Holiday rentals in Londonderry

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Top-rated holiday rentals in Londonderry

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Top guest favourite
A cozy tiny cabin, constructed with wooden beams and a sloped roof, is situated among tall trees. The porch features a railing, inviting seating, and a lantern. Sunlight filters through the foliage, casting a soft glow on the forest floor covered in pine needles.
Treehouse in Brookline
4.98 out of 5 average rating, 257 reviews

Glamping Cabin with Hot Tub on Flower Farm

<b>Vermont's Most Wish Listed</b> ﹏﹏﹏ Nestled in a wooded grove on Tanglebloom Flower Farm, this unforgettable glamping-inspired farm stay invites you to escape the everyday & immerse yourself in nature - comfortably. Designed with a clear roof looking up to the trees and screened sides to let in the breeze, the handmade tiny cabin invites you to slow down. Explore southern Vermont's hikes, farmer's markets & swimming holes or stay put. Perfect for a romantic couples retreat or solo getaway.

Top guest favourite
Home in Londonderry
4.92 out of 5 average rating, 103 reviews

VT Cabin sitting above the West River and Village

Converted in 1967 this 1 bedroom, 1 bathroom cozy cabin was once a tractor shed for the historical William's Mills along the West River. It now sits on 12 acres on a country dirt road overlooking the river and the Village. Amenities (stores, dining) are a 1-minute drive, and there are walking trails at the end of the road. It's a great Vermont getaway with ski mountains, Stratton, Bromley, and Magic just minutes away! Cross-country skiing, snowshoeing, and the VT Country store nearby!Yes, Wi-fi!

Guest favourite
The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.
Cabin in Londonderry
4.95 out of 5 average rating, 240 reviews

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

Top guest favourite
A spacious living area features a central stone fireplace, surrounded by cozy seating. Large windows frame scenic views of the trees outside, filling the space with natural light. The rustic wooden beams and walls add warmth, while the open layout connects to the kitchen and loft above.
Barn in Andover
4.99 out of 5 average rating, 147 reviews

Fat Cat Barn - Close Okemo & Magic, Vermont

Welcome to Fat Cat Barn! This is an incredibly unique, family oriented 1850's Mennonite built Post & Beam barn on 10+ acres in the pastoral hills of Andover, VT. We are wedged between the wonderful villages of Weston, Ludlow & Chester. Just 15 minutes from Okemo and Magic ski mountains with Stratton, Bromley & Killington all within 40 minutes. This is a wonderful four season property with plenty of options for fun right outside our door step. The Stratton mountain views and sunsets are stunning

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, 154 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
A spacious lawn is shown, featuring two buildings. One is a charming cottage with large glass doors, while the other is a main house with a traditional exterior. The ground is covered with fallen leaves, and trees line the background.
Cottage in Weston
4.97 out of 5 average rating, 108 reviews

Charming Mountain Cottage **NO CLEANING FEE**

Enjoy a charming cottage on the side of a hill in beautiful Weston, Vermont. You'll have the entire building to yourself (it's a stand-alone structure) to come and go as you please. My goal is to provide a five-star experience for five-star guests. I think little details like Ralph Lauren bath sheets, freshly-pressed bed linens, and duvet covers that are laundered between each guest make a difference. If you agree, you're probably the type of guest I'd enjoy hosting! Motorcycle friendly!!

Guest favourite
A modern interior is showcased with wooden walls and flooring, featuring a cozy bed positioned near large windows. A compact dining area is visible, with a small table and two chairs. An air conditioning unit is installed on the wall, contributing to the space's comfort.
Home in Winhall
4.94 out of 5 average rating, 324 reviews

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

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, 210 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

Guest favourite
The tiny house exterior features a charming porch with colorful railings and vibrant green doors. Tall trees surround the cottage, and a light dusting of snow covers the ground, adding to the serene atmosphere of the setting.
Tiny home in Jamaica
4.94 out of 5 average rating, 1,334 reviews

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Top guest favourite
The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.
Cottage in Windsor
4.97 out of 5 average rating, 435 reviews

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

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 home in Athens
4.84 out of 5 average rating, 170 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.

Top guest favourite
A mid-century retreat is illuminated at dusk, surrounded by snow-covered trees. Floor-to-ceiling windows create a warm glow, inviting guests into the living space. The landscape features a serene atmosphere with gently falling snow, enhancing the peaceful setting of the property.
Home in Winhall
4.98 out of 5 average rating, 417 reviews

Stunning mid-century house on 2.5 private acres

Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.

Popular amenities for Londonderry holiday rentals

When is the best time to visit Londonderry?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Londonderry?

    Londonderry has more than 130 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Londonderry with our cabin rentals, starting at about $90 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.

  • 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 house rentals in Londonderry have wifi?

    Absolutely! We offer over 100 house rentals with wifi in Londonderry. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Londonderry have free parking?

    Absolutely! We offer over 100 house rentals with free parking in Londonderry. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Londonderry

  • Total holiday rentals

    Explore 170 holiday rentals in Londonderry

  • Nightly prices starting at

    Londonderry holiday rentals start at $115 SGD per night before taxes and fees

  • Verified guest reviews

    Over 10,530 verified reviews to help you choose

  • Family-friendly holiday rentals

    130 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 80 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    160 of Londonderry holiday 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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