Holiday rentals in Bridgton

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Top-rated holiday rentals in Bridgton

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Home in Bridgton
5 out of 5 average rating, 112 reviews

Sauna*Hot Tub*Game Room*King Beds*Firepit*Near Ski

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

Top guest favourite
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
4.98 out of 5 average rating, 313 reviews

Barn on Pleasant- walk to town-no cleaning fee

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 fall & winter 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

Top guest favourite
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.
Home in Bridgton
4.91 out of 5 average rating, 338 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.

Guest favourite
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
4.89 out of 5 average rating, 259 reviews

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!

Top guest favourite
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
4.94 out of 5 average rating, 668 reviews

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.

Top guest favourite
A modern kitchen features sleek countertops and high-end appliances, including a stainless steel oven and range. Black pendant lights hang above a spacious island with bar stools. Multiple windows allow for abundant natural light, with a patterned rug adding warmth to the wooden floors.
Guest house in Hiram
5 out of 5 average rating, 123 reviews

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

Top guest favourite
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
4.99 out of 5 average rating, 109 reviews

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

Guest favourite
Home in Bridgton
4.95 out of 5 average rating, 228 reviews

Hot Tub & Dreamy Mountain Views w/ 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.
Guest house in Bridgton
4.85 out of 5 average rating, 147 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!

Top guest favourite
A cozy cabin interior features warm wooden walls and flooring. Twinkling string lights adorn the ceiling, creating a soft glow. A comfortable armchair is positioned beside a small lamp, with a spacious bed visible in the background, framed by large windows allowing natural light.
Cabin in Lovell
4.97 out of 5 average rating, 383 reviews

Secluded, cozy cabin nestled in the Maine woods

Kick back and relax in this calm, stylish space with a semi-remote cabin experience while keeping the gentle daily living comforts. Right at the edge of the White Mountain National Forest in one direction and in the other direction, a short five minute drive to Kezar Lake this secluded cabin has it all for the nature lover in you! Close to local favorite trailheads for hiking and mountain biking as well having nearby ski mountains and snowmobile trails.

Guest favourite
The living area features high wooden ceilings and large windows, allowing natural light to fill the space. A comfortable couch is positioned near the windows, while a television is mounted on the opposite wall. The warm wooden flooring complements the rustic design.
Guest house in Brownfield
4.88 out of 5 average rating, 481 reviews

Mountain Treehouse Guesthouse

Spacious second story post and beam room adorned with king bed, full kitchen, bath, living area, and laundry. The guest house is located on 40 acres of wilderness with mountain views, and walking trails on the property. Just two miles from Stone Mountain Arts Center, 15 minutes from Fryeburg village, and only 25 minutes to neighboring North Conway, NH. A great retreat for all seasons. TV, High-Speed Internet, AC, Heat, Ceiling Fans, New Construction.

Top guest favourite
A lofted bedroom features a spacious bed adorned with a vibrant striped blanket. Light filters through a window, highlighting the sloped whitewashed ceilings and simple artwork on the walls. Warm wood accents complement the soft, neutral tones throughout the room.
Home in Bridgton
4.98 out of 5 average rating, 140 reviews

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

Popular amenities for Bridgton holiday rentals

When is the best time to visit Bridgton?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$293 SGD$310 SGD$290 SGD$260 SGD$267 SGD$285 SGD$327 SGD$332 SGD$291 SGD$298 SGD$277 SGD$303 SGD
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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Bridgton?

    Yes! Work meets play with ease at over 160 vacation rentals in Bridgton featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Bridgton?

    Four-legged friends are welcome in Bridgton. Choose from more than 140 vacation rentals for guests traveling with pets.

  • Are there Bridgton vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Bridgton, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in house rentals in Bridgton?

    Experience the best of Bridgton with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Bridgton have self check-in?

    Absolutely! We offer over 70 house rentals with self check-in in Bridgton. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Bridgton have a bbq area?

    Absolutely! We offer over 60 cabin rentals with a bbq area in Bridgton. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly chalet rentals in Bridgton?

    Bridgton has more than 10 family-friendly chalet rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Bridgton?

    Enhance your stay in our House Rentals with the most popular amenities: over 100 homes with a bbq area, over 70 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Bridgton

  • Total holiday rentals

    Explore 380 holiday rentals in Bridgton

  • Nightly prices starting at

    Bridgton holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 14,640 verified reviews to help you choose

  • Family-friendly holiday rentals

    300 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 160 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wifi availability

    360 of Bridgton holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Lake access and Gym across Bridgton rentals

  • 4.9 Average rating

    Bridgton stays are highly rated by guests – averaging 4.9 out of 5!

Destinations to explore

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  3. Maine
  4. Cumberland County
  5. Bridgton