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

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

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

The Plum Bush House: Victorian farmhouse retreat

Welcome to The Plum Bush House! Your secluded 15-acre 1865 Victorian estate with heated pool, minutes from Chautauqua Institution. Designed for gathering, the home offers spacious living areas and en suite bedrooms for comfort and connection. Wineries, premier golf, and an expansive county trail system, the estate balances adventure-retreat with history and what lasts. Micro-weddings, wellness, and creative retreats! Minutes from Chautauqua Lake, culture, dining, and year-round recreation.

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

Ski and Golf SkiBirdie Lodge at Peek N' Peak

Bring the whole family to this great place with lots of room for fun! A true four seasons resort property located at the top of Peek N' Peak mountain resort. Ski-in/ski-out 40 yards to lifts #1 and #2 in the winter, or watch golfers play the first and eighth hole from the deck in the summer and fall. Main level open floor plan allows for gathering with beautiful views. A large game room is perfect for family fun complete with shuffle board, arcade games and comfy seating.

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!

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!

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!

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**