Family-friendly vacation rentals in Wilmington

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Wilmington

  • Total vacation rentals

    Explore 240 vacation rentals in Wilmington

  • Nightly prices starting at

    Wilmington vacation rentals start at G$18,825 GYD per night before taxes and fees

  • Verified guest reviews

    Over 10,110 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 110 rentals that welcome pets

  • Vacation rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wi-Fi availability

    240 of Wilmington vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Wilmington rentals

  • 4.9 Average rating

    Wilmington stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Wilmington

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

1 of 1 pages1 / 1
Top guest favorite
The entryway features a welcoming entrance with a wooden door, adorned with a green wreath. A glimpse into the bright interior reveals modern seating and natural light streaming through large windows, enhancing the inviting space that awaits inside.
Chalet in Wilmington
4.97 out of 5 average rating, 145 reviews

Snug Chalet - Wi-Fi + Close to Mount Snow

This stylish 1971 chalet is a country retreat with modern comforts for you and your family... complete with strong WiFi and a fenced-in dog yard! The minimal cabin is tucked in the trees and set up for families and friends, pet & kid-friendly. 10-15 Minutes to Mount Snow 10-15 Minutes to Downtown Wilmington This is a country house, not a boutique hotel :) If booking during winter or spring months, we HIGHLY recommend a 4wd vehicle as the weather can cause some tough road conditions (snow/mud).

Guest favorite
A cozy living area features a dark sofa adorned with colorful throw pillows. Natural light enters through a window, illuminating the space. A coffee table rests in front, complemented by a comfortable side chair and ottoman. Wall décor includes vintage items, enhancing the inviting atmosphere.
Apartment in Wilmington
4.89 out of 5 average rating, 336 reviews

Globetrotter Retreat - Minutes to the Mountain

Newly renovated, fully furnished apt in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt sleeps 4 people in comfort. Private balcony overlooks rolling river. Steps from many restaurants, bars & shopping. Supermarket is a short walk. FreeMoover bus stop across the street - leave your car parked & ride for free to local destinations! No guest under 18 years old.

Superhost
A cozy living area features a dark gray sofa with decorative cushions, complemented by two wooden armchairs. A timber-framed window offers a view of the outdoors. A coffee table holds a small centerpiece, and vintage skis are mounted on the wall above the seating.
Home in Wilmington
4.85 out of 5 average rating, 142 reviews

MtSnow HotTub Pool Table AirHockey PingPong *Darts

Welcome to our ❄newly listed❄lodge style home! HOT TUB✅ Our home is located on private 2.6 acre lot with beautiful views of Mount Snow in the distance. Our home offers easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our home. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in southern Vermont!

Top guest favorite
A inviting outdoor space features two blue Adirondack chairs paired with a fire pit, where flames reflect off colored glass. A hot tub is visible nearby, surrounded by greenery, enhancing the tranquil ambiance of the area.
Home in Wilmington
4.96 out of 5 average rating, 143 reviews

Walk To Town, Hottub, Firepit, Games, Mt Snow

Welcome to our family-friendly home in Wilmington, Vermont! Perfect for group getaways. Our home offers a blend of comfort and convenience. Just a short walk from Wilmington's charming downtown, with easy access to restaurants, shops, and groceries. Mount Snow is only a 12-minutes away, making this an ideal base for both winter skiing adventures and summer hikes. Whether you're here for outdoor fun or cozy nights by the fire pit, our home is ready to make your Vermont getaway unforgettable!

Top guest favorite
A spacious deck is showcased with several outdoor chairs arranged to overlook a lush landscape. The surrounding trees and rolling hills create a serene backdrop, with partially cloudy skies above, inviting relaxation and enjoyment of the natural setting.
Chalet in Wilmington
4.95 out of 5 average rating, 188 reviews

Mountain View Retreat: 5 Mi to MT Snow, Hot Tub

Come escape to Wilmington, Vermont. Stunning views of Mt. Snow, a small stream, and a large hot tub on 12 secluded acres. Only 10 minutes to Mount Snow and 30 minutes to Stratton our home is the perfect getaway for your VT adventure with all of your family and friends. Come ski, snowboard, snowmobile, hike, kayak, mountain bike, swim, or fish just minutes away! After your long day exploring come relax in the hot tub, by the fire, in the game room, or just out on our deck taking in the sunset!

Guest favorite
A bathroom features natural wood paneling and a brick accent wall. A compact vanity with a sink is complemented by a mirror and overhead lighting. Shelves hold neatly folded towels, while a washer and dryer unit is integrated into the design, presenting a functional space.
Home in Wilmington
4.91 out of 5 average rating, 260 reviews

Wilmington A-Frame- Cozy and Convenient

Entire charming and chic A-frame chalet conveniently located to all the amenities Wilmington has to offer. Walk into town to enjoy dining, shopping and trail hiking or take a short 15 minute drive to Mount Snow for a day of outdoor adventure. Relax on the water at Harriman Reservoir, just a 2 mile drive from the house. House is conveniently located along the Moover route. Relax back at the house while enjoying time on the front porch or an evening on the couch. Located on Main Street.

Top guest favorite
Cabin in Wilmington
5.0 out of 5 average rating, 135 reviews

Mid-mod VT Dream Chalet near skiing, lake & forest

Surround yourself in nature and cozy modern comfort. The romantic mid-mod-styled chalet backs to 10 acres of peaceful forest yet is just 12 min drive to Mount Snow for great skiing. 3 min. to the boat launch of gorgeous Lake Whitingham where you can rent jetskis & boats or go swimming & fishing. Hike trails to the charming town of Wilmington with its coffee shops & restaurants. Pools & hot tub up the road at clubhouse. Just steps away from iceskating, pickleball, hiking & snowmobile trails.

Top guest favorite
Treehouse in Wilmington
5.0 out of 5 average rating, 112 reviews

Beautiful timber-frame treehouse

The timber frame treehouse is a perfect couples retreat. The home is custom built with hardwood maple trees cut down and milled right on the property. The deck has a barrel sauna, cold or hot cedar soaking tub, a propane fire pit, a wood burning chiminea fire pit, and a bar top for outdoor dinning. The inside has a stone fireplace, fully equipped kitchen, tile shower, projector with dvds, books, board games, chandelier, and dimmable lighting for any mood. This home is truly one of a kind.

Top guest favorite
A spacious great room features a comfortable seating area with a white couch, eclectic armchair, and colorful floor design. Artistic decorations are placed on the walls and shelves, with a kitchenette visible in the background. A piano and drums are positioned nearby for guest use.
Guest suite in Wilmington
4.92 out of 5 average rating, 840 reviews

Architectural GuestSuite

The Guest Suite is located on the first floor of an architectural studio in historic Wilmington, Vermont. Please enjoy the piano, drums, and art supplies! The Guest Suite is both UNIVERSALLY ACCESSIBLE, TOBACCO FREE, and ANIMAL FREE due to allergies in our family. LineSync Architecture staff will be working from 8:30am - 5ish upstairs, and once in a while on the weekends. When guests are in we try to be super sensitive and quiet, but footsteps will be heard!

Guest favorite
A well-maintained home features a spacious porch with green chairs and is surrounded by a lush lawn and trees. The gravel driveway offers ample parking space, while the bright blue sky enhances the serene outdoor setting.
Home in Wilmington
4.94 out of 5 average rating, 319 reviews

Wilmington. In Town Village Home

Beautifully renovated bright, 125 year old home in town. House thoroughly cleaned and sanitized after each stay. Touchless flushing toilets. Mini-Split air conditioning in each bedroom and on the main level. Minutes to MT Snow. Easy walk to town for food and shopping. Deerfield river directly across the street. 2 min from the lake. Valley hiking trails within sight. There is a 2 car limit. A request for additional vehicles needs to be made prior to check-in.

Guest favorite
A large outdoor pool is surrounded by a wooden deck with lounge chairs and umbrellas. The background features a multi-story building with expansive windows. Vibrant autumn trees with colorful foliage frame the scene, providing a serene and inviting atmosphere.
Home in Wilmington
4.89 out of 5 average rating, 180 reviews

Cozy 4BR Cabin | Pools & Hot Tub | Near Mt Snow

Escape to the mountains in this cozy 4BR, 2BA Chimney Hill cabin, just 15 minutes from Mt. Snow and minutes from downtown Wilmington. Gather around the outdoor fire pit, cozy up by 2 fireplaces, or enjoy access to the nearby community clubhouse with indoor & outdoor pools, hot tub, fitness room, and more. Sleeping up to 8, the home is perfect for families and groups looking for skiing, hiking, lake days, foliage, or a relaxing Vermont getaway year-round.

Superhost
A uniquely designed raised container home features multiple levels and large windows that offer expansive views of the surrounding landscape. The structure includes a covered outdoor area below, and the combination of dark wood and metal creates a striking exterior appearance.
Shipping container in Whitingham
4.87 out of 5 average rating, 119 reviews

The House of Pi

WE now pay your 15.5% Guest Service fee!!! Welcome to The House of Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock and Kayaks. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views. Hot Tub and Custom Cedar Sauna!

Popular amenities for Wilmington family-friendly rentals

When is the best time to visit Wilmington?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$84,922 GYDG$84,922 GYDG$67,770 GYDG$59,822 GYDG$61,077 GYDG$59,822 GYDG$60,449 GYDG$58,148 GYDG$57,521 GYDG$62,750 GYDG$65,260 GYDG$81,994 GYD
Avg. temp-5°C-4°C1°C8°C14°C18°C21°C20°C16°C9°C4°C-2°C

Destinations to explore