The Best Romantic Hotels in Chesapeake, VA from AED 1,549 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

Coffee/tea maker, fridge, microwave, oven

1. Norfolk Beach Cottage Rental

East Ocean View

Jessie m.

AED 643

AED 1,549 total

includes taxes & fees

19 Oct - 20 Oct

4 bedrooms, iron/ironing board, travel crib, WiFi

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

Sandbridge

Dana H.

AED 1,358

AED 3,001 total

includes taxes & fees

20 Sep - 21 Sep

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Top Chesapeake Hotel Reviews

Holiday Inn & Suites Virginia Beach North Beach by IHG

8/10 Good

"Fabulous location and view from our oceanfront room! The mattress was very firm and uncomfortable. Front desk staff was excellent as well as Isle of Capri staff, housekeeping staff was just ok. We enjoyed all the restaurants, pools and the hot tub. We would stay again."

Hilton Vacation Club Ocean Beach Club Virginia Beach

10/10 Excellent

"Pros: Loved my stay, big spacious room with kitchen and balcony, very kid friendly and right on the boardwalk. Cons: The deposit was $200 and parking is across the street in a parking garage! Will definitely be back to visit soon!"

Sandcastle Resort On The Beach

8/10 Good

"Great balcony views Quiet at night Only complaints was how loud the toilet was when you flushed scared me to death the first time"

Hilton Virginia Beach Oceanfront

8/10 Good

"It was a very expensive night for a hotel that lacked any true luxury."

Schooner Inn

10/10 Excellent

"Convenient. Need to enforce no smoking policy. Shouldn’t be allowed to smoke on balconies and outside doors"

Oceans 2700

10/10 Excellent

"soon as you walked through the door we smelled bleach and the staff was very nice and helpful"

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 Lake Drummond. 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 Lake Drummond 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

Holiday Inn & Suites Virginia Beach North Beach by IHG

Hilton Vacation Club Ocean Beach Club Virginia Beach

Sandcastle Resort On The Beach

Hilton Virginia Beach Oceanfront

Schooner Inn

Oceans 2700

Frequently asked questions

Explore a world of travel with Expedia