Vacation rentals with a pool in Chautauqua County

Private Pool, Cabana, Tiny House &RusticBarn Games

Lola’s Oasis is a peaceful retreat on my private property not a commercial Airbnb. I host guests in a cozy tiny guest house with your own sparkling pool to enjoy sunny days in complete privacy. The perfect romantic getaway in a charming small town near wineries &outdoor adventures. EXTRA Amenities:Rustic Barn Game Room, pergola patio, bonfire, bars, 2 charcoal grills, hammock&Bikes. Central location:Hiking 5 min, Lily Dale/Lake Erie 20 min, Jamestown/Ellicottville 30 min, Buffalo/Niagara 50 min.

Location · Value · Wifi

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

Value · Family · Indoor spaces

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 · Comfort

Steps from slopes and all amenities !

Renovated in 2026, this beautiful second-floor condo is the perfect getaway for a family or couples. fully equipped with all the comforts of home, it offers everything you need for a relaxing stay. Prime location within walking distance of slope and main hotel, where you’ll find a Starbucks, dining, an indoor/outdoor spa, adventure course, and mini golf Whether you’re here for skiing, outdoor activities, or simply to unwind, this condo provides the perfect home base for your mountain escape.

Family · Hospitality · Cleanliness

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.

Location · Family · Decor

Fall Colors await your group or family! 4 BR 3 BA

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!

Family · Location · Indoor spaces

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 · Checkout

Charming Lakefront Condo w/Pool.

Welcome to the Charming Seneca Retreat on Chautauqua Lake Features amazing sunset lake views on the patio. Open modern design with a plush sofa and plush queen beds. Well supplied kitchen and baths. Amenities include, pool, tennis, pickle ball, picnic area, playground, lake access. This condo 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.

Location · Nearby · View

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.

Family · Location · View

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 Peek n' Peak, our 4-bedroom condo at the top of the hill inside the Peek n' Peak Resort. The lift is just steps away and the golf course wraps the back. Gas fireplace and hot chocolate after a ski day, pool table in the game room, golf course views from the deck. King, queen, and bunk rooms plus a loft sleep up to 14, 16 with the loft trundles. Ski in winter, golf in summer.

Family · Location · View

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!

Value · Family · Outdoor spaces

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**

Value · Location · Cleanliness