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

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Oct 4 - Oct 5
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Oct 5 - Oct 6
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Oct 9 - Oct 11
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Oct 16 - Oct 18

Our top choices for Chesapeake hotels with a pool

A swimming pool with lounge chairs and a view of the beach.
A bar area with wooden furniture, a surfboard decoration, and a large ceiling with a wooden design.
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.

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.
$76 nightly
$89 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 hotel room with two beds, a desk, a chair, and artwork on the walls.
A banquet table set for a formal event with white tablecloths, gold chargers, and blue napkins.
A modern bar area with multiple seating arrangements and hanging spherical light fixtures.

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 2 - Nov 3
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 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.
A modern lobby with a wooden reception desk, seating area, and a vending machine.

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.
$84 nightly
$99 total
Nov 3 - Nov 4
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 multi-story hotel with balconies, a flag, and a well-maintained lawn.
A beachfront hotel with a long, straight promenade leading to the beach.
A hotel room with a bed, a desk, a chair, a lamp, and a view of the ocean through a large window.

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.
$94 nightly
$110 total
Nov 1 - Nov 2
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 beachside balcony with lounge chairs and a view of the ocean.
A rooftop patio with outdoor seating, a white coffee table, and a view of the ocean.
A high-rise building with a visible "Hyatt Place" sign, a rooftop terrace with outdoor seating, and a beach view.

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 modern bar area with a neon sign, a fireplace, and a seating area with sofas and ottomans.
An outdoor seating area with cushioned benches, a fire feature, and ambient lighting.

6. Aloft by Marriott Chesapeake

Aloft by Marriott Chesapeake
Greenbrier
  • Splash into year-round aquatic bliss at this hotel's immaculate indoor pool sanctuary.
$91 nightly
$107 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 lobby with a reception desk, seating area, and dining tables.
A hotel room with a flat-screen TV, a wooden desk, a grey sofa, and a large window with curtains.
A hotel room with a gray sofa, a small table, a lamp, a patterned carpet, and a wooden desk with a lamp.

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.
$78 nightly
$92 total
Nov 1 - Nov 2
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 hotel lobby with a reception desk, seating area, and a large abstract wall.

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.
$96 nightly
$112 total
Nov 4 - Nov 5
Total with taxes and fees
Hyatt Place Virginia Beach Town Center
An indoor swimming pool with blue-tiled walls and a modern design.
A high-rise hotel with multiple balconies, a beachside location, and a well-lit facade.
A gym with large windows overlooking the ocean, exercise equipment, and a wooden floor.
A hotel room with a large window offering a view of the beach and ocean.

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.
$92 nightly
$108 total
Oct 5 - Oct 6
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.
An outdoor patio area with tables and chairs, string lights, and a canopy.
A gym with treadmills, weight machines, and dumbbells.

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 11 - Oct 12
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 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'.
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.

Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk
Greenbrier
$84 nightly
$99 total
Nov 3 - Nov 4
Total with taxes and fees
Comfort Suites Chesapeake - Norfolk
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.
A hotel room with a flat-screen TV, a wooden desk, a grey sofa, and a large window with curtains.
A hotel room with a gray sofa, a small table, a lamp, a patterned carpet, and a wooden desk with a lamp.

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake
Chesapeake
$78 nightly
$92 total
Nov 1 - Nov 2
Total with taxes and fees
Wingate by Wyndham 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 modern hotel room with a built-in coffee maker, a flat-screen TV, and a wooden desk.
A snack and beverage vending area with multiple shelves stocked with various products.

Holiday Inn Express Chesapeake - Norfolk by IHG

Holiday Inn Express Chesapeake - Norfolk by IHG
Chesapeake
$101 nightly
$118 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Express Chesapeake - Norfolk 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 modern hotel building with a prominent sign for Delta Hotels Marriott.
A gym with treadmills, weight machines, and dumbbells.

Delta Hotels by Marriott Chesapeake Norfolk

Delta Hotels by Marriott Chesapeake Norfolk
Chesapeake
$102 nightly
$119 total
Oct 11 - Oct 12
Total with taxes and fees
Delta Hotels by Marriott Chesapeake Norfolk
A large indoor swimming pool with a sunlit floor, a reception desk, and a seating area with chairs.
An interior hallway with a patterned carpet, an exit door, framed pictures on the wall, and an elevator.
A hotel room with two beds, a desk with a chair, a flat-screen TV, a mirror, and a bedside lamp.
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.

Hampton Inn & Suites Chesapeake-Battlefield Blvd.

Hampton Inn & Suites Chesapeake-Battlefield Blvd.
Greenbrier
$97 nightly
$113 total
Nov 2 - Nov 3
Total with taxes and fees
Hampton Inn & Suites Chesapeake-Battlefield Blvd.
An outdoor seating area with cushioned benches, a fire feature, and ambient lighting.
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.

Aloft by Marriott Chesapeake

Aloft by Marriott Chesapeake
Greenbrier
$91 nightly
$107 total
Nov 1 - Nov 2
Total with taxes and fees
Aloft by Marriott 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 hotel room with a large bed, a desk with a chair, a small table, and a lamp.
A snack and beverage area with shelves stocked with snacks and a refrigerator with beverages.

Fairfield Inn and Suites By Marriott Chesapeake

Fairfield Inn and Suites By Marriott Chesapeake
Greenbrier
$100 nightly
$117 total
Oct 18 - Oct 19
Total with taxes and fees
Fairfield Inn and Suites By Marriott 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 Staybridge Suites hotel with a brick facade, multiple windows, and a parking lot with cars.
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
$101 nightly
$118 total
Nov 1 - Nov 2
Total with taxes and fees
Staybridge Suites Chesapeake by IHG
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.
Reception
A hotel with a modern design, featuring a prominent entrance with a covered area and a clear sky in the background.
An indoor swimming pool with blue-tiled walls, seating areas, and potted plants.

SpringHill Suites by Marriott Chesapeake Greenbrier

SpringHill Suites by Marriott Chesapeake Greenbrier
Greenbrier
$101 nightly
$118 total
Nov 1 - Nov 2
Total with taxes and fees
SpringHill Suites by Marriott Chesapeake Greenbrier
A modern lobby with a grey sofa, yellow armchairs, and a wooden coffee table.
A modern Hyatt Place hotel with a covered entrance, a parking area, and a landscaped garden.
An indoor swimming pool with clear windows, a ladder, and a lifeguard chair.
A modern lobby with a curved wall, seating area, and a fireplace.

Hyatt Place Chesapeake

Hyatt Place Chesapeake
Greenbrier
$114 nightly
$133 total
Nov 2 - Nov 3
Total with taxes and fees
Hyatt Place Chesapeake
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Hotels with pools and hot tubs in Chesapeake

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.
A hotel room with a flat-screen TV, a wooden desk, a grey sofa, and a large window with curtains.
A hotel room with a gray sofa, a small table, a lamp, a patterned carpet, and a wooden desk with a lamp.

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake
Chesapeake
$78 nightly
$92 total
Nov 1 - Nov 2
Total with taxes and fees
Wingate by Wyndham Chesapeake
A large indoor swimming pool with a sunlit floor, a reception desk, and a seating area with chairs.
An interior hallway with a patterned carpet, an exit door, framed pictures on the wall, and an elevator.
A hotel room with two beds, a desk with a chair, a flat-screen TV, a mirror, and a bedside lamp.
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.

Hampton Inn & Suites Chesapeake-Battlefield Blvd.

Hampton Inn & Suites Chesapeake-Battlefield Blvd.
Greenbrier
$97 nightly
$113 total
Nov 2 - Nov 3
Total with taxes and fees
Hampton Inn & Suites Chesapeake-Battlefield Blvd.
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 Staybridge Suites hotel with a brick facade, multiple windows, and a parking lot with cars.
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
$101 nightly
$118 total
Nov 1 - Nov 2
Total with taxes and fees
Staybridge Suites Chesapeake by IHG
A spacious lobby with a reception desk, green seating, and a large TV screen.
A hotel with a brick facade, a flat roof, and a large entrance.
An indoor swimming pool with clear water, a reception desk, and a few lounge chairs.
A hotel lobby with a patterned carpet, a central sofa, and a dining area with wooden chairs and tables.

Holiday Inn Express Hotel & Suites Chesapeake by IHG

Holiday Inn Express Hotel & Suites Chesapeake by IHG
Western Branch North
$84 nightly
$99 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Express Hotel & Suites Chesapeake by IHG
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.
A buffet with various food items including fruits, pastries, and beverages.
An outdoor patio with stone walls, a round table, and green chairs.
A lobby with a reception desk, a fireplace, and a seating area.

Great Studio | Pool & Hot Tub. Your Next Vacation

Great Studio | Pool & Hot Tub. Your Next Vacation
Chesapeake
$147 nightly
$169 total
Nov 1 - Nov 2
Total with taxes and fees
Great Studio | Pool & Hot Tub. Your Next Vacation
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.
A buffet with various food items including fruits, pastries, and beverages.
A lobby with a reception desk, a fireplace, and a seating area.
An outdoor patio with stone walls, a round table, and green chairs.

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Chesapeake
$158 nightly
$182 total
Nov 1 - Nov 2
Total with taxes and fees
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.
An outdoor patio with stone walls, a round table, and green chairs.
A lobby with a fireplace, potted plants, and wooden decor.
A buffet with various food items including fruits, pastries, and beverages.

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Chesapeake
$158 nightly
$182 total
Nov 1 - Nov 2
Total with taxes and fees
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.
A buffet with various food items including fruits, pastries, and beverages.
A lobby with a fireplace, potted plants, and wooden decor.
An outdoor patio with stone walls, a round table, and green chairs.

Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
$158 nightly
$182 total
Oct 11 - Oct 12
Total with taxes and fees
Studio | Free Breakfast. Indoor Pool & Hot Tub.
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.
A lobby with a reception desk, a fireplace, and a seating area.
A buffet with various food items including fruits, pastries, and beverages.
A lobby with a fireplace, potted plants, and wooden decor.

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
$147 nightly
$169 total
Nov 1 - Nov 2
Total with taxes and fees
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.
A lobby with a reception desk, a fireplace, and a seating area.
A buffet with various food items including fruits, pastries, and beverages.
An outdoor patio with stone walls, a round table, and green chairs.

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Chesapeake
$169 nightly
$194 total
Nov 1 - Nov 2
Total with taxes and fees
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
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

Schooner Inn

Schooner Inn

8/10 Good
"Nice location at the end of the boardwalk. The climate control system would not allow us to increase the temperature to a comfortable level for the evening. It would not go over 68.5 degrees. Otherwise very pleased with the stay."
Sam 3-night trip
Posted 4 hours ago
Schooner Inn
Holiday Inn & Suites Virginia Beach North Beach by IHG

Holiday Inn & Suites Virginia Beach North Beach by IHG

10/10 Excellent
"I would book again nice clean stay"
Tonya 1-night trip
Posted 6 hours ago
Holiday Inn & Suites Virginia Beach North Beach by IHG
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

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

10/10 Excellent
"Welcome to the Neptune Festival during a Nor Easter… lol, no one controls the weather but the room is beautifully situated with a view of rough seas, walking distance to everything. The staff were great at check in, the room is clean, well laid out and breakfast is yet to be decided but it is early, 5am to 9am. If people had decorum of any kind the weed smoking would be better managed but really in the world today who cares about others… RIGHT!!! Nothing staff can do and that’s okay… Our room smells fine it’s the idiots above us and the wind lowing it to us. The hotel is in a great location. Great stay, highly recommend."
Chaz 2-night trip
Posted 7 hours ago
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
Hilton Virginia Beach Oceanfront

Hilton Virginia Beach Oceanfront

8/10 Good
"Positive: Good views to the beach and close proximity to stores, wheel chair access in bathroom, balcony, room service Negative:AC takes awhile to cool, no ventilation in bathroom, elevators take too long to come, pay to park"
Kevin 3-night trip
Posted 12 hours ago
Hilton 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 $92 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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