Family-friendly holiday rentals in Pittsfield

Guest suite in Stockbridge

5.0 out of 5 average rating, 116 reviews

Studio Suite with Vermont Style & Amazing Views

Central to Killington, Pico & Sugarbush Ski Areas. Breathtaking views. Features all Vermont has to offer in any season - Golf, Downhill & X-country Skiing, nearby VAST trails, Snowshoeing, Hiking, Trail & Road Biking. Unit is en suite w/sitting area, dining table/desk, kitchenette (no stove). Shower and toilet with ADA bars. Handicap accessible. Large closet, dresser. Streaming TV/DVD/VHS, selection of games, discs and tapes. 2 entrances - public and private. Stone patio and fire pit. Quiet.

FamilyIndoor spacesAccuracy

Earthen home in Granville

The interior of a cozy yurt features an orange clay wall and a wooden ceiling with exposed beams. A spacious bed is dressed in white linens, and a small desk with a chair sits nearby. A wood stove is positioned next to a area rug, enhancing the inviting atmosphere.

4.93 out of 5 average rating, 177 reviews

Sculpted Earthen Yurt in Green Mtns

Get away from it all in a wild mountain wonderland! Beautifully appointed yurts & a cabin surrounded by 25 acres of private forest, all to yourself. Hand-sculpted earth design, persian rugs, organic linens, & full kitchen w/many artisan touches. Explore local waterfalls and MTB trails, hike from the doorstep, make a campfire under a glittering, light-pollution-free sky. A private paradise for couples & outdoorsy families; a haven for writers & creatives; a quiet refuge to find yourself again.

FamilyIndoor spacesSkiing

4.98 out of 5 average rating, 194 reviews

Cabin in Pittsfield

Tiny Vermont Cabin!

Newly built tiny cabin in the woods of Vermont! Perfect for a quiet get away and close by outdoor fun! Killington and Pico Mountain is 15 minutes away! Sugarbush is 50 minute drive. Coming to Pittsfield for a wedding? Riverside Farm is only .7 of a mile down the road! Winter: MUST have AWD/4x4 for winter access on dirt road and driveway. Snow tires recommend. Cozy up by the newly added propane fireplace with an easy click of a button! Come experience the beauty Vermont has to offer!

Indoor spacesKitchenDecor

4.98 out of 5 average rating, 178 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 spacesKitchenNearby

4.98 out of 5 average rating, 123 reviews

An exterior view of the home showcases a patio adorned with string lights, providing a warm glow against the backdrop of rolling green hills. The hot tub is visible nearby, adding to the inviting outdoor space perfect for gatherings.

Cabin in Killington

Camp Poe: HotTub/AC/Game Room/6acres/Patio/EVchrgr

Experience the heart of the Green Mountains on our private 6 acre estate. Camp Poe at Estabrook is the ultimate Vermont getaway--wide plank floors, fully stocked farmhouse kitchen, wooden beams and a two story family room w/ a wood burning stove. This 3200 sq ft house is perfect for entertaining with two separate living rooms, bar, game room, 10ft dining tables (inside AND outside) and hot tub. 13 min to Killington Mtn & 4min to the #1 golf course in VT! EV Charger available for guest use.

Indoor spacesKitchenQuiet

4.97 out of 5 average rating, 305 reviews

A wooden cabin is set against a backdrop of colorful autumn foliage. The exterior features multiple large windows and a spacious deck with seating arrangements, including two lounge chairs. A grill and stacked firewood are visible on the deck, inviting outdoor gatherings.

Cabin in Roxbury

Off Grid Secluded Farm Stay Cabin

In a secluded, hand-crafted off the grid cabin, come and enjoy the elements with us at Drift Farmstead. A 3-minute walk leads you through gardens and pasture, to Ravenwood, a small, intimate cabin with everything you need. Be it an extended weekend tucked in seclusion, amongst the birds, river and trees, or find the comforts of a 37 acre small farm nestled in the mountains and settle in, working from afar. Top shelf skiing at Sugarbush is near, along with Vermont's finest grub and beer.

KitchenFamilyDecor

4.94 out of 5 average rating, 132 reviews

A spacious outdoor deck features a mix of seating, including lounge chairs and a table set for two. String lights are elegantly draped above, providing a warm glow. Surrounding trees add to the natural setting, enhancing the peaceful atmosphere.

Cabin in Stockbridge

1958 Classic "Hunting Cabin" w/ Breathtaking Views

Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a private mountain, surrounded by breathtaking views of Killington, Pico mountains, and the White River. Originally purchased from a Sears & Roebuck catalog as a hunting cabin owned by the same family until 2019. The cabin has since been transformed into its original vintage classic camp décor with antique furnishings and unique vintage finds that take you back in time.

FamilyKitchenBarbecue

A cozy living area features a deep leather sofa positioned near a stone fireplace. A large window opens to the balcony, inviting natural light. A TV is mounted above a wooden mantle, and a small table and chair provide a space for work or dining.

4.99 out of 5 average rating, 177 reviews

Alpine Condo - AC & Pool - Golf & Bike

Updated 1-bedroom Whiffletree condo with stylish alpine feel—steps from Killington Resort, golf course, and access road. Thoughtfully stocked with essentials, plus a private gear locker for convenience. Relax at the onsite outdoor pool (open Memorial Day–Labor Day). Sleeps 4 with a king bed and queen pullout sofa. Portable AC unit in the living room helps keep the condo comfortable Pack & Play crib, mattress and sheets available upon request for $25 per stay. Reg #007718

Indoor spacesKitchenAccuracy

4.97 out of 5 average rating, 146 reviews

A bright living area features large windows that frame views of the surrounding forest. Natural light enhances the wood-paneled walls. A comfortable sofa and chair are positioned around a central coffee table. A small, modern wood stove provides warmth, creating a cozy atmosphere.

Cabin in Goshen

The Berghüttli: Glowing Swiss Hut in the Forest

The Berghüttli ("little mountain hut") is a Swiss-inspired hut and farm stay surrounded by National Forest in Goshen, VT (pop. 168). A completely private escape—no other structures in sight, just woods and quiet. Inside, a wall of windows brings the forest right up to you, while glowing maple plywood fills the space with warm light. High-speed fiber internet runs a reliable 300 Mbps. Stay connected or switch off completely. Search "The Berghüttli" on YouTube for a video tour.

Indoor spacesFamilyNearby

4.99 out of 5 average rating, 330 reviews

A modern house with wooden exterior is shown from an elevated perspective, surrounded by autumn foliage. A hot tub is positioned on a spacious deck, which includes a seating area with four chairs and a small table. Scenic mountain views and vibrant trees enhance the natural setting.

Tiny home in Warren

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*

KitchenIndoor spacesCondition

4.85 out of 5 average rating, 256 reviews

A welcoming living area features a large fieldstone fireplace, with a soft couch and several armchairs arranged for comfort. A coffee table sits in the center of the space. Above, warm lighting illuminates an adjacent dining area, enhancing the cozy atmosphere.

Home in Pittsfield

Killington area home - 4 seasons - hot tub and A/C

Set on a private road in the hills of Pittsfield, our house welcomes you year-round. Right in the heart of the Northeast’s best winter-sports, it's convenient to Killington ski resort, VAST snowmobile trails, Mountain Meadows cross country skiing and Green Mountain National Golf course. Furthermore, there are wonderful hikes and mountain biking to be done on the property and beyond - particularly beautiful in the fall.

Indoor spacesKitchenBiking

4.94 out of 5 average rating, 148 reviews

A private deck with a hot tub is surrounded by colorful planters filled with seasonal flowers and pumpkins. The entrance to the cabin features a welcoming door framed by autumn decorations, backed by lush greenery from the surrounding forest.

Cabin in Chittenden

Outside Inn - Hot Tub/Killington/MtnTop Inn/VAST

Reconnect with nature at the Outside Inn, a four season retreat, locally known as the Labor of Love. A man fell in love with a woman, but when he asked for her fathers blessing he said, first you must build her a home. So he built this beautiful post and beam cabin and they lived happily ever after! *Decorated seasonally!* IG/TikTok: outside_inn_vt FB: Outside Inn VT

Indoor spacesKitchenComfort

Popular amenities for Pittsfield family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 109 reviews

Chalet in Killington

The Overlook - Views | Hot Tub | Fire Pits | Games

Indoor spacesFamilyQuiet

A warm living area is highlighted by a wood-burning fireplace, providing a cozy focal point. A comfortable sofa and coffee table fill the space, while a large flat-screen TV is mounted above the fireplace. A friendly dog sits on the floor, enhancing the welcoming vibe.

4.94 out of 5 average rating, 305 reviews

AC, Vermont Retreat, Dogs Welcome, Pool & Spa

KitchenFamilyBathroom

4.93 out of 5 average rating, 301 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 spacesLocation

4.91 out of 5 average rating, 108 reviews

A charming treehouse is perched among vibrant autumn foliage, surrounded by trees displaying shades of yellow and red. The wooden structure features a red roof and a spacious deck that offers a scenic view, harmonizing with the natural hillside landscape.

Treehouse in Warren

The Birch Perch! Treehouse with spa and fire pit!

Indoor spacesFamilyLocation

4.94 out of 5 average rating, 223 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

Indoor spacesFamilyGetting around

4.95 out of 5 average rating, 111 reviews

Tiny home in Ludlow

Alpine Reflection + Hot Tub

Indoor spacesKitchenAmenities

4.9 out of 5 average rating, 156 reviews

Treehouse in Stockbridge

Romantic Treehouse- AC, PVT Hot tub, 20 Min to KLT

KitchenFamilyOutdoor spaces

4.92 out of 5 average rating, 168 reviews

A bright dining area is highlighted by a large wooden table, surrounded by black chairs. Natural light floods the space through multiple windows, accentuating the warm wooden beams above. A chandelier adds a touch of elegance, complementing the simple decor.

Home in Killington

Atelier Killington, hottub and amazing location

Indoor spacesKitchenEV charging

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 136 reviews

Cabin in Corinth

Cabin Hill at Taplin Hill Farm in Corinth, Vermont

FamilyIndoor spacesComfort

4.94 out of 5 average rating, 142 reviews

A raised Treehut is nestled among trees, featuring a spacious deck and large windows. A cozy fire pit area is visible below, along with two adirondack chairs. Ferns and natural foliage surround the site, enhancing the secluded and peaceful ambiance of the retreat.

Treehouse in Braintree

Treehut - Secluded Treehouse in the Forest

Indoor spacesFamilyWalkability

4.97 out of 5 average rating, 239 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

KitchenFamilyHiking

4.85 out of 5 average rating, 204 reviews

An A-frame chalet features a sloped metal roof and wooden exterior, surrounded by verdant greenery. A welcoming wooden deck with stairs leads to the entrance, inviting guests to enjoy the natural setting. Large windows allow for sunlight to illuminate the space.

Chalet in Stockbridge

Vermont Chalet

Indoor spacesKitchenCleanliness

4.99 out of 5 average rating, 263 reviews

A charming cabin stands beneath a clear blue sky, featuring a metal roof and large windows that provide ample natural light. Grassy areas surround the structure, with trees bordering the background, creating a serene rural setting.

Cabin in Royalton

Genuine Vermont Sugar House on 70 peaceful acres.

Indoor spacesKitchenBathroom

4.99 out of 5 average rating, 168 reviews

Home in Woodstock

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

Indoor spacesKitchenBiking

4.92 out of 5 average rating, 249 reviews

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)

Indoor spacesKitchenParking

5.0 out of 5 average rating, 142 reviews

A rustic wooden cabin is set amidst trees, featuring a welcoming front porch with two chairs. Flower boxes adorn the windows, adding a touch of greenery. The natural wood siding blends harmoniously with the surrounding landscape, creating a serene and inviting exterior.

Farm stay in Washington

Casita Cabin -Sun drenched cozy cabin on homestead

KitchenIndoor spacesQuiet

Family-friendly home rentals with a pool

4.89 out of 5 average rating, 135 reviews

Home in Killington

Golf and Mountain Biking outside the door!

KitchenIndoor spacesGetting around

4.88 out of 5 average rating, 254 reviews

Home in Killington

Luxury Condo Tucked in the Heart of Killington

Indoor spacesFamilyBackyard

4.94 out of 5 average rating, 481 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

FamilyKitchenCondition

4.91 out of 5 average rating, 1015 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

FamilyIndoor spacesCondition

4.88 out of 5 average rating, 280 reviews

The exterior of a cozy ranch house is shown, framed by lush greenery and flowering shrubs. The front porch is accessible via steps, with a teal door welcoming visitors. A pathway leads through the manicured lawn, enhancing the inviting appearance of the property.

Home in Mendon

Ranch at Mendon Mt Orchards

Indoor spacesKitchenHeating

4.88 out of 5 average rating, 304 reviews

The cozy living area features a pair of gray sofas positioned around a circular wooden coffee table. A fireplace is set against a green accent wall, accompanied by a flat-screen TV mounted above. Natural light filters through the large window adorned with blinds.

Townhouse in Killington

Renovated 2bd/2.5bath/Den + Pool Access (pets ok)

Indoor spacesKitchenShared spaces

Aerial view captures a large cluster of buildings nestled among vibrant autumn foliage, showcasing shades of orange, yellow, and green. Majestic mountains rise in the background, while a spacious parking area is visible, surrounded by trees.

4.87 out of 5 average rating, 127 reviews

Updated large condo across from AT and skiing

FamilyKitchenCondition

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.