Chesapeake rentals with pool
We found 3,135 rentals with pool — enter your dates for availability
Explore Chesapeake rentals with pools
Tranquil Paradise Nature Sanctuary. Pool, red barns and horses, goats and more.
Sleeps 5 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Ultimate Vacation Home
Sleeps 10 · 4 bedrooms · 3 bathrooms
2.02.0 out of 10
2 reviews(2 reviews)
Comfortable Home | Long Stay Discount Available
Sleeps 6 · 3 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
6 reviews(6 reviews)
Beautiful home in Chesapeake
Sleeps 7 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Cozy 2-bedroom condo in wonderful Chesapeake with fitness room, WiFi
Sleeps 6 · 2 bedrooms · 1 bathroom
The Ocean Key Virginia Beach Resort
Sleeps 4 · 1 bedroom
7.87.8 out of 10
Goodgood
1,311 reviews(1,311 reviews)
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Frequently asked questions
Are there any holiday rentals with a pool in Chesapeake?
Consider one of our 3,135 holiday rentals with a pool and start planning your trip to Chesapeake. Whether you want to stay in South Norfolk, Greenbrier West, Deep Creek South or another well-known neighbourhood, you’ll discover the ideal poolside escape on Stayz.
How much does it cost to stay in a holiday rental with a pool in Chesapeake?
Prices vary according to length of stay, season and exact location, so enter your travel details to find a stay offering a splashing good time. No matter your plans or budget, Stayz has holiday rentals with a pool in Chesapeake for every type of guest.
When is the best time to book a holiday rental with a pool in Chesapeake?
With average temperatures ranging from 23ºC to 30ºC, August is popular with the majority of Stayz guests. Browse our holiday rentals with a pool in this corner of Chesapeake City County during other months too. There may be greater availability outside of Chesapeake’s peak months.
What holiday rentals with a pool in Chesapeake have nice views?
After a day of sightseeing fun, retreat to your holiday rental with a pool for a refreshing dip. The icing on the cake? Some of these Chesapeake properties also boast impressive views of historic areas.
Are there holiday rentals with a private pool in Chesapeake?
Chesapeake doesn’t have any holiday rentals with a private pool. But if you’re looking for a place that’s for your exclusive use and has all the comforts of home, we’ve got your back. Almost all our properties offer conveniences like separate bedrooms and a kitchen. If you want to add a little luxury to your holiday, use our handy filter tool to find options with a hot tub, among other premium perks.
What are the top things to do in Chesapeake?
Get your Chesapeake getaway off to a terrific start by visiting top attractions like Norfolk Botanical Garden, Nauticus National Maritime Centre and Chrysler Museum of Art. Stay in a Stayz holiday home rental with the family and then discover the best of this destination together.
Why should I book my holiday rental with a pool with Stayz?
No sharing your space, no uncomfortable encounters with people you don’t know. When you choose a Stayz holiday rental with a pool, you’ll have the whole place to yourself to splish splash around. Need to cancel or alter your travel plans? Our flexible cancellation policies let you book your rental house with complete peace of mind.