Holiday rentals with a pool in Chautauqua County

Cheerful 1-Bedroom Cabin with a Campfire & Pool

Relax with the whole family at this peaceful place to stay. You can reconnect with nature, take a dip in the pool, enjoy some s’mores next to a campfire, or escape from the hustle and bustle. This cabin is equipped with a ramp for easy access, electricity, lights, ceiling fan, apartment-sized refrigerator, and a small countertop. The property is located at Homestead Park Campground with plenty of weekend activities to enjoy. Bathrooms, Showers, and laundromat are all onsite. 5.3 miles from kinzu

Frost Farms - animals, country, and nature escape

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 just a few miles off I86

Tiny House, Private-Pool, Barn Game Room & More!

Lola’s Oasis is a hidden gem on beautiful grounds in a central location for hiking, wineries, water sports & more! The property has this Tiny house & several unique amenities private to yourselves; a Pool, pool house, Rustic Barn Bar & GameRoom. A pergola patio area w/bonfire, slate Bar & 2 charcoal grills. A hammock, swing & a small Orchard. Bikes available. It’s a central location- to Hike 5min,Lily Dale 20 mins, Jamestown 30min, Ellicottville 30mins, Lake Erie 20min & Buffalo/Niagara 50min

Lotus Bay Cabin- Re-Opening Friday, September 12th

*In-ground pool, hot tub & pool house open through Dec. 1st, 2025 *8-person stand alone hot tub opens Dec. 1st, 2025 Autumn, winter, is that you? A cold drink in the in-ground hot tub & pool, meals in the fully stocked kitchen, movies on the spacious sectional, book reading in the sunroom, cozy bomb-fires under the stars & beach strolls for gorgeous sunsets & walks along Lake Erie…simply cannot go wrong! Lake Erie Wine Country, Buffalo & Niagara Falls all within close reach!

Cozy Ski-in/Ski-out with room for the whole family

Welcome to our vacation home! At 2,500 sq ft, four bedrooms and two pull outs, our condo offers four season fun for the whole family. Located at Peek N’ Peak resort; guests staying during ski season enjoy true ski-in/ski out access to 27 lighted ski slopes and trails. Guests staying off season take advantage of a full service day spa, indoor/outdoor pools, restaurants, Peek Mountain Adventures, and a championship 18 hole golf course within walking distance.

Million $ view Lake Chautauqua

Immerse yourself in a private, perfect getaway with stunning Lakefront views from Living Room & Bedroom. Enjoy the crackling from the wood burning fireplace, warm & cozy. Welcome to our quiet, serene condo located in the M building at the end of the Chautauqua Lake Estates Property. This beautifully appointed 850 sq ft. residence features warm woods and is fully furnished with everything you need for a relaxing retreat. Come relax & then go out and play !

Hidden Lakefront Gem | Cozy Cottage Stay

Tucked down a quiet lane on Chautauqua Lake, Sunny Cottage blends cozy comfort with laid-back fun. With 3 bedrooms, a pool, a private dock, and room to play, it’s perfect for memory-making—whether you’re paddling, roasting s’mores, or relaxing on the porch. Guests enjoy 3 paddleboards, 2 kayaks, and a lakeside fire pit for sunset chats and starry nights. Just 10 minutes from Bemus Point, it’s your peaceful escape with a splash of adventure.

Enjoy Peek 'n Peak From a Luxury Upscale Condo

A great spot for families and couples, this exquisite condo features vaulted ceilings, a winding spiral staircase, and large windows that allow in plenty of light. Relax outside on the balcony or get cozy next to the fireplace in the living room. Condo is part of the Camelot complex at Peek ‘n Peak resort in Clymer, NY. Common space pictures show the Peek hotel lobby, coffee shop & pools Principal renter must be a minimum 25 years of age.

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.