Family-friendly vacation rentals in Greenwood

Find and book unique family-friendly homes on Airbnb

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$20,924 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,920 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    130 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!

Top-rated family-friendly rentals in Greenwood

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

1 of 1 pages1 / 1
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

Mt Abram ski in ski out Log Home. NO GUEST FEE

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.

Indoor spacesKitchenRiver

4.92 out of 5 average rating, 157 reviews
Top guest favorite
A private hot tub is situated outdoors, surrounded by greenery and offering views of the lake and mountains in the background. Two glasses of sparkling wine are placed on the tub's edge, reflecting the natural scenery under a clear blue sky.
Home in Woodstock

Sunset & Lake View, Theater, HTub, Xbox, Mini Golf

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!

FamilyKitchenHospitality

4.99 out of 5 average rating, 159 reviews
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

Fall Mountain Escape! Hot Tub | Fire Pit | Foliage

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!

KitchenIndoor spacesAccuracy

4.93 out of 5 average rating, 170 reviews
Top guest favorite
Home in West Paris

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.

FamilyKitchenAccess

4.99 out of 5 average rating, 145 reviews
Top guest favorite
A charming chalet is set amidst lush greenery, featuring a unique wooden exterior and large glass windows. The inviting entryway leads to a spacious deck supported by wooden beams, with surrounding landscaping that includes natural stone walls and various plants.
Chalet in Greenwood

Log Home Upper Unit - Hot Tub - Fall Foliage

Do you want to truly get away and have no neighbors in sight? I want to welcome you to our secluded chalet in the woods. The chalet has everything you need for a restful and luxurious stay near Bethel and the beautiful surrounding area. We are located across the street from Round Pond and have access to some of Maine's best uncrowded fishing spots. Hiking abounds in the surrounding mountains along with the beautiful town of Bethel nearby. Also Mt. Abram is only a 5 minute car ride away.

Indoor spacesKitchenHospitality

4.94 out of 5 average rating, 116 reviews
Guest favorite
The chalet-style cabin is surrounded by lush greenery and features a wooden exterior with large windows. A quaint balcony adorns the front, allowing for natural light to fill the space. A gravel pathway leads to the inviting red front door.
Cabin in Woodstock

Sunday River & Lake Chalet, 2 Kitchens, Hot Tub

Family-friendly Chalet-Style cabin on three acres. Minutes away from world class skiing and across the street from Glover's Marsh Wildlife Sanctuary and beautiful North Pond, with lake access minutes away. Kayaks available for rent during summer months! Updated recently with upgrades including luxurious Egyptian cotton sheets, memory foam mattress toppers, & plush down alternative comforters. Hot Tub with Pavilion next to new stone firepit! Come relax and enjoy the beautiful Maine landscape!

KitchenIndoor spacesLaundry

4.97 out of 5 average rating, 177 reviews
Top guest favorite
Treehouse in Pownal

The Copper Fox Treehouse

Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse

Indoor spacesKitchenView

4.99 out of 5 average rating, 198 reviews
Top guest favorite
Cabin in Greenwood

Sun&Fun on the Pond! Swim, Fish, Kayak, Paddle

Summer at Camp Wigwam! Lake cottage on North Pond. Swim, paddle, hike, enjoy the firepit. 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*

Indoor spacesKitchenComfort

4.95 out of 5 average rating, 279 reviews
Top guest favorite
The waterfront camp is situated amid tall trees, featuring large windows that allow natural light to fill the living space. A grassy area slopes gently toward the sandy shore, creating an inviting outdoor space. The tranquil lake reflects the surrounding greenery.
Cottage in Woodstock

Cozy Camp on North Pond

Charming waterfront camp on a quiet dead end road. Freshwater lake is great for fishing, swimming, boating and simply relaxing! Watch for the family of bald eagles that call this lake their home and listen to the loons as you watch the sunset. Plenty of room for the whole family with two bedrooms and trundle beds . Hike Bucks Ledge right from the camp or make the 5 mile loop around the pond. Cookout on the gas grill, propane provided, and then toast marshmallows over the campfire.

Indoor spacesKitchenView

4.95 out of 5 average rating, 118 reviews
Top guest favorite
Chalet in Bryant Pond

Sunday River | Mt Views | Dog Fndly | 20% Off 3+

Luxury mountain retreat minutes from Sunday River slopes. Designed for discerning guests, this upscale estate features breathtaking panoramic views, a private hot tub, a gourmet chef’s kitchen, and an open living space with a cozy fireplace. Whether you're here for world-class skiing, hiking, or a premium alpine getaway, enjoy high-end finishes and ultimate comfort. Perfect year-round Maine escape for families and groups seeking outdoor adventure and relaxation. Book your stay!

FamilyIndoor spacesWalkability

4.93 out of 5 average rating, 198 reviews
Guest favorite
A backyard space features a circular fire pit surrounded by several black wooden Adirondack chairs. In the background, the modern, three-story home is partially obscured by trees and showcases a combination of gray and white siding.
Home in Bethel

Brand New 4BR- fire pit, hot tub, game room.

North Star Hideaway – Cozy Retreat Near Sunday River Escape to North Star Hideaway, a brand-new, 4BR/3.5BA home just 10 minutes from Sunday River! Sleeps 12 with a game room & fire pit. 🛏️ Bedrooms: (4 bedrooms) Upstairs: 2 King suites w/ Smart TVs, mini-split AC & ensuite baths. Downstairs: 1 Queen room, 1 Bunk room (2 sets), plus a bonus room w/ sleeper sofa. 🔥 Fireplace | Starlink Wi-Fi | Xbox Game Room | Ski Mudroom | S’mores Kit Book now for adventure & relaxation!

Indoor spacesFamilySkiing

4.97 out of 5 average rating, 128 reviews
Top guest favorite
Home in Greenwood

Bright, Vintage Maine Home, Awaiting Adventure!

Ahh, FALL! 🍁 Enjoy the slower pace and countless hiking, biking and exploring opportunity in the mountains right here! Classic 3 bedroom, 1 bath centrally located Western Maine home, with hot tub! Much of the vintage charm remains in this early 1900's home, with modern comforts added throughout. This area offers four seasons of fun and you won't have to go far to find it! A mile to skiing & biking at Mt. Abram/15 minutes to Sunday River and five minutes to Bethel Village.

Indoor spacesFamilyCleanliness

4.95 out of 5 average rating, 181 reviews

Popular amenities for Greenwood family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favorite
A spacious lakefront home is depicted against a backdrop of lush greenery. A large deck with seating is visible, complemented by colorful landscaping. The yard, featuring well-kept grass, offers ample space, while the sun casts gentle shadows across the scene, inviting outdoor relaxation.
Home in Woodstock

One of a kind Lakefront home near Sunday river

Indoor spacesKitchenLayout

4.88 out of 5 average rating, 139 reviews
Top guest favorite
Cabin in Chesterville

Off-Grid Cabin with Wood Fired Hot Tub. 4 Kayaks

KitchenIndoor spacesSleep quality

5.0 out of 5 average rating, 213 reviews
Top guest favorite
Cabin in West Paris

Log cabin, stunning views, hot tub, fire pit

Indoor spacesFamilyLocation

4.96 out of 5 average rating, 227 reviews
Guest favorite
A tranquil scene featuring a modern cabin nestled among vibrant autumn foliage. Rushing water flows gently in the foreground, with smooth stones lining the riverbank. Soft light emanates from the windows of the cabin, creating a cozy ambiance amidst the natural surroundings.
Tiny home in Norway

Glass Wall Waterfront Hot Tub Fireplace Private

Indoor spacesFamilyDecor

4.93 out of 5 average rating, 270 reviews
Top guest favorite
Yurt in Woodstock

Luxury Romantic Yurt •Hot Tub •Mt Views •AC •WiFi

KitchenIndoor spacesGetting around

5.0 out of 5 average rating, 291 reviews
Top guest favorite
Chalet in Bethel

Hot Tub | Game Room | Dog-Friendly | Sleeps 14

FamilyKitchenCheckout

4.99 out of 5 average rating, 113 reviews
Top guest favorite
Chalet in Bethel

Cozy Chalet | Hot Tub*Sauna*Game Room*Fire Pit*BBQ

FamilyIndoor spacesNearby

4.99 out of 5 average rating, 104 reviews
Top guest favorite
The game room features vibrant murals depicting video game characters and arcade themes. A ping pong table occupies the center, surrounded by a cozy leather couch and a large TV. The space is brightened by natural light from overhead fixtures, enhancing the lively atmosphere.
Cabin in Newry

Mountain View Chalet with Hot Tub and Game Room

KitchenIndoor spacesLaundry

4.96 out of 5 average rating, 159 reviews

When is the best time to visit Greenwood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$73,234 GYDG$73,443 GYDG$63,399 GYDG$57,541 GYDG$58,378 GYDG$60,261 GYDG$62,562 GYDG$62,144 GYDG$55,867 GYDG$57,750 GYDG$56,285 GYDG$68,421 GYD
Avg. temp-10°C-9°C-3°C4°C11°C16°C19°C18°C14°C7°C1°C-6°C