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

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Check availability on Chesapeake Romantic Hotels

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Chesapeake romantic hotels

A kitchen with white cabinetry, a granite countertop, and a dining area with a staircase.

1. Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental
East Ocean View
9.0 out of 10, Wonderful, (306 reviews)
"Great space, close to a great beach, loved that it’s pet friendly with space for our dog to run around, a good park within walking distance, and host was very communicative. Loved our time here!"
United States
Anonymous traveler
The price is AED 643
AED 1,549 total
includes taxes & fees
3 Nov - 4 Nov
Norfolk Beach Cottage Rental
A view from a room with a large window overlooking a deck with wicker furniture and a view of a distant building by the water.

2. 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
Norfolk
8.8 out of 10, Excellent, (92 reviews)
"Nice small rustic cottage right on the beach. Enjoyed my time there."
United States
Mary W.
The price is AED 493
AED 996 total
includes taxes & fees
28 Oct - 29 Oct
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
A balcony with turquoise chairs and a view of a parking lot and buildings.

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

Penthouse By The Sea | Huge Home w/ Amazing Views
Sandbridge
9.0 out of 10, Wonderful, (43 reviews)
"Was use to ocean front beach house, all the codes and elevators took some getting use to.Loved the space in the condo and convenience of the store and restaurant across the street."
United States
Dana H.
The price is AED 933
AED 2,532 total
includes taxes & fees
28 Oct - 29 Oct
Penthouse By The Sea | Huge Home w/ Amazing Views
A spacious room with wooden floors, a balcony with a rope barrier, and a large window overlooking the outside.

4. WHO IS READY FOR SUNSHINE AND SAND?! PACK YOUR SENSE OF ADVENTURE & COME VISIT!

WHO IS READY FOR SUNSHINE AND SAND?! PACK YOUR SENSE OF ADVENTURE & COME VISIT!
Corolla
9.4 out of 10, Exceptional, (36 reviews)
"Great location! Very private! Hot tub and pool were great! Saw ponies everyday but they always left “presents”!"
United States
Greta H.
The price is AED 973
AED 1,938 total
includes taxes & fees
2 Nov - 3 Nov
WHO IS READY FOR SUNSHINE AND SAND?! PACK YOUR SENSE OF ADVENTURE & COME VISIT!
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.
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Top Chesapeake Hotel Reviews

Hilton Vacation Club Oceanaire Virginia Beach

Hilton Vacation Club Oceanaire Virginia Beach

10/10 Excellent
"Staff were nice and helpful. The room was great with everything we needed for the weekend to include cell phone chargers. We also enjoyed the pool and hot tub."
Christian 3-night trip
Posted 2 hours ago
Hilton Vacation Club Oceanaire Virginia Beach

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 Veterans' Memorial. 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 Veterans' Memorial 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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