Vacation rentals with a pool in Chautauqua Lake

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Top-rated rentals with a pool in Chautauqua Lake

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

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Top guest favorite

Tiny home in Cherry Creek

4.98 out of 5 average rating, 121 reviews

Barn Games & Cozy Nights, Fall Tiny House Escape

Lola’s Oasis is a hidden gem on beautiful grounds, the perfect romantic escape in a small town for fall foliage, wineries & autumn adventures!The property has this cozy Tiny House & several unique amenities private to yourselves: a Rustic Barn Bar & Game Room, pergola patio with bonfire, slate bar & 2 charcoal grills, plus a hammock, swing & small orchard. Bikes available. It’s a central location-Hiking 5 min, Lily Dale & Lake Erie 20 min,Jamestown & Ellicottville 30 min, &Buffalo/Niagara 50 min

Superhost

A charming two-story lake house is surrounded by well-maintained gardens and vibrant flowerbeds. The entrance features a welcoming path leading to a front door framed by greenery. A large driveway provides easy access, with a glimpse of lake Chautauqua visible in the background.

Home in Mayville

5 out of 5 average rating, 4 reviews

Lovely house on a hill w/a view

Relax with the whole family at this peaceful place to stay. Lovely lake house, with great view of lake Chautauqua from 2 outdoor decks, and large picture windows in large living area. Large dining table. 3 full baths, 3 full bedrooms, 1 bedroom small with sleeper sofa and closet. Full kitchen, washer dryer, pool (closed after 9/2) tennis court access. Propane grill. Shared outdoor shelter for larger gatherings. Fire pit. Boat launch + dock rental available by day or season (during the summer).

Top guest favorite

A sparkling blue pool glistens under the sun, framed by a smooth concrete patio. In the background, a rustic black barn stands against a vibrant green landscape, flanked by tall trees and a clear sky dotted with soft clouds.

Home in Mayville

5 out of 5 average rating, 21 reviews

The Plum Bush House: Victorian farmhouse retreat

An 1865 Italianate, Victorian farmhouse where guests can retreat and gather within a serene, historic landscape and modern comforts. Enjoy charming common areas amidst towering black locusts and quiet meadows. Explore the spacious outdoors and gardens; relax and rest in luxury; take in scenic views, and feel at home in this charming treasure. The main house rental sleeps 12; inquire if you’d like to expand your space to an open floor plan, vaulted ceiling, queen-bed apartment as an ADD-ON FEE.

Guest favorite

A swimming pool is illuminated in soft blue tones, creating a calming atmosphere at night. A ladder is positioned at one end, and a white lifebuoy hangs on a post nearby. The surrounding area is enclosed by a fence, with trees visible in the background.

Cabin in Frewsburg

5 out of 5 average rating, 25 reviews

Cheerful 1-Bedroom Cabin with a Campfire & Pool

Relax with the whole family at this peaceful place to stay. You can reconnect with nature, take a dip in the pool, enjoy some s’mores next to a campfire, or escape from the hustle and bustle. This cabin is equipped with a ramp for easy access, electricity, lights, ceiling fan, apartment-sized refrigerator, and a small countertop. The property is located at Homestead Park Campground with plenty of weekend activities to enjoy. Bathrooms, Showers, and laundromat are all onsite. 5.3 miles from kinzu

Guest favorite

Farm stay in Sinclairville

4.9 out of 5 average rating, 10 reviews

Frost Farms - animals, country, and nature escape

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 just a few miles off I86

Superhost

An indoor pool is situated in a spacious room with stone accent walls and wooden beams. Surrounding the pool, multiple chairs are arranged for seating. Natural light filters through skylights above, illuminating the water surface. A cozy seating area is visible in the background.

Home in Asheville

4.77 out of 5 average rating, 73 reviews

Lake Getaway w/ Indoor Pool!

A true mid century house on an amazing plot of land situated on 3.5 acres. The ONLY property in the CHQ area with an indoor pool! Come enjoy this four season home with your friends and family. The lake is just down the hill and you’re just a few minutes to Bemus Point, Southern Tier, the Institution, and Peek n’ Peak Beautiful patio with walkout. Dog friendly! Now taking rentals of 30 days or more exclusively (local laws) contact me about about fractional ownership for shorter stays!

Guest favorite

A charming cottage exterior is presented, featuring a welcoming front porch adorned with rocking chairs. The yellow siding is complemented by a classic chimney, while a well-maintained lawn surrounds the building. Large windows allow natural light to fill the interior spaces.

Cottage in Dewittville

4.88 out of 5 average rating, 16 reviews

Hidden Lakefront Gem | Cozy Cottage Stay

Tucked down a quiet lane on Chautauqua Lake, Sunny Cottage blends cozy comfort with laid-back fun. With 3 bedrooms, a pool, a private dock, and room to play, it’s perfect for memory-making—whether you’re paddling, roasting s’mores, or relaxing on the porch. Guests enjoy a dock for relaxing, 3 paddleboards, 2 kayaks, and a lakeside fire pit for sunset chats and starry nights. Just 10 minutes from Bemus Point, it’s your peaceful escape with a splash of adventure.

Guest favorite

A living area is presented with a floral-patterned couch and a cozy green chair. A rectangular wooden table is positioned nearby, with a bowl of fruit visible. Large windows allow natural light to illuminate the space, and a stone fireplace is featured against one wall.

Vacation home in Clymer

4.97 out of 5 average rating, 36 reviews

Cozy Ski-in/Ski-out with room for the whole family

Welcome to our vacation home! At 2,500 sq ft, four bedrooms and two pull outs, our condo offers four season fun for the whole family. Located at Peek N’ Peak resort; guests staying during ski season enjoy true ski-in/ski out access to 27 lighted ski slopes and trails. Guests staying off season take advantage of a full service day spa, indoor/outdoor pools, restaurants, Peek Mountain Adventures, and a championship 18 hole golf course within walking distance.

Superhost

A serene bedroom features a queen size bed dressed in yellow and blue linens. Large windows provide scenic lake views, while a soft armchair complements the decor. Two nightstands are positioned beside the bed, and natural light fills the space.

Apartment in Mayville

5 out of 5 average rating, 3 reviews

Million $ view Lake Chautauqua

Immerse yourself in a private, perfect getaway with stunning Lakefront views from Living Room & Bedroom. Enjoy the crackling from the wood burning fireplace, warm & cozy. Welcome to our quiet, serene condo located in the M building at the end of the Chautauqua Lake Estates Property. This beautifully appointed 850 sq ft. residence features warm woods and is fully furnished with everything you need for a relaxing retreat. Come relax & then go out and play !

Guest favorite

An open living space is highlighted by wooden beams across the ceiling, with a circular dining table surrounded by four black chairs. A cozy seating area with a fireplace is visible in the background, while natural light enters through a nearby window.

Chalet in Clymer

4.85 out of 5 average rating, 26 reviews

Sun and Snow Escape: Ski/Golf Condo in Peek'n Peak

Welcome to our upper-level condo at Peek’n Peak Resort, featuring a Master bedroom, loft bedroom, and 3 full bathrooms. Enjoy four seasons of fun with skiing, golfing, ziplining, swimming, a spa, and a gym nearby. Our condo is close to Chair Lift #8 for winter skiing and summer adventures. Note: Resort amenities are not included. No rescheduling within 30 days of arrival. Travel insurance strongly recommended, due to our strict cancellation policy.

Guest favorite

The living room features a spacious sofa and a leather armchair, complemented by a stone fireplace. Large windows allow natural light to enter, with a view of snowy surroundings visible outside. Decorative greenery and art enhance the cozy atmosphere.

Condo in Clymer

4.94 out of 5 average rating, 68 reviews

Enjoy Peek 'n Peak From a Luxury Upscale Condo

A great spot for families and couples, this exquisite condo features vaulted ceilings, a winding spiral staircase, and large windows that allow in plenty of light. Relax outside on the balcony or get cozy next to the fireplace in the living room. Condo is part of the Camelot complex at Peek ‘n Peak resort in Clymer, NY. Common space pictures show the Peek hotel lobby, coffee shop & pools Principal renter must be a minimum 25 years of age.

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

4.95 out of 5 average rating, 43 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.