Vacation rentals with a pool in Chautauqua County

The Poolside Tiny House & Rustic Barn Game Lounge

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

Ideal Family Home on 5 private Acres. FILLS FAST!

Escape to Lakeside Meadows, a serene retreat nestled on 5 acres. Just 10 minutes from Mayville. This spacious 4-BDR, 3-BTH home offers the perfect blend of comfort and luxury, with easy access to all major local attractions. Enjoy complete tranquility, surrounded by lush woods and plenty of open space for outdoor fun. Relax around the outdoor fire pit with free firewood, and experience thoughtful touches and top-notch amenities throughout. HEATED Pool Chautauqua Lake awaits you and your family!

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).

Frost Farms - animals, country, snowmobile, 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

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

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!

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!

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.

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!

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.

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**

Hidden Lakefront Gem | Cozy Cottage Stay

Sunny Cottage is your lake escape. 3 bedrooms, pool, dock, kayaks, paddleboards, and room for both quiet mornings and laughter-filled nights. Whether it’s family, friends, or a getaway for two, you’ll find space to relax, play, and explore, with Bemus Point just minutes away.