Search for Cheap Deals on
Hotels in Chesapeake

Check Last Minute Chesapeake Hotel Deals

Tonight Feb 22 - Feb 23Next weekend Feb 27 - Mar 1

Choose from 3396 Chesapeake Hotel Deals

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

2.5 out of 5
817 Greenbrier Circle Chesapeake VA
  • 16 min walk from Greenbrier Mall
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,008 reviews)
Everything was first-class!

Reviewed on Feb 15, 2026

Wingate by Wyndham Chesapeake
Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd Chesapeake VA
  • 9 min walk from Greenbrier Mall
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,012 reviews)
Room was very clean and spacious. Everyone was very nice from front desk to breakfast and cleaning peraonnel. I did like the red velvet waffles w hearts for Valentines weekend. Its a continental.breakfast afterall Close to stores. Love pops diner. Id come back and do recommend. Area was tranquil

Reviewed on Feb 16, 2026

Comfort Suites Chesapeake - Norfolk
Fairfield Inn and Suites By Marriott Chesapeake

Fairfield Inn and Suites By Marriott Chesapeake

2.5 out of 5
1560 Crossways Blvd Chesapeake VA
  • 9 min walk from Greenbrier Mall
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,000 reviews)
Room was clean, staff very friendly. Bed was soft. Bathroom clean . Will return

Reviewed on Feb 15, 2026

Fairfield Inn and Suites By Marriott Chesapeake
WoodSpring Suites Chesapeake - Norfolk South

WoodSpring Suites Chesapeake - Norfolk South

2.5 out of 5
137 Kempsville Rd Chesapeake VA
  • 8 min drive from Greenbrier Mall
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the helpful staff in our ...
5.8/10 (659 reviews)
Staff was really welcoming and nice.. I plan on returning.

Reviewed on Dec 8, 2025

WoodSpring Suites Chesapeake - Norfolk South
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

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

3 out of 5
1801 Atlantic Ave Virginia Beach VA
  • 29 min drive from Greenbrier Mall
Book a stay at this beach hotel in Virginia Beach. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the breakfast and the helpful staff ...
8.2/10 Very Good! (2,509 reviews)
Great hotel

Reviewed on Feb 19, 2026

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
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
  • 30 min drive from Greenbrier Mall
Book a stay at this 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 ...
8.2/10 Very Good! (1,224 reviews)
Nice room. Excellent view of the boardwalk. Would book again.

Reviewed on Feb 18, 2026

Hilton Vacation Club Ocean Beach Club Virginia Beach
Hilton Vacation Club Oceanaire Virginia Beach

Hilton Vacation Club Oceanaire Virginia Beach

3.5 out of 5
3421 Atlantic Ave Virginia Beach VA
  • 30 min drive from Greenbrier Mall
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, a beach locale, and a fitness center. Our guests praise the pool and the helpful staff in ...
8.2/10 Very Good! (1,010 reviews)
Very nice

Reviewed on Feb 18, 2026

Hilton Vacation Club Oceanaire Virginia Beach
Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

3 out of 5
3601 ATLANTIC AVENUE Virginia Beach VA
  • 30 min drive from Greenbrier Mall
Book a stay at this beach hotel in Virginia Beach. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (2,197 reviews)
Room was updated and clean! Beds were comfortable!

Reviewed on Feb 16, 2026

Hyatt Place Virginia Beach / Oceanfront
Hyatt Place Hampton Convention Center

Hyatt Place Hampton Convention Center

3 out of 5
1905 Coliseum Dr Hampton VA
  • 47 min drive from Greenbrier Mall
Book a stay at this business-friendly hotel in Hampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,345 reviews)
The room was clean, spotless, and comfortable. I needed a microwave and the staff got it to me quickly. There was noise above my room and that handled promptly. Enjoyed my stay.

Reviewed on Feb 20, 2026

Hyatt Place Hampton Convention Center
Holiday Inn Va Beach-Oceanside (21st St) by IHG

Holiday Inn Va Beach-Oceanside (21st St) by IHG

3 out of 5
2101 Atlantic Avenue Virginia Beach VA
  • 29 min drive from Greenbrier Mall
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (1,003 reviews)
Great staff and location

Reviewed on Feb 16, 2026

Holiday Inn Va Beach-Oceanside (21st St) by IHG
Norfolk Waterside Marriott

Norfolk Waterside Marriott

3.5 out of 5
235 E Main St Norfolk VA
  • 13 min drive from Greenbrier Mall
Book a stay at this business-friendly hotel in Norfolk. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,005 reviews)
Staff were great

Reviewed on Feb 21, 2026

Norfolk Waterside Marriott
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave Virginia Beach VA
  • 31 min drive from Greenbrier Mall
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff ...
7.6/10 Good! (1,807 reviews)
Stayed there several times during our travels south. Great location, we have dog but not too many guests with pets, this time I made mistake and booked 1 night when we needed 2! Texted, tried to change, when we arrived told front desk. She insisted we had to check in b4 she could check in Addtl night! ...

Reviewed on Feb 15, 2026

Wyndham Virginia Beach Oceanfront
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.

Find cheap hotels in Chesapeake

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Chesapeake hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Chesapeake.

Choosing the right hotel in Virginia has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Chesapeake’s 3,396 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $81. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Chesapeake hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Chesapeake. No matter your reason for visiting Chesapeake, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Chesapeake hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Chesapeake for as low as $81.

How many hotels are there in Chesapeake?

With over 3,396 hotels in Chesapeake, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $81.

How to find cheap car rentals in Chesapeake?

Finding a cheap car rental deal in Chesapeake is as easy as scoring cheap hotels in Chesapeake. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.