 3.6 acre private lot 🎿 Within minutes to Stratton, Magic, Bromley, Mt Snow, & Okemo ski resorts! 1 hour to Killington! 📍 Under 30 minutes to wonderful Manchester! ⛰️ 5 miles to Lowell State Park, 8 miles to Appalachian Trailhead ♥Sleeps 4 ♥2nd Bedroom is open loft with full bath ☒ Booking Guest must be 25. ☒ NO PARTIES, NO SMOKING, NO PETS @deerwoodhill

Top guest favourite
A rustic cottage is surrounded by vibrant flower pots, with a stone wall framing the entrance. A deck extends from the structure, featuring outdoor seating under a green umbrella. Trees provide shade in the background, while distant mountain views enhance the natural setting.
Cottage in Londonderry
4.96 out of 5 average rating, 231 reviews

Vermont Treehouse - Romantic Private Elegant

3 night minimum, unless prior approval, self checkin. Work remotely. This romantic, elegant, private getaway for two (or one) in our "Treehouse" with sleeping loft, full kitchen & bathroom, screened porch, deck, sauna, WiFi, BBQ grill, etc. Overlooking pasture & mountains. Enjoy the property with 3 miles hiking/snowshoe trails. Guest house on 160 acre private horse farm. Lots to do at nearby ski areas, shopping, hiking, biking, theater in summer. Or just relax. Discount for longer stays.

Top guest favourite
The rustic cabin sits amidst a lush green landscape, framed by towering trees. The stone chimney adds character, while the two separate structures showcase a combination of wood siding and modern roofing. Clear blue skies create a serene backdrop for the natural beauty.
Cabin in Landgrove
4.99 out of 5 average rating, 215 reviews

The Owl’s Nest in Landgrove

Our recently renovated cabin is the perfect escape during any season! Located within minutes of Bromley, Magic, and Stratton, Wild Wings, and Viking. Also nestled in an amazing network of hiking, biking and ski trails. Guests will never be more than a few minutes away from outdoor adventure. With two bedrooms and one bonus loft, guests can enjoy the comforts of our cozy cabin, including a full kitchen, bathroom, outdoor shower, HOT TUB, fire pit, WiFi and FREE EV CHARGING. @owlsnestvt

Top guest favourite
The chalet is set against a backdrop of trees, showcasing a combination of natural stone and wood siding. Multiple outdoor seating areas are visible, featuring colorful chairs with a fire pit nearby. Dim evening light gently illuminates the home, highlighting the windows and inviting ambiance.
Chalet in Jamaica
4.99 out of 5 average rating, 102 reviews

Designer Chalet w/ Mountain Views close to it all

A perfect little getaway. This stylish 3 bedroom/2 bath chalet is surrounded by endless outdoor activities. Swimming, hiking, biking, visiting the local waterfalls, golf courses, or rent an ATV from local outfit. This beautiful home is perfect for 6-8 people. Situated on 2.5 acres, this private setting with mountain views, has everything you need to feel at home. Multiple restaurants, cafes, markets for food, beer & wine less than a 5 min drive as well to sporting stores for supplies.

Guest favourite
Chalet in Jamaica
4.98 out of 5 average rating, 286 reviews

Classic Vermont A-Frame | Fire Pit | Near Stratton

Escape to a classic Vermont A-Frame in Jamaica, Vermont on a private wooded 3-acre property along scenic Route 100. Near Stratton Mountain, Mount Snow, Jamaica State Park, and Pike Falls, this peaceful mountain retreat is perfect for hiking, swimming holes, fall foliage, scenic drives, and outdoor adventures. Enjoy mornings on the screened porch and evenings around the fire pit listening to the river across the street under the Vermont stars.

Superhost
A modern cabin features a contrasting black exterior and wooden accents, nestled among lush trees. A wide deck with railing leads to the entrance, offering a welcoming space to enjoy the surrounding nature. Large windows provide ample natural light and views of the forest.
Tiny homes in Athens
4.86 out of 5 average rating, 176 reviews

LUXE Forest Retreat

Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

Guest favourite
Chalet in Peru
4.83 out of 5 average rating, 109 reviews

A-Frame | Floor-to-Ceiling Windows, Bromley 1mi

Floor-to-ceiling windows, soaring wood-paneled ceiling, and a natural brook outside the door. Classic Vermont A-Frame on a quiet gravel road in Peru — 1 mile from Bromley Mountain and the Appalachian Trail. King master with its own fireplace and French doors to the backyard. Living room fireplace, renovated kitchen and baths, lofted twin bedroom. Fast WiFi. Superhost Michael, 5.0 communication rating.

Guest favourite
A dining area is highlighted by a wooden table set for four, surrounded by light green chairs. Natural light fills the space through two large windows, while a vintage hutch displays colorful items against a contrasting gray wall.
Home in Londonderry
4.97 out of 5 average rating, 159 reviews

Wild Blossom Farmhouse - a lovely family getaway

Welcome to Wild Blossom Farmhouse! Conveniently located near Magic, Bromley, Stratton, and Okemo! At our little piece of Vermont, you will find farmhouse-style decor and furnishings, beautiful bright daytime light, and a delightful garden complete with treehouse, tree swing, and fire pit! ***Longterm Stays Allowed*** Four-legged friends welcome with an additional $75 per pet fee.

Popular amenities for Londonderry vacation rentals

When is the best time to visit Londonderry?

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Avg. price$490 CAD$465 CAD$381 CAD$268 CAD$275 CAD$275 CAD$310 CAD$310 CAD$296 CAD$344 CAD$310 CAD$476 CAD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Londonderry?

    Londonderry has more than 140 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Londonderry?

    Experience the best of Londonderry with our apartment rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Londonderry?

    Four-legged friends are welcome in Londonderry. Choose from more than 80 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Londonderry?

    Yes! Work meets play with ease at over 80 vacation rentals in Londonderry featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Londonderry vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Londonderry, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Londonderry have air conditioning?

    Absolutely! We offer over 50 house rentals with air conditioning in Londonderry. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Londonderry have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in Londonderry. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Londonderry have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Londonderry. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Londonderry have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in Londonderry. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Apartment Rentals in Londonderry?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with free parking, over 10 homes with wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Londonderry

  • Total vacation rentals

    Explore 170 vacation rentals in Londonderry

  • Nightly prices starting at

    Londonderry vacation rentals start at $124 CAD per night before taxes and fees

  • Verified guest reviews

    Over 10,690 verified reviews to help you choose

  • Family-friendly vacation rentals

    140 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    170 of Londonderry vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Londonderry rentals

  • 4.9 Average rating

    Londonderry stays are highly rated by guests—averaging 4.9 out of 5!

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