
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.

Attitash Retreat
Cozy spot for 4, plus your furry friend! (Must be 21 to check-in, no cats) Less than a mile from Attitash Mountain Resort, this spot is home base for your next adventure. IF YOUR DOG IS JOINING YOU, please provide advanced notice, a $25/night pet fee for the first 4 nights (max$100), that rabies vaccination records be provided at check in, and that your dog have access to a crate for times that you must leave him/her behind! One dog is permitted per room, no cats. Thank you for understanding.

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.

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Your crew will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular shops and restaurants. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, no loud partying after 10 pm. City of Portland License #: STHR-004465-2022

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. Just minutes from Story Land, Attitash, and North Conway, Summit Vista offers access to top ski resorts, hiking trails, restaurants, and shopping. Blending mountain style with modern comfort, Summit Vista celebrates the natural beauty and timeless charm of the White Mountains.

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.

Historic Schoolhouse c1866 Winter & Summer Dates
Stay at our one-room Schoolhouse c1866. Winner of Maine Homes Small Space Design Award 2023 and consistently top 1-5% of Airbnb homes for exceptional hospitality, comfort, cleanliness & quintessential romantic New England vibes. The Schoolhouse is 1 of 3 homes on our family's resort-like retreat, Camp Tall Pines: Featuring tennis/pool/gym/sauna, 1000-feet of frontage along the private 80-acre Shapleigh pond (boat/swim/fish), and nestled amongst a majestic 50-acre forest of tall pine trees.

Bartlett Condo; Great Views, Resort Access
Located at one of Mount Washington Valley's Premier family resorts, this 1 BR condo is the perfect destination for a family weekend or romantic getaway. Enjoy all that MWV has to offer and then return home to a cozy space to relax and unwind. Access to resort amenities is available including pools, rec room, trails and more. Minutes from Storyland and Jackson Village. Just a short drive to numerous downhill and x-country skiing venues as well as tax free shopping and dining in North Conway.

Cozy Condo at Attitash!
Enjoy activities & beautiful scenery offered at Attitash Mountain Village, in the White Mountains! This cozy one bedroom, 2nd floor condo sleeps four, and includes a completely renovated kitchen/living area and bathroom! You will be just steps away from a beautiful pool pavilion, tennis courts, playgrounds, the Saco River Beach, hot tubs, fire pits, an arcade, and a fitness center. Nestled among all the summer attractions of the area- 10 minutes to Story Land! Always something fun to do!

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.

Cozy Condo at The Seasons- 2 Bedrooms
Very cozy and inviting space to enjoy a White Mountain vacation or quick getaway! Clean and very comfortable 2 bedroom, 2 bath condo at Seasons at Attitash. Located on Rte 302 in Bartlett it is minutes away from Attitash Mountain, Storyland, Echo Lake Park and more. The center of North Conway with shops, Conway railroad and Cranmore Adventure Park is 12 min away. This is the ideal location as we are nestled in a quiet and remote area yet just a short drive to many attractions.

Private Bungalow w/ Hot Tub, Free Parking & Pool
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
Popular amenities for Bridgton rentals with a pool
House rentals with a pool

Treehouse Farm - Sebago

Witts' End- quiet neighborhood in Knights Hill

Silent Nights 5 Min to Mt Ice Fish & Wood Stove

The Lodge at Hidden Pines

Ski Resorts 15 mins, Updated Family Friendly Condo

Bear Brook House

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

River Access|Gas stove|Min to N. Conway, Attitash
Apartment rentals with a pool

Attitash Studio | 5min to Storyland| Pools

Remodeled Condo - Storyland & Santa’s Village

Across from Storyland & in the Heart of the Mtns

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

Elevate Your Adventure: Book Slope side Now!

Million $ View of Lake Winni Flexible check in/out

Bartlett N. Conway, NH condo ski near Storyland

Cozy Fireplaced Mountain King Suite w/Hot Tubs & P
Other holiday rentals with a pool

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

Pristine Log Cabin w/Lake Access NO Cleaning Fees!

6 miles from Sunday River with heated outdoor pool

Unique Church Stay • Sebago Lake • Pool • Fire Pit

Secluded Rustic Log Cabin on Beautiful Frye Island

Peaceful Pines Saco River Getaway

Luxury Retreat In Back Cove | 10 Min to Downtown

Retreat In The Orchards
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 £106 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!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Island of Montreal Holiday rentals
- Jersey City Holiday rentals
- House rentals Bridgton
- Rentals with a washing machine and dryer Bridgton
- Rentals with breakfast Bridgton
- Ski-in/ski-out rentals Bridgton
- Cottage rentals Bridgton
- Fitness-friendly rentals Bridgton
- Rentals with a kayak Bridgton
- Rentals with lake access Bridgton
- Beachfront rentals Bridgton
- Rentals with outdoor seating Bridgton
- Waterfront rentals Bridgton
- Rentals with a firepit Bridgton
- Cabin rentals Bridgton
- Rentals with a hot tub Bridgton
- Rentals with beach access Bridgton
- Rentals with a patio Bridgton
- Family-friendly rentals Bridgton
- Pet-friendly rentals Bridgton
- Rentals with a fireplace 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
- Weirs Beach
- Loon Mountain Resort
- Scarborough Beach
- Mount Washington Cog Railway
- Cranmore Mountain Resort
- Willard Beach
- King Pine Ski Area
- Gunstock Mountain Resort
- Franconia Notch State Park
- East End Beach
- Omni Mount Washington Resort
- Cannon Mountain Ski Resort
- Diana's Baths
- Funtown Splashtown USA
- Waterville Valley Resort
- Crescent Beach State Park
- Wolfe's Neck Woods State Park
- Pleasant Mountain Ski Area
- Conway Scenic Railroad




