Family-friendly vacation rentals in Wilmington

4.97 out of 5 average rating, 144 reviews

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

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).

Indoor spacesKitchenAccess

4.95 out of 5 average rating, 152 reviews

A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.

Home in Guilford

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

FamilyIndoor spacesTV

4.89 out of 5 average rating, 336 reviews

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

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.

Indoor spacesFamilyRiver

4.99 out of 5 average rating, 397 reviews

Tiny home in Wilmington

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

KitchenIndoor spacesWifi

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.

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.

KitchenFamilyDecor

5.0 out of 5 average rating, 134 reviews

Cabin in Wilmington

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.

Indoor spacesFamilyHiking

4.85 out of 5 average rating, 101 reviews

A cozy living area features a grey sectional sofa and a wooden table. Natural light enters through windows adorned with simple frames. A subtle rug lies beneath the furniture, enhancing the room's warmth, while a doorway leads to a separate sleeping area.

Apartment in Wilmington

Modern river apartment near lake, hiking, golf #1

Cozy, comfortable, and robust 2 bedroom that can fit 7 people. TV with chromecast and wifi provided, super close to Mount Snow, perfect for skiing/snowboarding, summer family trips or just a getaway/short or long term stay! AC window unit in primary bedroom with queen bed! Parking for 2 cars included, clean, cozy, and very roomy, up to 7 guests. Newly renovated unit overall. You'll have a great time at Mount Snow, the cute and quaint town of Wilmington, all 4 seasons!

FamilyIndoor spacesWalkability

Guest suite in Wilmington

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.

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!

FamilyIndoor spacesParking

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.

4.94 out of 5 average rating, 318 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.

KitchenFamilyNearby

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!

Indoor spacesFamilyComfort

4.98 out of 5 average rating, 536 reviews

A well-lit kitchen and dining area features a wooden dining table surrounded by six chairs. Light hardwood flooring complements the gray cabinetry. A potted plant sits on the table, and modern appliances are visible in the background, including a refrigerator and stove.

Apartment in Wilmington

**Happy Hour! Gorgeous & Modern Downtown Retreat**

Come enjoy our beautiful apartment above our liquor store in downtown Wilmington! Lots of local shops and dining right in town! We are along a river and next to a hiking trail system! Walking distance to the serene 10+ mile lake; kayaks, stand-up paddle boards or motor boat/jet ski rentals nearby. In the winter, enjoy local trails on snowshoes or cross-country skies; only 15 minutes to Mount Snow! We look forward to meeting you!!!

FamilyIndoor spacesBiking

5.0 out of 5 average rating, 131 reviews

Chalet in Wilmington

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Escape to the serene beauty of Vermont's Green Mountains at the Mount Snow Chalet, a charming retreat nestled on a private wooded lot in the desirable Chimney Hill community of Wilmington. 🏠🌳 Just minutes from the slopes of Mount Snow, our chalet offers the perfect blend of rustic charm and modern amenities for an unforgettable getaway. Designed with love and care, we invite you to relax and stay awhile! 🥰

KitchenIndoor spacesGrill

Popular amenities for Wilmington family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A cozy living area features a leather sectional sofa adorned with patterned throw pillows. Natural light flows through large windows, illuminating warm wood paneling and a brick fireplace. A game table stands nearby, accompanied by rustic decor and hardwood flooring.

4.89 out of 5 average rating, 180 reviews

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

KitchenIndoor spacesCheck-in

4.92 out of 5 average rating, 471 reviews

Cabin in Wilmington

Picturesque Cabin near Mt Snow

KitchenIndoor spacesCheckout

4.96 out of 5 average rating, 169 reviews

Chalet in Dover

Brook House: Hot Tub, Fire Pit, Ping Pong, Mt Snow

KitchenFamilyHiking

4.95 out of 5 average rating, 187 reviews

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

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

Indoor spacesKitchenHiking

4.98 out of 5 average rating, 777 reviews

An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.

Cottage in Shaftsbury

Schoolhouse Spa Retreat on a Vermont Farm

Indoor spacesKitchenComfort

4.98 out of 5 average rating, 124 reviews

The spacious A-frame home is set against a backdrop of vibrant trees and lush greenery. A well-manicured hill leads to the house, which features large windows allowing natural light to fill the interior. The bright blue sky complements the tranquil outdoor scenery.

Chalet in Dover

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB

Indoor spacesFamilyDecor

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.

4.96 out of 5 average rating, 143 reviews

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

KitchenFamilyBackyard

4.96 out of 5 average rating, 114 reviews

A serene backyard features a fire pit surrounded by white adirondack chairs and a small side table. Green grass stretches towards a wooden deck, while lush trees and shrubs provide natural privacy. The house, painted in blue, stands elevated in the background.

Home in Dover

Wonderful House! Rec Room HotTub Firepit Garden!

KitchenFamilyCondition

Family- and pet-friendly home rentals

4.86 out of 5 average rating, 314 reviews

The A-Frame chalet is set amidst vibrant autumn foliage, showcasing a wrap-around deck with wooden railings. A balcony extends above, offering a view of the surrounding trees and an inviting outdoor space with seating.

Chalet in Dover

The Mountain A-Frame at Mount Snow

Indoor spacesKitchenQuiet

Place to stay in Stratton

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.

4.99 out of 5 average rating, 218 reviews

The Chal-A-Frame Vermont

Indoor spacesFamilyHeating

4.94 out of 5 average rating, 1376 reviews

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

Indoor spacesFamilyBathroom

4.94 out of 5 average rating, 132 reviews

A modern cabin is set amidst lush greenery, elevated on stilts for an unobstructed view. The exterior features a mix of wood and dark finishes, with large windows allowing natural light to fill the interior. A gravel path leads to the entrance.

Home in Jamaica

The Post Haus - One-of-A-Kind Modern VT Experience

KitchenIndoor spacesHospitality

4.85 out of 5 average rating, 388 reviews

Cabin in Woodford

400+ Airbnb Visits: Incredible Mountain Cabin

Indoor spacesKitchenGetting around

4.96 out of 5 average rating, 129 reviews

The cabin is situated among lush greenery, featuring a light green exterior that complements the natural surroundings. Large windows allow for ample light, while ferns frame the building at the front. The wooded area provides a sense of privacy and tranquility.

Cabin in Whitingham

The Hideaway Camp

Indoor spacesFamilySleep quality

4.93 out of 5 average rating, 307 reviews

A gently sloping lawn leads up to the light-colored building, framed by lush gardens and vibrant greenery. A pair of purple Adirondack chairs sits invitingly on the grass, offering a serene spot to enjoy the surrounding landscape.

Apartment in Marlboro

Shakespeare’s Folly Side Farm and AirBnB.

FamilyIndoor spacesWifi

4.99 out of 5 average rating, 106 reviews

A cozy living area features wooden paneling and a warm brown sofa, complemented by a natural wood coffee table on a cowhide rug. A vibrant wall displays green foliage and the phrase 'Green Mountain State.' Four bar stools are positioned nearby, offering additional seating.

Chalet in Wardsboro

Brook Haven Retreat - Minutes to Mt Snow&Stratton

KitchenFamilyDecor

Family-friendly home rentals with a pool

4.93 out of 5 average rating, 113 reviews

MountSnow ski on/off condo in Vermont

FamilyKitchenGrill

4.99 out of 5 average rating, 295 reviews

Exposed wooden beams frame the room, complemented by warm brick walls. A cozy fireplace sits centered against the wall, with decorative art above it. A comfortable chair and lamp are positioned nearby, while a television and small dresser provide functional elements in the living space.

Cottage in Newfane

Cozy Vermont Antique Sugar House with Fireplace

FamilyIndoor spacesAccuracy

4.92 out of 5 average rating, 128 reviews

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna

KitchenIndoor spacesGetting around

A spacious living area features a large sectional sofa adorned with decorative cushions. A wooden coffee table sits in front, with a lamp beside it. A dining area is visible, accompanied by a window allowing ample natural light and a view of the surrounding trees.

4.94 out of 5 average rating, 106 reviews

Cozy Mt Snow Ski In / Out

Indoor spacesFamilyPool

A spacious living area is introduced, featuring a stone fireplace and a large sectional sofa arranged around a coffee table. A dining table and chairs are positioned nearby, with natural light filtering through large windows adorned with curtains.

4.94 out of 5 average rating, 105 reviews

Great Amenities-Season Condo gym-sport center-pool

Indoor spacesFamilyGrill

4.8 out of 5 average rating, 276 reviews

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

KitchenFamilyCheck-in

Superhost

Townhouse in Dover

4.86 out of 5 average rating, 105 reviews

The Rooster - Mt Snow Townhome w/ Heated Pool!

Indoor spacesFamilyCondition