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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Superhost

Condo in Clymer

4.83 out of 5 average rating, 47 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

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, 3 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).

Guest favorite

A spacious outdoor pool area is surrounded by a landscaped environment, showcasing a rustic pavilion with a sloped roof. Lounge chairs are arranged near the pool, with tables and umbrellas providing shaded seating options. Rolling green hills create a tranquil backdrop under a clear blue sky.

Townhouse in Ellicottville

4.96 out of 5 average rating, 52 reviews

Red Stove Retreat @Wildflower - Holiday Valley

You will be close to everything when you stay at this centrally-located townhome. In the winter, walk or take the shuttle to the Holiday Valley ski slopes. Take a quick 1 mile walk/drive into the village to explore quaint shops, great restaurants, and a charming atmosphere. When the snow is gone, Holiday Valley keeps the fun going with additional adventures like Sky High Adventure Park and the Double Black Diamond golf course. Be sure to check out our guestbook for activities in all seasons!

Top guest favorite

A clear blue in-ground pool is framed by a concrete patio. Sun loungers are positioned nearby, with vibrant flowers lining the fence. Lush green fields and trees are visible in the background, contributing to a tranquil outdoor setting.

Farm stay in Cattaraugus

5 out of 5 average rating, 142 reviews

The Guest House at Burdick Blueberries Farm

Share the peaceful beauty of our working family blueberry and flower farm with organic and sustainable practices. Located in East Otto, New York. During the blueberry season experience the joyful bustle of the pick-your-own blueberries and flowers, Mid-July - August. Private guest house attached to farmhouse. Enjoy our patio and spacious lawns plus in-ground pool. Walk along the blueberry bushes, farm roads and woodland trails. Guest space has a simple & natural aesthetic, a relaxing haven.

Guest favorite

A well-maintained swimming pool is illuminated by soft underwater lighting, casting a calming blue hue over the water. The surrounding deck features a safety ladder and a lifebuoy. A fenced area can be seen in the background along with faint tree outlines.

Camper/RV in Frewsburg

5 out of 5 average rating, 25 reviews

Lovely 2-Bedroom Keystone Sydney Outback 5th Wheel

Reconnect with nature at this unforgettable escape. You'll always remember your time at this unique place to stay. The property is located at Homestead Park Campground with plenty of weekend activities to enjoy. Whether it is swimming at the pool, having s’mores at a camp fire, or watching the beautiful sunset from the deck. The restaurant is open Sunday for breakfast. There is a playground on site, laundromat, showers with bathrooms, & camp store. Onsite camp owners can assist with any needs.

Superhost

A light-filled living area features large windows that provide views of the lake. Two soft sofas in neutral tones are positioned around a coffee table adorned with decorative elements. Subtle lighting from lamps enhances the inviting ambiance, while a patio view offers additional outdoor seating.

Home in Dewittville

5 out of 5 average rating, 3 reviews

New! Lake Front Condo w/Pool

The Cayuga Retreat on Lake Chautauqua! Features a modern coastal design with high end finishes throughout. Furnished with everything you need to feel right at home. Amazing sunset lake views on the patio. Amenities include, pool, tennis, pickle ball, picnic area, playground, lake access. This property is close to shopping, dining, Bemus Point, Chautauqua Institution, Lucille Ball Museum, National Comedy Center, Breweries, several wineries, ski resort, amusement park and other lake attractions.

Top guest favorite

The pool area is enclosed by a wooden fence, with a rectangular pool featuring a clear blue surface. Two lounge chairs are positioned nearby on a stone surface. A shaded pergola overhead provides a resting spot, with the sky visible beyond.

Tiny home in Cherry Creek

4.98 out of 5 average rating, 112 reviews

Country Tiny House, POOL, Barn GameRoom & MORE!

Lola’s Oasis is a hidden gem on beautiful grounds in a central location for hiking, wineries, water sports & more! The property has this Tiny house & several unique amenities private to yourselves; a Pool, pool house, Rustic Barn Bar & GameRoom. A pergola patio area w/bonfire, slate Bar & 2 charcoal grills. A hammock, swing & a small Orchard. Bikes available. It’s a central location- to Hike 5min,Lily Dale 20 mins, Jamestown 30min, Ellicottville 30mins, Lake Erie 20min & Buffalo/Niagara 50min

Top guest favorite

A warm wood-sided exterior of a two-story house is visible, featuring a steeply pitched roof and an entrance with steps leading to a front porch. An American flag is displayed on the porch, and the area is surrounded by trees, casting gentle shadows.

Home in Clymer

5 out of 5 average rating, 18 reviews

Slopeside Condo Haasienda

Have fun with the whole family at this stylish place on the slopes/hillside of Peak n Peek Resort! Ski in Ski out in winter! Great Mountain views from the deck, less than 5 minutes to Findlay Lake and its great restaurants and small-town shops. SKI winter. golf summer (90 seconds to champ golf course on top of hill), ziplining and tree course mini golf 2 minutes away on resort as well! Pools, golf, hike, fish, shop, dine, spa, close to Chatauqua Institute and Lake (Bemiss Point), on resort !

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, 14 reviews

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.

Top guest favorite

Home in Irving

5 out of 5 average rating, 207 reviews

Lotus Bay Cabin- Pool/Hot Tub/Lake

*Pool, spa & pool house open May 1st, 2025* Summer is that you? Sipping a drink in the in-ground hot tub & pool, preparing meals in the fully stocked kitchen, enjoying movies on the spacious sectional, reading a book in the sunroom, cozy bomb-fires under the stars & strolling down for sandy beach days, sunsets & walks along Lake Erie…simply cannot go wrong! Lake Erie Wine Country, Buffalo & Niagara Falls all within close reach! *8-person stand alone hot tub re-opens Dec. 1st, 2025*

Guest favorite

A cozy seating area includes a gray sleeper sofa adorned with decorative pillows. Vintage ski posters are displayed on the wall, alongside ski equipment. A wooden trunk serves as a coffee table beneath soft lighting, while natural light filters in through the sliding glass door.

Condo in Ellicottville

4.9 out of 5 average rating, 229 reviews

Wildflower Studio Retreat

Clean and cozy ground floor studio townhouse less than 5 minutes away from Holiday Valley Resort/Pools/Golf Course and Driving Range/Sky High Adventure Park Located in Wildflower Complex Queen Murphy bed and sleeper sofa bed (queen with memory foam) Free WiFi Fully equipped kitchen Private patio Charcoal grill available to use at the gazebo Shuttle service to the slopes during winter season Walk to town for brewery/winery/restaurants/shops Bike and hiking trails

Guest favorite

An outdoor hot tub is positioned on a wooden deck, with gentle bubbling water visible. Surrounding the tub, hanging light fixtures offer illumination, and a scenic view of rolling hills and trees is present in the background, suggesting a peaceful atmosphere at sunset.

Home in Ellicottville

4.86 out of 5 average rating, 14 reviews

The Eagles Nest – Couples Escape

Experience The Eagles Nest in Ellicottville, a private 2-acre retreat with stunning views of Holimont Ski Resort. Enjoy the heated pool (seasonal from May 1-October 15), outdoor hot tub, fire pit, and the best sunrise in Western New York! This two-bedroom getaway offers a full kitchen, washer/dryer, and plenty of space for families or couples. Perfect for year-round relaxation or adventure, it stands out with its privacy, space, and serenity.