Vacation rentals with a pool in Chautauqua County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Chautauqua County

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

Guest favorite
Tiny home in Cherry Creek
View Eclipse! Tiny House, Pool, goat & GameBarn!
Lola’s Oasis is a hidden gem on beautiful grounds. Which includes this Tiny house (2 guests max),a Tree House(Separate Listing OPENING IN JUNE 2024, 2 guests max) w/several unique amenities(Shared 6/24); a Pool, pool house,Rustic Barn Bar &GameRoom.A pergola patio area w/bonfire, slate Bar &charcoal grill. A hammock,Swing & a small Orchard. Stay in one & make new friends or bring friends & family to have the grounds to yourself! .5 miles to town,35 mins to Ellicottville,Allegheny &Chaut. Lake.
Jan 6 – 13
$157 per night
4.98 out of 5 average rating, 92 reviews
Guest favorite
Home in Mayville
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.
Nov 18 – 25
$382 per night
4.9 out of 5 average rating, 31 reviews
Guest favorite
Home in Irving
Lotus Bay Cabin - All Seasons Oasis
*8-person hot tub open thru 04/30/2024* *In-ground pool & attached spa opens 05/01/2024* Spring, Summer is that you? Host an unforgettable stay at Lotus Bay Cabin! A glass of wine in the 8-person stand alone hot tub, mouth watering meals from the fully stocked kitchen, movie on the oversized sectional, a book by the fireplace, marshmallows outdoors & strolls down for sunsets & sea glass hunting at the neighborhood-only private beach! Hiking, skiing, Wine Country, Buffalo, Niagara Falls!
Jan 3 – 10
$380 per night
4.99 out of 5 average rating, 172 reviews

Popular amenities for Chautauqua County rentals with a pool

House rentals with a pool

Guest favorite
Home in Angola
Lake Erie Family & Pet Friendly Home + Pool
Apr 13 – 20
$133 per night
4.88 out of 5 average rating, 26 reviews
Guest favorite
Home in Bemus Point
Roomy Historic Lake House with pool and huge yard
Aug 27 – Sep 3
$816 per night
4.89 out of 5 average rating, 37 reviews
Guest favorite
Home in Irving
Sunset Bay Luxe Family Fun House - Buffalo Region
Mar 19 – 26
$500 per night
5.0 out of 5 average rating, 7 reviews
Home in Clymer
New Listing! Ski In&Ski Out - Next to Lift #8
Oct 15 – 22
$215 per night
5.0 out of 5 average rating, 3 reviews
Home in French Creek
Peak Retreat
Dec 25 – Jan 1
$186 per night
5.0 out of 5 average rating, 4 reviews
Guest favorite
Home in Clymer
Peek'n Peak Clubhome Condo
Nov 20 – 27
$553 per night
5.0 out of 5 average rating, 5 reviews
Home in Ashville
Lake Getaway w/ Indoor Pool!
Nov 10 – 17
$553 per night
4.42 out of 5 average rating, 24 reviews
Home in Sherman
Lakeside Meadows serene getaway.
Aug 14 – 21
$503 per night
New place to stay
Home in Mayville
Victorian farmhouse retreat
Oct 22 – 29
$749 per night
New place to stay
Home in Chautauqua
NorthShore Unit A4
Mar 23 – 30
$217 per night
New place to stay
Guest favorite
Home in Mayville
Secluded Cottage Near CHQ Institution & CHQ Lake
Nov 14 – 21
$274 per night
4.83 out of 5 average rating, 30 reviews
Home in Chautauqua
NorthShore Unit A1
May 2 – 9
$222 per night
New place to stay

Condo rentals with a pool

Guest favorite
Condo in Clymer
Roomy Beautiful Golf/Ski Condo
Nov 20 – 27
$479 per night
5.0 out of 5 average rating, 15 reviews
Guest favorite
Condo in Bemus Point
Lakeside Brand New Luxury Condo
Oct 30 – Nov 6
$375 per night
4.96 out of 5 average rating, 23 reviews
Guest favorite
Condo in Clymer
Enjoy Peek 'n Peak From a Luxury Upscale Condo
Mar 22 – 29
$228 per night
4.95 out of 5 average rating, 62 reviews
Guest favorite
Condo in Clymer
8409PEAK SLOPE SIDE, IN/OUT,GOLF,SKI LIFT8,FIREPIT
Oct 29 – Nov 5
$468 per night
4.89 out of 5 average rating, 36 reviews
Guest favorite
Condo in Bemus Point
Bemus Point Luxury Condo
Oct 14 – 21
$360 per night
4.98 out of 5 average rating, 40 reviews
Guest favorite
Condo in Clymer
New: Remodeled Peek n Peak Camelot condo, sleeps 6
Jun 26 – Jul 3
$213 per night
4.99 out of 5 average rating, 68 reviews
Condo in Mayville
Lakeside Retreat in Dewittville w/ Pool Access!
Nov 4 – 11
$221 per night
New place to stay
Condo in Mayville
Lakefront Dewittville Condo with Private Deck!
May 5 – 11
$281 per night
New place to stay
Condo in Mayville
Waterfront Dewittville Condo w/ Furnished Balcony!
Oct 9 – 16
$280 per night
New place to stay

Destinations to explore