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Vacation rentals with a pool in Bridgton

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Bridgton

  • Total vacation rentals

    Explore 40 vacation rentals in Bridgton

  • Nightly prices starting at

    Bridgton vacation rentals start at ﺩ.ﺇ441 per night before taxes and fees

  • Verified guest reviews

    Over 980 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Bridgton vacation rentals include wi-fi 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!

Top-rated rentals with a pool in Bridgton

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
The spacious loft is highlighted by 16-foot ceilings and multiple skylights. A queen bed is positioned near a cozy seating area, complemented by a wooden dining table. Eye-catching artwork adorns the walls, and natural light fills the room through large windows.
Loft in Falmouth
4.95 out of 5 average rating, 685 reviews

Loft Apartment on Tree-Lined Street in Falmouth

Staying in this huge second floor loft (32'x25’), you will find a quiet oasis in the treetops. The 16' ceilings and stylish decor provide sanctuary after a busy day of sight seeing. We offer a queen bed and two twins. You are surprisingly close to Portland's restaurants and shops, well located for day trips up and down the Maine coast. Start the day with a self-brewed local coffee. Relax at the end of the day streaming your favorite entertainment on a 55" 4K-HD TV paired with a Sony sound bar. Soak in the secluded backyard HOT TUB, OPEN YEAR ROUND, with a pool available in the summer. The loft is bright and airy given its 16 foot cathedral ceilings, four sky lights and five large windows. Each window has room darkening blinds and full curtains that can darken the room for an afternoon nap. It is accessed through a private entrance up a wide stairwell in the stand alone garage. An In-Suite thermostat allows you to control a comfortable room temperature. The newly renovated space is equipped with queen bed and a twin trundle bed, which pulls out a second twin bed (sleeps two). The beds are fitted with 100% cotton sheets. The living room lounge area has a 55" 4K Ultra UHD flat screen TV equipped with a Roku streaming device. Spectrum TV streaming app provides the broadcast networks, as well as ESPN, TNT, AMC, Bravo and others. Bring your log-in ID to access your favorites programming, such as NETFLIX, HBO-Go, HULU and SlingTV. A Blu-ray/DVD player is available upon request. (There are 3 redbox locations within 2 miles.) The full bath has a shower stall (no tub). Plush towels and premium soap, shampoo and conditioner are provided. Enjoy use of backyard hot tub year round and in ground pool during summer season. Children are welcome. The loft is stocked with books and board games. There is a baby gate available. We are happy to assist you in making plans to see the area. Please ask us if you need recommendations to things to do during your stay. While you will have your own private space and free standing four walls, we will generally be nearby and available. The setting of this property is a long and winding street with large, open lots and eye-catching homes. Stroll to the mouth of the Presumpscot River, which empties into Casco Bay. Dine and shop in the heart of the Old Port, only 14 minutes away. There are no bus lines close to the house. One could manage navigating the area via Uber if not driving a car. The loft has an efficiency kitchen with toaster oven, mini fridge, coffee maker, electric tea kettle, two burner hot-plate, pans, utensils, plates and silverware. We keep the loft stocked with Wicked Joe Sumatra blend. Wicked Joe is a local family-owned company committed to producing exceptional coffees using sustainable business practices from crop to cup. Additional large beach towels provided for hot tub and pool use. We can connect you with local area shops for surf board, stand-up paddle board and bike rentals. We have plenty of ideas on restaurants, shops and points of interest which we are happy to share. Local area magazines and tourist information available in the loft.

Guest favorite
A spacious room features a large bed with plush bedding against a warm-toned wall. A relaxing jetted tub is positioned beside it, with soft lighting provided by bedside lamps. A window allows natural light to enter, enhancing the overall calm and comfortable ambiance.
Apartment in Bartlett
4.89 out of 5 average rating, 303 reviews

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.

Guest favorite
A hot tub is positioned on a wooden deck, overlooking expansive views of rolling hills and a tranquil pond. The sky displays a blend of soft colors during sunset, creating a serene atmosphere. Nearby, outdoor chairs are visible, inviting relaxation.
Home in Harrison
4.89 out of 5 average rating, 348 reviews

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.

Top guest favorite
A private pool area features a colorful inflatable parrot floating in clear water. Surrounding the pool are several lounge chairs arranged for relaxation. Lush trees provide shade, and a fence ensures privacy for the space, which is brightly illuminated by natural sunlight.
Home in Portland
4.96 out of 5 average rating, 160 reviews

"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

Guest favorite
A spacious dining area with a round wooden table is positioned near a cozy living space featuring a large sectional sofa. The kitchen is equipped with modern appliances and a breakfast bar, illuminated by stylish overhead lighting. Large windows provide natural light and views of the outdoors.
Condo in Bartlett
4.85 out of 5 average rating, 203 reviews

Fantastic condo in best location in MWV.

One of the nicest units in Nordic Village wonderful location 1 mile from Storyland and close to the best skiing, hiking and finest dining in the Mount Washington Valley. This is unit A which has full kitchen, dining room, breakfast bar and separate bedroom. Unit B which is below it is listed separately as 'Brand new..." and is more suited for a couple w/ child or solo looking for getaway vacation, It does not have a stove or dishwasher. It is a studio with a queen bed and a queen sleeper couch.

Top guest favorite
Condo in Bartlett
4.96 out of 5 average rating, 111 reviews

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.

Top guest favorite
Apartment in Portland
4.97 out of 5 average rating, 490 reviews

Apt in Victorian Mansion w/ Hot Tub, Parking, Pool

Contemporary styling with old-world charm, the Apartment in the Leonard Bond Chapman House offers a relaxing stay only 10 min to downtown. Whether you plan to soak in the shared hot tub, cool down in our seasonal pool, or relax by one of our fire pits, our half-acre yard offers a tranquil stay. The apartment boasts a newly renovated bathroom, radiant heated floors in both kitchen & bath, and a chef's kitchen. This grand apartment won't disappoint. L2 EV charging outlet on site #allarewelcome

Top guest favorite
Condo in Intervale
5 out of 5 average rating, 105 reviews

Spectacular Mountain Views, at Eagle Ridge !

Eagle 🦅 Ridge North Conway/ Intervale NH . You have the entire condo to share with family/ friends. Mountain Adventures with get togethers right here. Hiking Trails Frogs pond Swimming Tennis Kite flying & more. Trails End “Ice Cream” Rated best ski town in NH. Easy access to Mt. Washington and the Valley. Mt. Cranmore Wildcat Attitash Brenttwoods King Pines Story land Scenic Railroad Saco River canoeing/tubing Fishing StoryLand Saco River canoeing/tubing Tax free shopping

Top guest favorite
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.
Home in Bridgton
4.89 out of 5 average rating, 174 reviews

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.

Top guest favorite
Place to stay in Shapleigh
5 out of 5 average rating, 125 reviews

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

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.

Guest favorite
A welcoming living area features warm wood flooring and natural light from multiple windows. Comfortable seating includes a sofa and chairs arranged around a central table. A ceiling fan provides gentle airflow, while double French doors lead to an outdoor space.
Guest suite in Standish
4.92 out of 5 average rating, 116 reviews

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.

Guest favorite
The living room features a cozy arrangement with a dark sofa and loveseat adorned with decorative throw pillows. A round coffee table is positioned centrally, with natural light filtering through the window adorned with blinds. A piece of aviation-themed wall art adds character to the space.
Townhouse in Bartlett
4.97 out of 5 average rating, 226 reviews

3 Bears Glen, Across St. from Story Land, AC, pool

Welcome to Three Bears Glen! A cozy condo located right across the street from Story Land on a golf course! 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. New pool coming this summer! Located just a short drive to North Conway. Enjoy all the valley has to offer!

Popular amenities for Bridgton rentals with a pool

Destinations to explore

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