Family-friendly vacation rentals in Greenwood

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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

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, 151 reviews

MtAbram ski in ski out. Mountain biking in Summer

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.

Superhost

A modern living area features a comfortable seating arrangement with a sofa and accent chairs. A coffee table sits at the center, surrounded by wooden side tables. Warm light is provided by stylish floor lamps, and colorful artwork decorates the walls, enhancing the relaxed ambiance.

Apartment in Norway

4.82 out of 5 average rating, 439 reviews

Remodeled Downtown Norway 1.5 Bedroom, 1 Bath Apt

Newly renovated and remodeled 1.5 Bedroom (both Queen Beds), and 1 full Bathroom on the 1st floor of a 2 floor Townhouse. In Downtown Norway Maine, 3 doors down from the local coffee shop (Cafe Nomad), and steps from downtown shops and the farmers market. Less than a 5min drive from Lake Pennesseewassee and great restaurants like 76 Pleasant. 10 minute drive from Norway Country Club, 20min from the Oxford Casino, and 40minutes from Bethel. Bright, airy, modern relaxed feel to the apartment.

Guest favorite

A small, wooden dock extends into Jewett Pond, featuring two teal Adirondack chairs positioned towards the water. Lush green hills rise in the background, reflecting the serene setting. The calm water invites relaxation and offers unobstructed views of the surrounding nature.

Cabin in Waterford

4.9 out of 5 average rating, 155 reviews

Jewett Pond Retreat

Relax in the Western Maine Foothills at our cabin on Jewett Pond. The main cabin has 672 sq ft of finished living space with bedroom (queen bed), bathroom, basic kitchen, great room (queen sleeper sofa), and screened porch. There is an additional rustic bunkhouse with two twin beds. This space is ideal for a couple or adventurous family who enjoys swimming, canoeing, hiking, fishing, or sitting on the screened porch with a good book and pine forest backdrop. Canoe included with booking.

Superhost

Two wooden chairs are positioned on a deck, facing a serene pond surrounded by vibrant autumn foliage. A small table rests between the chairs, and the expansive sky is filled with clouds, adding to the tranquil atmosphere of the natural setting.

Home in Harrison

4.9 out of 5 average rating, 308 reviews

Riverfront Luxury in the woods, Million $ Views.

Secluded A-frame nestled along Crooked River, breathtaking views and world-class fly fishing beckon. Swim in the river or explore scenic hiking trails right from your doorstep. Inside, savor modern comforts including central AC. Just minutes from pristine lakes, primo golf courses, and thrilling ski slopes, this charming private oasis offers an ideal mix of tranquil relaxation and outdoor adventure. Book your unforgettable getaway today and immerse yourself in this one-of-a-kind retreat!

Guest favorite

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

4.85 out of 5 average rating, 239 reviews

Maine Lakes Region house (private hot tub)

Cozy new construction, Chalet style, year-round house, on 9 wooded acres. Lots of Privacy, Short drive to Ski slopes, snowmobile trails, hiking, or beautiful lake to swim, or kayak. Gage beach a 10-minute drive. Close to great hiking, Also Shawni peak and Sunday River. Great restaurants, Mt Washington, NH shopping outlets. Full Desk / office, 200 mb of streaming. Wi-Fi, Netflix via ROKU, Canines only, NO CATS, NO EXCEPTIONS. Portable generator in the event of a power failure provided.

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

4.94 out of 5 average rating, 106 reviews

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.

Guest favorite

The cottage features a rustic wooden exterior with a large wrap-around porch. Two Adirondack chairs are positioned on the porch, offering a welcoming spot to enjoy the surrounding nature. A large window allows light to enter the space, enhancing the warm atmosphere.

Cottage in Bridgton

4.91 out of 5 average rating, 186 reviews

True Maine Artist Cottage with Outdoor Shower

Featured on Huckberry!! Beautifully decorated seasonal artist cottage with brand new soaking tub and outdoor shower. Solo stove fire pit and Adirondack chairs. Huge wrap-around porch with outdoor seating and glorious sunset views across blueberry fields. Also amazing stargazing!! Close to Naples, Bridgton, Sebago Lake. Tons of lakes nearby, hiking, swimming, boating, restaurants, music and local beer! Great place to stay to explore the area or also just relax and hang out.

Superhost

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, 259 reviews

Maine Paradise at North Pond-Paddle, Fish, Swim

Camp Wigwam! Lake cottage on North Pond. Swim, fish, kayak, paddleboard and more. 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*

Guest favorite

A spacious living area is highlighted by a brown leather sectional sofa, complemented by a small wooden stool. Nautical maps adorn the walls, alongside a ship's wheel, offering a coastal theme. Natural light fills the room through large windows, creating a bright atmosphere.

Vacation home in Bethel

4.97 out of 5 average rating, 118 reviews

The Cape Ann Ranch

Our beautiful one level home in the Western Foothills of Maine is situated on two acres, equal distance between Sunday River Resort , Mt. Abram Ski and Bike Resort , Black Mountain is 45 minutes away. Explore all our area has to offer. Skiing, Snowmobiling, ATV, hiking trails for all abilities, boating, fishing and swimming in our lakes, ponds and rivers and biking. Breweries, Town festivals, art shows, music concerts and so much more.

Top guest favorite

The exterior of the renovated school house is displayed, featuring light blue siding and a prominent arched window above the double glass doors. A wooden deck surrounds the front entrance, and planters are positioned along the edges, contributing to the inviting appearance.

Guest suite in Mexico

4.94 out of 5 average rating, 226 reviews

Beautiful Renovated Schoolhouse w/Private Entrance

Come stay in our renovated school house! This guest suite has great history. It has a spacious room with private entrance and private bathroom. Original wood floors, ornate copper ceilings, private driveway and private deck. Minutes from great hiking, waterfalls, lakes and ponds, and gorgeous scenic views. I have a 5 star cleanliness rating and can ensure that every surface is thoroughly sanitized between guests.

Guest favorite

A charming two-story blue house with a welcoming front porch is surrounded by lush green grass and trees. The structure features multiple windows and a contrasting red house visible in the background, providing a sense of space and community.

Home in Bethel

4.96 out of 5 average rating, 116 reviews

Sunday River Bethel Village ! Walk to Restaurants

2 Bdrm, 1 Bth, Cozy Rental located in Bethel Village. 400 yds from The Bethel Inn. Walk to Bethel Village Restaurants & Shops. Home is in residential area with plowed sidewalks and well lit street. Ideal for a mature quiet couple or similar who are into skiing / enjoying the Bethel area and respectful of the property and neighbors. small dog ok, no cats.

Top guest favorite

A stunning view of distant mountains is captured at sunset, with soft hues of pink and purple in the sky. A modern house is positioned in the foreground, framed by trees, providing a serene backdrop to the surrounding natural landscape.

Cabin in Greenwood

4.99 out of 5 average rating, 230 reviews

The Lookout at The Cross Farm

An ultra modern Icelandic style house with 2+ bedrooms. The property is on 80+ acres with nice trails for walking and biking, but no motorized off-road vehicles are allowed. A vacation here is a green vacation, through a large solar array we produce more than 100% of our power needs.