Family-friendly vacation rentals in Greenwood

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Greenwood

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

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Guest favorite
A charming wooden chalet is surrounded by vibrant fall foliage, showcasing a welcoming deck with red Adirondack chairs. An American flag gently flutters outside, while the natural landscape offers a serene backdrop to the cozy exterior.
Cabin in Greenwood
4.93 out of 5 average rating, 150 reviews

Cozy Cabin w/ Hot Tub & Fire Pit-Walk to Ski Lift!

Whether you want to relax by the fire pit or chill in the hot tub under the stars, grill out on deck w/ mountain views, get cozy by the fireplace playing board games, hike local trails & waterfalls, swim/boat/fish at the beach, or walk to Mt Abram 2 min from cabin to hike/mountain bike/ski/snowmobile &enjoy live music, dinner & drinks at the outdoor beer garden-The Mountain House truly has it all! Explore surrounding area with a quick drive to downtown Bethel,Sunday River,& The White Mountains!

Top guest favorite
Home in West Paris
4.99 out of 5 average rating, 124 reviews

Four Season Western Maine Adventure Base

Make some memories at this family-friendly property. Enjoy panoramic views of Maine's western foothills. Owned by an outdoor-loving family, complete with hounds and chickens, this is a perfect spot to launch your Maine adventures. On the doorstep of skiing, hiking, biking, hunting, fishing, kayaking,canoeing. Enjoy beautiful sunrises and sunsets, sightings of eagles, moose, deer, sounds of peepers, woodcock, wild turkey gobbles and whip-o-wills. Enjoy the lifestyle that makes this Vacationland.

Guest favorite
A calm lake reflects the surrounding greenery under a partly cloudy sky. A wooden dock extends into the water, while a canoe rests alongside, ready for exploration. The stillness of the scene invites tranquility and outdoor adventure.
Farm stay in Norway
4.94 out of 5 average rating, 223 reviews

Waterfront Home on Norway Lake - Hillcrest Farm

Serene parklike setting on 11-acres with 1,300-ft of frontage on Norway Lake. Newly renovated 1 bedroom apartment with full kitchen in historic farmhouse has separate access for complete independence. Only 35 min to Sunday River & 1 mile to downtown Norway. Direct connection to miles of hiking, biking & ski trails on Shepherd's Farm Preserve. Fish from our dock, use our canoes and kayaks, rent boats from the local marina or watch abundant wildlife from the deck - unlimited outdoor activities!

Guest favorite
A modern tiny house is nestled among tall trees, showcasing two large glass walls that allow sunlight to stream inside. The cabin is elevated on stilts, with a snowy landscape surrounding it, creating a serene and private retreat in nature.
Tiny home in Jay
4.93 out of 5 average rating, 261 reviews

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak

Immerse yourself in our forest and serene pond. Quiet 40-acre commune consists of two tiny house cabins + barn on private pond. Book one of the simple yet elegant cabins/barn for more guests. Modern, off-grid, solar-powered retreat. Two solid glass walls to bring you closer to nature while staying in our simple yet elegant tiny house with all comforts of home. 5 min walk to shared fire pits, kayaks, pond & seasonal picnic shelter. AWD SUV or truck required. Off-grid, so no A/C. Pet fee $89.

Top guest favorite
Cabin in Woodstock
4.95 out of 5 average rating, 154 reviews

Private Lakefront Cabin in Woods near Sunday River

Private waterfront Cabin in woods, nestled off private dirt road near Mt. Abrams and Sunday River. Kayak, swim & fish in pristine lake in Summer. Skate, XC Ski, Ice Fish, Snowshoe, Hike in Winter. Fireplace and Fire Pit. Excellent wifi - Private, quiet remote workspace. Rustic modern cozy decor: fully-equipped stainless steel kitchen with full sized appliances, dishes, utensils, coffee maker. Organic linens. Pristine bathroom-large hot shower area, heat lamp, soaking tub.

Top guest favorite
The kitchen features a mix of cabinetry and counter space with a double sink, electric stove, and refrigerator. A tiled floor with a patterned design provides a clean and functional aesthetic. Natural light enters through the window, illuminating the space.
Apartment in West Paris
4.98 out of 5 average rating, 243 reviews

Private Apartment in the Foothills! A Gem!

One mile from Route 26! Charming apartment with private locked entrance and separate driveway attached to historic 1880s farmhouse in the foothills of Western Maine. Clean and cozy, it has one bedroom with a queen bed and two sofa sleepers which make it a great spot for a couple or a family of four. We're only fifteen minutes to Mt. Abram and 30 minutes to Sunday River. There's easy-access to snowmobile trails and Moose Pond right across the road. Oxford Casino is 30 minutes south.

Guest favorite
The living area features a cozy blue sectional sofa complemented by an accent chair and a decorative pouf. Natural light fills the space through large windows, which are adorned with woven shades. Wall art and unique decor, including a moose silhouette, enhance the welcoming atmosphere.
Cabin in Greenwood
4.94 out of 5 average rating, 267 reviews

Mins to Slopes, Snow & fun on the Pond, Let's Ski!

Winter at Camp Wigwam! Lake cottage on North Pond. Skate, hike, enjoy the firepit in the snow. Stay in comfort with all the amenities. Explore Western Maine or just relax at camp. Watch the nesting pair of bald eagles swoop down to capture fish, listen to the loons. Strong WiFi with Streaming. Enjoy the 100+ DVDs and the record turntable. Near Bethel with lovely restaurants, bars and other venues. Great for kids, couples and families. *Bring your 4-footed friend-pet fee applies*

Top guest favorite
Treehouse in Woodstock
4.98 out of 5 average rating, 278 reviews

Treehouse With Hot Tub Close to Sunday River!

This authentic, luxury treehouse was designed by B'Fer Roth, DIY Network TV host of The Treehouse Guys and built by the Treehouse Guys. Nestled in the woods on a quiet, private rd with no neighbors in sight, the treehouse is just 15 minutes to Sunday River Ski Resort, 5 minutes to Mt. Abram and 10 minutes to downtown Bethel. The treehouse is abutted by 626 acres of Bucks Ledge Community Forest (7 miles of hiking/snowshoeing trails accessible from the treehouse).

Top guest favorite
A cozy cabin interior features warm wooden walls and flooring. Twinkling string lights adorn the ceiling, creating a soft glow. A comfortable armchair is positioned beside a small lamp, with a spacious bed visible in the background, framed by large windows allowing natural light.
Cabin in Lovell
4.97 out of 5 average rating, 397 reviews

Secluded, cozy cabin nestled in the Maine woods

Kick back and relax in this calm, stylish space with a semi-remote cabin experience while keeping the gentle daily living comforts. Right at the edge of the White Mountain National Forest in one direction and in the other direction, a short five minute drive to Kezar Lake this secluded cabin has it all for the nature lover in you! Close to local favorite trailheads for hiking and mountain biking as well having nearby ski mountains and snowmobile trails.

Top guest favorite
A cozy cottage is nestled among the trees, featuring large windows that invite natural light. A small deck with seating is visible in front, surrounded by lush greenery and a wooden base that enhances the connection to nature.
Guesthouse in Greenwood
4.96 out of 5 average rating, 112 reviews

The Burrow at Patch Mountain

Surrounded by nature, this is a perfect getaway for anyone seeking an active outdoor adventure or a quiet restful retreat. The Burrow is a small studio cottage, set between two other buildings, on a wooded 4.2 acre property. It’s a cozy space with a full kitchen, views of the river and abundant natural light. It has its own sunny patio for eating and shares a fire ring, sitting area and driveway with my other AirBnB- The Haven at Patch Mountain.

Top guest favorite
The spacious interior features wooden beams and warm, rustic tones. A large bed is centrally positioned, accompanied by a wooden chest. A cozy seating area includes a rocking chair and lamps, while a dining table near windows offers natural light and views of the surroundings.
Guest suite in Conway
5 out of 5 average rating, 367 reviews

CloverCroft - "Far from the madding crowd."

CloverCroft, a 200+/- year old farmhouse, is located in the rich farmland of the Saco River Valley at the foot of the White Mountains. We go the extra mile to make your stay enjoyable and comfortable. (Please note our mattress is FIRM and there is a long flight of outdoor stairs to access the suite.) COME ENJOY PRIVACY AND THE GREAT OUTDOORS. There are many summer and winter activities very close by and we look forward to hosting you.

Guest favorite
A tranquil lake scene is captured, featuring an isolated island adorned with trees. The water reflects soft hues of orange and pink from the sunset, while gentle mist hovers over the landscape, enhancing the serene atmosphere of the natural setting.
Home in Greenwood
4.96 out of 5 average rating, 121 reviews

Lakefront summer getaway cabin for 6

Located along Main Street, this beautifully restored lake front home had a private dock and yard facing the lake. Come enjoy summer on the lake with our canoes, kayaks and corn hole. In the winter come to ice skate in the front yard and ski at Sunday River (20mins) or Mt Abrams (5mins). House offers high speed internet, a smart TV and modern amenities. Custom dining nook, custom kitchen and modern, yet cozy finishes throughout.

Popular amenities for Greenwood family-friendly rentals

When is the best time to visit Greenwood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$73,730 GYDG$76,446 GYDG$66,838 GYDG$53,679 GYDG$52,008 GYDG$52,426 GYDG$62,452 GYDG$62,034 GYDG$55,768 GYDG$55,350 GYDG$54,306 GYDG$69,762 GYD
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Quick stats about vacation rentals that are family-friendly in Greenwood

  • Total vacation rentals

    Explore 130 vacation rentals in Greenwood

  • Nightly prices starting at

    Greenwood vacation rentals start at G$18,798 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,910 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Greenwood vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Greenwood rentals

  • 4.9 Average rating

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