Holiday rentals with a pool in Chautauqua County

Private Pool, Cabana, Tiny House &RusticBarn Games

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.

Location · Family · Condition

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

Family · Location · Laundry

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

Family · Location · Walkability

Lake Erie Retreat with Pool & Hot Tub

Unwind on your own, bring the family or gather with friends at this private retreat, perfectly located between Buffalo, NY and Erie, PA. With accommodations for 6 guests, this location offers the perfect blend of relaxation and convenience! This home features 3 queen beds, 1.5 bathrooms, a full kitchen and updated open spaces! Spend your afternoons poolside or soak in the hot tub after a day of exploring! Nearby Attractions • Lake Erie beaches
• SUNY Fredonia
• Music on the Pier
• Wine Trail

Family · Value · Accuracy

4BR Paradise with Pool & Fire Pits Chautauqua Lake

Escape to your own private paradise at Lakeside Meadows — a spacious 4-bedroom, 3-bathroom retreat nestled on 5 serene, wooded acres just outside Mayville, NY. Only 10 minutes from the prettiest stretch of Chautauqua Lake, this custom-built home is perfect for families, multi-generational getaways, and groups who want space to relax, play, and make lasting memories. Close to Chautauqua Institution, Bemus Point and Lakewood for shopping convenience. One of CHQ's most sought after properties!

Location · Family · Quiet

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

Value · Location · Check-in

Ski & Golf Retreat | Steps to Lifts | Game Room

"Our stay was magical and made Christmas feel like a Hallmark movie." That's how a guest described our 4-bedroom home at the top of the hill inside the gated Peek n' Peak Resort. The lift sits across the street and the golf course wraps the back, so summer afternoons end with a round out back. Gas fireplace, pool table in the lower-level game room, golf course views from the deck. King primary plus queens and a bunk room sleep up to 14. Walk to the lifts in winter, golf in summer.

Location · Family · Parking

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.

Location · Family · Amenities

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!

Family · Location · Comfort

Historic 1880 Farmhouse• Walk to everything

Step back in time in this charming 1880 farmhouse in the heart of Bemus Point. Enjoy original character, a large deck, fire pit, spacious yard, and front porch with lake views just a block away. Walk to shops, restaurants, bars, and the waterfront-park your car and explore on foot. Guests have exclusive use of the main house. The owner and her friendly dog, Goldstein, live in a separate private apartment at the rear of the property.

Family · Location · Hospitality

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!

Family · Location · Pets

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**

Location · Family · Hospitality