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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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Cabin in Londonderry

4.94 out of 5 average rating, 343 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Cabin in Londonderry

4.95 out of 5 average rating, 150 reviews

Summit ViewCottage:Cozy 3bd 2ba w/Fireplace&HotTub

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 6 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

Home in Weston

4.96 out of 5 average rating, 249 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!

Cottage in Londonderry

4.96 out of 5 average rating, 213 reviews

Vermont Treehouse - Romantic Private Elegant

SPECIAL 2 night minimum, self checkin. Work remotely. Enjoy 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 on property. 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.

Cabin in Londonderry

4.94 out of 5 average rating, 113 reviews

Green Mountain base camp for year-round adventure!

Featured on Levi Kelly's Cabin Tours & Lincoln Car Ad! Deerwood Hill is a 3.6 acre base camp for all Green Mountain adventures. Perfect retreat for all seasons! Within minutes to Stratton, Magic, Bromley, Mt Snow, & Okemo ski resorts! 1 hour to Killington! Under 30 minutes to wonderful Manchester! Let us take care of you in beautiful South Londonderry! ♥Comfortably sleeps 6 ♥2nd Bedroom is open loft with full bath ☒ Booking Guest must be 25. ☒ NO PARTIES, NO SMOKING, NO PETS @deerwoodhill

Home in Winhall

4.95 out of 5 average rating, 196 reviews

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Just minutes to skiing at Stratton Mountain, Bromley and Magic. Explore 27+ acres of forest with trails, river, sculpture gardens and private pond. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. A short drive to Manchester with shops and restaurants. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

Home in South Londonderry

4.85 out of 5 average rating, 133 reviews

Lovers Honey Pond Treehouse with hot tub & sauna

This VERY NEW and VERY romantic treehouse is finished!!! The Honey Pond Treehouse is made especially for you and yours! It’s constructed of all natural materials, has breathtaking views, and is outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…You will enjoy private hot tubbing, sauna time, relaxing, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes…biking & disc golf at Magic Mnt!

Cabin in Landgrove

4.99 out of 5 average rating, 172 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

Barn in Chester

4.99 out of 5 average rating, 575 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Home in Londonderry

4.98 out of 5 average rating, 115 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min).

Home in Londonderry

4.97 out of 5 average rating, 130 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.

Guesthouse in Putney

4.97 out of 5 average rating, 270 reviews

Cozy cottage loft and retreat

Returning guests, please ask about our discount! Relax and recharge in our peaceful Vermont cottage. Enjoy this sweet getaway with hardwood floors, fast wifi, a fully equipped kitchen, a quiet sleeping loft with a queen size bed, gorgeous natural light, views of surrounding hills and pond, gardens, and your own private entrance and back deck next to the Putney Brook.

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Popular amenities for Londonderry vacation rentals

Free parking on premises

Air conditioning

Stay near Londonderry's top sights

Magic Mountain Ski Area136 locals recommend

Honeypie122 locals recommend

SoLo Farm & Table98 locals recommend

Taylor Farm51 locals recommend

Clark's Quality Foods Londonderry VT44 locals recommend

Lowell Lake State Park44 locals recommend

Other great vacation rentals in Londonderry

Cabin in Winhall

4.96 out of 5 average rating, 27 reviews

PROMO: 3rd Night 25% off. Inquire before booking!

Rental unit in Winhall

5 out of 5 average rating, 13 reviews

Private & Quiet Apartment near Stratton Access Rd

Barn in Londonderry

5 out of 5 average rating, 11 reviews

Cozy Barn in Londonderry

Home in Londonderry

4.93 out of 5 average rating, 15 reviews

Tallwood Pine Chalet

Home in Londonderry

4.99 out of 5 average rating, 98 reviews

A Modern Cottage in Southern Vermont

Cottage in Londonderry

4.85 out of 5 average rating, 53 reviews

Vermont Country Cottage (Near Village)

Home in Londonderry

4.98 out of 5 average rating, 43 reviews

Cozy Family/Pet Friendly Cabin w/ Modern Upgrades

Home in Londonderry

5 out of 5 average rating, 22 reviews

Black Star Barn, Mountain Retreat

Quick stats about vacation rentals in Londonderry

Total rentals
170 properties
Nightly prices starting at
$80 before taxes and fees
Total number of reviews
9K reviews
Family-friendly rentals
140 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with a pool
10 properties have a pool

Frequently Asked Questions

Are there pet-friendly vacation rentals in Londonderry?
Four-legged friends are welcome in Londonderry. Choose from more than 70 vacation rentals for guests traveling with pets.
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.
Are there vacation rentals with a dedicated workspace in Londonderry?
Yes! Work meets play with ease at over 90 vacation rentals in Londonderry featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Londonderry have a bbq area?
Absolutely! We offer over 60 house rentals with a bbq area in Londonderry. Enjoy a tailored experience with all the comforts you desire.
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!
How much does it cost to stay in chalet rentals in Londonderry?
Experience the best of Londonderry with our chalet rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cabin rentals in Londonderry have air conditioning?
Absolutely! We offer over 10 cabin rentals with air conditioning in Londonderry. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Londonderry?
Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with a bbq area, over 100 homes with wireless internet, over 40 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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