Family-friendly holiday rentals in Woodstock

4.99 out of 5 average rating, 153 reviews

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!

FamilyIndoor spacesOutdoor spaces

5.0 out of 5 average rating, 204 reviews

Cabin in Chesterville

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

Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- beautiful swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Indoor spacesFamilySleep quality

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.

FamilyIndoor spacesBathroom

4.88 out of 5 average rating, 135 reviews

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

Amazing large lakefront home right on the water near Sunday river ski resort. Sleeps upwards of 25 people. There is a small surcharge per person for groups larger than 20. At certain times of year we rent to smaller than average groups at an other than listed price. Great for family reunions, weddings etc. Largest yard on the lake! And our hot tub is very invigorating after a day of skiing or hiking! Hot tub is charged separately. NOTE: From late June to late August we only rent by the week.

KitchenIndoor spacesAmenities

4.94 out of 5 average rating, 260 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

Indoor spacesKitchenQuiet

4.99 out of 5 average rating, 543 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.

KitchenFamilyComfort

4.96 out of 5 average rating, 171 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.

KitchenIndoor spacesQuiet

4.97 out of 5 average rating, 175 reviews

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!

FamilyIndoor spacesSleep quality

5.0 out of 5 average rating, 281 reviews

Yurt in Woodstock

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

Escape to Birdsong Yurt, a romantic and luxurious retreat nestled in the mountains of Maine. Enjoy beautiful mountain views, serene privacy on 2 acres, and a cozy yurt experience you won’t forget. Perfect for couples, friends, or small families seeking a magical getaway. Whether sipping wine under the stars, relaxing sunsets in the hot tub, or cozying up by the fire, Birdsong Yurt is your perfect mountain escape. Book your unforgettable experience today! •Full Kitchen/Bathroom •WiFi/AC

KitchenFamilyBarbecue

4.99 out of 5 average rating, 391 reviews

A tiny house with a grey exterior sits nestled among lush greenery and colorful flower beds. It features tall windows that allow natural light to flow in, and a bright red door that adds a pop of color. Surrounding steps made of stones lead up to the entrance.

Tiny home in Durham

Crow’s Nest Tiny House at Old Crow Ranch

The Crow's Nest Tiny House sits nestled on Old Crow Ranch, a 70-acre working livestock farm, a true example of thriving Maine farmland. You'll be surrounded by fields and pine woods in Durham, Maine. Just outside Freeport and only 30 minutes from Portland, this cozy space makes a calming retreat away from the city - for a night or for a week. Fall asleep listening to the peepers and gazing at the stars, drink your morning coffee while looking out at the cattle grazing in the fields.

KitchenFamilyComfort

4.99 out of 5 average rating, 185 reviews

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 spacesFamilyGetting around

4.94 out of 5 average rating, 272 reviews

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 spacesFamilyOutdoor spaces

Popular amenities for Woodstock family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 114 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

Indoor spacesFamilyDecor

Tiny home in New Gloucester

4.94 out of 5 average rating, 271 reviews

Tiny house in the Birch Grove with private HOT TUB

FamilyKitchenLocation

4.85 out of 5 average rating, 273 reviews

A glamping Geodome stands elevated against a twilight sky, illuminated by warm lights. A small fire burns in a metal pit near a seated figure. Surrounding trees add greenery to the serene outdoor setting, creating a calming atmosphere.

Dome in Buckfield

StreamSide Getaway- HOT TUB / AC/ Wi-Fi

FamilyKitchenSolo travel

4.96 out of 5 average rating, 221 reviews

A hot tub is positioned on lush green grass, surrounded by wildflowers and tall trees. The sun sets behind the forest, casting a warm glow across the landscape. A natural, serene ambiance is created as the sky transitions to evening.

Cabin in West Paris

Cabin w/mtn views, hot tub, fire pit, dog friendly

KitchenIndoor spacesComfort

4.99 out of 5 average rating, 106 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

KitchenIndoor spacesBackyard

4.97 out of 5 average rating, 129 reviews

An open-concept living area features comfortable couches adorned with yellow pillows. A glass coffee table sits on a plush rug, and hardwood floors add warmth. The space is complemented by modern kitchen elements, including a large hooded range and sleek cabinetry, visible in the background.

Home in Bethel

Sunday River Escape | Sauna, Hot Tub, Dog-Friendly

FamilyIndoor spacesAmenities

4.95 out of 5 average rating, 151 reviews

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

Indoor spacesKitchenCleanliness

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, 166 reviews

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

Indoor spacesKitchenWi-Fi

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 116 reviews

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

KitchenFamilyBarbecue

4.98 out of 5 average rating, 271 reviews

An aerial view captures a secluded log cabin surrounded by lush greenery on a private island. A wooden dock extends over the tranquil water, providing access to the cabin, which is nestled among trees. Sunlight glistens on the lake's surface.

Island in Monmouth

Naughty Dog Private Island Log Cabin

KitchenFamilyValue

4.97 out of 5 average rating, 360 reviews

Home in Bethel

Sunday River Orchard w/Fireplace, Firepit & Hens!

KitchenIndoor spacesBackyard

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.

4.99 out of 5 average rating, 260 reviews

The Lookout at The Cross Farm

Indoor spacesKitchenHospitality

4.95 out of 5 average rating, 139 reviews

A log cabin with a welcoming design features four prominent gabled windows on the upper level. The earthy tones of the wood blend harmoniously with the surrounding greenery. A wooden walkway leads from the lakeside, enhancing accessibility to the cabin's entrance.

Cabin in Weld

Camp Bai Yuka/Little Camp (Log Cabin on Webb Lake)

FamilyKitchenDecor

4.95 out of 5 average rating, 602 reviews

A rustic cabin is nestled among tall trees, showcasing wooden logs and a slanted roof. Sturdy stairs lead to a porch, where a warm entry invites nature lovers. Leafy surroundings create a serene atmosphere, highlighting the cabin's rustic charm.

Treehouse in Conway

Tree House at the Shire

FamilyIndoor spacesCheckout

4.93 out of 5 average rating, 220 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

KitchenIndoor spacesNearby

4.92 out of 5 average rating, 173 reviews

A bright sitting area features large windows offering scenic views of Porter Lake and surrounding mountains. Wooden walls create a cozy atmosphere. A comfortable couch sits adjacent to a flat-screen TV. Nearby, a bookshelf displays a variety of books, enhancing the inviting space.

Cabin in Strong

Lakefront Home with Dock | Porter Lake | Sugarloaf

FamilyIndoor spacesAccuracy

Family-friendly home rentals with a pool

4.93 out of 5 average rating, 188 reviews

Cabin in Freeport

Cozy romantic A-frame by a woodland stream - 25

KitchenIndoor spacesHot tub

Superhost

Home in Newry

4.86 out of 5 average rating, 111 reviews

Farmhouse: Hot Tub, Mini Golf, Pickleball, POOL

FamilyKitchenTV

4.94 out of 5 average rating, 235 reviews

A log cabin is nestled among tall trees on a gentle slope. Large windows create airy views from the exterior, showcasing a front deck that extends along the house. The natural surroundings provide a peaceful and serene setting.

Home in Peru

the lake house

FamilyKitchenView

4.93 out of 5 average rating, 128 reviews

An outdoor pool area is seen, surrounded by snow-covered ground and trees. A hot tub is situated beside the pool, with steam rising into the cool air. A sign that reads 'Welcome To The Brookeggs' is visible on the fence. Mountains are in the background.

Condo in Newry

Cozy 1 br condo with ski in/out lift access & Pool

FamilyKitchenDecor

4.95 out of 5 average rating, 695 reviews

The spacious loft is highlighted by 16-foot ceilings and multiple skylights. A queen bed is positioned near a cozy seating area, complemented by a wooden dining table. Eye-catching artwork adorns the walls, and natural light fills the room through large windows.

Loft in Falmouth

Loft Apartment on Tree-Lined Street in Falmouth

Indoor spacesFamilyAmenities

4.82 out of 5 average rating, 179 reviews

A modern living area is equipped with a large flat-screen TV mounted on the wall. A wooden coffee table sits in the center, surrounded by two floral armchairs. A dining table with white chairs is positioned against the wall, illuminated by natural light from two windows.

Apartment in Berlin

White Mountain Renovated 1 Bdrm + queen sleep sofa

KitchenIndoor spacesCondition

4.94 out of 5 average rating, 335 reviews

The living area is highlighted by a spacious sectional sofa and a wooden spiral staircase leading to the upper level. Natural light fills the space, accentuating the wooden flooring and cozy decor. A coffee table sits centrally, complementing the overall inviting atmosphere.

Condo in Bartlett

An Amazing Mountain Getaway!

FamilyIndoor spacesShared spaces