
Family-friendly vacation rentals in Londonderry
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Londonderry
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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!

Glamping Cabin with Private Pond and Mountain View
This little glamping cabin with cozy woodstove is set at the far edge of a field overlooking a wildlife pond, seasonal fountain, and mountain. It is a peaceful place, surrounded by beauty, and special not just for these amenities but because it is improbably located on four private acres right in Manchester Center. The property abuts 70 acres of preserved land, but is steps from Main Street and all the shopping, dining, and outdoor options that this lovely year-round tourist town has to offer.

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

Vermont Botanical Studio Apartment
This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

Monadnock Sunrise Forest Hideaway
Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for two adults (queen bed) and one kid (63" long fold down couch).

New Cabin in Jamaica
Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Clean, Captivating VT Farmhouse near Stratton!
Let us welcome you to our beautifully appointed, circa 1901 Vermont farmhouse resting on four acres of lush, rolling pastures--the quintessential Vermont experience! The house exudes warmth, coziness and tranquility with no detail left untouched. 4 BR 2 bath with huge family room. Minutes to 3 of the best ski-mountains on the east coast - Stratton, Bromley, Magic Mtn and close to Manchester shopping. A few miles from renowned Solo Farm & Table, HoneyPie and West River Farmer's market.

Treehouse Haven in Putney-All Seasons
Peaceful, private & fully equipped four-season treehouse, surrounded by nature. ☽ Private & secluded ☽ Central to activities & necessities ☽ Firepit, pellet stove, deck, grill & fully stocked kitchen ☽ Scrupulously clean, unscented products ☽ Clean composting toilet ☽ Tea & local coffee ☽ Hot outdoor shower ☽ 45min to ski resorts ☽ Swimming holes & hikes ☽ WiFi & electricity Visit for romance, time with the family, a retreat from the business of life, or even a remote work sanctuary.

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

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.

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.

Love Shack Yurt on Star Lake (100% off grid)
Glamping at its finest. Bring everything but the bed. Enjoy sunsets and star gazing lakeside. No running water or electricity. Clean & custom built outhouse for a toilet. You will need to bring bedding, size king. Please note: self cleaning policy. Leave it in great condition for your fellow travelers. Woodstove for heat, provide your own wood. One King Bed with mattresses and top sheet ONLY. IG@YURTlilyPAD
Popular amenities for Londonderry family-friendly rentals
Family-friendly home rentals with a hot tub

Beautiful Timber Frame Retreat

Vermont Retreat Luxe Yurt, Romantic & in Nature

Cozy condo within walking distance to the slopes.

Mountain side acres

Glamping Cabin with Hot Tub on Flower Farm

Secluded tiny house resort - DOG FRIENDLY

Barrel Sauna + Hot Tub & Mtn Views

Modern Cabin with Outdoor Spa on Vermont Farm
Family- and pet-friendly home rentals

Cabin on the Hill

Stunning Studio in historic Downtown Bellows Falls

Moon Valley Country Retreat no clean fee pets yes

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

Cabin - 7 min to Ski Stratton - Woodstove - Views - Dog OK

Gristmill Cabin overlooking peaceful brook.

The Rafters Lodge

Sunrise Cabin
Family-friendly home rentals with a pool

Bear's Den - Mt Snow Townhome w/ Ski Home Trail!

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

⛷☃️Close to lifts. Rustic. Mountain Green Resort🏂❄️…

Beautiful Spacious Condo at Killington Resort

Beautiful rustic woods and fields retreat.

Cozy Vermont Antique Sugar House with Fireplace

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Hotel Chic - Home Comfort -Ski Easy.
When is the best time to visit Londonderry?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$69,637 GYD | G$77,375 GYD | G$57,927 GYD | G$47,052 GYD | G$47,052 GYD | G$48,934 GYD | G$56,254 GYD | G$51,235 GYD | G$52,071 GYD | G$54,790 GYD | G$53,326 GYD | G$69,010 GYD |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Quick stats about vacation rentals that are family-friendly in Londonderry

Total vacation rentals
Explore 140 vacation rentals in Londonderry

Nightly prices starting at
Londonderry vacation rentals start at G$18,821 GYD per night before taxes and fees

Verified guest reviews
Over 6,910 verified reviews to help you choose

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
130 of Londonderry vacation rentals include wi-fi 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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- Family-friendly rentals Windham County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- West Mountain Ski Resort
- Mount Snow Ski Resort
- Pico Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Hildene, The Lincoln Family Home
- Lake George Expedition Park
- Dorset Field Club
- The Shattuck Golf Club
- Hooper Golf Course
- Lucky Bugger Vineyard & Winery
- National Museum of Racing and Hall of Fame
- Northern Cross Vineyard
- Bromley Mountain Ski Resort
- Autumn Mountain Winery
- Whaleback Mountain




