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Family-friendly vacation rentals in Londonderry

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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$23,009 GYD per night before taxes and fees

  • Verified guest reviews

    Over 6,740 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    140 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!

Top-rated family-friendly rentals in Londonderry

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
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

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

4.93 out of 5 average rating, 271 reviews
Top guest favorite
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

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!

4.95 out of 5 average rating, 324 reviews
Guest favorite
The log cabin features a two-story structure, harmonizing rustic wooden siding with a white lower section. A spacious deck extends from the second level, complemented by large windows. Vibrant autumn foliage surrounds the home, adding warmth to the scenic outdoor landscape.
Cabin in Londonderry

Authentic Log Cabin Near Bromley, Magic & Stratton

This authentic 4-bed, 2.5-bath Vermont log cabin sits on 1.5 wooded acres—fireplace, firepit and enough vintage charm to feel like a genuine escape. After the slopes, play a classic arcade machine, make s'mores outside, or decompress by the fire with a board game. Ski Bromley, Magic, and Stratton—all minutes away. Manchester's outlets, the Stone House Antique Center, and the Vermont Country Store are a short drive. Feels remote, but you're minutes from a walkable coffee shop, diner, and market.

4.94 out of 5 average rating, 103 reviews
Top guest favorite
Cottage in Londonderry

Vermont Country Cottage(Near Village w/Magic View)

This cute, country cottage offers 2 bedrooms, 1 bath with a treehouse loft in the bunk room. The floors are wood, kitchen is custom built with stainless steel appliances, bathroom vanity is custom built using the original kitchen sink from the home, and the twin size bunks are built in as well. There is a very large yard. There are 4 ski resorts within 20 minutes, the Weston Country Store and play house are 5 minutes up the road, and you can walk to the local farmers market every Saturday.

4.9 out of 5 average rating, 110 reviews
Top guest favorite
A cozy log cabin is nestled among tall trees, with sunlight filtering through the leaves. The surrounding ground is covered in vibrant autumn leaves, and a winding path leads to the front entrance of the home, offering a serene and inviting atmosphere.
Chalet in Londonderry

10 min from Stratton! Log Cabin w/ Beautiful Views

Spectacular views of Stratton Mountain! This cozy log cabin is set on 10 acres of land offering a quiet year round Vermont getaway. The home offers 3 bedrooms (all with mountain views), 2 baths and comfortably sleeps 7. Located 10-15 minutes from skiing (Stratton, Bromley and Magic), 25 minutes from shopping and dining in Manchester, and ½ mile from Gale Meadows Pond for hiking and water activities in the summer. If you’re looking for the ultimate Vermont experience, you’ve found your spot!

4.95 out of 5 average rating, 128 reviews
Guest favorite
A charming cabin nestled in a wooded area, showcasing a rustic blue exterior. Large windows illuminate the space, highlighting the inviting porch. Autumn foliage surrounds the home, adding warm colors to the serene landscape.
Cabin in Londonderry

Idyllic 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

4.95 out of 5 average rating, 192 reviews
Top guest favorite
The exterior of a two-story house is depicted, featuring a welcoming entrance with wooden steps and a green door. Window boxes with plants are positioned below each window on the light gray facade, surrounded by a landscaped yard with a gravel pathway leading to the front door.
Apartment in Londonderry

Bread and Butter Apartment

Our house is located just a few minutes from Magic Mountain and less than thirty minutes from Bromley, Stratton and Okemo. Chester and Londonderry are a short drive away, and there are many wonderful hikes nearby. The apartment occupies the entire second floor of our house and has a private entrance. It includes two cozy bedrooms, a 3/4 bath, a small kitchen and a comfy living room. The apartment still has that old Vermont charm and is perfect for a relaxed weekend in the Green Mountains.

4.99 out of 5 average rating, 105 reviews
Top guest favorite
The rustic barn structure features a combination of dark wood siding and a gabled roof, highlighted by a central chimney. Large wooden doors and multiple small windows create an inviting appearance, while the surrounding natural landscape includes lush trees and open fields.
Barn in Jamaica

The Rafters Lodge

A unique VT experience! This 1860s barn was converted into a Girl Scout camp in the 1950s and served many years training leaders and scouts. Today, the Rafters continues to be a special part of many families lives, who come to enjoy the rustic camping experience and beautiful ninety acre farm. The lodge has accommodated large youth groups, families and even the occasional wedding party. With the close proximity to Stratton and Bromley, visitors enjoy countless recreational opportunities.

4.97 out of 5 average rating, 117 reviews
Top guest favorite
An interior view showcases a modern staircase with wooden steps and a metal railing, leading to a second floor. Natural light floods the space through large glass windows, illuminating the wooden walls and a stone fireplace. A green plant adds a touch of nature.
Home in Londonderry

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). STR License 26-23-185

4.99 out of 5 average rating, 155 reviews
Top guest favorite
A spacious living area features large floor-to-ceiling windows offering a view of the green outdoor space. A plush sofa, accented with colorful cushions, sits in front of a wooden coffee table. A modern dining area is visible in the background, illuminated by soft lighting.
Home in Winhall

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 4wd or awd vehicle is recommended. Important note: The grill is put in storage and not accessible November-April due to inclement weather. 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. The house has a non-working fireplace.

4.98 out of 5 average rating, 433 reviews
Top guest favorite
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

Designer Chalet w/ Mountain Views close to it all

Private 3-bedroom, 2-bath chalet on 2.5 peaceful acres with beautiful mountain views. Comfortably sleeping 6 guests, it’s the perfect Vermont escape for ski weekends, foliage trips, outdoor adventure, or simply relaxing with family and friends. Enjoy nearby hiking, biking, swimming, waterfalls, golf, and scenic drives. Close to Jamaica State Park, Bondville, Stratton, and Mount Snow, with Manchester’s shopping and dining an easy day trip away.

4.98 out of 5 average rating, 113 reviews
Top guest favorite
The exterior showcases a rustic wooden building surrounded by lush greenery and vibrant shrubs. A winding stone path leads to the entrance, while large glass doors provide a welcoming view into the interior. The setting is serene and integrated with nature.
Apartment in Londonderry

Vermont Getaway Apartment

A 2 bedroom apartment attached to our home, close to Stratton, Bromley, Magic, Okemo & Mt Snow Skiing, hiking, fishing, golfing, tennis, outlet shopping and fine dining all close by. Manchester a short drive. Hot tub available from 8am-8pm. Level 2 EV charger available for a $10 cash fee (and give us advance notice if possible so we can open the garage for you).

4.96 out of 5 average rating, 620 reviews

Popular amenities for Londonderry family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
Chalet in Winhall

Stratton Chalet | Barrel Sauna, Hot Tub & Views

4.97 out of 5 average rating, 157 reviews
Top guest favorite
The chalet is positioned on a gently sloping grassy area, featuring a spacious deck with a hot tub and several outdoor seating options arranged around a fire pit. Large windows reflect warm interior light, framing a serene natural backdrop of trees, enhancing the inviting ambiance.
Chalet in Winhall

Mountain view chalet with hot tub & fire pit!

4.99 out of 5 average rating, 140 reviews
Top guest favorite
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

The Owl’s Nest in Landgrove

4.99 out of 5 average rating, 222 reviews
Superhost
Cabin in Londonderry

Stunning Rustic Apple Barn - hot tub & sauna

4.81 out of 5 average rating, 510 reviews
Guest favorite
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

Modern Cabin with Hot Tub & EV Charging Station

4.95 out of 5 average rating, 363 reviews
Guest favorite
Cabin in Winhall

A frame cabin with Hot tub near Stratton, VT

4.92 out of 5 average rating, 130 reviews
Top guest favorite
The bedroom is designed with a spacious bed adorned with crisp white linens. A large triangular window provides a serene view of lush greenery outside, allowing natural light to fill the room.
Cabin in Townshend

Modern Cabin with Outdoor Spa on Vermont Farm

4.96 out of 5 average rating, 208 reviews
Top guest favorite
Treehouse in Wilmington

Beautiful timber-frame treehouse

5.0 out of 5 average rating, 124 reviews

Family- and pet-friendly home rentals

Top guest favorite
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

Fat Cat Barn - Close Okemo & Magic, Vermont

4.99 out of 5 average rating, 155 reviews
Top guest favorite
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

Apple Blossom Cottage: A Tiny House

4.94 out of 5 average rating, 1384 reviews
Top guest favorite
The A-frame house is framed by tall trees, featuring large triangular windows that enhance natural light. A wooden deck extends to a seating area with two rocking chairs and a picnic table. A person walks their dog along the path leading to the entrance.
Place to stay in Stratton

The Chal-A-Frame Vermont

4.99 out of 5 average rating, 225 reviews
Guest favorite
A charming cottage entrance is depicted with natural wood siding and a small porch area. Soft lighting enhances the ambiance. A friendly dog sits on the gravel path, surrounded by lush greenery, indicating a tranquil forest setting.
Cottage in Jamaica

Cottage-Swim-View-Firepit-7min to Stratton-Dog OK

4.85 out of 5 average rating, 641 reviews
Superhost
The timber frame house is surrounded by dense trees, showcasing a natural setting. Large windows illuminate the exterior, providing glimpses of the interior. Sturdy wooden steps lead to the door, enhancing accessibility amid the forest environment.
Tiny home in Athens

Luxury “Tiny” House With Sauna (Timbery)

4.91 out of 5 average rating, 253 reviews
Guest favorite
A stationary white bus sits on a gravel path surrounded by green grass. In the background, sparse trees and expansive fields are visible. Two outdoor chairs and a small shed can be seen nearby, highlighting the serene, rural setting.
Bus in Granville

Serene Bus Getaway Among Rolling Farm Land

4.89 out of 5 average rating, 223 reviews
Guest favorite
Chalet in Jamaica

Classic Vermont A-Frame | Fire Pit | Near Stratton

4.97 out of 5 average rating, 295 reviews
Top guest favorite
A bright interior is featured, showcasing a mix of seating options including a blue sofa and an upholstered armchair. A small dining table is complemented by wooden chairs. The kitchen area is visible, equipped with diverse utensils, while large windows on two sides allow natural light to fill the space.
Apartment in Andover

Private Hilltop farm apartment

4.97 out of 5 average rating, 481 reviews

Family-friendly home rentals with a pool

Top guest favorite
A bright and airy great room features high wooden ceilings with large windows showcasing mountain views. A spacious sectional sofa is arranged around a colorful area rug, complemented by blue armchairs. Contemporary lighting and artistic decor add to the inviting ambiance.
Home in Springfield

Luxury Mid-Century Modern Vermont Home, Okemo View

4.99 out of 5 average rating, 101 reviews
Guest favorite
A spacious ski home is surrounded by snow-covered trees, featuring a modern design with a sloped metal roof. Large windows allow natural light to enter, while a gravel driveway leads to the entrance. This bustling wooded area provides a serene backdrop during winter.
Home in Peru

Beautiful Bromley/Manchester VT Retreat w/hot tub

4.9 out of 5 average rating, 184 reviews
Top guest favorite
The exterior of the chalet is shown in twilight, with soft light emanating from a window. The rustic wooden structure features a sloped roof and is surrounded by snow-covered ground and trees in the background.
Guesthouse in Granville

Moon Valley Country Retreat no clean fee pets yes

4.91 out of 5 average rating, 1027 reviews
Guest favorite
A rustic log cabin features a porch with seating arrangements, including Adirondack chairs. The front yard is partially landscaped with small plants. Stacked firewood is visible next to the cabin, and the structure is surrounded by trees and greenery, providing a natural, secluded setting.
Cabin in Wardsboro

Log Cabin Near Stratton/Mt Snow

4.79 out of 5 average rating, 279 reviews
Top guest favorite
A spacious family room features a vaulted ceiling with wooden beams. Seating includes a sectional sofa and two lounge chairs. A large smart TV is mounted above a minimalist fireplace. Natural light floods in from the expansive glass doors leading to a balcony.
Cottage in Wardsboro

Modern Cottage between Stratton and Mount Snow VT

4.97 out of 5 average rating, 113 reviews
Top guest favorite
A cozy living area features a pair of brown sofas with decorative cushions. A wooden coffee table is centered in front of the seating. Artwork is displayed on the light green walls, and a lamp provides soft illumination, complementing the natural light from the window.
Condo in Stratton

Cozy condo within walking distance to the slopes.

4.96 out of 5 average rating, 182 reviews
Top guest favorite
A gravel road leads through open fields bordered by manicured greenery. In the distance, rustic buildings and trees with autumn foliage are visible against a clear blue sky, creating a serene rural landscape.
Farm stay in Clarendon

Dream Catcher Farm

5.0 out of 5 average rating, 115 reviews
Superhost
A spacious living area is highlighted by large windows that provide a panoramic view of the surrounding hills. The room features a comfortable sofa, a wooden coffee table, and a dining set. A fireplace and a fully equipped kitchen are situated in the background.
Condo in Stratton

~10% OFF~Walk To Mountain~Amenities

4.88 out of 5 average rating, 111 reviews

When is the best time to visit Londonderry?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$84,297 GYDG$83,669 GYDG$64,216 GYDG$52,084 GYDG$52,084 GYDG$52,712 GYDG$56,268 GYDG$51,247 GYDG$52,084 GYDG$59,614 GYDG$52,293 GYDG$80,741 GYD
Avg. temp-5°C-4°C1°C8°C14°C18°C21°C20°C16°C9°C4°C-2°C

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