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Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Chesapeake vacation rentals

Interior
The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The Speakeasy Downtown Newport News
Beach nearby
The Atrium Resort, Virginia Beach by Vacatia

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, (1,479 reviews)
"Staff was very nice and attentive!"
United States
Darryl
The price is NT$14,497
NT$18,550 total
includes taxes & fees
Jan 23 - Jan 24
The Atrium Resort, Virginia Beach by Vacatia
Terrace/patio
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
3.0 star property
Northeast Virginia Beach
8.2 out of 10, Very Good, (1,180 reviews)
"The room was very clean and nice! Enjoyed the ocean view. We had nothing but positive interactions with the staff. It was very easy to use all the wonderful facilities such as the pool hot tub and the sauna."
United States
Bonnie
The price is NT$3,685
NT$6,117 total
includes taxes & fees
Jan 23 - Jan 24
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
House (4 Bedrooms) | Interior
Centrally Located Hampton Roads Home w/ Game Room!

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$8,306
NT$19,533 total
includes taxes & fees
Jan 12 - Jan 13
Centrally Located Hampton Roads Home w/ Game Room!
Indoor pool
The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort
3.0 star property
Northeast Virginia Beach
7.8 out of 10, Good, (1,457 reviews)
"Great stay, great recovery from other ocean front places! Great room for a family or girls sleepover!!"
United States
Aja-Brianne A
The Ocean Key Virginia Beach Resort
Terrace/patio
stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
2.5 star property
Suffolk
9.4 out of 10, Exceptional, (58 reviews)
"Beautiful and clean. The staff was amazing. "
United States
Robin
The price is NT$3,758
NT$4,316 total
includes taxes & fees
Jan 18 - Jan 19
stayAPT Suites Suffolk-Chesapeake
Property entrance
Angie's Guest Cottage

Angie's Guest Cottage

Angie's Guest Cottage
2.0 star property
Northeast Virginia Beach
8.6 out of 10, Excellent, (225 reviews)
"The best place I have ever stayed at"
United States
Robin
The price is NT$2,501
NT$3,249 total
includes taxes & fees
Jan 11 - Jan 12
Angie's Guest Cottage
Studio | Interior
Beach Side Studio #3 Apts by RedAwning

Beach Side Studio #3 Apts by RedAwning

Beach Side Studio #3 Apts by RedAwning
3.0 star property
Cottage Line
The price is NT$2,276
NT$6,169 total
includes taxes & fees
Feb 5 - Feb 6
Beach Side Studio #3 Apts by RedAwning
On the beach, beach towels
Buckroe Bungalow Buckroe Bungalow Escape to the Beach 2mins Away

Buckroe Bungalow Buckroe Bungalow Escape to the Beach 2mins Away

Buckroe Bungalow Buckroe Bungalow Escape to the Beach 2mins Away
2.0 star property
Hampton
The price is NT$2,669
NT$10,949 total
includes taxes & fees
Jan 11 - Jan 12
Buckroe Bungalow Buckroe Bungalow Escape to the Beach 2mins Away
Interior
Penthouse By The Sea Huge Home w Amazing Views

Penthouse By The Sea Huge Home w Amazing Views

Penthouse By The Sea Huge Home w Amazing Views
2.0 star property
Sandbridge
The price is NT$9,106
NT$22,621 total
includes taxes & fees
Jan 11 - Jan 12
Penthouse By The Sea Huge Home w Amazing 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.
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Top Chesapeake Hotel Reviews

La Quinta Inn & Suites by Wyndham Virginia Beach

La Quinta Inn & Suites by Wyndham Virginia Beach

10/10 Excellent
"Vyron and Deepa were fantastic! Customer service was on point with everything. Breakfast was good and the rooms were clean. I will recommend family and friends to this hotel!"
Alexandre 1-night trip
Posted 3 days ago
La Quinta Inn & Suites by Wyndham 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 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 39 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 Oak Grove Lake Park and Chesapeake Arboretum are a couple of great spots to enjoy the outdoors. Greenbrier Mall and Chesapeake Conference Center are other places to visit while you're in town.

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.