The Best Hotels with a Pool in Chesapeake, VA from ₩157,276 in 2026

Q: What are some hotels with pools in Chesapeake?

Comfort Suites Chesapeake - Norfolk : Hotel located near Greenbrier Mall. Features buffet, a seasonal outdoor pool, and complimentary wired internet access. Hyatt Place Chesapeake : Hotel located near Greenbrier Mall. Offers buffet, an indoor pool, and free self parking.

Check availability on Chesapeake Hotels with a Pool

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Our top choices for Chesapeake hotels with a pool

Comfort Inn & Suites Chesapeake - Portsmouth

Chesapeake

Splash into year-round aquatic bliss in this business district hotel featuring an inviting indoor pool with extended hours.

₩200,116 total

includes taxes & fees

Jul 12 - Jul 13

SpringHill Suites by Marriott Chesapeake Greenbrier

Greenbrier

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

₩198,014 total

includes taxes & fees

Jun 28 - Jun 29

Hampton Inn & Suites Chesapeake-Battlefield Blvd.

Greenbrier

Dive into relaxation at this hotel's pristine indoor pool and hot tub sanctuary.

₩244,827 total

includes taxes & fees

Jun 21 - Jun 22

Holiday Inn Express Hotel & Suites Chesapeake by IHG

Western Branch North

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

₩238,584 total

includes taxes & fees

Jul 12 - Jul 13

Sleep Inn & Suites Chesapeake - Portsmouth

Chesapeake

Cool, refreshing indoor pool oasis awaits at this comfortable hotel with a fitness center.

₩157,276 total

includes taxes & fees

Jul 6 - Jul 7

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.

₩226,159 total

includes taxes & fees

Jun 28 - Jun 29

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.

₩212,408 total

includes taxes & fees

Jun 28 - Jun 29

Aloft by Marriott Chesapeake

Greenbrier

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

₩210,667 total

includes taxes & fees

Jun 28 - Jun 29

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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

₩244,827 total

includes taxes & fees

Jun 21 - Jun 22

SpringHill Suites by Marriott Chesapeake Greenbrier

Greenbrier

₩198,014 total

includes taxes & fees

Jun 28 - Jun 29

Comfort Inn & Suites Chesapeake - Portsmouth

Chesapeake

₩200,116 total

includes taxes & fees

Jul 12 - Jul 13

Holiday Inn Express Hotel & Suites Chesapeake by IHG

Western Branch North

₩238,584 total

includes taxes & fees

Jul 12 - Jul 13

Suite, 1 King Bed, Non Smoking, Hot Tub, Kitchenette | Desk, iron/ironing board, free WiFi, bed sheets

Sleep Inn & Suites Chesapeake - Portsmouth

Chesapeake

₩157,276 total

includes taxes & fees

Jul 6 - Jul 7

Fairfield Inn and Suites By Marriott Chesapeake

Greenbrier

₩226,159 total

includes taxes & fees

Jun 28 - Jun 29

Delta Hotels by Marriott Chesapeake Norfolk

Chesapeake

₩212,408 total

includes taxes & fees

Jun 28 - Jun 29

Homewood Suites by Hilton Chesapeake-Greenbrier

Greenbrier

₩262,171 total

includes taxes & fees

Jun 21 - Jun 22

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Top Chesapeake Hotel Reviews

Schooner Inn

10/10 Excellent

"Was a nice room with a great view! Nice price! Beds were so comfortable and got a great sleep. Only suggestion I have is get bigger TVs for the rooms."

Wingate by Wyndham Chesapeake

6/10 Okay

"The Wi-Fi connection is terrible it would not hold a connection for longer than about 10 minutes and then would disconnect. The hot water is non-existent on the third floor - I let it run for more than 15 minutes and it still was barely lukewarm. The room was clean, but the hallways are dark and have a strange smell (maybe some type of cleaner). The bathroom tubs are not really practical for someone who needs assistance in and out of the shower - the grab bars are not in the right location or they need more than one."

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

10/10 Excellent

"Comfortable bed, very clean, wonderful. Helpful front desk. I left my phone and the housekeeper brought it to me. The only problem we had was on the day of departure all the ice machines were broken. But overall an excellent hotel"

Wyndham Virginia Beach Oceanfront

2/10 Terrible

"I have stayed at Wyndham properties before, including locations in Dallas and Las Vegas. Unfortunately, this property was poorly maintained throughout. From the moment I entered the lobby, it was apparent that the facility was not being properly cared for. The furniture was stained, scratched, and visibly worn. It appeared that management was either unaware of these conditions or had chosen not to address them. The lack of maintenance extended throughout the property. From the pool area to the elevators, floors, and fixtures throughout the property, there was visible dirt, damage, and general neglect. It appeared that routine cleaning and maintenance were not being performed. My initial room had a ceiling leak that had been poorly repaired. The leak had clearly existed for some time, as mold was present and the wallpaper was bubbling and peeling away from the wall. In addition, the furniture was broken, the balcony showed signs of mold and rust, and the outdoor furniture was dirty and unclean. Overall, the room resembled accommodations several levels below what one would reasonably expect from a Wyndham property—more akin to a student dormitory than a hotel charging premium rates. I paid more than $1,400 in advance for this 7-day stay, and the condition of the hotel did not justify that expense. Had I known the true condition of the property, I would not have booked this hotel. The experience was extremely disappointing and far below the standard I have come to expect."

Frequently asked questions

What are some hotels with pools in Chesapeake?

Comfort Suites Chesapeake - Norfolk: Hotel located near Greenbrier Mall. Features buffet, a seasonal outdoor pool, and complimentary wired internet access. Hyatt Place Chesapeake: Hotel located near Greenbrier Mall. Offers buffet, an indoor pool, and free self parking.

What is there to see and do in Chesapeake?

Explore places like Sandbridge Beach and Naval Station Norfolk while you're in the area. Make a point to visit attractions like Riverwalk Parkway Park and Playground and Chesapeake Arboretum. Chesapeake appeals to visitors with its beautiful beaches, major shopping area, and array of dining options.

When is the best time to book a hotel with a pool in Chesapeake?

You may want to consider an accommodation with an outdoor swimming pool if you plan to visit Chesapeake in the warmest months of July, August, or June when the average temperature is 77°F. Lodging with an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temp is 45°F.

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Check availability on Chesapeake Hotels with a Pool

Our top choices for Chesapeake hotels with a pool

Comfort Inn & Suites Chesapeake - Portsmouth

SpringHill Suites by Marriott Chesapeake Greenbrier

Hampton Inn & Suites Chesapeake-Battlefield Blvd.

Holiday Inn Express Hotel & Suites Chesapeake by IHG

Sleep Inn & Suites Chesapeake - Portsmouth

Fairfield Inn and Suites By Marriott Chesapeake