Photo by Sarah Chiricosta
Search Hotels with Pool in Chesapeake
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check availability on Chesapeake Hotels with Pool
Our top choices for Chesapeake hotels with a pool

8.6 out of 10, Excellent, (1004)
The price is ฿2,114
฿2,494 total
includes taxes & fees
21 Dec - 22 Dec

Holiday Inn Express Hotel & Suites Chesapeake by IHG
Holiday Inn Express Hotel & Suites Chesapeake by IHGWestern Branch North
7.4 out of 10, Good, (797)
The price is ฿2,644
฿3,104 total
includes taxes & fees
21 Dec - 22 Dec

8.0 out of 10, Very good, (1004)
The price is ฿2,493
฿2,930 total
includes taxes & fees
20 Dec - 21 Dec

Hampton Inn & Suites Chesapeake-Battlefield Blvd.
Hampton Inn & Suites Chesapeake-Battlefield Blvd.Greenbrier West
8.0 out of 10, Very good, (1001)
The price is ฿2,524
฿2,966 total
includes taxes & fees
4 Jan - 5 Jan 2026

SpringHill Suites by Marriott Chesapeake Greenbrier
SpringHill Suites by Marriott Chesapeake GreenbrierGreenbrier East
8.2 out of 10, Very good, (1008)
The price is ฿2,707
฿3,176 total
includes taxes & fees
1 Jan - 2 Jan 2026

Fairfield Inn and Suites By Marriott Chesapeake
Fairfield Inn and Suites By Marriott ChesapeakeGreenbrier East
9.0 out of 10, Wonderful, (1002)
The price is ฿2,676
฿3,140 total
includes taxes & fees
21 Dec - 22 Dec

8.4 out of 10, Very good, (1004)
The price is ฿2,776
฿3,256 total
includes taxes & fees
4 Jan - 5 Jan 2026
The price is ฿2,618
฿3,074 total
includes taxes & fees
4 Jan - 5 Jan 2026
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.
Hotels with pools and free breakfast in Chesapeake

Holiday Inn Express Chesapeake - Norfolk by IHG
Holiday Inn Express Chesapeake - Norfolk by IHGChesapeake
8.6 out of 10, Excellent, (1002)
The price is ฿2,487
฿2,923 total
includes taxes & fees
21 Dec - 22 Dec
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.
Top Chesapeake Hotel Reviews

Hilton Vacation Club Oceanaire Virginia Beach
10/10 Excellent











































