Holiday rentals with a pool in New Haven County

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Popular amenities for New Haven County rentals with a pool

House rentals with a pool

Guest favourite
Home in Fairfield
4.94 out of 5 average rating, 17 reviews

Once a Pond - time and stress slow down.

CailinRating, 5 stars2 weeks ago
We loved our weekend stay here! It’s such a peaceful retreat. From the cozy interior to the beautiful land surrounding the house we absolutely loved it! Johanna and her husband were friendly and responsive. We’d love to come back—especially in autumn!
Superhost
Home in Clinton
4.91 out of 5 average rating, 11 reviews

Clinton Beach House & Cottage w/ Pool, Near Shore

HannahRating, 5 stars2 months ago
We had a group of 8 adults and 7 kids (5 and under) and the space was great for a large group! There was plenty of room for the kids to run around downstairs and the large yard was fantastic. We were there in the winter so couldn’t take advantage of the pool but we did make a trip to the local beach (5 min drive) and use the fire pit. I definitely recommend Gregory’s place for both larger groups and families! We would love to return!
Superhost
Home in Milford
4.86 out of 5 average rating, 78 reviews

Spacious 4 bedroom, oasis with ocean views galore

HollyRating, 5 stars2 months ago
Great house, we wish we could have stayed longer but due to weather we were only there one night. Very comfortable home, plenty of space, we would love to come back in the warmer months to enjoy the pool! We have stayed in many rentals in the area (family nearby) and this has been the nicest one.
Guest favourite
Home in Middletown
4.95 out of 5 average rating, 40 reviews

Hot Tub and pool Home away from home

KristenRating, 5 stars2 months ago
Jan's house was a great stay with plenty of room for six adults. We loved the game room and outdoor hot tub. Instructions for the hot tub were clear and easy to follow. We'd definitely stay again!
Guest favourite
Home in Fairfield
5 out of 5 average rating, 16 reviews

4BR/2.5BA Refuge Near University, Downtown & Beach

CourtneyRating, 5 stars6 months ago
Our family visited Connecticut for a concert and we absolutely loved our weekend stay at Adam & Shelly’s! The place was clean and beautifully designed. Plus, our kiddos loved the pool! Shelly was responsive and accommodating. We couldn’t have asked for more. Would love to stay again!
Guest favourite
Home in Fairfield
4.95 out of 5 average rating, 20 reviews

Old Post Road w/Pool and Cottage, walk to Beach

SophiaRating, 5 stars5 months ago
We had a great stay at Rose and Tom’s place and can’t wait to go back. From the start, Rose’s communication was super timely and clear. Tom met us at check in to show us the property and answer any questions, and remained available the rest of the weekend in case we needed anything. The house is extremely comfortable, clean, spacious. All the bedrooms were comfortable with plenty of towels and linens. The house has plenty locations to work from home as well. The location is a perfect 5 minute walk to town. We didn’t get to go to the beach, but it was very close and the house also had beach chairs/ towels in case we needed them. The pool house was an extra great and comfortable space to watch sports on the big TV with our group. The yard is perfectly manicured and the pool was heated, making our September stay even better. It was truly a great stay and wish we could have stayed longer.
Guest favourite
Home in Roxbury
4.89 out of 5 average rating, 19 reviews

Zoom Map 5* Town Roxbury! "SentryHill" PoshPadsCT

BrittRating, 5 stars3 months ago
Beautiful property and well equipped home in a quiet neighborhood. Great for a relaxing getaway with friends or family. The yard has additional amenities for kids to enjoy outside time. The house has great WiFi but would be helpful to know that cell service is limited.
Superhost
Home in Milford
5 out of 5 average rating, 8 reviews

Huge Family House w/Waterviews

LynnRating, 5 stars4 months ago
We had a wonderful stay! The house can accommodate large family gatherings - there were a lot of spaces for folks to spread out as well as gather. The kitchen is very well stocked. We would definitely rent again!

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