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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Guest favorite

The cabin exterior features a rustic wooden structure with a welcoming entrance. A spacious deck with seating is visible, surrounded by lush greenery. A grill and prep area are set up near the entrance, providing an inviting spot for outdoor meals. A friendly pet can be seen nearby.

Tiny home in Machias

4.86 out of 5 average rating, 411 reviews

Lucky Day Cabin Ellicottville/Ashford 30 acres

Family built cabin on 30 acre country estate, just outside exciting year round resort village of Ellicottville. Perfect for nature lovers and outdoor enthusiasts, the cabin has all necessities, similar to a tiny house. Nestled near the gardens, and surrounded by quiet rolling hills. Enjoy with door step delivered breakfast, or book a guided hike with estate owner and learn about medicinal plants and flowers, the topography of the land and a farm fresh picnic lunch on the peninsula of our lake.

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).

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.

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

Tiny House, Private-Pool, Barn Game Room & 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

Guest favorite

A covered porch seating area is furnished with a floral-patterned sectional sofa, accented by plush pillows. A small table sits in front, alongside a decorative sculpture. Expansive green fields and trees are visible in the background, enhancing the tranquil outdoor setting.

Home in Mayville

4.89 out of 5 average rating, 38 reviews

Revitalized Historic Inn on Private 15-Acre Estate

This refurbished, historic Manor previously housed an Inn and has recently been updated and modernized for today's travelers. Enjoy the privacy of the 28-acre estate estate while you drink in stunning lake views from the covered porch, whip up a delicious meal in the gourmet kitchen, or find the perfect spot to curl up with a book, all without giving up the convenience of being a short drive from all of the culture and activity Chautauqua Institution and Chautauqua Lake have to experience.

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

A clear blue pool is surrounded by a smooth deck, featuring a connected hot tub. Comfortable lounge chairs with vibrant cushions sit under a colorful umbrella in the background, and lush greenery frames the area, enhancing the inviting outdoor space.

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

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 !

Superhost

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

4.88 out of 5 average rating, 17 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.

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

4.74 out of 5 average rating, 66 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 Chautauqua Lake 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. Gas fireplaces. Beautiful patio with walkout from main living area. Dog friendly!