The Best Romantic Hotels in Chesapeake, VA from AED 1,503 in 2026

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

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Our top choices for Chesapeake romantic hotels

1. Norfolk Beach Cottage Rental

East Ocean View

Penny H.

AED 614

AED 1,503 total

includes taxes & fees

15 Sep - 16 Sep

2. ❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views

Sandbridge

Cindy S.

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Top Chesapeake Hotel Reviews

Schooner Inn

10/10 Excellent

"We were able to check in early, and the pool and room were in great condition."

Sandcastle Resort On The Beach

8/10 Good

"Location is perfect, has everything you could possibly want at the property, groceries, alcohol, clothes, beach items, rental items and restaurants Down side was one very rude front desk women but there were also a couple very nice and helpful Especially the younger man with the big hair😊.Elevators were either broken or very slow and it wasn’t even busy. I asked for housekeeping and they never showed up and I had to go to the desk to change towels. Never once was there house keeping on our floor that I saw."

Wyndham Virginia Beach Oceanfront

10/10 Excellent

"Oceanfront, great quiet beach, staff were friendly, definitely worth the price."

Hilton Vacation Club Ocean Beach Club Virginia Beach

8/10 Good

"Always love the pools, especially the 21 and over pool. Outside pools seemed a little too dirty. Staff was great! Room was clean but poorly maintained and stocked. Only had a partial roll out of toilet paper and paper towels. Took too long to get the TP. No ice bucket, no dish drainer. Lamp was not working and outlet in the kitchen area wasn’t working. Overall decent experience but did get tired of calling for things."

Oceans 2700

10/10 Excellent

"One of my fave places to stay when I come to the beach! The staff is always super friendly and helpful."

Crowne Plaza Virginia Beach Town Center by IHG

10/10 Excellent

"Property was very nice and well kept. The Kascade Restaurant on the Lobby level was fantastic."

Ocean Resort

10/10 Excellent

"My favorite place to stay i stay there every time I go to the beach staff is like family ill be back in October"

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 Chesapeake Arboretum. 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 Chesapeake Arboretum 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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Norfolk Vacations

Find Romantic Hotels in Chesapeake, VA

Change your mind

Treat yourself

Be picky

Check availability on Chesapeake Romantic Hotels

Our top choices for Chesapeake romantic hotels

1. Norfolk Beach Cottage Rental

2. ❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views

Top Chesapeake Hotel Reviews

Schooner Inn

Sandcastle Resort On The Beach

Wyndham Virginia Beach Oceanfront

Hilton Vacation Club Ocean Beach Club Virginia Beach

Oceans 2700

Crowne Plaza Virginia Beach Town Center by IHG

Ocean Resort

Frequently asked questions

Explore a world of travel with Expedia