
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.

Family Ready Home Close to Town Trails and Outlets
This gorgeous townhouse that is just steps away from North Conway, walk to the Muddy Moose for dinner and drinks. Every smart device you can think of has been thought of, less than 5 minutes to Cranmore, the outlets for shopping, 15 minutes to Attitash, tons of trails for hiking, mountain biking, cross country skiing, snowshoeing. Three full bathrooms, three queen beds, 2 single beds. WIFI, cable, 70 inch TV set up for gaming, foosball table, three levels of space so everyone can spread out.

Attitash Mt. Escape - Pool+Hot Tub, Near N Conway
Spacious, tastefully renovated 2 bedroom condo at base of Attitash Mountain. Condo is on 2nd and 3rd floors of building. Resort has full amenities such as pools, jacuzzis, restaurant, pub, riverfront beach, 24-hour hospitality desk and more. Pedestrian tunnel to ski lifts at Attitash Mountain. Gas fireplace. Central location just minutes to White Mountain and North Conway attractions such as Story Land, Echo Lake and Bretton Woods. Relax slopeside and enjoy amenities, or venture out and explore.

Summit Vista | 3br Mountain Paradise | Epic Views
Escape to Summit Vista, a classic chalet style home in the heart of the White Mountains. With 3 bedrooms, 2 baths, a loft, and many thoughtful upgrades, this home is built for comfort, connection, and mountain adventure. Conveniently located between North Conway & Jackson, Summit Vista offers easy access to top ski resorts, hiking trails, restaurants, and shopping. Blending mountain style with classic comfort, Summit Vista is a nod to the natural beauty & timeless charm of the White Mountains.

Apt in Victorian Mansion w/ Hot Tub & Parking
Mixing contemporary styling with old-world charm, the Apartment in the nationally registered Chapman House offers a relaxing, private stay, only minutes to downtown! Whether you plan to soak in the shared hot tub, cool down in our pool or relax by the fire pit, our half-acre yard offers a tranquil space for all. The apartment has a chef's kitchen, dining, and living room with gas fireplace. NB., use of the living room bed may incur a charge. We have a L2 EV charging outlet. #allarewelcome

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.

KimBills’ on the Saco
KimBills' is a newly renovated, cozy, first floor condo located at Attitash Mtn. Village, just minutes from the Saco River. Full kitchen well stocked with necessities, gas fireplace, A/C, Murphy bed and pull-out sofa bed with new, comfortable mattresses. Cable/internet, 55" TV, & board games. Large deck with lighting. Guests enjoy full use of all Attitash Mtn. Village amenities including river access, pools, sauna, hot tubs, tennis & basketball. Close to shopping and area attractions.

Romantic New England Historic Schoolhouse c1866
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 and tennis court.

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.

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.

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!
Popular amenities for Bridgton rentals with a pool
House rentals with a pool

Treehouse Farm - Sebago

Silent Nights 5 Min to Mt Ice Fish & Wood Stove

The Lodge at Hidden Pines

Peaceful Retreat

Moose Pond Cottage - 3 mins to Pleasant Mountain!

Ski Resorts 15 mins, Updated Family Friendly Condo

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

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

Ski in/ski out Sunday River Condo Brookside 2a210

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

Ski Condo on Cranmore Mountain-Pool and Hot tub!

Cute & cozy Attitash Studio Condo

Cozy Condo at The Seasons- 2 Bedrooms

Spectacular Mountain Views at Eagle Ridge

3 bd / 2 bth, SLOPE SIDE at Cranmore! Unit#1104

Slope Side | Ground floor | Hot Tub, Pool, Sauna
Other holiday rentals with a pool

HotTub+Sauna+6Private Acres+15 min to Sunday River

Pristine Log Cabin w/Lake Access NO Cleaning Fees!

Witts' End- quiet neighborhood in Knights Hill

Cozy Maine Church • Fire Pit • Hammock • WoodStove

Heated SwimSpa, Sauna, Games + 7mi to Sunday River

3 mins to Pleasant Mt/Moose Pond w/hot tub & sauna

“Tangerine” @ Cranmore

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 $121 NZD per night before taxes and fees

Verified guest reviews
Over 980 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Bridgton holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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- Sebago Lake
- Squam Lake
- Story Land
- Sunday River Resort
- Scarborough Beach
- Loon Mountain Resort
- Weirs Beach
- Mount Washington Cog Railway
- Franconia Notch State Park
- East End Beach
- Diana's Baths
- Omni Mount Washington Resort
- King Pine Ski Area
- Dunegrass Golf Club
- Willard Beach
- Funtown Splashtown USA
- Cannon Mountain Ski Resort
- Waterville Valley Resort
- Cliff House Beach
- Wolfe's Neck Woods State Park
- Crescent Beach State Park
- Ferry Beach
- Black Mountain of Maine
- White Lake State Park




