Family-friendly vacation rentals in Bridgton

4.99 out of 5 average rating, 139 reviews

Family & Friends Retreat*Hot Tub*Game Room*King Be

MAKE MEMORIES together in the school's large classroom which is an impressive gathering spot for the whole group with the modern kitchen, massive dining table and comfy living room. Endless entertainment in the brand new barn game room! This lovingly restored schoolhouse is a unique mixture of historic charm, warmth, character and modern ease. Gather outside on the 7 acre property for a cookout, chat by the fire or relax in the sauna and hot tub after hiking, swimming, boating, skiing, dining or

4.95 out of 5 average rating, 271 reviews

Dreamy Mountain Home w/ Hot Tub, Firepit, + Views!

Perched at the summit with complete privacy and sweeping views of Mount Washington, the White Mountains, and Woods Pond, Mainely Mountain Views is a 4-bedroom Maine retreat that earns its name the moment you step onto the deck. Perfect for large groups with easy access to Pleasant Mountain, Long Lake, Sebago Lake, and the Saco River - plus hiking, mountain biking, and snowmobile trails. Watch the sun set over the mountains from the hot tub. The kind of place you come to relax, unwind, and enjoy.

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.

4.92 out of 5 average rating, 374 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.

4.89 out of 5 average rating, 288 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!

4.94 out of 5 average rating, 284 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

4.98 out of 5 average rating, 63 reviews

The exterior of the house features a light-colored wooden façade with green shutters. Surrounded by lush trees, the home includes a front porch with steps leading to the entrance and ample outdoor space covered in grass and gravel.

Cottage in Bridgton

Beach | Pool | High-end kitchen | Bunkbeds| AC

Lake Haus Bridgton offers Maine luxury living with a beautiful pine interior, an open concept kitchen/dining/living area, three bedrooms, one and a half baths, and a spacious sunny living space. Located in the beautiful shared waterfront community of Knights Hill, situated on Moose Pond in Bridgton, Maine. The association amenities include a shared sandy beach on Moose Pond, a pool, tennis courts, a basketball court, and two playgrounds. Skiing at Pleasant Mountain is only 5 minutes away.

A hot tub is positioned on a spacious deck, offering a stunning view of a mountain during sunset. The scenery features a blend of warm hues in the sky, with gentle slopes visible in the background. Steps lead up to the hot tub, enhancing accessibility.

4.95 out of 5 average rating, 174 reviews

*1MMview*Bar,Hot Tub,3mins2Pleasant Mnt, Pool tab.

This special, completely renovated place can host your family gathering or group of friends in an inviting setting. This unique house with a private bar, spa, and a pool table will satisfy all your vacation needs! Located close to everything, but absolutely quite and private 20 acres property! It is situated on a ridge with a spectacular mountain view. Our house offers comfort & entertainment. The property will give you the full vacation in the woods experience. This is just what you need!

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.

4.92 out of 5 average rating, 136 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, 111 reviews

Cabin in Bridgton

The Barnhaus | Unique 5-Star Experience | Hot Tub

Welcome to The Barnhaus. This brand-new construction custom-built home with an outdoor hot tub was specifically to be a vacation home, we have thought of everything! This cabin has all solid wood furnishings, real leather upholstery, 1080p 40 inch TV's in each bedroom and great water pressure! Perched up on a hill in a quiet neighborhood, our home is secluded & quiet yet less than 5 min. from Shawnee Peak and Moose Pond. We cut no corners while building this house and hope to have you soon!

4.98 out of 5 average rating, 388 reviews

A spacious bedroom is highlighted by a king-size bed adorned with subtle patterns. Natural light pours in through large windows, illuminating the beautiful stone fireplace, which provides a cozy focal point. A comfortable reclining couch sits nearby, enhancing the relaxing atmosphere.

Guest suite in Bridgton

Barn on Pleasant- Walk to Highland Beach

Welcome to our charming loft in a peaceful neighborhood, ideal for comfort and convenience. This well-maintained property provides a cozy living space. The loft features a kitchenette, a beautiful stone fireplace and a big, comfy reclining couch. Visit Bridgton this summer walking distance highland lake, shops, and restaurants. Just minutes from Pleasant Mountain for hiking, skiing, 30 minutes from North Conway, and an hour from Portland a perfect central location to relax after exploring.

4.94 out of 5 average rating, 726 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.

4.95 out of 5 average rating, 117 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.

Popular amenities for Bridgton family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

4.88 out of 5 average rating, 114 reviews

Manor Suite cozy downtown walk to beach & hot tub

4.91 out of 5 average rating, 163 reviews

An aerial view captures a log cabin surrounded by lush green trees, showcasing its isolated position on three private acres. The cabin features a blue-green roof, with a driveway leading to parked vehicles nearby, emphasizing a serene and wooded environment.

Cabin in Bridgton

Private cabin with lake access, hot tub & firepit!

A large wooden house with multiple windows is positioned among tall trees. The sun is setting in the background, casting a warm glow on the deck and surrounding lawn, which features natural landscaping and a few large rocks.

4.98 out of 5 average rating, 153 reviews

Bridgton Getaway

4.98 out of 5 average rating, 201 reviews

Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

5.0 out of 5 average rating, 107 reviews

Cabin in Norway

Secluded Cabin: Mountain View, Hot Tub + Fireplace

5.0 out of 5 average rating, 249 reviews

Home in Oxford

The Modern Lakehouse

4.9 out of 5 average rating, 164 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

4.85 out of 5 average rating, 230 reviews

Cabin in Intervale

Riverside|Sauna|Hot tub|Pizza Oven|Dogs

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 140 reviews

The living area features high, wooden ceilings with exposed beams and large windows, allowing natural light to flood the space. A stone fireplace serves as a focal point, while a cozy seating area is complemented by a dining table surrounded by red chairs.

Home in Naples

Best Ski & Lake House

4.97 out of 5 average rating, 147 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

4.87 out of 5 average rating, 130 reviews

A spacious living area features warm wood paneling and a cozy wooden fireplace. Comfortable seating is arranged around a coffee table, and large glass doors allow natural light to fill the room, leading to the scenic outdoors. A ladder provides access to the loft area.

Chalet in Bridgton

Charming Chalet 3 min to SKIING & PVT beach access

4.97 out of 5 average rating, 100 reviews

Cabin in Denmark

Moss Hill Cabin

4.98 out of 5 average rating, 64 reviews

Lake Front Cabin on Desirable Highland Lake

A cozy blue cottage sits surrounded by tall trees near the water's edge. A screened porch is visible, providing outdoor seating. The structure features a sloped roof and a wooden deck that extends toward the lake, highlighting the peaceful natural setting.

5.0 out of 5 average rating, 14 reviews

Lakeside Cottage with beautiful sunsets!

The outdoor area features a circular stone fire pit surrounded by multiple wooden chairs on a gravel surface. A hot tub is positioned nearby, while a wooden structure offers sheltered space. The backdrop showcases the farmhouse exterior and lush greenery under a sunset sky.

5.0 out of 5 average rating, 40 reviews

Fowler Farmhouse | Downtown | Beach | Hot tub +Bar

4.97 out of 5 average rating, 77 reviews

A spacious kitchen features wooden cabinetry and a large granite island with seating. A modern stainless steel refrigerator and oven are present, along with a range hood. Natural light enters through the window, highlighting the white subway tile backsplash and various kitchen appliances.

Apartment in Bridgton

The Blueberry House (no silly fees!)

Family-friendly home rentals with a pool

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.

4.9 out of 5 average rating, 181 reviews

Moose Pond Mountain Escape

4.96 out of 5 average rating, 125 reviews

The modern cabin features a sleek design surrounded by lush greenery. Soft bistro lights create a warm glow, illuminating the outdoor seating area with two Adirondack chairs. The deck can be seen in the background, enhancing the inviting atmosphere of the natural setting.

Cabin in Freeport

Romantic hideaway cabin w/ access to spa - 26

4.96 out of 5 average rating, 179 reviews

A welcoming living area is furnished with two dark sofas adorned with vibrant orange cushions. A rustic coffee table is centered on a colorful area rug, while large windows allow natural light to fill the space, highlighting the wall art above.

Home in Portland

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

4.87 out of 5 average rating, 113 reviews

Home in Newry

Farmhouse: Hot Tub, Mini Golf, Pickleball, 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.

Family friendly + Mountain Views @amountainplace

4.96 out of 5 average rating, 406 reviews

4.93 out of 5 average rating, 128 reviews

Condo in Conway

Cranmore Mountain Condo | Pool, Hot Tub | Sleeps 6

4.88 out of 5 average rating, 179 reviews

A gentle river flows over smooth, rocky surfaces, creating soft white rapids. Surrounding the water, a mix of evergreen and deciduous trees line the banks. A clear blue sky is visible above, enhancing the natural landscape.

Condo in Bartlett

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