Family-friendly holiday rentals in Greenwood

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.

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.

4.99 out of 5 average rating, 209 reviews

The exterior of the chalet showcases a striking design with a sloped roof and large windows. Soft lighting emanates from within, creating a warm glow against the dark wood finish. Surrounding greenery enhances the natural setting, while a deck with a patio umbrella is visible.

Cabin in Stoneham

Mad Moose Lodge• Secluded Cabin w/ Mountain View’s

Welcome to the Mad Moose Lodge! Year-round adventures begin at this 2-bed, 2.5-bath Stoneham chalet. This vacation rental provides incredible fall foliage views and easy access to mountains and lakes! Close by to cross-country skiing and snowshoeing in the winter and hiking, mountain biking, boating and swimming in the summer there are endless options of outdoor enjoyment. Enjoy stunning sunsets over the mountains from the comfort of the couch, or while enjoying a game of pool in the game room!

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.

4.93 out of 5 average rating, 162 reviews

Cozy Cabin w/ Hot Tub & Fire Pit - Hike/Bike/Swim!

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!

4.99 out of 5 average rating, 136 reviews

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.

4.94 out of 5 average rating, 249 reviews

A private hot tub is surrounded by trees displaying vibrant autumn leaves, with a gentle stream flowing nearby. A fire pit sits beside the hot tub, offering a cozy gathering space. The cabin's exterior features wooden siding and large windows that invite natural light.

Tiny home in Norway

Glass Wall Waterfront Hot Tub Fireplace Tiny Home

Wake up to rushing waterfalls right outside your glass wall in this romantic waterfront tiny home in Norway, Maine! Private hot tub with river views, see-through gas fireplace, cozy raised queen bed overlooking the water, outdoor shower, hammocks, and direct access to hiking trails. Total privacy—no neighbors in sight. Modern kitchen, heated floors, fast WiFi, and thoughtful touches for couples or solo escapes. Romantic getaway near Sunday River skiing, golf & Maine adventures. Nature's oasis

4.99 out of 5 average rating, 523 reviews

A cozy cabin is nestled among snow-covered trees, showcasing a wooden exterior in warm tones. The entrance features a welcoming pathway lined with snow, while the nearby deck offers a glimpse into the winter landscape, creating a serene atmosphere in the snowy environment.

Cabin in Hanover

Cabin retreat just steps from adventure

Nestled on 80 acres in the woods alongside a stream, this cabin is the perfect retreat. Whether you are looking for a romantic getaway, a family vacation, or a gathering of your closest friends-this cabin is ideal. It is located on a private road and close to Howard Pond, Androscoggin River, and Sunday River skiing. No matter the season, opportunities await, whether you decide to stay close or venture out. There are plenty of trails nearby to explore, canoe rentals, skiing and so much more.

4.93 out of 5 average rating, 107 reviews

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

Secluded home-Upper Unit, Hot Tub & Pond Access

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.

4.96 out of 5 average rating, 164 reviews

A wooden dock extends into a calm lake, flanked by lush greenery and colorful foliage. Two Adirondack chairs are positioned invitingly at the end of the dock, with a brightly colored blanket draped over one. Reflections of clouds and trees are visible on the water's surface.

Cabin in Woodstock

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 dishes, utensils, pots, pans, coffee maker & espresso machine. Organic linens. Pristine bathroom-large hot shower area, heat lamp, soaking tub.

4.94 out of 5 average rating, 271 reviews

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

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*

4.93 out of 5 average rating, 180 reviews

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!

4.98 out of 5 average rating, 305 reviews

Treehouse in Woodstock

LuxuryTreehouse w/ Hot Tub Near Sunday River

Escape to an authentic luxury treehouse designed by B’Fer Roth of DIY Network’s Treehouse Guys and built by The Treehouse Guys. Hidden on a private wooded road with no neighbors in sight, this unique retreat borders 626 acres of Bucks Ledge Community Forest with 7 miles of trails right outside your door. Enjoy peaceful seclusion just 15 minutes to Sunday River, 5 minutes to Mt. Abram, and 10 minutes to Bethel for the perfect mix of adventure and relaxation.

4.93 out of 5 average rating, 119 reviews

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.

Guest house in Greenwood

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.

Popular amenities for Greenwood family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Tiny home in New Gloucester

A modern tiny house is set amidst lush greenery, featuring a spacious wooden deck with clear railings. A swing hangs from a nearby frame, and rustic stone landscaping encircles a small fire pit. Sunlight filters through the trees, highlighting the tranquil outdoor space.

4.94 out of 5 average rating, 244 reviews

Tiny house in the Birch Grove with private HOT TUB

4.96 out of 5 average rating, 277 reviews

A scenic view showcases the vivid colors of autumn foliage across rolling hills under a blue sky. Pine trees frame the foreground, while distant mountains provide a tranquil backdrop.

Flat in Woodstock

Ski, Swim, Hike, Bike, Repeat!

4.94 out of 5 average rating, 119 reviews

Chalet in Newry

3 min to Sunday River w/ Views, Game room, Hot tub

Superhost

A modern two-story wooden retreat, situated amidst a snowy landscape. Large windows and sliding doors dominate the facade, allowing ample natural light. A spacious deck is visible with seating options, and a hot tub is accessible beneath the upper level, blending seamlessly with the surrounding nature.

Home in Bethel

4.89 out of 5 average rating, 121 reviews

Aspen East at Sunday River

4.85 out of 5 average rating, 249 reviews

The image showcases a bright interior with vaulted ceilings, featuring large angular windows that allow natural light to fill the space. A rustic brick fireplace with a black stove is centered against a wall. A wooden ceiling fan hangs above, enhancing the cabin-like atmosphere.

Home in Waterford

Maine Lakes Region house (private hot tub)

4.94 out of 5 average rating, 288 reviews

A well-lit chalet is visible in the background, showcasing its large windows. In the foreground, a stone fire pit surrounded by five adirondack chairs is highlighted, with glowing embers and flames creating a warm ambiance against the night sky.

Cabin in Fryeburg

Avail. 6/5*Hot Tub*Lake Access+Beach*A/C*Dogs OK

4.97 out of 5 average rating, 115 reviews

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.

4.99 out of 5 average rating, 103 reviews

An open living area features large windows with red accents, allowing natural light to enhance the space. A plush sectional sofa offers seating, complemented by decorative throw pillows, while a dining area with red stools is visible in the background. Fresh floral arrangements add a touch of color.

Chalet in Bethel

Chasing Affinity Riverside, Modern, Hot Tub

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 116 reviews

A modern kitchen is equipped with a stainless-steel microwave and stove beneath a stylish backsplash. The countertop features a sink and invites meal preparation. A comfortable nook with a raised twin bed can be seen in the background, surrounded by decorative plants.

Guest suite in Freeport

Studio Apartment in Freeport

4.89 out of 5 average rating, 106 reviews

A spacious outdoor setting features a fire pit surrounded by multiple wooden Adirondack chairs in varying colors. The cozy cottage is visible in the background, nestled among trees and greenery. A picnic table and a shed are also present, contributing to the inviting atmosphere.

Cottage in Bethel

Cozy Cottage w/ Lil' Pond, Fenced Yard & Firepit

5 out of 5 average rating, 8 reviews

The image captures a serene landscape of rolling mountains under a colorful sky at sunset. Soft hues of orange and blue blend with the silhouettes of the distant peaks, set against a lush green foreground of trees and foliage.

Barn in Greenwood

The Barn North at The Cross Farm

4.98 out of 5 average rating, 135 reviews

A modern exterior of the eco-friendly retreat is displayed, showcasing a sloped roof and large windows. The deck features comfortable seating and steps leading to the welcoming entryway. Surrounding greenery adds a natural backdrop, enhancing the serene atmosphere of the waterfront sanctuary.

Home in Sweden

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit

4.9 out of 5 average rating, 235 reviews

A comfortable living area is highlighted by a light-colored sofa adorned with 'ski' throw pillows. A wooden coffee table sits in front, with a magazine on top. A cozy armchair is positioned nearby, and natural light streams in through the window, revealing snowy outdoor scenery.

Guest house in Hanover

Sunny Cabin Near Sunday River River Front

4.93 out of 5 average rating, 206 reviews

A modern cabin exterior is surrounded by lush greenery, featuring a spacious outdoor area with a fire pit at the center. Four wooden chairs are arranged around the fire pit, while a picnic table is nearby. String lights are hung to enhance evening ambiance.

Cabin in Madison

Cedar Hideaway: Walk to Pond, 15m N. Conway

5 out of 5 average rating, 43 reviews

A modern living area features large windows that provide views of the surrounding hills. A cozy seating arrangement includes a spacious leather sofa and two armchairs, positioned around a wooden coffee table. A television is mounted on the wall above a stylish fireplace, enhancing the inviting ambiance.

Home in Greenwood

Chic Greenwood Chalet

4.97 out of 5 average rating, 29 reviews

360* Mountain Views Where Sunsets Steal The Show

Family-friendly home rentals with a pool

4.89 out of 5 average rating, 304 reviews

A spacious room features a large bed with plush bedding against a warm-toned wall. A relaxing jetted tub is positioned beside it, with soft lighting provided by bedside lamps. A window allows natural light to enter, enhancing the overall calm and comfortable ambiance.

Flat in Bartlett

Attitash Retreat

Townhouse in North Conway

The open kitchen features modern stainless steel appliances, including a refrigerator and stove. A spacious island with Quartz countertops provides seating for four, complemented by white bar stools. The dining area is visible, showcasing a dining table set for six, with natural light flowing in from nearby windows.

4.96 out of 5 average rating, 381 reviews

Family friendly + Mountain Views @amountainplace

4.83 out of 5 average rating, 127 reviews

A game room is provided, featuring two vintage arcade machines prominently displayed against light-colored walls. A colorful rug with a playful design brightens the floor space, while a small table and chair are positioned nearby, offering additional seating options.

Townhouse in Bartlett

Spacious Vaca! N-Conway, Storyland, Hiking, Saco

4.87 out of 5 average rating, 174 reviews

Apartment in Bartlett

Spacious Condo-Attitash Ski-Storyland-Saco & More!

Serviced apartment in Berlin

The living room features a comfortable gray sofa, complemented by vibrant throw pillows. Natural light floods in through the large windows, offering views of the outdoors. A coffee table rests on a colorful rug, while a modern light fixture illuminates the space.

4.84 out of 5 average rating, 207 reviews

Spacious White Mountain renovated 2 bedroom, Apt 3

4.97 out of 5 average rating, 226 reviews

The living room features a cozy arrangement with a dark sofa and loveseat adorned with decorative throw pillows. A round coffee table is positioned centrally, with natural light filtering through the window adorned with blinds. A piece of aviation-themed wall art adds character to the space.

Townhouse in Bartlett

3 Bears Glen, Across St. from Story Land, AC, pool

4.96 out of 5 average rating, 125 reviews

A living room showcases a cozy seating area with two black sofas facing a television. A coffee table is centrally placed, adorned with a candle and a snack. A brick fireplace adds warmth, while natural light filters through the dual windows, dressed with light curtains.

Apartment in Conway

Cozy, clean, 2nd floor condo in Conway, NH!