Find Romantic Hotels in Chesapeake, VA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chesapeake Romantic Hotels

Tonight
2 May - 3 May
Tomorrow
3 May - 4 May
Next weekend
8 May - 10 May
In two weeks
15 May - 17 May

Our top choices for Chesapeake romantic hotels

Terrace/patio

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

❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views
Sandbridge
9.2 out of 10, Wonderful, (35 reviews)
"Excellent host! "
United States
Cindy S.
The price is AED 1,273
AED 2,829 total
includes taxes & fees
5 May - 6 May
❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views
Exterior

Spacious 2 BR Townhouse Walking Distance to the Beach and Boardwalk (410B)

Spacious 2 BR Townhouse Walking Distance to the Beach and Boardwalk (410B)
Northeast Virginia Beach
9.4 out of 10, Exceptional, (62 reviews)
"Great townhouse in a convenient location. It was the perfect place for weekend family getaway."
United States
Anonymous traveler
The price is AED 630
AED 2,625 total
includes taxes & fees
5 May - 6 May
Spacious 2 BR Townhouse Walking Distance to the Beach and Boardwalk (410B)
Outdoor dining

Ground Floor 2 BR Cottage Walking to Everything!

Ground Floor 2 BR Cottage Walking to Everything!
Northeast Virginia Beach
9.2 out of 10, Wonderful, (63 reviews)
"Great stay "
United States
Brendan M.
The price is AED 597
AED 2,243 total
includes taxes & fees
4 May - 5 May
Ground Floor 2 BR Cottage Walking to Everything!
Property grounds

Upstairs 1BR Beach Apartment in the Heart of the Vibe District - 5 Minute Stroll to Beach (508B)

Upstairs 1BR Beach Apartment in the Heart of the Vibe District - 5 Minute Stroll to Beach (508B)
Northeast Virginia Beach
9.2 out of 10, Wonderful, (39 reviews)
"This was a cute house. It was in a great location for our needs. There were plenty of restaurants and shops within walking distance as well as the beach. "
United States
Lisa P.
The price is AED 479
AED 1,914 total
includes taxes & fees
4 May - 5 May
Upstairs 1BR Beach Apartment in the Heart of the Vibe District - 5 Minute Stroll to Beach (508B)
Property grounds

2 BR, 2 Story Townhouse by the Beach (410A)

2 BR, 2 Story Townhouse by the Beach (410A)
Northeast Virginia Beach
9.4 out of 10, Exceptional, (71 reviews)
"The place was very clean, close to shops, gas stations, and the beach! We absolutely loved our stay here definitely would stay here again. The owners was nice to communicate back and forth with and answered instantly with anything you may need! Definitely a very clean and nice house to stay in!"
United States
Caitlyn W.
The price is AED 630
AED 2,625 total
includes taxes & fees
5 May - 6 May
2 BR, 2 Story Townhouse by the Beach (410A)
Exterior

Newly Refreshed 2 BR Townhouse Walking Distance to the Beach and Boardwalk (406A)

Newly Refreshed 2 BR Townhouse Walking Distance to the Beach and Boardwalk (406A)
Northeast Virginia Beach
9.4 out of 10, Exceptional, (73 reviews)
"Great location"
United States
Josh M.
The price is AED 630
AED 2,625 total
includes taxes & fees
5 May - 6 May
Newly Refreshed 2 BR Townhouse Walking Distance to the Beach and Boardwalk (406A)
Property grounds

VB Townhouse 2BR • Pet‑Friendly • Short Walk to Beach & Boardwalk (406B)

VB Townhouse 2BR • Pet‑Friendly • Short Walk to Beach & Boardwalk (406B)
Northeast Virginia Beach
9.6 out of 10, Exceptional, (117 reviews)
"We enjoyed our stay. The townhouse was clean and comfortable. Easy walking distance to restaurants and boardwalk."
United States
Deborah S.
The price is AED 719
AED 2,730 total
includes taxes & fees
10 May - 11 May
VB Townhouse 2BR • Pet‑Friendly • Short Walk to Beach & Boardwalk (406B)
Smart TV, fireplace, DVD player

Updated Condo | Short Stroll To VB Boardwalk

Updated Condo | Short Stroll To VB Boardwalk
Northeast Virginia Beach
9.4 out of 10, Exceptional, (45 reviews)
"Close to the beach and very clean!"
United States
Danielle C.
The price is AED 1,067
AED 3,500 total
includes taxes & fees
9 May - 10 May
Updated Condo | Short Stroll To VB Boardwalk
On the beach, beach towels

OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission

OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission
Northeast Virginia Beach
8.0 out of 10, Very Good, (15 reviews)
"Loved the location and the avtivitoes/events in the neighborhood."
United States
Smain K.
The price is AED 1,833
AED 2,761 total
includes taxes & fees
3 May - 4 May
OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission
Sun loungers, beach towels

Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental
East Ocean View
9.0 out of 10, Wonderful, (283 reviews)
"Great place loved it cozy beach house "
United States
JaLiylah M.
The price is AED 611
AED 1,469 total
includes taxes & fees
3 May - 4 May
Norfolk Beach Cottage Rental
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.
View all properties

Top Chesapeake Hotel Reviews

Schooner Inn

Schooner Inn

10/10 Excellent
"Good view and clean room. "
Michael 2-night trip
Posted 3 hours ago
Schooner Inn

Explore a world of travel with Expedia

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.