Search for Cheap Deals on
Hotels with Pools in Chesapeake Bay

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking!


Featured Chesapeake Bay Hotels with a Pool

Washington Plaza Hotel
Washington Plaza Hotel
4 out of 5
10 Thomas Circle NW, Washington, DC
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Washington. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the breakfast and the ...
Washington Plaza Hotel
Capitol Skyline Hotel
Capitol Skyline Hotel
3.5 out of 5
10 I Street S.W, Washington, DC
Stay at this 3.5-star business-friendly hotel in Washington. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Popular attractions National Mall and ...
Capitol Skyline Hotel
Hilton Vacation Club The Historic Powhatan Williamsburg
Hilton Vacation Club The Historic Powhatan Williamsburg
3.5 out of 5
3601 Ironbound Rd, Williamsburg, VA
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star golf resort in Williamsburg. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the restaurant in our reviews. ...
Hilton Vacation Club The Historic Powhatan Williamsburg
Omni Shoreham Hotel
Omni Shoreham Hotel
4 out of 5
2500 Calvert St Nw, Washington, DC
Fully refundableReserve now, pay when you stay
Stay at this 4-star family-friendly hotel in Washington. Enjoy an outdoor pool, 2 bars/lounges, and breakfast (surcharge). Our guests praise the pool and the ...
Omni Shoreham Hotel
Days Inn by Wyndham Virginia Beach At The Beach
Days Inn by Wyndham Virginia Beach At The Beach
2 out of 5
1000 Atlantic Ave, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
Stay at this motel in Virginia Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Days Inn by Wyndham Virginia Beach At The Beach
Hilton Vacation Club Ocean Beach Club Virginia Beach
Hilton Vacation Club Ocean Beach Club Virginia Beach
3.5 out of 5
3401 Atlantic Ave, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star beach hotel in Virginia Beach. Enjoy free WiFi, 2 indoor pools, and a beach locale. Our guests praise the helpful staff and the clean rooms ...
Hilton Vacation Club Ocean Beach Club Virginia Beach
Wingate by Wyndham Williamsburg
Wingate by Wyndham Williamsburg
2.5 out of 5
2007 Richmond Rd, Williamsburg, VA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Wingate by Wyndham Williamsburg
Turtle Cay Resort
Turtle Cay Resort
2.5 out of 5
600 Atlantic Ave, Virginia Beach, VA
Stay at this hotel in Virginia Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular ...
Turtle Cay Resort
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
3 out of 5
105 Visitors Center Dr, Williamsburg, VA
Fully refundableReserve now, pay when you stay
Stay at this 3-star golf hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
The Ven at Embassy Row, Washington, D.C., a Tribute Portfolio Hotel
The Ven at Embassy Row, Washington, D.C., a Tribute Portfolio Hotel
4 out of 5
2015 Massachusetts Ave NW, Washington, DC
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Washington. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the helpful staff and the ...
The Ven at Embassy Row, Washington, D.C., a Tribute Portfolio Hotel
Sheraton Pentagon City Hotel
Sheraton Pentagon City Hotel
3.5 out of 5
900 S Orme St, Arlington, VA
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star business-friendly hotel in Arlington. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the breakfast ...
Sheraton Pentagon City Hotel
Days Inn by Wyndham Williamsburg Historic Area
Days Inn by Wyndham Williamsburg Historic Area
2.5 out of 5
706 Bypass Road, Williamsburg, VA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly motel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the clean rooms ...
Days Inn by Wyndham Williamsburg Historic Area
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.