Vacation rentals with a pool in Chautauqua County

Private Pool, Tiny House & Rustic Barn Game Room

Lola’s Oasis is a private escape on beautiful grounds, featuring your own sparkling pool perfect for cooling off & enjoying sunny days in privacy. The ideal romantic getaway in a charming small town near wineries &outdoor adventures. Enjoy The Tiny House w/amenities: Rustic Barn Game Room, pergola patio, bonfire, slate bar, 2 charcoal grills, hammock & small orchard.Bikes available.Centrally located Hiking 5min, Lily Dale &Lake Erie 20min, Jamestown & Ellicottville 30min, Buffalo/Niagara 50min.

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

Peek n' Peak 4BR—Steps to lifts—On the golf course

"A few steps to the ski slope." Peek n' Peak Condo lives up to it. The Tudor condo sits at the top of the hill inside the gated Peek n' Peak Resort, with the lift across the street and the golf course out back. Boots on at sunrise for first chair, gas fireplace and hot chocolate after, pool table in the lower-level game room, golf course view from the deck. King master plus queens and a twin-over-full bunk room sleep up to fourteen. Walk to lifts in winter, golf in summer.

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!

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!

Chautauqua Retreat: 5 Private Acres. Heated Pool.

Escape to Lakeside Meadows, a private 4-bed, 3-bath retreat on 5 acres near Chautauqua Lake. Perfect for families, this home features a heated pool, two fire pits, volleyball, basketball, and an arcade. Enjoy serene countryside views and easy access to local attractions. Comfortably sleeps up to 12 guests in a spacious, well-appointed home designed for making memories.

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.

Adorable Ski/Golf Condo at Peak N Peek

My place is close to family-friendly activities and nightlife. You’ll love my place because of the people, the ambiance, and the outdoors space. My place is good for couples, solo adventurers, families (with kids), big groups.