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Family-friendly vacation rentals in Plymouth

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Plymouth

  • Total vacation rentals

    Explore 140 vacation rentals in Plymouth

  • Nightly prices starting at

    Plymouth vacation rentals start at ﺩ.ﺇ 404 per night before taxes and fees

  • Verified guest reviews

    Over 5,820 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    140 of Plymouth vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Plymouth rentals

  • 4.9 Average rating

    Plymouth stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Plymouth

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
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

KitchenIndoor spacesCleanliness

4.99 out of 5 average rating, 170 reviews
Top guest favorite
Cabin in Plymouth

Mountain Views, Hot tub, Trails, Pond, BBQ

Private Pond | Post & Beam | Nature Retreat | Hot Tub Sleeps up to 8 Welcome to your peaceful escape in the woods. This custom-built, post-and-beam home sits on 5 wooded acres with private frontage on a tranquil 6+ acre pond—perfect for nature lovers, quiet seekers, and family or friend groups looking to unwind. Highlights: * 4 bedrooms | 2.5 baths * 3 King beds & 1 Twin Bunk. All memory foam mattresses * 30-ft ceilings, reclaimed beams * Fully equipped kitchen * 75” TV, arcade, board games

FamilyIndoor spacesHeating

4.99 out of 5 average rating, 92 reviews
Guest favorite
Home in Bridgewater

Breathtaking Riverfront Retreat w/Mountain Views

Thoughtfully designed to elevate every moment of your Vermont getaway, our home offers a comfortable & uniquely historic experience, along with panoramic views of the beautiful Ottauquechee River. Perfectly nestled between the vibrant towns of Woodstock and Killington, guests have incredible hiking, skiing, golfing, shopping, leaf peeping, delicious dining, and so much more right at your finger tips. Wonderful for families, couples, or small groups looking to explore all that VT has to offer!

Indoor spacesFamilyCheck-in

4.97 out of 5 average rating, 107 reviews
Top guest favorite
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!

Welcome to one of the most unique "retreats" in Vermont! Perched atop a private mountain with beautiful 100 mile views! Ideally located between Killington (7 miles) & Okemo resorts, near Woodstock. Relax in the Jacuzzi while enjoying the views and stars. Private, peaceful hiking trails and waterfalls, with trail maps. Direct access to the Green Mtn. Forest, new BlackStone Grill! There's a picnic table near the water falls and Buddha Rocks. Enjoy your own nature paradise! Small private beach!

KitchenFamilyHot tub

4.96 out of 5 average rating, 273 reviews
Guest favorite
A large hot tub is positioned under a wooden structure, offering a view of the snow-covered building in the background. The exterior is characterized by dark accents against white walls, and natural scenery is visible through the open roof.
Apartment in Plymouth

Moguls Unit: Skyeship Gondola 2 miles w/ HOT TUB

The Mogul's Unit is a recently updated, fully separate, ground level, 2 bedroom/ 1 bathroom apartment in our four-family French Chalet. Located 1 mile to lakes and summer camps and 2 miles from Skyship Gondola. 15 minutes to Killington’s main base area and 20 minutes to Okemo or Woodstock. If you would like to book multiple units, check out our other listings by clicking my Host Profile Picture below. The units at this location are called "the Canyons Unit", "The Ledges", and "The Glades".

FamilyIndoor spacesHot tub

4.93 out of 5 average rating, 207 reviews
Guest favorite
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

KitchenFamilyCleanliness

4.99 out of 5 average rating, 131 reviews
Top guest favorite
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.

FamilyKitchenAir conditioning

4.93 out of 5 average rating, 102 reviews
Top guest favorite
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.
Home in Ludlow

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.

Indoor spacesFamilyHiking

4.99 out of 5 average rating, 141 reviews
Top guest favorite
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.

Indoor spacesKitchenCondition

4.94 out of 5 average rating, 402 reviews
Guest favorite
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.
Home in Ludlow

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!

Indoor spacesFamilyComfort

4.87 out of 5 average rating, 102 reviews
Top guest favorite
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.

KitchenFamilyTV

4.97 out of 5 average rating, 464 reviews
Top guest favorite
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

KitchenFamilyHot tub

4.96 out of 5 average rating, 115 reviews

Popular amenities for Plymouth family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
Chalet in Killington

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

KitchenFamilyCheckout

4.97 out of 5 average rating, 109 reviews
Top guest favorite
The spacious living area features warm wood paneling and a polished floor. A dining area with a wooden table is elevated, while a cozy seating arrangement with colorful cushions is nestled on the ground. Soft lighting from overhead fixtures creates a welcoming ambiance.
Loft in Ludlow

Spacious Renovated Barn Apt on 100 acres!

KitchenIndoor spacesQuiet

4.95 out of 5 average rating, 906 reviews
Top guest favorite
Condo in Killington

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

KitchenFamilyBiking

4.96 out of 5 average rating, 217 reviews
Guest favorite
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

KitchenFamilySolo travel

4.94 out of 5 average rating, 226 reviews
Guest favorite
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

KitchenFamilyParking

4.95 out of 5 average rating, 267 reviews
Guest favorite
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 Incredible View & Private Hot Tub!

FamilyKitchenParking

4.93 out of 5 average rating, 113 reviews
Guest favorite
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

KitchenIndoor spacesHeating

4.92 out of 5 average rating, 170 reviews
Guest favorite
Cabin in Cavendish

Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board

Indoor spacesFamilyNearby

4.96 out of 5 average rating, 114 reviews

Family- and pet-friendly home rentals

Top guest favorite
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

FamilyKitchenBathroom

4.84 out of 5 average rating, 188 reviews
Top guest favorite
A bright interior is featured, showcasing a mix of seating options including a blue sofa and an upholstered armchair. A small dining table is complemented by wooden chairs. The kitchen area is visible, equipped with diverse utensils, while large windows on two sides allow natural light to fill the space.
Apartment in Andover

Private Hilltop farm apartment

KitchenFamilyRiver

4.97 out of 5 average rating, 478 reviews
Guest favorite
The modern timber frame cabin features a covered porch with wooden beams, providing a welcoming entry. Large windows offer views of the surrounding forest, while a landscaped path leads to the entrance, framed by lush greenery and natural stone steps.
Cabin in Ludlow

Modern Okemo Smart Cabin - As Seen On DIY Channel

FamilyKitchenSkiing

4.95 out of 5 average rating, 111 reviews
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

KitchenFamilyBathroom

4.93 out of 5 average rating, 104 reviews
Top guest favorite
A log cabin is set amidst a snowy landscape, featuring a large wrap-around deck that offers outdoor seating. Snow blankets the ground and the roof, while evergreen trees frame the property, enhancing the secluded ambiance. The stone chimney rises from the cabin, suggesting warmth inside.
Cabin in Cavendish

Cozy VT Log Cabin Minutes to Okemo & Killington

KitchenFamilyView

4.96 out of 5 average rating, 110 reviews
Top guest favorite
Cabin in Mount Holly

Private Cabin/PetsOK/AC/Minutes to Okemo/Fast Wifi

Indoor spacesKitchenCleanliness

4.97 out of 5 average rating, 274 reviews
Guest favorite
Apartment in Ludlow

Very Cute Suite

KitchenIndoor spacesQuiet

4.95 out of 5 average rating, 102 reviews
Guest favorite
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.
Home in Ludlow

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

FamilyIndoor spacesSleep quality

4.93 out of 5 average rating, 101 reviews

Family-friendly home rentals with a pool

Top guest favorite
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.
Condo in Killington

PEEP Pico Hike out back door 1 Bedrm 1 night okay

FamilyIndoor spacesParking

4.93 out of 5 average rating, 500 reviews
Guest favorite
Townhouse in Killington

Ski In/Out Spruce Glen B, AC, Sauna, Fireplace

FamilyIndoor spacesHospitality

4.78 out of 5 average rating, 120 reviews
Top guest favorite
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

Indoor spacesFamilyValue

5.0 out of 5 average rating, 112 reviews
Guest favorite
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

Indoor spacesFamilyBiking

4.95 out of 5 average rating, 152 reviews
Guest favorite
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.
Condo in Killington

Mtn Green Condo-Ski/Bike Lifts, Covered Parking

KitchenFamilyCondition

4.92 out of 5 average rating, 226 reviews
Top guest favorite
Home in Killington

Golf and Mountain Biking outside the door!

KitchenFamilyCleanliness

4.89 out of 5 average rating, 139 reviews
Superhost
Home in Killington

Luxury Condo Tucked in the Heart of Killington

FamilyKitchenTV

4.86 out of 5 average rating, 257 reviews
Top guest favorite
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

Indoor spacesKitchenComfort

4.99 out of 5 average rating, 100 reviews

When is the best time to visit Plymouth?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 1,682ﺩ.ﺇ 1,840ﺩ.ﺇ 1,381ﺩ.ﺇ 1,010ﺩ.ﺇ 1,039ﺩ.ﺇ 1,065ﺩ.ﺇ 1,153ﺩ.ﺇ 1,065ﺩ.ﺇ 1,028ﺩ.ﺇ 1,194ﺩ.ﺇ 1,083ﺩ.ﺇ 1,616
Avg. temp-7°C-6°C0°C7°C14°C18°C21°C20°C15°C9°C3°C-3°C

Destinations to explore