Top Chester rentals with pool or private pool - Connecticut

Explore Chester rentals with pools

Premier Host

Charming beach home, complete with pool & cozy guest house!

Sleeps 14 · 5 bedrooms · 3+ bathrooms

Back Patio-Pool, Hot tub, Fireplace, firepit, Bar & TV, Bathroom, Outdoor Shower

Premier Host

Spacious 5-bedroom, 6 bath vacation home just 30 min drive to beaches and casino

Sleeps 14 · 5 bedrooms · 5+ bathrooms

Historic 1853 two-family home on 6 acres

Country getaway in 2 family home, huge yard & grounds, minutes from lakes & more

Sleeps 8 · 3 bedrooms · 1 bathroom

Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston

Sleeps 9 · 5 bedrooms · 2 bathrooms

Top rated rentals with pools - Chester

Premier Host

Cute cottage just a block from the beach!

Easy to book and Mel was very quick to answer any questions we had.

Tracey G.

Stayed Mar 2022

Find spaces that suit your style

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to stay in a holiday home with a pool in Chester?

Where you stay, when you want to travel and the length of your escape will determine the price of a holiday home with a pool in Chester. Key in your travel details on Stayz, then pick the ideal one for you and prepare to make a splash.

When is the best time to book a holiday home with a pool in Chester?

July is when the majority of guests book a holiday home with a pool in Chester, which is in Middlesex County. Average temperatures range from 17ºC (17ºC) to 29ºC (29ºC) during this time of year.

What holiday homes with a pool in Chester have nice views?

Use the "Location" filter to find a holiday home with a pool and the views you dream of waking up to. Start by entering the dates you plan to travel to Chester, then narrow your search based on the type of area you'd prefer to stay in. All that's left is to pack your swimsuit and you're all set for a splashing good time.