Family-friendly holiday rentals in Weston

4.94 out of 5 average rating, 369 reviews

The rustic cabin features a red exterior with a metal roof, framed by lush greenery. Flower pots with colorful blooms adorn the porch, which includes a small table and chairs. Large windows allow natural light to illuminate the interior.

Cabin in Londonderry

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

4.95 out of 5 average rating, 288 reviews

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!

4.8 out of 5 average rating, 239 reviews

A small red cabin is nestled under large trees, surrounded by lush greenery and autumn foliage. The backdrop features distant mountains, creating a serene and natural setting. Soft light filters through the leaves, enhancing the peaceful atmosphere of the landscape.

Guesthouse in Manchester

Glamping Cabin with Private Pond and Mountain View

This little glamping cabin with cozy woodstove is set at the far edge of a field overlooking a wildlife pond, seasonal fountain, and mountain. It is a peaceful place, surrounded by beauty, and special not just for these amenities but because it is improbably located on four private acres right in Manchester Center. The property abuts 70 acres of preserved land, but is steps from Main Street and all the shopping, dining, and outdoor options that this lovely year-round tourist town has to offer.

4.97 out of 5 average rating, 108 reviews

A spacious lawn is shown, featuring two buildings. One is a charming cottage with large glass doors, while the other is a main house with a traditional exterior. The ground is covered with fallen leaves, and trees line the background.

Cottage in Weston

Charming Mountain Cottage **NO CLEANING FEE**

Enjoy a charming cottage on the side of a hill in beautiful Weston, Vermont. You'll have the entire building to yourself (it's a stand-alone structure) to come and go as you please. My goal is to provide a five-star experience for five-star guests. I think little details like Ralph Lauren bath sheets, freshly-pressed bed linens, and duvet covers that are laundered between each guest make a difference. If you agree, you're probably the type of guest I'd enjoy hosting! Motorcycle friendly!!

4.94 out of 5 average rating, 177 reviews

A cozy outdoor living area features wooden seating, including a swing and chairs surrounding a fire pit. The camper is positioned on a deck nestled among trees, providing a sense of seclusion. A small table is visible, completing the inviting gathering space.

Campervan/RV in Guilford

Monadnock Sunrise Forest Hideaway

Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for two adults (queen bed) and one kid (63" long fold down couch).

4.99 out of 5 average rating, 268 reviews

The cabin's exterior showcases a warm wooden facade with large, strategically placed windows. A spacious screened porch extends from the building, inviting natural light and outdoor enjoyment. A stone pathway leads to the entrance, surrounded by landscaped gravel and native vegetation.

Cabin in Jamaica

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

4.99 out of 5 average rating, 200 reviews

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

Our recently renovated cabin is the perfect escape during any season! Located within minutes of Bromley, Magic, and Stratton, Wild Wings, and Viking. Also nestled in an amazing network of hiking, biking and ski trails. Guests will never be more than a few minutes away from outdoor adventure. With two bedrooms and one bonus loft, guests can enjoy the comforts of our cozy cabin, including a full kitchen, bathroom, outdoor shower, HOT TUB, fire pit, WiFi and FREE EV CHARGING. @owlsnestvt

Apartment in Middletown Springs

The historic Italianate home features a white exterior, with classic green shutters adorning tall windows. A spacious porch is supported by graceful columns, providing numerous seating options. The surrounding yard displays mature trees, enhancing the charm of the property set against a serene backdrop.

4.9 out of 5 average rating, 268 reviews

Apartment in Vermont Historic Home

This lovely renovated 3-room apartment is attached to our 1885 Vermont italianate home, located is historic Middletown Springs, Vermont. We have been working on restoring this house, listed on Vermont's registry of historic homes, for a dozen years now. The apartment has its own entrance, full kitchen, and one spacious bedroom. The third room is a large sitting room with a shower and closet bath. Enjoy your morning coffee on the front porch, meet our chickens, and explore our garden.

4.97 out of 5 average rating, 230 reviews

Icicles hang from a ledge, glistening in the sunlight. The backdrop features rolling mountains with patches of snow and a clear blue sky, creating a serene winter landscape visible through the ice formations.

Guest suite in Weston

Spacious King Spa Suite Weston Hills

Spacious 750 sqft guest suite king bed, table & chairs, kitchenette & sitting area & large, private spa bathroom featuring walk through mosaic shower area 4 shower heads, jets, wands & two person roman jacuzzi tub featuring aroma & chroma therapy & heated back rests. Ensuite bidet, elongated toilet & urinal. Pull-out sofa & comfy king bed with views from 5 glass doors to private deck. Xfinity high speed Internet and streaming TV with Peacock Premium. Private entrance from deck.

4.99 out of 5 average rating, 696 reviews

A cozy living area features a mixture of seating options, including a tufted sofa and a vintage-style sofa adorned with decorative cushions. Natural wood floors enhance the warmth of the space, while artwork on the walls and a circular coffee table complete the inviting atmosphere.

Barn in Chester

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

4.94 out of 5 average rating, 272 reviews

A group of twelve alpacas stands in a lush outdoor setting, showcasing various colors including white, brown, black, and grey. A wooden structure is visible in the background, surrounded by greenery and fencing.

Farm stay in Hoosick

Airbnb @ Sweet & Savory Farmette

Welcome to the AirBnB situated on a small working farm. You are welcome to tour the grounds to say hello to all the animals. This place is for the birds! No really you will enjoy watching chickens, ducks, emus, geese, guinea fowl, and peafowl. The farm is also home to a herd of beautiful alpaca and resident llama, curious goats, and barn cats. There are working livestock guardian dogs who watch over the herd who will greet you from behind the fence.

4.85 out of 5 average rating, 287 reviews

An aerial view captures the yurt nestled in a green landscape, surrounded by trees and a body of water. A fire pit and outdoor seating are visible nearby, with a custom-built outhouse located to the side, enhancing the rustic glamping experience.

Yurt in Mount Holly

Love Shack Yurt on Star Lake (100% off grid)

Glamping at its finest. Bring everything but the bed. Enjoy sunsets and star gazing lakeside. No running water or electricity. Clean & custom built outhouse for a toilet. You will need to bring bedding, size king. Please note: self cleaning policy. Leave it in great condition for your fellow travelers. Woodstove for heat, provide your own wood. One King Bed with mattresses and top sheet ONLY. IG@YURTlilyPAD

Popular amenities for Weston family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 122 reviews

The cabin entrance is framed by freshly fallen snow, with wooden siding that blends into the winter landscape. A lantern on the left provides a soft glow, illuminating the path. Tranquil trees surround the area, enhancing the serene atmosphere.

Cabin in Plymouth

~The ClubHaus~

4.87 out of 5 average rating, 141 reviews

An A-frame cabin is nestled among trees with autumn leaves in vibrant shades. A large deck extends from the cabin, featuring a hot tub and outdoor dining area. A barrel sauna is positioned nearby, completing the inviting outdoor space.

Cabin in Mount Holly

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

4.99 out of 5 average rating, 322 reviews

Tiny home in Wilmington

Beautiful Timber Frame Retreat

4.97 out of 5 average rating, 158 reviews

The exterior of Bearfoot Cottage is highlighted, featuring a combination of wood and metal finishes. A spacious deck with steps leads to the entrance, framed by large windows. A fire pit sits nearby, complemented by comfortable seating arrangements on the gravel surface.

Tiny home in Chester

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

4.97 out of 5 average rating, 509 reviews

A yurt is surrounded by nature, featuring a wooden deck with two Adirondack chairs. A storage shed with a sloped roof is adjacent. The landscape includes fields and trees, with a sunset sky casting soft colors above.

Tiny home in Putney

Vermont Retreat Luxe Yurt, Romantic & in Nature

4.85 out of 5 average rating, 157 reviews

The custom home features warm wood siding and a welcoming porch with flower boxes. A spacious deck with rustic railings extends from the second floor, while a covered area includes seating. Surrounding greenery enhances the natural setting, creating a serene outdoor ambiance.

Cabin in Wardsboro

Mountain side acres

4.9 out of 5 average rating, 247 reviews

A wooden deck is featured in the foreground, leading to a small sitting area with a patterned chair beside a black side table. Lush greenery surrounds the space, providing a natural setting, while a gravel path and stacked firewood are visible in the background.

Tiny home in Clarendon

Secluded tiny house resort - DOG FRIENDLY

4.96 out of 5 average rating, 593 reviews

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

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 199 reviews

The cabin features a wooden exterior surrounded by lush greenery, with large windows allowing natural light to enter. A wooden deck extends from the side, leading to a cozy outdoor area and an adjacent structure, contributing to the rustic charm of the setting.

Tiny home in Dover

Rustic Cabin in foothills of Green Mountains

4.97 out of 5 average rating, 223 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

4.91 out of 5 average rating, 337 reviews

The exterior of a red cabin is framed by green grass and colorful yellow flowers. The building features multiple windows and a gabled roof, creating a charming and rustic appearance. A clear pathway leads to the welcoming front door.

Guesthouse in Pawlet

Picturesque Cabin on the Mettowee

4.95 out of 5 average rating, 164 reviews

The exterior of a red cabin is surrounded by a snowy landscape. Large windows allow natural light to illuminate the front space, while a simple wooden bench rests on the porch. Pine trees are visible in the background, creating a serene atmosphere.

Cabin in Cavendish

The Cozy Little Red Cabin

Apartment in Bellows Falls

A spacious studio is depicted, featuring a cozy seating area with a blue couch and a patterned loveseat. A large wooden dining table is positioned nearby. The room is accented by vibrant artwork and is illuminated by natural light from two windows, complementing the warm wood flooring.

4.94 out of 5 average rating, 295 reviews

Stunning Studio in historic Downtown Bellows Falls

4.91 out of 5 average rating, 947 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

4.95 out of 5 average rating, 243 reviews

A wide view of colorful autumn foliage is captured, showcasing a variety of trees with hues of red, orange, and yellow. A clear blue sky sets a backdrop against the distant mountains, creating a serene landscape.

Home in Danby

Comfortable farmhouse with stunning views

4.96 out of 5 average rating, 134 reviews

A cabin made of wood features a covered front porch, surrounded by vibrant autumn foliage. A hammock can be seen hanging between the trees, alongside a picnic table. A carpet of fallen leaves enhances the natural setting, while tall trees provide a shaded atmosphere.

Tiny home in Granville

Gristmill Cabin overlooking peaceful brook.

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 186 reviews

A view from the balcony showcases the surrounding landscape, highlighting green hills and clear blue skies. Two adjoining buildings are visible, featuring sloped roofs and a variety of architectural styles. The area appears tranquil, with open spaces and scattered trees enhancing the natural scenery.

Condo in Killington

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

4.99 out of 5 average rating, 124 reviews

A modern living room features a traditional wood-burning fireplace framed by a brick facade. A large TV is mounted above the mantle, while a plush recliner, a small seating area, and a neatly stacked firewood display complete the cozy setting.

Condo in Dover

Winter Dream! The Handle Lodge at Snowtree Condos

4.95 out of 5 average rating, 103 reviews

The living area features a cozy fireplace surrounded by stone, with a wooden mantel. A dining table with white chairs is positioned near the kitchen, complemented by bar stools at the counter. Light floods in through large windows, enhancing the open layout.

Condo in Ludlow

Winterplace - Steps away from Slopes

4.92 out of 5 average rating, 106 reviews

The spacious great room features a wood-burning fireplace and is furnished with two comfortable sofas and a wooden coffee table. A large flat-screen TV hangs on the wall, and natural light emanates from the surrounding windows. A dining area with a circular table is visible in the background.

Home in Ludlow

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

4.93 out of 5 average rating, 114 reviews

A view of an open-concept suite showcases a kitchen countertop with a sink and decorative flowers. A cozy living area is visible, featuring a red sofa and a dining table. The master bedroom is visible in the background, fitted with a king bed and soft lighting.

Condo in Proctorsville

One Bedroom Suite Near Okemo

4.98 out of 5 average rating, 164 reviews

A red wooden cabin nestled among trees, showcasing a welcoming front porch. Air conditioning units are situated to the side. Natural light filters through the foliage, creating a serene and shaded outdoor atmosphere.

Barn in Newfane

Beautiful rustic woods and fields retreat.

4.96 out of 5 average rating, 125 reviews

A cozy living area features a brick fireplace with a warm fire. A comfortable sofa adorned with decorative pillows is positioned nearby, accompanied by a wooden coffee table. Wall-mounted art and soft lighting enhance the welcoming ambiance.

Townhouse in Killington

Beautiful Spacious Condo at Killington Resort