Family-friendly holiday rentals in Plymouth

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

4.99 out of 5 average rating, 155 reviews

A spacious living area features a central stone fireplace, surrounded by cozy seating. Large windows frame scenic views of the trees outside, filling the space with natural light. The rustic wooden beams and walls add warmth, while the open layout connects to the kitchen and loft above.

Barn in Andover

Fat Cat Barn - Close Okemo & Magic, Vermont

Welcome to Fat Cat Barn! This is an incredibly unique, family oriented 1850's Mennonite built Post & Beam barn on 10+ acres in the pastoral hills of Andover, VT. We are wedged between the wonderful villages of Weston, Ludlow & Chester. Just 15 minutes from Okemo and Magic ski mountains with Stratton, Bromley & Killington all within 40 minutes. This is a wonderful four season property with plenty of options for fun right outside our door step. The Stratton mountain views and sunsets are stunning

The exterior of the fully renovated home is surrounded by greenery, featuring a spacious yard and a fenced area. A large deck is visible on the back of the house, along with a detached garage and ample outdoor space for gatherings.

4.92 out of 5 average rating, 102 reviews

Updated 6BR Home 4 min to Okemo w fenced in yard!

Fully renovated! This single-family home is a perfect getaway for you and your friends or family to enjoy some of the best terrain in the Northeast at Okemo Mountain, located just 5 minutes away. After a day on the slopes come home, unwind and relax or head to downtown Ludlow area to enjoy restaurants, bars, shopping and more. Pet-friendly, large fenced in yard. Nearby attractions: - Camp Plymouth State Park & Echo Lake - Fox Run Golf - Buttermilk Falls hiking and swimming - Killington Skiing!

4.93 out of 5 average rating, 103 reviews

Home in Reading

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

Okemo & Killington Ski House Large 4 bedroom 2.5 bath, 3,000+ sq ft home located close to Okemo Ski Resort and surrounded by 10 acres of land at the end of a private road! This recently renovated home features 3 levels, a large game room, 5 separate sleeping areas and a large covered porch! Enjoy ultimate privacy with proximity to multiple outdoor adventures including skiing, golfing, hiking and mountain biking. Just a short drive to downtown Ludlow and other surrounding stores in Cavendish.

4.99 out of 5 average rating, 132 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~

Appreciate life at our peaceful home away from home in the Vermont Woods... Located a short drive from Killington and Okemo ski mountains, The ClubHaus is the perfect spot to unwind after enjoying four season New England activities. Breweries and great food are nearby in Woodstock, Manchester, and Dorset. Huge fireplace, hot tub, comfortable beds, and lots of thoughtful touches provided to welcome you to the ClubHaus family. Wifi, Netflix, and Disney+ included, no cable. @clubhausvt on IG

4.97 out of 5 average rating, 184 reviews

Ski Chalet with Hot Tub on Okemo Mountain

Escape to this spacious 3-level, 1,700+ sq. ft. ski chalet, just 4 minutes from Okemo Mtn Resort and downtown Ludlow, 6 minutes from Jackson Gore, and 30 minutes from Killington. Floor-to-ceiling windows frame beautiful 180-degree views of the wooded backyard, creating a peaceful mountain retreat. After skiing, hiking, or exploring, unwind by the fireplace or soak in the private Jacuzzi hot tub. With plenty of space and a fantastic location, this chalet is an ideal Vermont getaway year-round.

Adirondack chairs and a small side table are positioned on a spacious deck, offering an unobstructed view of Okemo resort. The winter landscape features snow-covered ground, complemented by a clear blue sky and distant mountain views.

4.99 out of 5 average rating, 142 reviews

Stunning Okemo Views - 3BD 3BA on 10 Private Acres

Recently constructed on ten private acres with captivating views of Okemo. Three BR, three full bath, air conditioned modern chalet, just 1.5 miles from downtown and 3 miles from Okemo’s base areas. Epic views of Okemo and surrounding mountains from every room. Cozy around the fireplace in the living room or enjoy smores outside by the firepit, or unwind on the deck. Lower level has second living room great for kids with large TV, comfy couches, Pac Man arcade, foosball and board games.

4.93 out of 5 average rating, 408 reviews

Cabin in Poultney

Waterfront Vermont Lake House w/ Panoramic Sauna

Waterfront on Lake St. Catherine, with almost 100ft of private lake frontage and a view that's hard to beat. Watch the sunrise from the deck or from inside our new panoramic barrel sauna. Explore the lake by kayak or canoe — both included for guests. Keep an eye out for both bald eagles and loons. There's also a fire pit for evening s'mores — firewood included as well. Great for families — we've got a crib, a bunk room for the kids, and a bookshelf of board games for those rainy days.

4.99 out of 5 average rating, 320 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

A newly renovated lakefront home is showcased, featuring a spacious deck with comfortable seating and a covered lower level area. Soft lighting illuminates the exterior, highlighting the modern finishes and architectural details against a twilight sky.

4.88 out of 5 average rating, 104 reviews

VT Lakefront House, Lake Fun, Fall Foliage and Ski

Newly renovated, air conditioned, lake front home with a hot tub, fire pits and modern finishes. Tons of space, super comfortable beds. Plus TWO LARGE bonus rooms. Year-round fun; swim, kayak, golf and fish in the summer; hike and fall foliage in the fall and ski in the winter. 7 minutes from Okemo and 22 minutes from Killington. Cook with a stunning view of the lake, watch a movie by the fire or hottub. Outdoor shower, game room, movie room, screened porch and much more!

4.97 out of 5 average rating, 471 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.

4.96 out of 5 average rating, 119 reviews

Tiny home in Ludlow

Alpine Reflection + Hot Tub

Escape to this luxury glass tiny home perched at 1,500 feet in elevation in Ludlow, Vermont—architect-designed and built in Estonia with stunning views of Okemo Mountain. Tucked away in a private forest setting, this one-of-a-kind retreat features a hot tub, fire pit, outdoor shower under the trees, radiant heated floors, and floor-to-ceiling windows that immerse you in nature. Designed for quiet luxury relaxation and unforgettable mornings, it’s the perfect escape every season

Popular amenities for Plymouth family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 274 reviews

A captivating sunset paints the sky with hues of orange, pink, and purple, with rolling hills silhouetted in the foreground. The distant mountains create a serene backdrop, accentuating the natural beauty of the secluded setting.

Home in Plymouth

Top of the World! Jacuzzi! Private Hiking Trails!

4.97 out of 5 average rating, 112 reviews

Chalet in Killington

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

4.89 out of 5 average rating, 106 reviews

A cozy living room features a stone fireplace at its center, surrounded by natural wood paneling. Two red accent chairs are positioned beside a window, while a large gray sofa and green armchair offer ample seating. A coffee table rests in front, adorned with a textured blanket.

Home in Killington

Brookview Lodge, Killington, VT

4.94 out of 5 average rating, 141 reviews

A contemporary ski house is featured, set against a snowy landscape. The structure showcases large glass windows and a spacious deck, elevated on stilts. Surrounding trees and a light dusting of snow enhance the serene atmosphere of the property, inviting a cozy retreat.

Chalet in Ludlow

Okemo Ski Chalet with Hot Tub

4.89 out of 5 average rating, 100 reviews

A spacious living area is highlighted by a large gray sectional sofa, complemented by decorative cushions. Natural light enters through adjacent doorways, illuminating the open layout that connects to a well-equipped kitchen, featuring light wood cabinetry and modern appliances.

Apartment in Killington

BearNecessities- Pool, Hot Tub, Gym

4.93 out of 5 average rating, 115 reviews

A vibrant autumn landscape is visible, featuring a two-story green townhome bordered by a well-maintained lawn. Colorful foliage on nearby trees and surrounding hills creates a warm ambiance, highlighting the natural beauty of the area in this scenic outdoor view.

Townhouse in Killington

Topridge 3BR w Foliage Views & Private Hot Tub!

4.99 out of 5 average rating, 112 reviews

An aerial view captures the chalet nestled among lush greenery, with mountains rising gently in the background. The warm hues of sunset fill the sky, while string lights illuminate the exterior, creating an inviting atmosphere amidst the natural landscape.

Chalet in Mendon

Close to Killington-Loaded with Amenities-Hot Tub

4.93 out of 5 average rating, 271 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

Family- and pet-friendly home rentals

Superhost

A inviting corner of the cabin showcases a light-colored armchair beside a wooden cabinet. Soft natural light filters through two windows adorned with simple treatments, illuminating the warm wooden walls. A wood-burning stove stands nearby, enhancing the rustic charm of the space.

Cabin in Cavendish

Copper Hill House - VT getaway near Ludlow & Okemo

4.93 out of 5 average rating, 104 reviews

4.97 out of 5 average rating, 110 reviews

Home in Bridgewater

Breathtaking Riverfront Retreat w/Mountain Views

4.99 out of 5 average rating, 155 reviews

An interior view showcases a modern staircase with wooden steps and a metal railing, leading to a second floor. Natural light floods the space through large glass windows, illuminating the wooden walls and a stone fireplace. A green plant adds a touch of nature.

Home in Londonderry

Modern 3-bedroom A-frame in Londonderry w/ Pond

4.95 out of 5 average rating, 229 reviews

A spacious living room features a comfortable sofa and armchair, enhancing relaxation. A large television is positioned in front, with decorative elements and artwork on the walls. Soft lighting from lamps and windows creates a welcoming ambiance in the well-designed space.

Guest suite in Clarendon

River House Apartment - Dog friendly

4.84 out of 5 average rating, 190 reviews

An old barn features weathered wooden siding and large windows, set against a backdrop of vibrant autumn foliage. A maple tree with bright orange leaves provides a natural canopy, while a carpet of fallen leaves covers the grassy ground, creating a serene outdoor scene.

Barn in Mount Holly

Mapleside Escape: Sugar/Ski/Green Mountains

4.97 out of 5 average rating, 138 reviews

A charming red exterior defines the recently built house, surrounded by lush greenery and a clear sky. The spacious porch features rustic columns, while comfortable seating invites relaxation. Large windows ensure natural light fills the interior, offering a connection to the serene outdoor environment.

Home in Windsor

Custom cabin on Mt Ascutney, Fall and Winter Days…

4.94 out of 5 average rating, 177 reviews

Cottage in Hartland

Cottage 5 miles from Woodstock-Dog Friendly w/FIOS

4.94 out of 5 average rating, 1384 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

Family-friendly home rentals with a pool

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.

4.91 out of 5 average rating, 227 reviews

Mtn Green Condo-Ski/Bike Lifts, Covered Parking

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, 308 reviews

Vermont Retreat, Dogs Welcome, Pool & Spa

5.0 out of 5 average rating, 115 reviews

A gravel road leads through open fields bordered by manicured greenery. In the distance, rustic buildings and trees with autumn foliage are visible against a clear blue sky, creating a serene rural landscape.

Farm stay in Clarendon

Dream Catcher Farm

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, 503 reviews

Book Peep now Stay on Pico 1 Bedroom free shuttle

A tranquil sleeping area features a cozy bed with soft bedding and accent pillows. Nightstands with lamps are placed on either side, providing gentle light. A large horse portrait adorns the wall above the bed, contributing to the serene ambiance.

4.91 out of 5 average rating, 110 reviews

Great PeeP rates Hike Golf Tennis 2 Bed on Mtn

4.89 out of 5 average rating, 141 reviews

Home in Killington

Golf and Mountain Biking outside the door!

4.99 out of 5 average rating, 101 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

Superhost

A cozy living area features a brick fireplace at its center, surrounded by two comfortable armchairs and a wooden coffee table. A Roku Smart TV is positioned next to large glass doors leading to the balcony, while a mirror reflects the warm ambiance. Natural light enhances the wooden accents on the walls.