Family-friendly holiday rentals in Bridgton

A spacious kitchen features white cabinetry with modern hardware and a large island with a wooden countertop. Black appliances, including a refrigerator and stove, complement the granite countertops. A window above the sink allows natural light to enter, enhancing the functionality of the space.

4.91 out of 5 average rating, 350 reviews

Lake Region Comfort, Close to Everything!

Come enjoy the Highland Lake area known for its clear water, boating and fishing! Just a few miles away from Shawnee Peak which offers both day/night skiing. Also a few miles away is downtown Bridgton where there is the Magic Lantern movie theater and the drive-in theatre. Downtown also offers shopping and many options for superb dining. This single-family residence will provide you with 3 bedrooms, a newly renovated kitchen, sliders to deck, bathroom, living room with large panel tv and WiFi.

4.99 out of 5 average rating, 185 reviews

An inviting living space features a cozy seating area with a dark sofa and accent chairs. A wooden dining table is positioned nearby. A steep staircase leads to the sleeping loft, while large windows provide views of the surrounding nature and allow natural light to fill the room.

Tiny home in Bridgton

Stunning Library Tiny Home *Private Hot Tub*King B

Welcome to The Tiny Library - Maine's most unique tiny home! This antique library building has been newly renovated into a cozy getaway for bibliophiles and library lovers alike. Its book-lined shelves and dark academia decor, along with modern amenities and high quality bedding ensure a memorable stay, while the gas fireplace and hot tub provide the perfect ambiance for rest and relaxation. Whether you're a bookworm or just in need of a quiet escape, The Tiny Library is the perfect retreat.

A chalet-style home is nestled among tall trees, featuring a wooden deck with a set of stairs leading down to the ground. Large windows provide glimpses into the living spaces, welcoming natural light into the interior.

4.89 out of 5 average rating, 174 reviews

Moose Pond Mountain Escape

A two minute walk to Moose Pond and one mile from Pleasant Mtn skiing in picturesque Bridgton, Maine. This cozy retreat is perfect for those who want a relaxing getaway in a fun-filled area in the heart of the lakes region. Guests enjoy a short walk to Association's beach/dock access and kayaks, and a short drive to tennis courts and pool. Hike, bike and explore Western Maine's mountains, lakes and villages. Bridgton shops are 5 miles away while N. Conway's outlets are 20 miles to the east.

4.89 out of 5 average rating, 271 reviews

The exterior of Pebble Cottage is shown, featuring a charming yellow facade with a welcoming front porch. Two large windows adorned with flower boxes are displayed, offering a glimpse of the landscaped yard framed by a white picket fence.

Cottage in Bridgton

Rustic Pebble Cottage in beautiful Bridgton, Maine

Pebble Cottage is a one hundred year old quirky camp that was enlarged some years back. It is located in Bridgton near plenty of lakes and skiing. The public beach is a short skip down the hill. The cottage is a rustic little haven that was saved from demolition, and updated with a brand new bathroom, a cute little kitchen with a dishwasher, with two heat pumps to keep the space cozy and three homey comfortable bedrooms, a large yard with a hammock, very quiet retreat. Please note it's old!

An aerial view captures a home set among tall trees near Highland Lake. The well-maintained yard stretches to the water's edge, showcasing direct lake access. A peaceful landscape is framed by greenery, while the calm lake reflects the surrounding nature.

4.91 out of 5 average rating, 128 reviews

Lakefront haven near Shawnee-25mi to North Conway

Located in a quiet neighborhood, our home on Highland Lake is perfect for families or a friendly gathering, boasting 3 BD-2 BA, with gorgeous lake views, and direct lake access with a common sandy walk out beach area. Enjoy the provided canoe and kayak, and spend an evening grilling on the deck, or roasting marshmallows in the common fire pit! Less than one mile to downtown Bridgton. Easy access to hiking and snowmobile trails, as well as skiing at Shawnee Peak (less than a 10 min drive).

4.94 out of 5 average rating, 272 reviews

A spacious great room features vaulted wooden ceilings and is adorned with large arched windows, allowing natural light to fill the space. A cozy seating area with plush sofas is complemented by a stone fireplace, creating an inviting environment. The kitchen area is visible in the background.

Cabin in Bridgton

Cozy Cabin, Close to everything

Charming Cabin located on a dead end road in a wooded setting. Ideal for four season activities. Walk to Long Lake for a swim or 15 minute drive to ski slopes, 30 miles to North Conway, 60 minutes to Portland or just walk the town of Bridgton to visit the restaurants and antique shops. If you like to snowmobile the (ITS) trail is 200 feet outside the back door. The Perfect vacation spot. The house has Wi-Fi (GIG Access) which is plenty of bandwidth for work or play. Please read House Rules

4.94 out of 5 average rating, 696 reviews

A spacious living area is highlighted by hardwood floors and tall ceilings with exposed beams. Large windows allow natural light to fill the room, illuminating the comfortable seating, modern coffee table, and decorative lamps. A piece of wall art adds a touch of character.

Loft in Bridgton

Tap House Loft~Sunny & Spacious, Private Hot Tub

Conveniently located in the heart of Downtown Bridgton, the Tap House Loft is ready for you, your friends and your family to enjoy! Walk to vibrant Main Street, Pondicherry Park, the Magic Lantern Theater, Highland Lake and all the downtown shops, gallerias and restaurants...or simply relax in the peace and quiet of our newly restored, historic warehouse. Located above the Sundown Lounge, this 900 sq ft space offers a large Master Suite with French Doors leading to a deck and hot tub.

An aerial view showcases a spacious home surrounded by lush greenery and a golf course. Nearby, a parking area is visible, along with manicured fairways and trees in the distance, providing a sense of tranquility and openness.

4.94 out of 5 average rating, 107 reviews

Beautiful Views, Bridgton Maine

Vacation getaway for all seasons. Enjoy mountain and golf course views from this 3,800 square foot home. Pleasant Mountain Ski Area beckons from 10 minutes away. Sunday River Ski Area is 40 minutes away. Or bring your clubs and test your skills on the challenging 18 holes at Bridgton Highlands Golf located steps away. At the end of the day, sip on an adult beverage in the spacious timber frame great room and marvel at the field-stone fireplace that stretches from floor to the ceiling.

4.98 out of 5 average rating, 129 reviews

A modern chalet-style exterior is visible, partially covered in fresh snow. Large windows reflect the snowy landscape, while the deck area is blanketed with a layer of snowflakes. The surrounding trees create a serene winter scene, enhancing the retreat’s natural charm.

Home in Sweden

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit

Escape to Camp Sweden, an eco-friendly waterfront sanctuary in the foothills of the White Mountains. Paddle across the private pond, go for a hike in the Mountains nearby, or jump in the new outdoor panoramic barrel sauna and let your worries evaporate away. Enjoy a unique and rejuvenating experience that connects you to nature without sacrificing comfort. This retreat offers all-season enjoyment for nature lovers and outdoor enthusiasts alike. Experience Maine’s beauty today

4.95 out of 5 average rating, 247 reviews

Dreamy Mountain Views w/ Hot Tub + Wood Stove

Dreamy mountainside home with views of Mt Washington and the White Mountains! Boasting 4 bedrooms and 2 bathrooms, this house is perfect for large groups seeking easy access to Pleasant Mountain Ski Area, Long Lake, Sebago Lake, and Saco River, along with nearby mountain biking, hiking, and snowmobile trails. After a long day of adventure, enjoy a soak in our 6-person hot tub, fully equipped kitchen, fire burning wood stove, and a cozy living room with a large screen TV!

Superhost

The image captures a lush green landscape in front of a charming red building. A winding drive leads towards the residence, while mountains rise in the background under a partly cloudy sky. Colorful flowers and greenery frame the scene, enhancing its natural beauty.

Guesthouse in Bridgton

4.83 out of 5 average rating, 157 reviews

Private apart with luxury view, mins to everything

Welcome to the Peak View Apartment! This lovely and stylish place is perfect for a honeymoon, anniversary or romantic getaway or for those who crave for retreat. This is what you imagine when you want to relax in the house in the mountains!!! But also great for a small family with kids! Sitting on the ridge of Pleasant Mountain, the place is minutes away from all the attractions and beautiful lakes. The property will give you the full vacation in the woods experience!

A two-story cabin is surrounded by snow-covered trees, showcasing a green metal roof and warm wood siding. Large windows offer views of the winter scenery. A wooden deck with a railing extends from the main level, inviting outdoor relaxation in the serene setting.

4.97 out of 5 average rating, 135 reviews

Fish Tales Cabin

Everything for your perfect Maine getaway! Use our private dock for your boat, but don't worry about kayaks and paddle boards - use ours. Enjoy a tranquil sunrise, the song of a loon, and the the quaint Bridgton village. Enjoy foliage in the fall and skiing at Pleasant Mountain (formerly Shawnee Peak) only 5 minutes away. White Mountains are very close too! Follow us on FB for more pictures, news and offers! Search for 35 Moose Pond, Bridgton, ME.

Popular amenities for Bridgton 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, 231 reviews

Tiny house in the Birch Grove with private HOT TUB

4.89 out of 5 average rating, 298 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.

Apartment in Bartlett

Attitash Retreat

4.91 out of 5 average rating, 145 reviews

The A-Frame cabin features a striking black exterior accentuated by bright yellow trim. A large umbrella shades a wooden deck with seating, inviting relaxation. Surrounding trees create a serene atmosphere, enhancing the cabin's secluded charm within the natural landscape.

Chalet in Denmark

Maine A-Frame with Hot Tub, Game Room, Lake Access

4.91 out of 5 average rating, 148 reviews

A charming log cabin is surrounded by snow-covered trees, creating a serene atmosphere. A snow-covered path leads to the entrance, highlighting the cabin's inviting design against the winter landscape. The sloped roof showcases a layer of fresh snow, complementing the rustic wood exterior.

Cabin in Bridgton

Private cabin w hot tub,skiing,firepit & mountains

4.96 out of 5 average rating, 204 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

Private Log Cabin w/mtn views, hot tub, BBQ

4.86 out of 5 average rating, 200 reviews

An aerial view captures a vibrant riverside cabin, surrounded by lush greenery and tall trees. The property sits beside a rocky stream, with a pathway leading up to the cabin's entrance, creating a serene and inviting outdoor setting.

Cabin in Intervale

Riverside|Sauna|Hot tub|Pizza Oven|Dogs

4.92 out of 5 average rating, 119 reviews

A private courtyard is illuminated at night, featuring a hot tub and a fire pit surrounded by gravel. Four wooden chairs are arranged around the fire pit, which has a glowing flame. Soft lights are strung along the wooden fence and cabin walls, creating a cozy atmosphere.

Cabin in Conway

Troy’s Cabin: N. Conway w/ Hot Tub, A/C, Fireplace

4.95 out of 5 average rating, 129 reviews

Cabin in Fryeburg

White Mountain Dream Cabin | 4 Acres + Hot Tub

Family- and pet-friendly home rentals

Guesthouse in New Gloucester

A wooden dock extends toward calm water, with a gentle sloping pathway leading down from the boathouse. The clear water reveals stones at the bottom, while green trees frame the picturesque lakeside view.

4.89 out of 5 average rating, 161 reviews

On the water Boathouse!

4.94 out of 5 average rating, 79 reviews

The exterior of a gray barn features a peaked roof and a large wooden door. An American flag is displayed, and a window is positioned above the entrance. Surrounding trees exhibit autumn foliage, and a white picket fence is visible in the background.

Barn in Hiram

Peaceful Barn Loft

A charming cottage is nestled among trees, featuring a sloped roof and large glass windows. A wooden pathway leads to a covered porch, furnished with red chairs. Surrounding ferns and greenery enhance the natural setting, inviting relaxation and connection with nature.

5 out of 5 average rating, 15 reviews

Moose Pond Cottage - 3 mins to Pleasant Mountain!

4.97 out of 5 average rating, 36 reviews

A cozy cabin sits nestled among colorful autumn foliage, reflecting on the calm lake surface. The exterior features a charming blue facade and a screened porch, surrounded by trees and boulders leading to the water’s edge.

Cabin in Bridgton

Lakefront Getaway Cabin/Private Sandy Beach!

A cozy dining area is equipped with a marble-topped table and two wooden chairs. White cabinetry contrasts with natural wood flooring. A small kitchen area features a sink and a compact refrigerator. Decorative plants and a hanging light fixture add subtle charm to the space.

4.87 out of 5 average rating, 82 reviews

Manor Suite,cozy newly renovated,downtown & beach

4.99 out of 5 average rating, 184 reviews

An inviting living area is highlighted by a plush blue sectional sofa, paired with a modern coffee table. Natural light enters through multiple windows with soft drapes, illuminating the warm wood accents and an area rug on the polished floor.

Guesthouse in Yarmouth

Private Guesthouse in the Woods

4.99 out of 5 average rating, 513 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

4.83 out of 5 average rating, 6 reviews

Apartment in Bridgton

Pleasant Mountain Affordable Clean Apartment

Family-friendly home rentals with a pool

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, 378 reviews

Family friendly + Mountain Views @amountainplace

4.86 out of 5 average rating, 101 reviews

Home in Newry

Farmhouse: Ice Rink | Movie Cave | Hot Tub

4.93 out of 5 average rating, 102 reviews

A cozy living area is highlighted by warm yellow walls and wooden beams. A sectional couch faces a TV, while a table with four chairs is positioned nearby. Bright light enters through a large window, and decorative items add character to the space.

Condo in Bartlett

Cozy Condo at The Seasons- 2 Bedrooms

4.96 out of 5 average rating, 153 reviews

A private pool area features a colorful inflatable parrot floating in clear water. Surrounding the pool are several lounge chairs arranged for relaxation. Lush trees provide shade, and a fence ensures privacy for the space, which is brightly illuminated by natural sunlight.

Home in North Deering

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Superhost

The image displays a cozy studio featuring a king-size bed, a gas fireplace, and a well-equipped kitchen area with modern appliances. A view of the indoor pool and hot tubs is highlighted, alongside a welcoming sign for Attitash Mountain, showcasing proximity to ski activities.

Condo in Bartlett

4.89 out of 5 average rating, 236 reviews

Cozy Fireplaced Mountain King Suite w/Hot Tubs & P

Place to stay in Shapleigh

5 out of 5 average rating, 118 reviews

Historic Schoolhouse c1866 Winter & Summer Dates

4.92 out of 5 average rating, 116 reviews

A welcoming living area features warm wood flooring and natural light from multiple windows. Comfortable seating includes a sofa and chairs arranged around a central table. A ceiling fan provides gentle airflow, while double French doors lead to an outdoor space.

Guest suite in Standish

Steep Falls Escape, river & falls just steps away