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

Chesapeake Vacation Rentals

  • 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 prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Chesapeake vacation rentals

A living room with a sofa, armchair, coffee table, and fireplace.

1. Nyakio Suite

Nyakio Suite
2.0 star property
Greenbrier
The price is ₩398,073
₩757,750 total
includes taxes & fees
Oct 11 - Oct 12
Nyakio Suite
A modern courtyard with white furniture, a central seating area, and a small lawn.

2. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (105 reviews)
"This property was like a home away from home. Rooms were spacious and location was good. Host was very friendly."
United States
Karen
The price is ₩160,216
₩183,993 total
includes taxes & fees
Oct 1 - Oct 2
stayAPT Suites Suffolk-Chesapeake
A multi-story building with balconies, a courtyard with seating, and a well-maintained lawn.

3. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
10.0 out of 10, Exceptional, (15 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
The price is ₩160,216
₩186,941 total
includes taxes & fees
Sep 17 - Sep 18
stayAPT Suites Hampton
A beach with a pier extending into the ocean, adjacent to a row of hotels with balconies overlooking the sea.

4. The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia
3.5 star property
Northeast Virginia Beach
8.2 out of 10, Very good, (1,668 reviews)
"Great stay"
United States
Denitra LaStacia
The price is ₩122,359
₩220,822 total
includes taxes & fees
Sep 29 - Sep 30
The Atrium Resort, Virginia Beach by Vacatia
An indoor swimming pool with clear glass ceilings, lounge chairs, and a view of the outside.

5. The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort
3.0 star property
Northeast Virginia Beach
7.6 out of 10, Good, (1,653 reviews)
"Everything was great, thank you so much!"
United States
Sarmiento
The price is ₩96,350
₩191,903 total
includes taxes & fees
Sep 30 - Oct 1
The Ocean Key Virginia Beach Resort
An outdoor seating area with wicker furniture and orange Adirondack chairs.

6. Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
4.0 star property
Northeast Virginia Beach
8.2 out of 10, Very good, (1,409 reviews)
"Wonderful family friendly hotel with beautiful ocean front view! Awesome balcony, great kitchenette and friendly staff. Will definitely be staying again!"
United States
craig
The price is ₩119,936
₩219,028 total
includes taxes & fees
Sep 29 - Sep 30
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
A two-story house with a white porch, a red door, and a small Christmas tree.

7. Angie's Guest Cottage

Angie's Guest Cottage
2.0 star property
Northeast Virginia Beach
8.4 out of 10, Very good, (243 reviews)
"This was our second time staying there. Location is wonderful. Owners are very friendly and accommodating. And the price was unmatched. Make sure to bring plates, utensils and cups."
United States
Bret
The price is ₩107,954
₩140,204 total
includes taxes & fees
Oct 1 - Oct 2
Angie's Guest Cottage
A modern house with a wooden exterior, a glass door, and a stone pathway leading to the entrance.

8. Private Virginia Beach Escape w/ Pool & Fire Pit!

Private Virginia Beach Escape w/ Pool & Fire Pit!
3.5 star property
Virginia Beach
The price is ₩285,426
₩626,430 total
includes taxes & fees
Sep 27 - Sep 28
Private Virginia Beach Escape w/ Pool & Fire Pit!
A spacious lounge area with a chandelier, sofas, and a round table.

9. Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
Downtown Newport News
7.4 out of 10, Good, (3 reviews)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
The price is ₩148,825
₩359,842 total
includes taxes & fees
Sep 17 - Sep 18
Ice Ice Baby Downtown Newport News
A spacious living room with a large window, a painting of a beach, and a ceiling fan.

10. 4BR Waterfront Penthouse Pool Views

4BR Waterfront Penthouse Pool Views
2.0 star property
Sandbridge
The price is ₩575,612
₩1,099,156 total
includes taxes & fees
Sep 17 - Sep 18
4BR Waterfront Penthouse Pool Views
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesapeake Hotel Reviews

Sandcastle Resort On The Beach

Sandcastle Resort On The Beach

10/10 Excellent
"We were very satisfied with everything and everyone"
Debra 2-night trip
Posted 3 hours ago
Sandcastle Resort On The Beach

Find out more about Chesapeake

Search for Vacation rentals in Chesapeake on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Chesapeake using one of the methods below:

  • View our selection of featured Vacation rentals in Chesapeake
  • Use the map to find apartments and other Vacation homes in the Chesapeake neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Chesapeake while they last

Look no further and take a look at our great range of rental properties in Chesapeake!

Frequently asked questions

Are there vacation rentals in Chesapeake?

Yes, there are vacation rentals in Chesapeake close to Broadmoor Play Area, or you can go with a more remote option if you're looking for a relaxing stay. Visitors like the array of shops and popular beaches in Chesapeake. While you're in the area, you can also enjoy the top-notch restaurants and live music.

How many vacation rentals are there in Chesapeake?

Expedia has 36 vacation rentals for your stay in Chesapeake.

What’s there to see and do in Chesapeake?

Family-friendly attractions include Broadmoor Play Area and Parkview Play Area, whereas Chesapeake City Park and Oak Grove Lake Park are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places like Naval Station Norfolk and Sandbridge Beach.

What’s a vacation rental in Chesapeake like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Chesapeake. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips.