Chesapeake Hotels with Pools

For travelers seeking relaxation, a hotel with a pool in Chesapeake offers the perfect respite. You can take a refreshing swim or lounge poolside without leaving the property. When booking, look for hotels with well-maintained pools to enhance your stay.

Trip.com Featured Hotels with Swimming Pools in Chesapeake

1. Staybridge Suites CHESAPEAKE - VIRGINIA BEACH by IHG

• Enjoy Fax/copying service, BBQ, and Conference room.

• Rated 8.8/10 based on 114 reviews.

• Steps from Liberty Live Church - Greenbrier (0.37 km).

• Price range: MYR 754-MYR 2,403.

2. Hyatt Place Chesapeake Greenbrier

• Offers Dry cleaning, Fax/copying service, and Multi-function room.

• Guest Rated: 8.1/10 (103 Reviews)

• Only 0.46 km away - easily reach Greenbrier Family Skating Center Roller Skating.

• Price range: MYR 611-MYR 1,977.

3. Delta Hotels Chesapeake Norfolk

• Offers Dry cleaning, Fax/copying service, and Snack bar.

• A 8.5/10 rating based on 100 reviews.

• Steps from Liberty Live Church - Greenbrier (0.26 km).

• Nightly rates: MYR 626 to MYR 2,109

All prices shown are for July 30-August 5, as listed on Trip.com.

Find Chesapeake hotels with a sprawling Pools.

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Top Hotels with Pools in Chesapeake

Seek out top Chesapeake hotels with proistine Pools.

Most Booked

Lowest price

Closest to downtown

Highest Rated

Wingate by Wyndham Chesapeake

Hotels in Chesapeake

Featured facilities: Gym

Good

103 reviews

7.9/10

1 night

From MYR 447

Check availability

99+

Staybridge Suites CHESAPEAKE - VIRGINIA BEACH by IHG

Hotels in Chesapeake

Featured facilities: Gym

Very Good

114 reviews

8.8/10

1 night

From MYR 716

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99+

Sleep Inn & Suites Chesapeake - Portsmouth

Hotels in Chesapeake

Featured facilities: Spa, Gym

94 reviews

6.8/10

1 night

From MYR 378

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Comfort Suites Chesapeake - Norfolk

Hotels in Chesapeake

Featured facilities: Gym

Very Good

103 reviews

8.7/10

1 night

From MYR 642

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Fairfield Inn & Suites Chesapeake

Hotels in Chesapeake

Featured facilities: Gym

Very Good

104 reviews

8.9/10

1 night

From MYR 623

Check availability

Delta Hotels Chesapeake Norfolk

Hotels in Chesapeake

Featured facilities: Bar, Gym

Very Good

99 reviews

8.5/10

1 night

From MYR 651

Check availability

99+

Hyatt Place Chesapeake Greenbrier

Hotels in Chesapeake

Featured facilities: Bar, Gym

Very Good

104 reviews

8.1/10

1 night

From MYR 815

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Comfort Inn & Suites Chesapeake - Portsmouth

Hotels in Chesapeake

Featured facilities: Spa, Gym

102 reviews

6.0/10

1 night

From MYR 551

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SpringHill Suites Chesapeake Greenbrier

Hotels in Chesapeake

Featured facilities: Gym

Very Good

105 reviews

8.3/10

1 night

From MYR 645

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Aloft Chesapeake

Hotels in Chesapeake

Featured facilities: Bar, Spa, Gym

Very Good

101 reviews

8.4/10

1 night

From MYR 647

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See More Hotels with Pools in Chesapeake

Latest Reviews for Chesapeake Hotels

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Read genuine traveler ratings & reviews to find your perfect stay.

Holiday Inn Express CHESAPEAKE - NORFOLK by IHG

8.8/10

Very Good

Posted on Jan 17, 2025

Guest User

Very good, very quiet and very convenient, because the itinerary was postponed, I kept renewing at this hotel. Although there are many hotels nearby, this price/performance ratio is still OK.

Price per night from:MYR 636

Residence Inn Chesapeake Greenbrier

8.4/10

Very Good

Posted on Jul 9, 2025

Guest User

직원들의 서비스는 좋지만 시설이 많이 낙후되었습니다. 특히 오래돤 천소파만 교체해도 많이 개선이 될 수 있을 것 같습니다.

Price per night from:MYR 888

Hampton Inn Norfolk/Chesapeake (Greenbrier Area)

8.1/10

Very Good

Posted on May 25, 2026

Guest User

Staff in the breakfast area was super grest,. Rooms that were reserved for me via the hotel staff were given away before we arrived, even though I called to verify our arriva timel when we were on our way. not happy!

Price per night from:MYR 509

Hampton Inn & Suites Chesapeake-Battlefield Blvd.

8.0/10

Very Good

Posted on Jul 31, 2020

Guest User

Hotel was exceptionally clean & staff was very nice & accommodating. However, our room was not ready until after 7:00 pm. I was promised a refund that never happened & have yet to receive a credit for a mystery charge on my card that I did not authorize.

Price per night from:MYR 657

Homewood Suites by Hilton Chesapeake-Greenbrier

7.8/10

Good

Posted on Jul 20, 2025

Guest User

직원들의 서비스는 너무나 좋았지만 객실내 시설은 너무나 낡았어요. 특히나 작고 오래된 낡은 천소파는 교체가 시급해 보입니다.

Price per night from:MYR 757

Holiday Inn Express & Suites CHESAPEAKE by IHG

7.4/10

Posted on Dec 31, 2021

Farmer

Great Service! It a must go!!

Price per night from:MYR 480

Frequently Asked Questions

What are the best hotels with Swimming Pools in Chesapeake?

If you are visiting Chesapeake for business or tourism, Staybridge Suites CHESAPEAKE - VIRGINIA BEACH by IHG (from MYR 754) , Delta Hotels Chesapeake Norfolk (from MYR 626) and Hyatt Place Chesapeake Greenbrier (from MYR 611) are popular choices.

How much is a hotel with Swimming Pools in Chesapeake?

For hotels with Swimming Pools in Chesapeake, the average price on weekdays is MYR 818, and on weekends (Friday–Saturday) is MYR 1,063.

What available deals for hotels with Swimming Pools in Chesapeake?

Trip.com always provides various promotions and discounts for both new and loyal users. You can check the promotions page to figure out what promotions are available for your stay.