Search for Cheap Deals on
Hotels in Chesapeake

Choose from 3451 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! (1,002 reviews)
5 star

Reviewed on Mar 24, 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 ...
8.8/10 Excellent! (1,001 reviews)
The hotel was clean, quiet, and it suited the purpose for our stay.

Reviewed on Mar 25, 2026

Comfort Suites Chesapeake - Norfolk
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
1570 CROSSWAYS BLVD Chesapeake VA
  • 5 min walk from Greenbrier Mall
Stay at this hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.6/10 Excellent! (408 reviews)
Everything was great! The room and bathroom were neat and clean. The bed was comfortable. Breakfast had many options, more than I was expecting. Check in was a breeze. It was very quiet. The location was perfect—very close to the freeway and there were restaurants very close. The only con I have ...

Reviewed on Mar 22, 2026

TRU by Hilton Chesapeake, VA
Holiday Inn Express Chesapeake - Norfolk by IHG

Holiday Inn Express Chesapeake - Norfolk by IHG

2.5 out of 5
721 Conference Center Drive Chesapeake VA
  • 16 min walk from Greenbrier Mall
Stay at this hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (1,000 reviews)
Holiday Inn Express Chesapeake - Norfolk is a clean and comfortable hotel. Their staff was very good. My family of four was very comfortable.

Reviewed on Mar 21, 2026

Holiday Inn Express Chesapeake - Norfolk by IHG
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 ...
8.4/10 Very Good! (2,512 reviews)
Clean. Great location. I wish the indoor pool was heated since our stay was in March.

Reviewed on Mar 25, 2026

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

3 out of 5
1101 Atlantic Ave Virginia Beach VA
  • 29 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 helpful staff and the clean rooms ...
8.4/10 Very Good! (1,229 reviews)
Could not stay in assigned room, or a replacement. Dirty, soiled, cigarette smoke and marijuana smell. Communication with staff was awful. Checked out and went to another hotel. Worst experience!

Reviewed on Mar 26, 2026

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
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 ...
8.4/10 Very Good! (1,273 reviews)
The staff was very friendly upon arrival. With it being marathon weekend, they were super helpful providing details on road closures. The room was clean and spacious. My only complaint was some mold on the bottom of the shower curtain. Aside from that, everything else was clean upon arrival. The ...

Reviewed on Mar 24, 2026

Hilton Vacation Club Ocean Beach Club Virginia Beach
Schooner Inn

Schooner Inn

2 out of 5
215 Atlantic Ave Virginia Beach VA
  • 28 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 helpful staff and the convenient ...
8.8/10 Excellent! (3,743 reviews)
Tim was clean, jets in hot tub worked, patio clean. It’s obviously older, but is clean, comfortable, the elevators always work and staff is always cordial and courteous! I’m a return visitor because it’s quiet at the end of the beach near the inlet and we love the hot tub!

Reviewed on Mar 26, 2026

Schooner Inn
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 ...
9.4/10 Exceptional! (2,213 reviews)
Great stay.

Reviewed on Mar 25, 2026

Hyatt Place Virginia Beach / Oceanfront
Hilton Virginia Beach Oceanfront

Hilton Virginia Beach Oceanfront

4 out of 5
3001 Atlantic Ave Virginia Beach VA
  • 30 min drive from Greenbrier Mall
Book a stay at this beach resort in Virginia Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,116 reviews)
Great location, nice place.

Reviewed on Mar 24, 2026

Hilton Virginia Beach Oceanfront
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 ...
8.4/10 Very Good! (1,023 reviews)
Just passing through

Reviewed on Mar 25, 2026

Hilton Vacation Club Oceanaire Virginia Beach
The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3 out of 5
424 Atlantic Avenue Virginia Beach VA
  • 28 min drive from Greenbrier Mall
Stay at this aparthotel in Virginia Beach. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our ...
7.8/10 Good! (1,479 reviews)
Absolutely lovely! The view, the pool, the staff were polite and informative 10/10 highly recommend

Reviewed on Mar 26, 2026

The Ocean Key Virginia Beach Resort
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 3,451 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 $82. 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 $82.

How many hotels are there in Chesapeake?

With over 3,451 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 $82.

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.