Vacation rentals with a pool in Chautauqua County

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Top-rated rentals with a pool in Chautauqua County

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Top guest favorite
An outdoor patio area is showcased, featuring a shaded pergola with comfortable seating. A swimming pool is visible behind a surrounding fence, with lounge chairs positioned beside it and a well-maintained grassy area in the background.
Tiny home in Cherry Creek
4.98 out of 5 average rating, 126 reviews

Private Pool, Tiny House & Rustic Barn Game Room

Lola’s Oasis is a private escape on beautiful grounds, featuring your own sparkling pool perfect for cooling off & enjoying sunny days in privacy. The ideal romantic getaway in a charming small town near wineries &outdoor adventures. Enjoy The Tiny House w/amenities: Rustic Barn Game Room, pergola patio, bonfire, slate bar, 2 charcoal grills, hammock & small orchard.Bikes available.Centrally located Hiking 5min, Lily Dale &Lake Erie 20min, Jamestown & Ellicottville 30min, Buffalo/Niagara 50min.

Guest favorite
A welcoming living area features a stone fireplace, accented by rustic decor. A large flat-screen television is mounted above the mantel. Comfortable seating arrangements include a sofa and armchairs, with sunlight filtering through large windows. A dining area is visible in the background.
Condo in Clymer
4.87 out of 5 average rating, 60 reviews

8409PEAK SLOPE SIDE, IN/OUT,GOLF,SKI LIFT8,FIREPIT

8409 Highlands Sleeps 19 condo located directly at top of Ski Lift/Chair 8 Sugar Shack on bottom of lift .Ski IN/OUT with a back door of condo into ski room lower level. The view from inside is great for watching skiers from the lift . Summer time this is one of the lifts that run all year around to get you down to the Resort for all the amenity's on site . Upper Golf course is walking distant to the Club House .This is the only 5 Bedroom Highland condo Slope side. Summer enjoy 2 Decks/Fire Pit

Guest favorite
A scenic view of a rustic farmhouse property, featuring multiple buildings amidst green trees and a field dotted with yellow wildflowers. The landscape showcases a clear sky and gently rolling terrain, reflecting the natural beauty of the farm environment.
Farm stay in Sinclairville
4.94 out of 5 average rating, 16 reviews

Frost Farms - animals, country, pool, nature

Reconnect with nature at this unforgettable escape. Experience the farm life on our 34 acres of paradise. Large pool with pool deck, fire pit and trails. Animals on premises, rustic and cozy farm house , near state forest and miles of snowmobile trails, hiking trails, and cross country skiing trails. Close to Lake Erie, Chautauqua Lake, Chautauqua Institution , Lily Dale , and the Ntl. Comedy Center. Bike trails and horse trail systems close. Hour from Niagara Falls and 45 min from Bills stadium

Guest favorite
A dining area features a table set for six, complemented by a stylish light fixture overhead. A comfortable gray sofa is positioned near glass doors, providing access to lake views and natural light. Tasteful wall art enhances the room's atmosphere.
Condo in Mayville
5 out of 5 average rating, 7 reviews

Sunset Shores: Lakefront Condo in Mayville (AC)

Incredible lake views, AC and heated pool! Welcome to this nautical condo in Mayville with unmatched lake views! With 3 bedrooms for 8 people, this fantastic property is perfect for families or groups of friends. Enjoy a day on the water and relax with the amazing sunsets right from your private deck! You'll find all the necessary amenities like laundry, WiFi, AC, and a fully stocked kitchen. Enjoy the heated inground pool from Father's Day to Labor Day! There's so much to do all year round!

Top guest favorite
Home in Irving
5 out of 5 average rating, 219 reviews

Lotus Bay Cabin- all seasons oasis

*8-person stand alone hot tub open Dec.-April* *In-ground pool with spill over hot tub & pool house open May 1st, 2026* Winter, Spring is that you? A drink in the above ground hot tub (or pool & hot tub), meals in the fully stocked kitchen, movies on the spacious sectional, reading in the sunroom, bomb-fires under the dark sky & gorgeous sunsets, walks and seasonal swimming along Lake Erie…simply cannot go wrong! Wine country, beaches, ski resorts, Buffalo & Niagara Falls all nearby

A well-lit outdoor patio features wooden beams and a railing, surrounded by lush shrubbery. The warm glow from string lights creates a cozy ambiance, enhancing the inviting atmosphere for outdoor relaxation.
Home in French Creek
4.7 out of 5 average rating, 10 reviews

Golf and Ski Peak and Peak

Perfect location for your ski or golf or wine tour getaway. Ski-in/ski-out, short drive to the golf course, 20 minute drive to several wineries in Lake Erie Wine Country. Roomy two bedroom extremely clean condominium sleeps 8 guests. The kitchen is equipped for cooking and serving 8 guests. In Unit laundry available. The lodge is minutes away giving you access to restaurants, shops and other entertainment activities. Pool workout facility and spa available for extra resort charge.

A bright living room features expansive windows offering views of the water. A spacious sectional sofa is complemented by a coffee table, while a small bench sits against the wall. A dining area with a table and chairs is visible in the background.
Condo in Mayville
5 out of 5 average rating, 4 reviews

Lakeside Retreat in Dewittville w/ Pool Access!

Embrace lake life at this 3-bedroom, 2.5-bathroom vacation rental in Dewittville! Situated on Chautauqua Lake, this lovely condo offers a cozy fireplace, a fully equipped kitchen, and a balcony with gorgeous water views. Unwind by the community pool, enjoy a delicious BBQ on the gas grill, or hit the nearby tennis court for some friendly competition. Whether you're seeking relaxation or adventure, you’ll love staying at this waterfront retreat during your next lake getaway!

Top guest favorite
Home in Mayville
4.95 out of 5 average rating, 20 reviews

Heated Pool 5 Acres Chautauqua Lake Pet Friendly.

Imagine waking up to birdsong on your own peaceful 5-acre retreat, just minutes from the sparkling shores of Chautauqua Lake. Nestled in tranquil countryside, this charming 4-bedroom, 3-full-bathroom home offers the perfect blend of comfort, space, and unforgettable memories for the whole family (or your favorite group of friends!). Come unwind, reconnect, and create stories you'll tell for years to come. We can't wait to host you at Lakeside Meadows!

Guest favorite
An open living area features a comfortable sofa and recliner, complemented by a coffee table. A dining table with multiple chairs is positioned near large windows and a sliding door leading to a deck. A stone fireplace adds a functional element to the space.
Townhouse in Clymer
4.84 out of 5 average rating, 44 reviews

4-Bedroom Ski & Golf Retreat

Enjoy every season at this mountain retreat located on the grounds of Peek N’Peak! This 4 bedroom, 3.5 bath condominium is perfectly located near ski, golf, and resort amenities (pool usage available through Peek N’Peak) - Perfect for the whole family! Ski-in, Ski-out during the winter, and walk on to the PGA rates golf course right next door. This home is sure to meet and exceed you expectations for a relaxing getaway!

Top guest favorite
The exterior of a spacious Condo is showcased, featuring a mix of brick and wood paneling. The two-story structure is surrounded by lush greenery, with well-maintained landscaping in front. A paved pathway leads to the entrance, framing the building's traditional architectural design.
Condo in Clymer
4.96 out of 5 average rating, 49 reviews

Roomy Beautiful Golf/Ski Condo

Nestled at the top of the hill inside the beautiful Peek n' Peak Resort; We are sure you will enjoy our beautiful 4 Bedroom Condo thats directly on the golf course and a few feet from the ski lift. This is a great spot for your family and friends to enjoy time on the slopes or round of golf and to gather in the evenings for fun and memories. There are plenty of TV's and a game space available in the lower level.

Top guest favorite
A well-equipped kitchen is presented with white cabinetry and granite countertops. Stainless steel appliances, including a microwave and oven, are visible. A dining table with dark chairs is set for several diners, while bright overhead lighting accentuates the vaulted ceiling.
Home in Mayville
4.92 out of 5 average rating, 63 reviews

Spacious Chautauqua Lake 4 Bedroom home

Make some memories at this unique and family-friendly place. While staying with us can access a boat launch and enjoy beautiful Chautauqua lake. Take a ride and go hiking at Panama Rocks or enjoy some spirits at Southerntier Brewery. Downtown Bemus Point is a great place to have dinner and relax and enjoy the sunset. Chautauqua institute is another near by place to visit with lots of entertainment!

Guest favorite
A charming multi-story building is displayed against a bright blue sky, featuring an intricate architectural design with multiple balconies. Lush greenery lines the street, enhancing the inviting appearance of the property, while the well-maintained road provides access to this lakeside accommodation.
Condo in Bemus Point
4.94 out of 5 average rating, 33 reviews

Lakeside Brand New Luxury Condo

Enjoy relaxing lakefront luxury accommodations in the center of Bemus Point. Top floor panoramic view of Chautauqua Lake. Restaurants, shops, grocery store, golfing and entertainment all within a block. Lakeside pool, hot tub and patio await you. **pool and hot tub closed September-May for off season** **NEWLY RENOVATED TOP TO BOTTOM**

Popular amenities for Chautauqua County rentals with a pool