Holiday rentals with a pool in Chautauqua County

The Plum Bush House: Victorian farmhouse retreat

An 1865 Italianate, Victorian farmhouse where guests can retreat and gather within a serene, historic landscape and modern comforts. Enjoy charming common areas amidst towering black locusts and quiet meadows. Explore the spacious outdoors and gardens; relax and rest in luxury; take in scenic views, and feel at home in this charming treasure. The main house rental sleeps 12; inquire if you’d like to expand your space to an open floor plan, vaulted ceiling, queen-bed apartment as an ADD-ON FEE.

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

Lake Getaway w/ Indoor Pool!

A true mid century house on an amazing plot of land situated on 3.5 acres. The ONLY property in the CHQ area with an indoor pool! Come enjoy this four season home with your friends and family. The lake is just down the hill and you’re just a few minutes to Bemus Point, Southern Tier, the Institution, and Peek n’ Peak Beautiful patio with walkout. Dog friendly! Now taking rentals of 30 days or more exclusively (local laws) contact me about about fractional ownership for shorter stays!

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.

Sun and Snow Escape: Ski/Golf Condo in Peek'n Peak

Welcome to our upper-level condo at Peek’n Peak Resort, featuring a Master bedroom, loft bedroom, and 3 full bathrooms. Enjoy four seasons of fun with skiing, golfing, ziplining, swimming, a spa, and a gym nearby. Our condo is close to Chair Lift #8 for winter skiing and summer adventures. Note: Resort amenities are not included. No rescheduling within 30 days of arrival. Travel insurance strongly recommended, due to our strict cancellation policy.

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.

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.