
Holiday rentals with a pool in Bridgton
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Bridgton
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Privacy, River, Pond, A frame Hot Tub EPIC Views,
14 Acres Secluded A-frame nestled along Clean Crooked River, Hot tub with breathtaking VIEWS and world-class fishing. Swim in the river, private pond or explore hiking trails right from your door. Central AC - Gas Fireplace - Modern Kitchen. 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. Invite a private chef, florist or yoga teacher to fully unwind. Heated bath floors.

Historic Schoolhouse c1866 / Sauna + Hot Tub + Gym
Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond, gym and tennis court.

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.

Cozy Family Retreat with Saco River Access
An ideal setting to enjoy Mt. Washington Valley's many year round outdoor activities or rest, relax and enjoy the peace. This cozy, comfortable condo has everything you and your guests might need to enjoy themselves. An upstairs, end unit with lots of natural light, and front and back decks. The inground pool is open in summer as are the tennis, shuffleboard and basketball courts. The common fields behind the condo are ideal for snowshoeing in the winter or walking in warm weather.

2 bedroom condo, mountain views, pools and jacuzzi
Nordic Village traditional spiral up 2 bedroom, 2 bath condominium with Mountain View’s in the Mount Washington Valley location close to skiing, golf, Storyland/Living Shores, hiking, snow shoeing, cross country skiing and more ... Beautiful stone faced gas log fireplace for heat and ambience, granite counters, jacuzzi, furnished with stylish decor. Perfect for children and couples with indoor and outdoor (heated) pools (free). spa, steam room, pond, tennis court, and a playground.

AttitashResort! 1-flr, studio, secure check-in
Location, Amenities, Convenience, All the things you're looking for in a perfect vacation get away! Enjoy every season at this well located mountain resort. Walk to all the Attitash Resort Activities like hiking, skiing, pools, hot-tubs and more all from this fully furnished condo studio that sleeps 2 adults (maybe more) at the base of some of the best skiing in the east! Stay on the grounds or travel in any direction to create memories, relax, experience your best life.

Romantic Bungalow w/ Hot Tub & Parking
The Bungalow is a private, luxury, en-suite, small, out-building on the property of the historic Chapman House. The space includes TV, fridge, microwave, and coffeemaker, access to the seasonal pool, and year-round shared hot tub. We are owner-operated. Relax outside on the lawn or the patio, at a picnic table (in season), one of the fire pits, or under the fir tree. Emily's beautiful garden could be in bloom. We now offer a Level 2 EV charging outlet. #AllAreWelcome

Steep Falls Escape, river & falls just steps away
Bright and pleasant 1 bedroom apt with separate entrance, gas fireplace, enclosed porch and large kitchen. Spacious yard to enjoy with pool, fire pit, grill and outdoor seating. Steep Falls is a rural village. Our home is a 5 min walk to the Saco River a favorite destination for canoeing, kayaking or tube floating (after the spring run off!) It is just a 10 min drive to the boat launch for Sebago Lake, one of Maine's largest and most beautiful bodies of water.

Peaceful Condo Near Storyland & Attitash Skiing
Comfortable and cozy two-bedroom, two-bath condo ready to fulfill your vacation needs. Located in a quiet spot close to the Clubhouse at The Seasons at Attitash, this condo offers seclusion while being located conveniently close to the shopping, dining and other fun activities found in N. Conway. Several Washington Valley Ski areas (Attitisash is only a 5-minute drive!), Santa’s Village, hiking, and beautiful scenic views can all be found within a short drive.

3 Bears Glen, Near Attitash, Wildcat & Black Mtn.
Welcome to Three Bears Glen! A cozy condo located just 4 miles from Attitash & Black Mtn., 12 miles to Wildcat! This 2 Bedroom 1st floor end unit condo is the perfect getaway. This family friendly home features a private entrance, fully equipped kitchen, heat, A/C, Wi-Fi, 3 Roku enabled TVs, games(adults & kids), washer/dryer & patio seating. Located across from Story Land and just a short drive to North Conway. Enjoy all the valley has to offer!

An Amazing Mountain Getaway!
Come and relax at our Nordic Village vacation condo! The 2-bedroom, 2-bath end unit features 2 stories with a spiral staircase, fireplace and a deck! Nordic Village amenities include pools, hot tubs, a sauna and more when you're not skiing at Attitash, Cranmore, Wildcat or Black Mountain! With Story Land 1 mile away, idyllic North Conway and all that's best of White Mountain National Forest within minutes, this getaway has it all!

Spacious Linderhof Condo Across from Storyland!
Spacious Linderhof Condo right across the street from Storyland! Great location! Right across from Storyland and close to 5 major ski areas. Spacious oversized 1 bedroom (863 sq. ft.) country club location. Golf, swimming, tennis, clubhouse on premises. Take a dip in the pool and have a bite to eat in the clubhouse (sandwiches, snacks, cocktails). Sofa pulls out for two more people . Pool is $55 week, $35 3 days, $20 1.
Popular amenities for Bridgton rentals with a pool
House rentals with a pool

Witts' End- quiet neighborhood in Knights Hill

Silent Nights 5 Min to Mt Ice Fish & Wood Stove

Moose Pond Cottage - 3 mins to Pleasant Mountain!

Ski Resorts 15 mins, Updated Family Friendly Condo

Farmhouse: Ice Rink | Movie Cave | Hot Tub

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Walkable Downtown North Conway w private hot tub!

There's No Place Like Home
Apartment rentals with a pool

Upscale retreat w/ panoramic White Mountain views

White Mountains Hiking Dogs Storyland Family

Remodeled Condo - Ski & Santa’s Village - Pool

Don’t miss out, book your ski trip now!

Cute & cozy Attitash Studio Condo

Across from Storyland & in the Heart of the Mtns

Bartlett Condo; Great Views, Resort Access

Cozy Condo at The Seasons- 2 Bedrooms
Other holiday rentals with a pool

Pristine Log Cabin w/Lake Access NO Cleaning Fees!

White Mountains Escape

The Lodge at Hidden Pines

Nordic Village Resort | Highland Top Floor Room

Cozy getaway at Attitash Mountain Village

Luxe Eco Studio near Back Cove

Cozy Family-Sized Condo Close To Everything

Cozy Condo In Gated Community Sleeps 4
Quick stats about holiday rentals with a pool in Bridgton

Total holiday rentals
Explore 30 holiday rentals in Bridgton

Nightly prices starting at
Bridgton holiday rentals start at £102 per night before taxes and fees

Verified guest reviews
Over 940 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Bridgton holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Bridgton rentals

4.8 Average rating
Bridgton stays are highly rated by guests – averaging 4.8 out of 5!
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- Ski-in/ski-out rentals Bridgton
- Rentals with pools Cumberland County
- Rentals with pools Maine
- Rentals with pools United States
- White Mountain National Forest
- Sebago Lake
- Squam Lake
- Story Land
- Sunday River Resort
- Scarborough Beach
- Loon Mountain Resort
- Weirs Beach
- Mount Washington Cog Railway
- Cranmore Mountain Resort
- King Pine Ski Area
- Franconia Notch State Park
- East End Beach
- Willard Beach
- Omni Mount Washington Resort
- Diana's Baths
- Cannon Mountain Ski Resort
- Funtown Splashtown USA
- Gunstock Mountain Resort
- Waterville Valley Resort
- Wolfe's Neck Woods State Park
- Crescent Beach State Park
- Palace Playland
- Conway Scenic Railroad




