Vacation rentals with a pool in Chautauqua County

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Top-rated rentals with a pool in Chautauqua County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost

Condo in Clymer

4.84 out of 5 average rating, 43 reviews

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

Guest favorite

Vacation home in Mayville

4.9 out of 5 average rating, 10 reviews

New! Lake Chautauqua Condo w/Lake Views

Welcome to The Seneca Retreat on Lake Chautauqua. This lake front 2 Bed 2 Bath Condo has left no details behind. The home comes furnished and well supplied with everything you will need to feel right at home. The stunning sunset lake views and outdoor patio space is perfect for entertaining while enjoying your stay with us. Amenities include, a pool, tennis courts, pickle ball, picnic area, and much more. Close to shopping, brew pubs, wineries, restaurants, ski resort and all lake attractions.

Guest favorite

Home in Irving

4.99 out of 5 average rating, 197 reviews

Lotus Bay Cabin - Autumn Oasis!

*In-ground pool & attached spa open until 12/1/2024* *8-person, stand alone hot-tub thereafter* Autumn, winter is that you? Sipping a drink in the always heated in-ground pool & spa (through 12/1), preparing meals in the fully stocked kitchen, movies on the oversized sectional, a book under the pergola, bomb-fires, strolls down for sunsets & sea glass hunting at the neighborhood-only private beach! You simply can’t go wrong. Lake Erie Wine Country, Buffalo, Niagara Falls all within reach.

Guest favorite

Camper/RV in Frewsburg

5 out of 5 average rating, 25 reviews

Lovely 2-Bedroom Keystone Sydney Outback 5th Wheel

Reconnect with nature at this unforgettable escape. You'll always remember your time at this unique place to stay. The property is located at Homestead Park Campground with plenty of weekend activities to enjoy. Whether it is swimming at the pool, having s’mores at a camp fire, or watching the beautiful sunset from the deck. The restaurant is open Sunday for breakfast. There is a playground on site, laundromat, showers with bathrooms, & camp store. Onsite camp owners can assist with any needs.

Guest favorite

Tiny home in Cherry Creek

4.98 out of 5 average rating, 112 reviews

County Tiny House, POOL,Barn GameRoom, Goat&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

Guest favorite

Home in Clymer

5 out of 5 average rating, 16 reviews

Slopeside Condo Haasienda

Have fun with the whole family at this stylish place on the slopes/hillside of Peak n Peek Resort! Ski in Ski out in winter! Great Mountain views from the deck, less than 5 minutes to Findlay Lake and its great restaurants and small-town shops. SKI winter. golf summer (90 seconds to champ golf course on top of hill), ziplining and tree course mini golf 2 minutes away on resort as well! Pools, golf, hike, fish, shop, dine, spa, close to Chatauqua Institute and Lake (Bemiss Point), on resort !

Guest favorite

Home in Mayville

4.89 out of 5 average rating, 38 reviews

Revitalized Historic Inn on Private 28-Acre Estate

This refurbished, historic Manor previously housed an Inn and has recently been updated and modernized for today's travelers. Enjoy the privacy of the 28-acre estate estate while you drink in stunning lake views from the covered porch, whip up a delicious meal in the gourmet kitchen, or find the perfect spot to curl up with a book, all without giving up the convenience of being a short drive from all of the culture and activity Chautauqua Institution and Chautauqua Lake have to experience.

Guest favorite

Home in Mayville

4.89 out of 5 average rating, 47 reviews

Spacious Chautauqua Lake 4 Bedroom home

Make some memories at this unique and family-friendly place. While staying with us, you can enjoy all of the wonderful amenities that CAMP CHAUTAUQUA has to offer. You can also 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!

Guest favorite

Vacation home in Clymer

4.96 out of 5 average rating, 27 reviews

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.

Superhost

Chalet in Clymer

4.86 out of 5 average rating, 14 reviews

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.

Guest favorite

Condo in Clymer

4.95 out of 5 average rating, 66 reviews

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.