A golf course, a large building complex, and a marina by a river.

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Check availability on Chesapeake Romantic Hotels

Tonight
Sep 24 - Sep 25
Tomorrow
Sep 25 - Sep 26
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Top Chesapeake Hotel Reviews

Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

10/10 Excellent
"The hotel and room were really nice, decent price and everyone was so friendly, the desk clerk, the maintenance workers, the sweet ladies in the restaurant, even the other guests. Definitely would stay again!!"
Tim 2-night trip
Posted 14 hours ago
Wyndham Virginia Beach Oceanfront
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

8/10 Good
"Room was spacious and comfortable. Balcony ocean view was perfect. Parking was atrocious. Only a dozen spots with only 2 handicapped spots. Otherwise it was a 2 block walk to park in a reserved lot. No breakfast available but bar attached had really good food and bar servers were great. Very convenient to nice restaurants. Hotel needs new room carpets. Mattresses could use an update too."
Susan 4-night trip
Posted 15 hours ago
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
Hilton Vacation Club Ocean Beach Club Virginia Beach

Hilton Vacation Club Ocean Beach Club Virginia Beach

8/10 Good
"Excellent location"
Jonathan 1-night trip
Posted 16 hours ago
Hilton Vacation Club Ocean Beach Club Virginia Beach
Holiday Inn Va Beach-Oceanside (21st St) by IHG

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

10/10 Excellent
"Staff very friendly and helpful. Rooms clean and up to date. Beds comfortable. Above average media hookups."
John 1-night trip
Posted 19 hours ago
Holiday Inn Va Beach-Oceanside (21st St) by IHG
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

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

8/10 Good
"Nice room with beach view. Clean and tidy. Wasn’t keen on the hotel situation being attached to a car park. Felt unsafe at times."
CAROLE 2-night trip
Posted 23 hours ago
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
Ocean Resort

Ocean Resort

8/10 Good
"Over all had a great stay. 8th floor air conditioners had condensation draining onto the balcony, No coffee pot but had the coffee and condiments. Staff was friendly and courtious. I would definitely stay again. Third year in row staying here for air show and vaction."
tim 3-night trip
Posted 2 days ago
Ocean Resort

Frequently asked questions

Searching for romantic hotels in Chesapeake?
Are you looking for a romantic escape? Our guests also love Chesapeake for its major shopping area, array of dining options, and sporting events. You might consider checking out some of the nearby sights and attractions such as Greenbrier Mall, Chesapeake Square Mall, or Northwest River Park and Campground. If you'd like to stay close to a certain attraction, you can sort properties by neighborhood or distance to top landmarks, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Chesapeake?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Chesapeake: The hottest months are usually July and August with an average temp of 77°F, while the coldest months are January and February with an average of 45°F. Average annual precipitation for Chesapeake is 54 inches.
What is there to do in Chesapeake?
There's nothing better than experiencing a new destination with your sweetheart, so consider checking out all that Chesapeake has to offer. If you're hoping to see some of the area's cultural attractions, you'll enjoy Chesapeake for its shopping, live music, and theater scene. You might think about stopping by Greenbrier Mall, Chesapeake Square Mall, or Northwest River Park and Campground while you're seeing the sights.
What's the best way to get to Chesapeake and around town during my romantic getaway?
These transportation options in Chesapeake might help your romantic getaway go off without a hitch: To get to Chesapeake, book a flight to Norfolk Intl. Airport (ORF), which is the closest major airport, located 10.1 mi (16.3 km) from the city center. If you'd like to explore around the area, consider renting a car to take in more sights.

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