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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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$8,926
NT$17,327 total
includes taxes & fees
Aug 31 - Sep 1
Nyakio Suite
A beach with a pier extending into the ocean, adjacent to a row of hotels with balconies overlooking the sea.

2. 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, (1,643 reviews)
"Great stay"
United States
Denitra LaStacia
The price is NT$2,698
NT$4,984 total
includes taxes & fees
Sep 14 - Sep 15
The Atrium Resort, Virginia Beach by Vacatia
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, (8 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
The price is NT$3,763
NT$4,390 total
includes taxes & fees
Aug 30 - Aug 31
stayAPT Suites Hampton
A modern courtyard with white furniture, a central seating area, and a small lawn.

4. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (103 reviews)
"Perfect! Will stay again and will look for this brand in my future travels."
United States
Melissa
The price is NT$3,763
NT$4,321 total
includes taxes & fees
Sep 1 - Sep 2
stayAPT Suites Suffolk-Chesapeake
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, (1,638 reviews)
"Staff was nice"
United States
Adrienne
The price is NT$2,180
NT$4,388 total
includes taxes & fees
Sep 14 - Sep 15
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, (1,384 reviews)
"Beach view great, clean room staff very helpful"
United States
James
The price is NT$2,713
NT$5,001 total
includes taxes & fees
Sep 15 - Sep 16
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)
"First, there was a $250 deposit, which was more than expected for a 2 night stay. It was returned within 48 hours of checkout. The staff was nice. The room had cheap wicker furniture and beds were more like cots. The upstairs room we were in had a huge roof slant and had to duck to use the bathroom and sleep with my head towards the headboard to fit. It had a kitchen but had no pots, pans, plates, silverware, cookware, or anything useful to prepare meals. The location was great for dining, the...
United States
DE
The price is NT$2,748
NT$3,532 total
includes taxes & fees
Sep 7 - Sep 8
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 NT$6,703
NT$14,712 total
includes taxes & fees
Sep 12 - Sep 13
Private Virginia Beach Escape w/ Pool & Fire Pit!
A modern living room with a large window, a flat-screen TV, a white desk, and a blue sofa.

9. The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is NT$4,245
NT$9,069 total
includes taxes & fees
Aug 30 - Aug 31
The Speakeasy Downtown Newport News
A beach with a wooden fence, a sandy path, and a few beach chairs.

10. Beach Front On The Bay 3 Bedroom Bungalow

Beach Front On The Bay 3 Bedroom Bungalow
3.0 star property
Cottage Park
10.0 out of 10, Exceptional, (1 review)
"This was excellent for my plans. The location was amazing and the beach access top tier. I would definitely rent this property again!"
United States
Simone
The price is NT$13,711
NT$21,961 total
includes taxes & fees
Sep 1 - Sep 2
Beach Front On The Bay 3 Bedroom Bungalow
A spacious lounge area with a chandelier, sofas, and a round table.

11. 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 NT$4,276
NT$9,115 total
includes taxes & fees
Sep 2 - Sep 3
Ice Ice Baby Downtown Newport News
A pool table in a room with wooden floors, a fireplace, and a window with purple curtains.

12. 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$9,201
NT$19,572 total
includes taxes & fees
Sep 1 - Sep 2
Centrally Located Hampton Roads Home w/ Game Room!
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

Sandcastle Resort On The Beach

Sandcastle Resort On The Beach

8/10 Good
"Beach view was great. Staff was great"
Fran 4-night trip
Posted less than an hour ago
Sandcastle Resort On The 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:

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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 Chesapeake Arboretum, 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 37 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.