A golf course, a large building complex, and a marina by a river.

Find Hotels with a Pool in Chesapeake, VA

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Check availability on Chesapeake Hotels with a Pool

Tonight
Oct 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Chesapeake hotels with a pool

A swimming pool with lounge chairs and a view of the beach.
A hotel room with two beds, a sofa, a small table, and a balcony with a view of the sea.
A balcony with a view of the beach and ocean during sunset.
An outdoor bar area with wooden tables and chairs, a brick wall, and a view of the ocean at dusk.

1. Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
Northeast Virginia Beach
  • Oceanfront pool sanctuary in Virginia Beach with beach cabanas and sunset views.
$80 nightly
$94 total
Oct 28 - Oct 29
Total with taxes and fees
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
A modern indoor swimming pool with clear glass walls, a high ceiling, and a seating area with chairs and a table.
A beach with a paved walkway, palm trees, and beach umbrellas.
A modern bar area with multiple seating arrangements and hanging spherical light fixtures.
A banquet table set for a formal event with white tablecloths, gold chargers, and blue napkins.

2. Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG
Northwest
  • Indoor pool relaxation awaits with 24-hour fitness center access at this hotel where friendly staff ensures a comfortable stay.
$75 nightly
$88 total
Nov 12 - Nov 13
Total with taxes and fees
Crowne Plaza Virginia Beach Town Center by IHG
A swimming pool with lounge chairs and umbrellas, surrounded by a building with multiple balconies.
A hotel room with a bed, a desk, a chair, a sofa, and a small table.
A modern lobby with a wooden reception desk, seating area, and a vending machine.
A hotel sign with a crescent moon logo and the name 'Comfort Suites'.

3. Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk
Greenbrier
  • Splash into a Virginia escape with a pristine pool and 24-hour fitness center near Norfolk attractions.
$89 nightly
$104 total
Nov 1 - Nov 2
Total with taxes and fees
Comfort Suites Chesapeake - Norfolk
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A hotel room with a wooden desk, a blue sofa, a small table, and a view of the ocean through large windows.
A hotel room with a bed, a desk, a chair, a lamp, and a view of the ocean through a large window.
A beachfront hotel with a long, straight promenade leading to the beach.

4. Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
Northeast Virginia Beach
  • Dive into ocean bliss with indoor pool comfort steps from Virginia Beach's iconic boardwalk.
$93 nightly
$109 total
Nov 3 - Nov 4
Total with taxes and fees
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
A poolside area with lounge chairs and a person reading a book.
A high-rise building with a visible "Hyatt Place" sign, a rooftop terrace with outdoor seating, and a beach view.
A pathway leading to a building with a view of the ocean.
A beachside balcony with lounge chairs and a view of the ocean.

5. Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront
Northeast Virginia Beach
  • Seasonal oceanfront pool beckons with boardwalk views and loungers for sun-soaked relaxation.
$110 nightly
$129 total
Nov 1 - Nov 2
Total with taxes and fees
Hyatt Place Virginia Beach / Oceanfront
An indoor swimming pool with clear lanes, a wooden ceiling, and lounge chairs.
A modern hotel lobby with a central seating area, a reception desk, and a staircase leading to an upper level.
A hotel with a modern facade, large glass windows, and a prominent 'aloft hotels' sign.
A modern bar area with a neon sign, a fireplace, and a seating area with sofas and ottomans.

6. Aloft by Marriott Chesapeake

Aloft by Marriott Chesapeake
Greenbrier
  • Splash into year-round aquatic bliss at this hotel's immaculate indoor pool sanctuary.
$107 nightly
$125 total
Nov 1 - Nov 2
Total with taxes and fees
Aloft by Marriott Chesapeake
A swimming pool with a tiled deck, a sign indicating spa hours, and a Whirlpool logo on the wall.
A hotel room with a gray sofa, a small table, a lamp, a patterned carpet, and a wooden desk with a lamp.
A hotel lobby with a reception desk, seating area, and dining tables.
A hotel room with a large bed, a desk, a chair, a television, and a small trash can.

7. Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake
Chesapeake
  • Poolside respite with heated indoor pool and hot tub, perfect for a refreshing dip year-round.
$82 nightly
$96 total
Nov 4 - Nov 5
Total with taxes and fees
Wingate by Wyndham Chesapeake
An indoor swimming pool with lounge chairs and a table, large windows, and a view of buildings outside.
A hotel room with a large bed, a TV, a desk with drawers, a suitcase, and a view of a shopping center.
A modern hotel room with a dining area, two armchairs, a coffee table, and large windows offering a view of trees and buildings.
A modern dining area with a long wooden table and black chairs, white cabinets, and a patterned backsplash.

8. Hyatt Place Virginia Beach Town Center

Hyatt Place Virginia Beach Town Center
Northwest
  • Splashy fun meets total comfort at this poolside retreat with sun loungers and 24-hour fitness center.
$101 nightly
$118 total
Nov 1 - Nov 2
Total with taxes and fees
Hyatt Place Virginia Beach Town Center
An indoor swimming pool with blue-tiled walls and a modern design.
A gym with large windows overlooking the ocean, exercise equipment, and a wooden floor.
A balcony with a view of a beach, a small table, and a chair.
A high-rise hotel with multiple balconies, a beachside location, and a well-lit facade.

9. Hilton Vacation Club Ocean Beach Club Virginia Beach

Hilton Vacation Club Ocean Beach Club Virginia Beach
Northeast Virginia Beach
  • Seaside pool bliss awaits with multiple aquatic options and beachside cocktail service.
$96 nightly
$113 total
Oct 21 - Oct 22
Total with taxes and fees
Hilton Vacation Club Ocean Beach Club Virginia Beach
An indoor swimming pool with clear glass walls, white lounge chairs, and a tiled floor.
A modern hotel building with a prominent sign for Delta Hotels Marriott.
A gym with treadmills, weight machines, and dumbbells.
An outdoor patio area with tables and chairs, string lights, and a canopy.

10. Delta Hotels by Marriott Chesapeake Norfolk

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.
$102 nightly
$119 total
Oct 18 - Oct 19
Total with taxes and fees
Delta Hotels by Marriott Chesapeake Norfolk
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Choose what matters most at hotels with a pool in Chesapeake

Breakfast included
Hot tub
Water park
Spa
4 stars

Hotels with pools and free breakfast in Chesapeake

A modern kitchen with a central island, bar stools, pendant lighting, and a large wall-mounted artwork.
A Fairfield by Marriott hotel with a modern design, featuring a covered entrance and a prominent sign.
A snack and beverage area with shelves stocked with snacks and a refrigerator with beverages.
A hotel room with a large bed, a desk with a chair, a small table, and a lamp.

Fairfield Inn and Suites By Marriott Chesapeake

Fairfield Inn and Suites By Marriott Chesapeake
Greenbrier
$100 nightly
$117 total
Nov 2 - Nov 3
Total with taxes and fees
Fairfield Inn and Suites By Marriott Chesapeake
A buffet with labeled containers of omelets and other dishes.
A room with a blue sofa, a small table, a microwave, a refrigerator, and a wall-mounted lamp.
A laundry area with a sign indicating it's for guest use only, a washing machine, and a dryer.
A hotel room with two beds, a desk with a chair, a TV, and a window with a city view.

Holiday Inn Express Chesapeake - Norfolk by IHG

Holiday Inn Express Chesapeake - Norfolk by IHG
Chesapeake
$101 nightly
$118 total
Nov 8 - Nov 9
Total with taxes and fees
Holiday Inn Express Chesapeake - Norfolk by IHG
A large indoor swimming pool with a sunlit floor, a reception desk, and a seating area with chairs.
A hotel lobby with multiple seating areas, including sofas, chairs, and round tables. There are wall-mounted lamps, a television, and framed pictures on the walls.
A hotel room with two beds, a desk with a chair, a flat-screen TV, a mirror, and a bedside lamp.
An interior hallway with a patterned carpet, an exit door, framed pictures on the wall, and an elevator.

Hampton Inn & Suites Chesapeake-Battlefield Blvd.

Hampton Inn & Suites Chesapeake-Battlefield Blvd.
Greenbrier
$97 nightly
$113 total
Nov 12 - Nov 13
Total with taxes and fees
Hampton Inn & Suites Chesapeake-Battlefield Blvd.
A modern lobby with a grey sofa, yellow armchairs, and a wooden coffee table.
An indoor swimming pool with clear windows, a ladder, and a lifeguard chair.
A bar area with a counter, a beverage dispenser, and several bar stools.
A modern lobby with a curved wall, seating area, and a fireplace.

Hyatt Place Chesapeake

Hyatt Place Chesapeake
Greenbrier
$114 nightly
$133 total
Nov 8 - Nov 9
Total with taxes and fees
Hyatt Place Chesapeake
A modern lobby with a wooden reception desk, seating area, and a vending machine.
A swimming pool with lounge chairs and umbrellas, surrounded by a building with multiple balconies.
A modern dining area with wooden flooring, yellow and blue chairs, and a central island with a coffee machine.
A hotel room with a bed, a desk, a chair, a sofa, and a small table.

Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk
Greenbrier
$89 nightly
$104 total
Nov 1 - Nov 2
Total with taxes and fees
Comfort Suites Chesapeake - Norfolk
A modern restaurant with a central bar area, multiple seating options including high tables and bar stools, and a flat-screen TV mounted on a wooden panel.
A hotel room with a large bed, two bedside tables with lamps, a sofa, a TV, and a painting on the wall.
Reception
A hotel with a modern design, featuring a prominent entrance with a covered area and a clear sky in the background.

SpringHill Suites by Marriott Chesapeake Greenbrier

SpringHill Suites by Marriott Chesapeake Greenbrier
Greenbrier
$114 nightly
$133 total
Nov 1 - Nov 2
Total with taxes and fees
SpringHill Suites by Marriott Chesapeake Greenbrier
A hotel lobby with a reception desk, seating area, and dining tables.
A hotel room with a gray sofa, a small table, a lamp, a patterned carpet, and a wooden desk with a lamp.
A hotel room with a large bed, a desk, a chair, a television, and a small trash can.
A swimming pool with a tiled deck, a sign indicating spa hours, and a Whirlpool logo on the wall.

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake
Chesapeake
$82 nightly
$96 total
Nov 4 - Nov 5
Total with taxes and fees
Wingate by Wyndham Chesapeake
A patio area with wicker furniture and a stone fire pit, surrounded by a stone wall and a pool.
A spacious living room with a fireplace, sofas, and a flat-screen TV mounted above the fireplace.
A hotel room with a kitchenette, a dining area, a bed, a TV, and a window with curtains.
A modern kitchen area with a stone wall, a flat-screen TV, a Coca-Cola refrigerator, a coffee machine, and a fruit bowl.

Staybridge Suites Chesapeake by IHG

Staybridge Suites Chesapeake by IHG
Chesapeake
$113 nightly
$132 total
Nov 1 - Nov 2
Total with taxes and fees
Staybridge Suites Chesapeake by IHG
An outdoor patio area with tables and chairs, string lights, and a canopy.
A modern kitchen with a breakfast bar, various food containers, and a 'PANTRY' sign.
A gym with treadmills, weight machines, and dumbbells.
A modern hotel building with a prominent sign for Delta Hotels Marriott.

Delta Hotels by Marriott Chesapeake Norfolk

Delta Hotels by Marriott Chesapeake Norfolk
Chesapeake
$102 nightly
$119 total
Oct 18 - Oct 19
Total with taxes and fees
Delta Hotels by Marriott Chesapeake Norfolk
An outdoor patio area with brick walls, a fire pit, and outdoor furniture.
A spacious living area with a stone fireplace, comfortable seating, and large windows.
A pool table with a billiard cue and balls, large windows, and a patterned carpet.
A spacious lobby with a fireplace, comfortable seating, and a dining area.

Residence Inn by Marriott Chesapeake Greenbrier

Residence Inn by Marriott Chesapeake Greenbrier
Greenbrier
$139 nightly
$162 total
Nov 1 - Nov 2
Total with taxes and fees
Residence Inn by Marriott Chesapeake Greenbrier
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesapeake Hotel Reviews

Hilton Vacation Club Oceanaire Virginia Beach

Hilton Vacation Club Oceanaire Virginia Beach

10/10 Excellent
"Well needed birthday vacation in a clean room right along the beach !!"
Katanya 2-night trip
Posted 1 hour ago
Hilton Vacation Club Oceanaire Virginia Beach
Schooner Inn

Schooner Inn

10/10 Excellent
"The Schooner is a great place to stay. Really friendly staff and really great location. It is a no frills hotel but the rooms and views are great and the price is superb."
John 1-night trip
Posted 1 hour ago
Schooner Inn
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

10/10 Excellent
"Everything was amazing. If I had to make a suggestion: the common hallway to my room, the carpet is riddled with unappealing stains, a light fixture cover was on the ground, it made the hotel feel low quality and that wasn’t the case but vibe matters, so I would suggest that. Maybe tile is better for the beach."
Laura 4-night trip
Posted 1 day ago
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
Hilton Vacation Club Ocean Beach Club Virginia Beach

Hilton Vacation Club Ocean Beach Club Virginia Beach

10/10 Excellent
"The property is clean. Staff exceptionally nice and helpful. View was spectacular. Remember please, you can't control your neighbors or other travelers, and you will enjoy YOUR stay."
Deborah 1-night trip
Posted 1 day ago
Hilton Vacation Club Ocean Beach Club Virginia Beach
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

10/10 Excellent
"It was quiet and clean. Good location!"
Alisa 2-night trip
Posted 1 day ago
Comfort Inn & Suites Hampton near Coliseum
Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG

10/10 Excellent
"My husband and I stayed for 2 nights and had a great visit. The hotel is close to the highway, Mount Trashmore and Town Center making very convenient for visitors. The staff was very pleasant and helpful. They have a restaurant in the hotel where we both enjoyed dinner one evening. The room was clean and the bed was more comfortable than we expected, which was a pleasant surprise. There were only two things I would alert others to before booking. We didn’t pay attention that there was not a microwave in the room while booking. This wasn’t a big deal for us but might be for others. And our room faced the highway so if you’re a light sleeper you might want to ask for a room on the opposite side. Neither were deal breakers for us. I would definitely recommend this hotel."
Amy 3-night trip
Posted 2 days ago
Crowne Plaza Virginia Beach Town Center by IHG
Marjac Suites Virginia Beach Oceanfront

Marjac Suites Virginia Beach Oceanfront

10/10 Excellent
"D"
Wilson 1-night trip
Posted 3 days ago
Marjac Suites Virginia Beach Oceanfront

Frequently asked questions

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 $96 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 option for families seeking a hotel with an outdoor pool near Greenbrier Mall. Guests consistently rave about the friendly and helpful staff, as well as the comfortable, clean rooms. With a traveller rating of 9.0, this hotel also offers free breakfast and internet, making it a convenient choice for busy families.Just a short drive away, the Holiday Inn Express Chesapeake - Norfolk by IHG presents another excellent choice. This hotel features an inviting outdoor pool with sun loungers, great for some fun in the sun after a day of shopping. Rated 8.6, guests appreciate the clean and quiet rooms, along with the great breakfast options and the friendly front desk service.For those looking for a spacious stay, the Comfort Suites Chesapeake - Norfolk, also rated 8.6, offers an outdoor pool and large rooms that are well-kept and comfortable. Families will love the free breakfast and the helpful staff who make your stay enjoyable.Lastly, the Hampton Inn Norfolk/Chesapeake (Greenbrier Area) has an inviting space with an outdoor pool and a traveller rating of 8.4. Guests enjoy the clean rooms, excellent breakfast service, and the inviting ambiance created by the friendly staff.
Is it cheaper to book flights and a Chesapeake hotel with a pool 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 vacation package.
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 in Chesapeake for you.

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