
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.
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Popular amenities for Chautauqua County rentals with a pool
House rentals with a pool
Guest favorite

Home in Sherman
4.88 out of 5 average rating, 8 reviewsLovely 4BD/3BTH on 5 Acres Heated Pool & Fire Pits
ShaylinRating, 5 stars3 weeks ago
Our stay was wonderful! Great place for both adults and kids. Patti’s descriptions were extremely accurate. So many games and activities to do right at the home. One of the cleanest Airbnbs I have seen too!

Home in Bemus Point
4.88 out of 5 average rating, 40 reviewsRoomy Historic Lake House with pool and huge yard
RachelRating, 5 stars8 months ago
We planed a LAST moment trip with our family. We had a group of 4 adults and 4 kids of multiple ages and we ALL had an amazing time and comfortable stay. We love Bemus point as a location and went and enjoyed walks around town and the sunset. Debbie was an absolute pleasure and a very gracious host. We loved her dog as well and will definitely book here again.

Home in Clymer
4.64 out of 5 average rating, 11 reviewsPrime Location! Ski In/Out,Steps to Lift#8 & Lodge
NicoleRating, 5 stars3 months ago
We took our kids up skiing for their second time. The place was convenient, clean and spacious. Check in and check out instructions are very detail and helpful. We loved it! We definitely want to go again. If this place is available BOOK IT

Home in French Creek
4.63 out of 5 average rating, 8 reviewsPeak Retreat
GarrettRating, 5 stars3 months ago
Had everything we needed. Place was clean and the host had good communication.
Guest favorite

Home in Mayville
4.89 out of 5 average rating, 38 reviewsRevitalized Historic Inn on Private 15-Acre Estate
ZaynahRating, 5 stars6 months ago
Michelle was very kind! Her empathy came to the forefront when she allowed us to keep one of our cars parked in the driveway for a few days after check out due to an emergency. If you'd like a quiet getaway with family, this is perfect! We also took a 45-minute car ride to Allegheny National Forest and spent several hours hiking. You can walk to the lake, and the public beach access is only a 15-minute drive (it has a very scenic view). Highly recommend!

Home in Clymer
5 out of 5 average rating, 6 reviewsPeek'n Peak Clubhome Condo
LindaRating, 5 stars12 months ago
The home was actually better than the photos! It was extremely clean, first class, and well appointed. The attention to detail was amzing. She even left little snack baskets out for us. We had 3 kids aged 5 to 14 with us and there were tons of games and activities in the house for them to use. The dining table was large enough to hold all of us comfortably (we had 7 people). The kitchen had everything we could have wanted. There was firewood already cut up and ready to use in the fireplace. We also like how the house was laid out. The kids pretty much had the lower level, the main level was parents and main living areas, and the grandparents had the nice upper loft level. We had several questions during our stay and Denise was expremely responsive in helping us out. We hope to be able to return for another vacation.
Guest favorite

Home in Irving
5 out of 5 average rating, 11 reviewsSunset Bay Luxe Family Fun House - Buffalo Region
JonRating, 5 stars5 months ago
Second year in a row staying and will be back for a third! Perfect house and an incredible host!
Condo rentals with a pool
Guest favorite

Condo in Clymer
4.94 out of 5 average rating, 68 reviewsEnjoy Peek 'n Peak From a Luxury Upscale Condo
MelodyRating, 5 stars1 month ago
Susan was amazing and the stay was so relaxiing and perfect for our Team's Rejuvenation Retreat!! Thank You So Much For Being Such An Amazing Host!!!
Top guest favorite

Condo in Clymer
4.97 out of 5 average rating, 39 reviewsRoomy Beautiful Golf/Ski Condo
ElizabethRating, 5 stars2 months ago
We were a group of two families - 6 adults and 6 teens. The location to the slopes was perfect. We had plenty of sleeping spaces. The kitchen was well equipped to make all of our meals at the condo. Julie and Michael reached out during our stay to make sure everything was as we expected. We will be back!
Top guest favorite

Condo in Bemus Point
4.98 out of 5 average rating, 47 reviewsBemus Point Luxury Condo
MarthaRating, 5 stars8 months ago
It was a perfect week! It was in a perfect location? Very comfortable and clean. It was everything we hoped for and more.

Condo in Mayville
5 out of 5 average rating, 3 reviewsSunset Shores: Lakefront Condo in Mayville (AC)
SusanRating, 5 stars9 months ago
We’ve stayed at CHQ Lake Estates a number of times over the years. This was by far one of the best places! Quiet, clean, and comfortable—We took AM walks (just the best) and people are so friendly. The pool is amazing. And you cannot beat the view of the lake anywhere. We even took time to sit out on the cushioned deck chairs at sunset and just relaxed—something we don’t do often enough. Well stocked with pots, pans, glasses, utensils etc.. Soft sheets & comfortable beds. It was great to have 3 bathrooms—having 2 showers meant we could all get ready in record time. Be sure to bring your TV sign-in information so you don’t have to reset your passwords! (Voice of experience… lol) Great instruction book with local recommendations and fast wi-fi. We had 4 adults and 3 kids. We would definitely stay again!
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