
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!

Summit View Cottage:Apres Ski| Hot tub|Fireplace
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

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

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.

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub
This historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 250 acre property.

Airbnb @ Sweet & Savory Farmette
Welcome to the AirBnB situated on a small working farm. You are welcome to tour the grounds to say hello to all the animals. This place is for the birds! No really you will enjoy watching chickens, ducks, emus, geese, guinea fowl, and peafowl. The farm is also home to a herd of beautiful alpaca and resident llama, curious goats, and barn cats. There are working livestock guardian dogs who watch over the herd who will greet you from behind the fence.
Popular amenities for Londonderry family-friendly rentals
Family-friendly home rentals with a hot tub

Log Cabin: Amazing Views, River Frontage, Hot Tub

Vintage Vermont Cabin, Hot Tub, Fire Pit, Private

Beautiful Timber Frame Retreat

Vermont Retreat Luxe Yurt, Romantic & in Nature

Cozy condo within walking distance to the slopes.

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

Stunning Studio in historic Downtown Bellows Falls

Log Cabin, King Beds & AC Near Hike/Swim/Golf/Bike

Gristmill Cabin overlooking peaceful brook.

Love Shack Yurt on Star Lake (100% off grid)

The Rafters Lodge

Sunrise Cabin

Serene Bus Getaway Among Rolling Farm Land

Cozy Hilltown Cottage
Family-friendly home rentals with a pool

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

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

Beautiful Spacious Condo at Killington Resort

Beautiful rustic woods and fields retreat.

Cozy Vermont Antique Sugar House with Fireplace

Walk to Mt. Snow-Spa-Summer Pool

Mt Snow Chalet: Peaceful Escape w/Hot Tub

In-law Apartment, Full Kitchen, Near Mt Wachusetts
When is the best time to visit Londonderry?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$69,654 GYD | G$77,393 GYD | G$57,940 GYD | G$47,064 GYD | G$47,064 GYD | G$48,946 GYD | G$58,568 GYD | G$55,012 GYD | G$51,247 GYD | G$56,267 GYD | G$53,339 GYD | G$69,027 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$18,825 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
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- 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
 - Lake George Expedition Park
 - Hildene, The Lincoln Family Home
 - Lucky Bugger Vineyard & Winery
 - Hooper Golf Course
 - Dorset Field Club
 - The Shattuck Golf Club
 - National Museum of Racing and Hall of Fame
 - Northern Cross Vineyard
 - Autumn Mountain Winery
 - Bromley Mountain Ski Resort
 - Whaleback Mountain