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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! (1,005 reviews)
The room seemed to be clean, but the towels had hair on them and the water pressure in the shower was very poor.

Reviewed on Mar 14, 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! (1,006 reviews)
Very polite , the room was clean , awesome job

Reviewed on Mar 14, 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 ...
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! (1,001 reviews)
Don't miss out on the tasty complimentary breakfast to start your day!

Reviewed on Mar 8, 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! (2,509 reviews)
Beds-comfortable. Room’s clean except the patio which had water dripping from above and soil from the lawn. This could be prevented by edging the cement edge. The breakfast was great. Typical hotel fare but the staff was amazingly friendly and on top of service. Rainy was super nice. The garage parking ...

Reviewed on Mar 14, 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! (1,214 reviews)
We had a room on the 7th floor right on the boardwalk with a perfect view of the ocean. The ice and vending machines were directly across from our room and they have a nice club/restaurant on the ground floor that leads right out to the boardwalk. The only downside is the parking is around the block ...

Reviewed on Mar 13, 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! (1,255 reviews)
Our stay was amazing! Staff was extremely friendly and courteous. Our room was clean . We had a city view but that was perfectly fine as we were right on the beach. Lastly our only complaint was the size of the bed. We booked for a queen and the bed was definitely a full size bed. Other than that ...

Reviewed on Mar 13, 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! (3,753 reviews)
Great place loved the nostalgia

Reviewed on Mar 14, 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! (2,200 reviews)
Nomas espero mi depósito gracias

Reviewed on Mar 13, 2026

Hyatt Place 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! (1,010 reviews)
Everything

Reviewed on Mar 11, 2026

Hilton Vacation Club Oceanaire Virginia Beach
Moxy Virginia Beach Oceanfront

Moxy Virginia Beach Oceanfront

3 out of 5
1201 Atlantic Ave 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 helpful staff and the clean ...
Moxy Virginia Beach Oceanfront
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 ...
9/10 Wonderful! (1,001 reviews)
The location is great, right on the beach which is definitely the best part of this hotel. However, the overall experience was just okay — nothing that really wowed me about the room. One thing that stood out was seeing a rat outside the back door near the beach bar area, which was concerning. I ...

Reviewed on Mar 11, 2026

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

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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 3,457 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 3,457 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.