Family-friendly vacation rentals in Woodstock

4.99 out of 5 average rating, 170 reviews

Home in Woodstock

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

Welcome to this charming 4-bedroom Cape Cod-style retreat in Woodstock, Vermont, a picture-perfect New England getaway set on a wooded hillside lot. With original wide-plank hardwood floors, a fully equipped chef's kitchen, and a spacious back deck with a 6-burner propane grill, this home offers the perfect blend of rustic character and modern comfort. Explore the covered bridges and artisan shops of Woodstock Village, or simply unwind in the peaceful garden setting. Please see: Other Things to

FamilyIndoor spacesCondition

4.97 out of 5 average rating, 215 reviews

A charming cottage is set against a backdrop of lush trees, with a deck extending from the front. The warm, orange sky creates a serene atmosphere, casting soft light on the exterior of the house and surrounding landscape.

Guesthouse in Hartland

Cozy - Killington 40 min. Woodstock-Hanover-Piano!

Luxurious, well appointed cottage - Beautiful sunrise view located between Woodstock VT and Hanover NH. Inspiring treat for musician’s getaway is a fully restored 1929 Steinway Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer. VERY comfortable queen bed. Romantic getaway in the woods, relax, work in peace, explore the beauty and history of the area. Hiking, biking, fishing, hot air balloon rides and shopping are all close by. Long (90 day) or weekend rental

KitchenFamilyBackyard

The bright kitchen showcases a spacious island with seating for four at sleek, modern bar stools. Stylish pendant lights hang above, and large windows provide natural light. Ample cabinetry lines the walls, with contemporary appliances positioned for easy access.

4.94 out of 5 average rating, 133 reviews

Quechee Getaway Book Your Ski Trip Now

New Build Multi family friendly home near Woodstock, Killington and Dartmouth – Sleeps 12, Modern Aesthetic, Private Porch & Fire Pit Escape to this stunning modern ski home, just 25 minutes from the Skyship Gondola of Killington, Vermont. Whether you're hitting the powder in winter or enjoying the breathtaking foliage and outdoor adventures in the warmer months, this luxurious retreat offers the perfect base for your next getaway. Hike the Gorge or stroll thru the quaint village of Woodstock.

Indoor spacesKitchenOutdoor spaces

4.98 out of 5 average rating, 120 reviews

A modern chalet is situated among lush greenery, featuring a sloped roof and large windows. A cozy outdoor seating area surrounds a fire pit on a grassy lawn, inviting relaxation in a natural setting. A storage area for firewood is visible beside the structure.

Chalet in Woodstock

Falcon House: VT Chalet w/Sauna, Bike to Village

Welcome to Falcon House! A modern VT chalet w/sauna at the edge of a 60 acre forest ∙ Outdoor Finnish sauna, shower, yoga platform & hiking trails ∙ 5 min to Woodstock village, 20 min to ski Killington ∙ Spotlessly clean, tastefully furnished, well stocked with thoughtful amenities ∙2 bedrooms, 2 full baths. Lofted king master has ensuite +Lower level den w/double futon ∙ Chefs kitchen, fireplace, 2 TVs & WiFi ∙ Brookside deck w/BBQ & dining ∙Follow Falcon House on Social @falcon_house_vt

Indoor spacesKitchenCheckout

4.98 out of 5 average rating, 182 reviews

A unique treehouse is seen perched among tall trees, with a blend of rustic wood siding and large windows that reflect the surrounding greenery. The structure stands elevated from the ground, supported by slender pillars, blending harmoniously with the natural forest environment.

Treehouse in Hancock

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

Indoor spacesKitchenValue

4.99 out of 5 average rating, 317 reviews

The kitchen area features a large island with seating and modern appliances. Natural wood paneling complements the high cathedral ceiling. Glass doors open to a scenic view of the surrounding hills, providing ample natural light and a connection to the outdoors.

Barn in Woodstock

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". A lofted space on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony. For more go to @theloft.vt

Indoor spacesFamilyLayout

4.97 out of 5 average rating, 465 reviews

The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.

Cottage in Windsor

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

FamilyIndoor spacesView

4.98 out of 5 average rating, 307 reviews

A cozy cabin is nestled among the trees, showcasing a rustic wooden exterior with large windows. It overlooks a gentle slope covered in green grass and wild plants, with sunlight filtering through the canopy above, creating a serene and inviting atmosphere.

Guesthouse in Woodstock

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED.

Indoor spacesKitchenPets

4.94 out of 5 average rating, 226 reviews

A cozy living space is highlighted by a modern pink chair positioned near a wood stove, which emits a warm glow. Large glass doors offer views of the wooded surroundings, while a Moroccan rug adds texture to the concrete floor.

Chalet in Royalton

Scandinavian design Chalet hiking trail + hot tub

This bright, well-designed Scandinavian-style chalet is the perfect cozy retreat. Nestled in the woods on a plot of 20+ acres, it offers scenic views and a private hiking trail leading to beautiful vistas, transforming into a winter wonderland for skiing adventures, a summer paradise for outdoor relaxation, and a vibrant canvas for leaf peeping during Vermont's stunning fall foliage season. Goodland wood burning hot tub is available 365 days a year.

FamilyIndoor spacesBathroom

4.94 out of 5 average rating, 175 reviews

Cottage in Hartland

Cottage 5 miles from Woodstock-Dog Friendly w/FIOS

Just 5 miles from Woodstock, the Cottage at StillwoodVT is a bright and cozy two-story home set on a peaceful 20-acre oasis of woods, pasture, and hill views. Two bedrooms (queen upstairs, full downstairs), one bath with shower, and open kitchen/living/dining area. Private, quiet, and surrounded by nature. One-bedroom use receives 10% back after checkout (not combinable with other discounts).

FamilyIndoor spacesLaundry

4.93 out of 5 average rating, 103 reviews

A historic barn house from the 19th century is surrounded by lush greenery. A large tree stands in the foreground, while the barn's wooden exterior and stone elements create a rustic charm. Various windows allow natural light to enhance the inviting atmosphere.

Home in Hartland

19th Century Bohemian Barn House

This 19th century barn-house has a welcoming, cosy, bright vibe and a funky bohemian flair. It's artsy, comfortable with touch of sophistication. Lots of sitting areas for reading, conversation and chilling out. Great view and backyard stream; perfect for nature lovers. Decks and wonderful outside space for a cook out or enjoying the brook & gardens on a nice day.

Indoor spacesKitchenSleep quality

A spacious living area features a modern wood-burning fireplace framed by light brick, with a mounted flat-screen TV above. Comfortable grey sofas and a wooden coffee table are arranged to encourage relaxation, while a wooden staircase leads to the upper level.

4.96 out of 5 average rating, 178 reviews

The Quechee Haus: VT Retreat with Outdoor Hot Tub

Relax, rejuvenate, and restore at the Quechee Haus. Located just 10 minutes from downtown Woodstock, 30 minutes from Killington, and around the corner from the family-friendly Quechee Ski Resort, this 3-bed, 3-bath modern retreat offers everything you need for the perfect winter getaway.

FamilyKitchenBathroom

Popular amenities for Woodstock family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 302 reviews

A rustic cabin is nestled among the trees, showcasing its wooden exterior and a metal roof. Tall windows allow natural light to fill the space. Surrounding greenery, including ferns and bushes, adds to the secluded atmosphere. A stone wall and picnic table can be seen in front.

Cabin in Sharon

forest retreat; off-grid writers cabin

KitchenIndoor spacesAccess

4.96 out of 5 average rating, 115 reviews

Tiny home in Ludlow

Alpine Reflection + Hot Tub

KitchenFamilyHospitality

A modern kitchen features a central island with a wooden countertop, surrounded by two stools. White cabinetry and ample counter space are present, with large windows providing natural light and garden views. A variety of appliances and kitchen tools are visible, enhancing functionality.

4.97 out of 5 average rating, 129 reviews

Quechee Ski Haus: Hot Tub, Sauna, & Mtn Views

Indoor spacesFamilyCleanliness

4.96 out of 5 average rating, 217 reviews

FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym

KitchenIndoor spacesHot tub

4.96 out of 5 average rating, 596 reviews

The uniquely shaped house, adorned with shingles, is surrounded by lush greenery. Large windows reflect the vibrant foliage, allowing natural light to illuminate the structure. The natural stone wall complements the rustic aesthetic, creating a harmonious blend with the wooded landscape.

Home in Fairlee

Cozy Bow House Perched in Trees w/ Hot Tub & View

Indoor spacesFamilyAccuracy

4.95 out of 5 average rating, 267 reviews

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

FamilyKitchenHeating

Guest suite in Brownsville/West Windsor

The exterior of a charming farmhouse features a green metal roof and white siding, surrounded by lush greenery. Flowering shrubs in the foreground add a touch of natural beauty, complementing the tranquil rural setting. Blue skies and scattered clouds provide a serene backdrop.

5.0 out of 5 average rating, 214 reviews

Cozy Guest Suite in VT Farmhouse

Indoor spacesKitchenHospitality

4.94 out of 5 average rating, 483 reviews

A custom-made yurt is nestled among lush greenery, surrounded by tall trees. Sunlight filters through the foliage, illuminating the yurt's circular structure and chimney. Wildflowers and grasses frame the foreground, creating a natural, serene setting.

Yurt in Randolph

Lower Yurt Stay on VT Homestead

Indoor spacesKitchenPets

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 166 reviews

A serene view captures a green field leading to distant mountains, with a weathered barn nestled among trees. A small shrub occupies the foreground, providing a sense of depth. The landscape reflects a tranquil countryside setting.

Home in Bethel

Vermont private retreat with gorgeous views.

Indoor spacesFamilyValue

4.97 out of 5 average rating, 107 reviews

Home in Bridgewater

Breathtaking Riverfront Retreat w/Mountain Views

FamilyIndoor spacesRiver

4.97 out of 5 average rating, 241 reviews

A charming cabin constructed from natural materials is nestled among lush trees in a forested area. Sunlight filters through the leaves, casting dappled shadows on the ground. The cabin features large windows that invite the surrounding greenery inside.

Tiny home in Hartland

Cabin on the Hill

FamilyIndoor spacesAmenities

4.98 out of 5 average rating, 240 reviews

A rustic cabin is nestled among vibrant wildflowers and lush greenery. A variety of flowers, including purple and yellow blooms, frame the scene, leading the eye towards the charming structure with a classic metal roof and wooden accents.

Home in West Windsor

Meadow View. 35 acres outside your door!

Indoor spacesFamilyAir conditioning

4.95 out of 5 average rating, 1067 reviews

Guesthouse in Hartland

Yurt In The Woods - Come to the Yurt.

Indoor spacesFamilyHospitality

4.93 out of 5 average rating, 102 reviews

Home in Reading

Private, Large 4BR home | Pet friendly | 10 Acres

Indoor spacesKitchenLaundry

A dining area is seen through an open doorway, featuring a wooden table surrounded by six chairs. Warm lighting is provided by a chandelier above, while a bowl of flowers centers the table. A patterned rug lies beneath, and cabinetry is visible in the background.

4.98 out of 5 average rating, 176 reviews

Charming, Cozy Cape

KitchenFamilyDecor

4.97 out of 5 average rating, 156 reviews

A large farmhouse is set against a backdrop of vibrant autumn foliage. The structure features a modern design with a metal roof and expansive glass windows, allowing for abundant natural light. A spacious lawn complements the serene rural setting.

Home in Rochester

Modern Farmhouse on 25 Acres - Superb Views

FamilyKitchenOutdoor spaces

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 120 reviews

A cozy living area features exposed beam ceilings and wood floors. Two comfortable sofas face each other, complemented by a coffee table and side tables with lamps. A staircase leads to the upper level, and a small workspace with a chair is visible in the corner.

Cabin in Hartford

Cozy Quechee Cabin near Woodstock and Killington

Indoor spacesKitchenCheck-in

4.91 out of 5 average rating, 1019 reviews

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

FamilyKitchenAccess

A cozy living area features a stone fireplace, providing warmth and a focal point in the room. Two brown sofas are positioned around a coffee table. Soft lighting from a nearby lamp creates a comfortable ambiance, complemented by large windows letting in natural light.

4.93 out of 5 average rating, 500 reviews

PEEP Pico Hike out back door 1 Bed free shuttles

KitchenIndoor spacesHot tub

4.99 out of 5 average rating, 100 reviews

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

KitchenFamilyQuiet

4.96 out of 5 average rating, 103 reviews

Home in Winhall

Heated Pool, EV Charging, Hot Tub & Barrel Sauna

Indoor spacesKitchenTV

4.93 out of 5 average rating, 142 reviews

Walk to Killington | Pool, Arcade + AC

Indoor spacesFamilyView

A modern kitchen with a circular dining table surrounded by four wooden chairs is featured. Stainless steel appliances, including a microwave and oven, are present. A stylish light fixture hangs above the table, while the fireplace and sports equipment are visible in the background.

4.92 out of 5 average rating, 226 reviews

Mtn Green Condo-Ski/Bike Lifts, Covered Parking

KitchenIndoor spacesLong stay

A modern studio space is presented with wood paneling and a vaulted ceiling. Stainless steel kitchen appliances are featured alongside a dining table and a comfortable seating area. Two vintage ski boards are mounted on the wall, and a sliding glass door provides access to a private balcony.