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. Hyatt Place Chesapeake Greenbrier

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

• Guest Rated: 8.2/10 (103 Reviews)

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

• Price range: CAD 164-CAD 402.

2. Comfort Suites Chesapeake - Norfolk

• Offers Garden, Fax/copying service, and BBQ.

• Rated 8.8/10 based on 103 reviews.

• Convenient to Chilled Ponds Ice Sports Complex, only 0.61 km.

• Price range: CAD 138-CAD 401.

3. Aloft Chesapeake

• Offers Eco tours, Dry cleaning, and Spa.

• Guest Rated: 8.4/10 (99 Reviews)

• Convenient to Chilled Ponds Ice Sports Complex, only 0.54 km.

• Price range: CAD 147-CAD 444.

All prices shown are for September 14-September 20, as listed on Trip.com.

Find Chesapeake hotels with a sprawling Pools.

Check-out

Swipe down to view more

Filter by:

Hotel Star Rating

≤2345

Guest Rating

Amazing 9+Great 8+Good 7+Pleasant 6+

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: Pool, Gym

Good

100 reviews

7.9/10

1 night

From CAD 131

Check availability

99+

Staybridge Suites CHESAPEAKE - VIRGINIA BEACH by IHG

Hotels in Chesapeake

Featured facilities: Pool, Gym

Very Good

115 reviews

8.9/10

1 night

From CAD 163

Check availability

99+

Sleep Inn & Suites Chesapeake - Portsmouth

Hotels in Chesapeake

Featured facilities: Pool, Spa, Gym

94 reviews

6.8/10

1 night

From CAD 109

Check availability

99+

Comfort Inn & Suites Chesapeake - Portsmouth

Hotels in Chesapeake

Featured facilities: Pool, Spa, Gym

100 reviews

5.9/10

1 night

From CAD 104

Check availability

Delta Hotels Chesapeake Norfolk

Hotels in Chesapeake

Featured facilities: Pool, Bar, Gym

Very Good

100 reviews

8.5/10

1 night

From CAD 159

Check availability

99+

Holiday Inn Express CHESAPEAKE - NORFOLK by IHG

Hotels in Chesapeake

Featured facilities: Pool, Gym

Very Good

109 reviews

8.8/10

1 night

From CAD 155

Check availability

99+

Hyatt Place Chesapeake Greenbrier

Hotels in Chesapeake

Featured facilities: Pool, Bar, Gym

Very Good

103 reviews

8.2/10

1 night

From CAD 165

Check availability

Holiday Inn Express & Suites CHESAPEAKE by IHG

Hotels in Chesapeake

Featured facilities: Pool, Gym

103 reviews

7.4/10

1 night

From CAD 128

Check availability

Comfort Suites Chesapeake - Norfolk

Hotels in Chesapeake

Featured facilities: Pool, Gym

Very Good

101 reviews

8.8/10

1 night

From CAD 140

Check availability

99+

Residence Inn Chesapeake Greenbrier

Hotels in Chesapeake

Featured facilities: Pool, Gym

Very Good

97 reviews

8.4/10

1 night

From CAD 187

Check availability

See More Hotels with Pools in Chesapeake

Latest Reviews for Chesapeake Hotels

See all

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

Fairfield Inn & Suites Chesapeake

8.9/10

Very Good

Posted on Feb 3, 2024

Guest User

The room is okay, but it's too close to the main road and very noisy! It is not recommended to book this hotel, breakfast is ok, but extra charge

Price per night from:CAD 179

Aloft Chesapeake

8.4/10

Very Good

Posted on Apr 4, 2024

Guest User

The pillow case and sheets had stains. The carpet in the room under the table hasn’t been vacuumed in a long time. The lobby sells like pool chlorine

Price per night from:CAD 147

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:CAD 137

SpringHill Suites Chesapeake Greenbrier

8.1/10

Very Good

Posted on Dec 8, 2023

Larrio Gray

The stay was great the people was great the food was great and it was very clean I will be staying there more often thanks so much

Price per night from:CAD 149

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:CAD 144

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:CAD 188

Frequently Asked Questions

What are the best hotels with Swimming Pools in Chesapeake?

If you are visiting Chesapeake for business or tourism, Hyatt Place Chesapeake Greenbrier (from CAD 164) , Comfort Suites Chesapeake - Norfolk (from CAD 138) and Delta Hotels Chesapeake Norfolk (from CAD 167) 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 CAD 239, and on weekends (Friday–Saturday) is CAD 289.

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.