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

Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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 NT$9,509
NT$18,101 total
includes taxes & fees
Oct 15 - Oct 16
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, (110 reviews)
"Theophilus was great at check in. Amazing customer service, quick check-in. The place was clean, the rooms were very clean. The overall atmosphere was great. I will definitely stay here again."
United States
Tarina
The price is NT$3,799
NT$4,363 total
includes taxes & fees
Oct 19 - Oct 20
stayAPT Suites Suffolk-Chesapeake
An outdoor seating area with wicker furniture and orange Adirondack chairs.

3. 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, (1,441 reviews)
"Great stay"
United States
Nancy
The price is NT$4,070
NT$6,594 total
includes taxes & fees
Nov 10 - Nov 11
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
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, (1,706 reviews)
"Great stay"
United States
Denitra LaStacia
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, (1,681 reviews)
"The room was nice and spacious. The hot tub wasn't working. Overall a great place to stay."
United States
Sharon
The price is NT$2,951
NT$3,468 total
includes taxes & fees
Oct 27 - Oct 28
The Ocean Key Virginia Beach Resort
A multi-story building with balconies, a courtyard with seating, and a well-maintained lawn.

6. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.4 out of 10, Exceptional, (28 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
The price is NT$3,799
NT$4,433 total
includes taxes & fees
Oct 15 - Oct 16
stayAPT Suites Hampton
A pool table in a room with wooden floors, a fireplace, and a window with purple curtains.

7. Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
The price is NT$9,359
NT$19,908 total
includes taxes & fees
Nov 5 - Nov 6
Centrally Located Hampton Roads Home w/ Game Room!
A two-story house with a white porch, a red door, and a small Christmas tree.

8. Angie's Guest Cottage

Angie's Guest Cottage
2.0 star property
Northeast Virginia Beach
8.4 out of 10, Very good, (249 reviews)
"Not a top of the line hotel, but it was clean, good location, and it served our needs. We would definitely stay here again."
United States
Cheryl
The price is NT$2,528
NT$3,284 total
includes taxes & fees
Oct 18 - Oct 19
Angie's Guest Cottage
A wooden deck with outdoor furniture, including a table with pastries and a vase of flowers.

9. 508 A The Shore Break Cottage

508 A The Shore Break Cottage
3.0 star property
Northeast Virginia Beach
508 A The Shore Break Cottage
A modern house with a wooden exterior, a glass door, and a stone pathway leading to the entrance.

10. 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 NT$6,768
NT$16,829 total
includes taxes & fees
Oct 27 - Oct 28
Private Virginia Beach Escape w/ Pool & Fire Pit!
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
"Easy and kind check in! Prime location! Right outside there were kids playground right on the beach and wonderful eateries. The staff the ambiance the pool the room was exceptional!!! 5 star!"
David 1-night trip
Posted 3 hours ago
Hilton Vacation Club Oceanaire Virginia Beach

Find out more about Chesapeake

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

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