Book the Best Hotels with POOL in Chesapeake in 2026

Check availability on Chesapeake Hotels with a Pool

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Our top choices for Chesapeake hotels with a pool

Holiday Inn Express Hotel & Suites Chesapeake by IHG

Western Branch North

Splash into relaxation at this indoor pool oasis near Chesapeake Square Mall.

CA $154 total

includes taxes & fees

May 3 - May 4

SpringHill Suites by Marriott Chesapeake Greenbrier

Greenbrier

Splash into refreshing elegance at this indoor pool oasis with post-adventure soaking awaits.

CA $184 total

includes taxes & fees

Apr 27 - Apr 28

Hampton Inn Norfolk/Chesapeake (Greenbrier Area)

Chesapeake

A seasonal outdoor pool awaits with refreshing waters and convenient poolside relaxation at this welcoming Chesapeake retreat.

CA $188 total

includes taxes & fees

Apr 29 - Apr 30

Wingate by Wyndham Chesapeake

Chesapeake

Poolside respite with heated indoor pool and hot tub, perfect for a refreshing dip year-round.

CA $151 total

includes taxes & fees

May 10 - May 11

Delta Hotels by Marriott Chesapeake Norfolk

Chesapeake

Dive into year-round aquatic bliss at this indoor pool sanctuary with nearby zoo adventures and hiking trails.

CA $188 total

includes taxes & fees

May 3 - May 4

Fairfield Inn and Suites By Marriott Chesapeake

Greenbrier

Splash into summer with a refreshing seasonal outdoor pool experience at this Chesapeake hotel near shopping destinations.

CA $189 total

includes taxes & fees

May 10 - May 11

Comfort Suites Chesapeake - Norfolk

Greenbrier

Splash into a Virginia escape with a pristine pool and 24-hour fitness centre near Norfolk attractions.

CA $187 total

includes taxes & fees

May 10 - May 11

Aloft Chesapeake

Greenbrier

Splash into year-round aquatic bliss at this hotel's immaculate indoor pool sanctuary.

CA $190 total

includes taxes & fees

May 10 - May 11

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Choose what matters most at hotels with a pool in Chesapeake

Breakfast included

Hot tub

Hotels with pools and free breakfast in Chesapeake

Hampton Inn & Suites Chesapeake-Battlefield Blvd.

Greenbrier

CA $202 total

includes taxes & fees

May 24 - May 25

Holiday Inn Express Hotel & Suites Chesapeake by IHG

Western Branch North

CA $154 total

includes taxes & fees

May 3 - May 4

SpringHill Suites by Marriott Chesapeake Greenbrier

Greenbrier

CA $184 total

includes taxes & fees

Apr 27 - Apr 28

Delta Hotels by Marriott Chesapeake Norfolk

Chesapeake

CA $188 total

includes taxes & fees

May 3 - May 4

Fairfield Inn and Suites By Marriott Chesapeake

Greenbrier

CA $189 total

includes taxes & fees

May 10 - May 11

Comfort Suites Chesapeake - Norfolk

Greenbrier

CA $187 total

includes taxes & fees

May 10 - May 11

Staybridge Suites Chesapeake by IHG

Chesapeake

CA $256 total

includes taxes & fees

May 17 - May 18

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Top Chesapeake Hotel Reviews

The Ocean Key Virginia Beach Resort

6/10 Okay

"Room was clean, plastic mattress cover did not make for a good night sleep and very noisy. People next door fighting in room until 130am. Room over looked a marina, nice view but lots of noise next to the highway. The AC wasn't working in the entire building but it did get fixed before departing. Good value for the room"

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

8/10 Good

"Beach view was excellent staff very friendly and helpful coffee in lobby all the time. Bar Resturant on site good bar food(not opened for breakfast though) parking was offsite , down the road a short walk .There was a small amount of parking at hotel but not many. Overall good for the price but needed some upgrades for sure"

Moxy Virginia Beach Oceanfront

10/10 Excellent

"The staff was a exceptional. Beach access was great. We only had two issues. One was cosmetic repairs - the ceiling had been repaired and the patched area was painted a slightly different color. They should have painted the entire ceiling. Also, there was some missing tile in bathroom and sloppy caulking around sink. The second issue was the mandatory valet parking. The lot was very accessible as it is across the street from the hotel. We would have preferred to park our car. Ultimately, we really enjoyed the other aspects of the hotel. So, those issues were very minor. We certainly would stay there again."

Frequently asked questions

What are the best hotels in Chesapeake with outdoor pools?

The Fairfield Inn and Suites By Marriott Chesapeake is a fantastic choice for families seeking relaxation and fun by the pool. With an impressive traveller rating of 9.0, guests rave about the friendly and helpful staff, alongside the clean and comfortable rooms. The hotel offers a refreshing outdoor pool, great for cooling off after a day of exploring the area. Plus, enjoy a complimentary continental breakfast to kickstart your day.

Another great option is the Holiday Inn Express Chesapeake - Norfolk by IHG, which boasts an inviting outdoor pool complemented by sun loungers, ideal for soaking up the sun. Rated 8.6 by travellers, this hotel is known for its clean and quiet rooms, excellent breakfast options, and friendly front desk staff. Families appreciate the combination of comfort and convenience, making it a solid choice for a family getaway.

The Hampton Inn Norfolk/Chesapeake (Greenbrier Area) is also worth considering, featuring an outdoor pool and a traveller rating of 8.4. Guests often highlight the great coffee and excellent breakfast service, along with the clean and inviting rooms. It's a fantastic spot for families looking to balance relaxation with outdoor fun.

For those desiring a spacious stay, Comfort Suites Chesapeake - Norfolk also offers an outdoor pool and is rated 8.4 by guests. Families will appreciate the large shower and the hotel's helpful staff, ensuring a pleasant experience throughout their stay.

Lastly, Homewood Suites by Hilton Chesapeake-Greenbrier presents a cozy and convenient environment, with a review rating of 8.0. This hotel features an outdoor pool and provides a complimentary breakfast, making it a favored choice among families who value comfort and convenience.

How much does a hotel with outdoor pool in Chesapeake cost?

Enjoy staying in a hotel in Chesapeake with an outdoor pool. You can find a great deal from CA $151 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.

Are there hotels with outdoor pools that are close to Greenbrier Mall?

The Fairfield Inn and Suites By Marriott Chesapeake is a fantastic choice for families seeking a comfortable stay near Greenbrier Mall. This hotel is not only rated 9.0 by travellers, but it also features a relaxing outdoor pool, superb for unwinding after a day of adventures. Guests rave about the friendly and helpful staff, as well as the clean and spacious rooms, making it an ideal spot for families with children.

Just a short drive away, the Hampton Inn Norfolk/Chesapeake (Greenbrier Area) also boasts an inviting outdoor pool. With a review score of 8.4, this hotel has an inviting space, complemented by well-kept rooms and a complimentary breakfast that travellers consistently find enjoyable. The hotel's location allows easy access to local attractions, while the friendly service enhances the overall experience for families looking for convenience and quality.

Is it cheaper to book flights and a hotel in Chesapeake as a package?

Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package.

How can I save on a hotel in Chesapeake with Expedia?

Before booking your Chesapeake hotel, remember to join Expedia's free travel rewards program—One Key™. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.

Can I cancel my hotel reservation on Expedia?

Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel with an outdoor pool in Chesapeake for you.

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Check availability on Chesapeake Hotels with a Pool

Our top choices for Chesapeake hotels with a pool

Holiday Inn Express Hotel & Suites Chesapeake by IHG

SpringHill Suites by Marriott Chesapeake Greenbrier