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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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Top guest favorite
Home in Woodstock
4.99 out of 5 average rating, 132 reviews

Sunset & Lake View, Theater, HTub, Xbox, Woodstove

Welcome to the Sunday River retreat in our luxury chalet with the best views in Maine. Our sanctuary can comfortably sleep 12 and boasts Lake Christopher panoramic views with Mt. Abram sights. Minutes from Sunday River Resort, a public boat launch and other area attractions. Private hot tub, fire pit, wood stove and deck await your arrival. Enjoy arcade games, Xbox, a movie theatre room, BBQ grill and speakeasy theme bar setup. Don't forget to take a picture in the gondola and to catch a sunset!

Guest favorite
The exterior of the log cabin features a large covered porch with wooden railings, complemented by stacked stone accents on the chimney. Surrounded by a grassy landscape, the cabin sits amidst tall trees, showcasing its rustic charm in a serene natural setting.
Cabin in Greenwood
4.92 out of 5 average rating, 156 reviews

Mt Abram ski in ski out Log Home

This cozy 15 year old log cabin sleeps 6 comfortable and has that log cabin and log furniture feeling and look. Situated on the slopes of Mt Abrams with very easy ski in and out. With a outdoor fireplace on large deck. This is truly your log cabin experience and sking adventure. The cabin has great views of the mountain range for viewing in Fall and Winter. it has 2 King beds, 2 Queen beds, 4 Twin beds, and 1 Full size bunk bed. This log cabin sits half way up Mount Abrams so you ski in and out.

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
4.94 out of 5 average rating, 154 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, 131 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.

Top guest favorite
The Great Room features a high cathedral ceiling and expansive windows that invite natural light and showcase woodland views. A comfortable sectional sofa and plush seating arrangements surround a modern stone fireplace, creating an inviting gathering space. Stairs lead to an upper level, adding to the open layout.
Chalet in Bethel
4.99 out of 5 average rating, 100 reviews

85in TV | Hot Tub | Huge Deck | Game Room | Playhouse

Welcome to The Retreat - a Just Happy Homes property! Nestled at the end of a private road and surrounded by beautiful wooded views, this new custom-built home blends coziness and amenities in a chic modern rustic design, just 12 min to Sunday River, 7 min to Mt Abram, and 5 min to downtown Bethel. This 5-bed, 3.5-bath home is meticulously crafted to offer an exceptional experience for family and friends seeking both adventure and relaxation. Create unforgettable memories at The Retreat!

Top guest favorite
A serene mountain view is presented, featuring rolling peaks partially shrouded in morning mist. Lush greenery in the foreground is accented by hints of autumn colors, creating a tranquil backdrop against the clear blue sky.
Apartment in Newry
4.97 out of 5 average rating, 131 reviews

Skiers Get-Away (1 BR near AT - w/views)

This newer House has a private 1-BR above-the-garage with a private back-entrance with a Living-room, Full Kitchen with a 2-person island, Large Bath with double-wide shower and a large BR w/ views of Sunday River as well as Mahoosuc Notch. Perfect for a two-person get-away, in the Western Mountains of ME. Great for Winter Sports at Sunday River, or Mt. Abrams, outdoor activities or quick-access to downtown Bethel. Accommodates Up to 2-Guests on our 9+ Acre lot. A/4WD required in Winter

Guest favorite
Two Adirondack chairs are positioned on the snowy shore, facing a serene lake framed by tall trees. The still water reflects the surrounding landscape, including snow-capped mountains under a partly cloudy sky. A peaceful winter scene is captured in this outdoor setting.
Cabin in Greenwood
4.94 out of 5 average rating, 269 reviews

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

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 Wii, 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
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, 250 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.

Top guest favorite
Treehouse in Woodstock
4.98 out of 5 average rating, 291 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 two-story home is set against a backdrop of lush greenery, featuring a spacious driveway in the foreground. A private balcony is visible on the second floor, while the garage doors provide additional functionality. Natural light enhances the inviting exterior.
Apartment in Bethel
4.97 out of 5 average rating, 261 reviews

Have you found YOUR Happy Space yet?

Come find YOUR Happy Space in My Happy Place! Set against Egypt Mountain with serene views, nature will nurture your soul as you reconnect with a simpler pace of life and rejuvenate in Your Happy Space. A two bedroom in-law apartment with private entrance, full kitchen, private balcony, queen bed in master full in second bedroom. Enjoy a campfire, stargazing, walk along the private road, fields, or hike the mountain. See "Your property" for booking information.

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, 116 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.

Guest favorite
Home in Greenwood
4.96 out of 5 average rating, 123 reviews

Lakefront winter 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$73,737 GYDG$76,452 GYDG$66,844 GYDG$53,684 GYDG$52,013 GYDG$52,430 GYDG$62,457 GYDG$62,039 GYDG$55,773 GYDG$57,653 GYDG$56,190 GYDG$68,306 GYD
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Quick stats about vacation rentals that are family-friendly in Greenwood

  • Total vacation rentals

    Explore 120 vacation rentals in Greenwood

  • Nightly prices starting at

    Greenwood vacation rentals start at G$20,889 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,320 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 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!