Find Romantic Hotels in Chesapeake, VA

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Check availability on Chesapeake Romantic Hotels

Next weekend
5 Jun - 7 Jun
In two weeks
12 Jun - 14 Jun

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 2,495
AED 4,397 total
includes taxes & fees
17 Jun - 18 Jun
❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views
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 668
AED 2,325 total
includes taxes & fees
31 May - 1 Jun
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 966
AED 2,575 total
includes taxes & fees
7 Jun - 8 Jun
Upstairs 1BR Beach Apartment in the Heart of the Vibe District - 5 Minute Stroll to Beach (508B)
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, (65 reviews)
"Great townhouse in a convenient location. It was the perfect place for weekend family getaway."
United States
Anonymous traveler
The price is AED 1,613
AED 3,967 total
includes taxes & fees
2 Jun - 3 Jun
Spacious 2 BR Townhouse Walking Distance to the Beach and Boardwalk (410B)
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, (118 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 986
AED 3,097 total
includes taxes & fees
31 May - 1 Jun
VB Townhouse 2BR • Pet‑Friendly • Short Walk to Beach & Boardwalk (406B)
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 1,525
AED 3,839 total
includes taxes & fees
1 Jun - 2 Jun
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 1,588
AED 3,975 total
includes taxes & fees
1 Jun - 2 Jun
Newly Refreshed 2 BR Townhouse Walking Distance to the Beach and Boardwalk (406A)
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
31 May - 1 Jun
OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission
On the beach

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Willoughby Spit
8.8 out of 10, Excellent, (74 reviews)
"We love this little quiet beach house "
United States
Annie N.
The price is AED 731
AED 1,299 total
includes taxes & fees
10 Jun - 11 Jun
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
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

Hampton Inn Virginia Beach-Oceanfront South

Hampton Inn Virginia Beach-Oceanfront South

2/10 Terrible
"The whole property smells like wet sewer. No real lobby and seating for waiting customers. Would not recommend stay at your own risk. Sounds like a dog pound when you get on your floor."
Edgar 4-night trip
Posted 1 hour ago
Hampton Inn Virginia Beach-Oceanfront South

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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.