Compare Chesapeake Vacation Rentals

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Chesapeake Rentals

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake

2.5 out of 5
5961 Harbour View Blvd Suffolk VA
Free Cancellation
Reserve now, pay when you stay
11.46 mi from city center
$119 nightly
The price is $137 total per night
$137 total
Apr 27 - Apr 28
Total with taxes and fees
Guests staying at stayAPT Suites Suffolk-Chesapeake enjoy free WiFi in public areas, laundry facilities, and a vending machine. If you drive, take advantage of free parking. This smoke-free aparthotel also has barbecue grills.
Kitchen
Parking included
Nantucket Charm | 280 ft from the Beach | Private Pool

Nantucket Charm | 280 ft from the Beach | Private Pool

Virginia Beach VA
19.32 mi from city center
At this vacation home, guests have access to an arcade/game room, laundry facilities, and barbecue grills.
Pool
Kitchen
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

Norfolk VA
13.4 mi from city center
$236 nightly
The price is $274 total per night
$274 total
Apr 13 - Apr 14
Total with taxes and fees
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
The Art Door Duplex only minutes from beach

The Art Door Duplex only minutes from beach

Virginia Beach VA
15.04 mi from city center
$196 nightly
The price is $227 total per night
$227 total
Apr 13 - Apr 14
Total with taxes and fees
Guests of this vacation home have access to designated smoking areas.
Pet friendly
Air conditioning
The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3 out of 5
424 Atlantic Avenue Virginia Beach VA
Free Cancellation
Reserve now, pay when you stay
18.04 mi from city center
$137 nightly
The price is $159 total per night
$159 total
Apr 29 - Apr 30
Total with taxes and fees
Guests staying at The Ocean Key Virginia Beach Resort enjoy an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The 24-hour front desk has staff standing by to help secure valuables, and answer any questions about the accommodations. Additional amenities include a business center, an arcade/game room, and laundry facilities.
Pool
Kitchen
Great Location ! 1 Short Block To The Boardwalk.

Great Location ! 1 Short Block To The Boardwalk.

Virginia Beach VA
17.99 mi from city center
At this condo, guests have access to features like laundry facilities.
Kitchen
Free WiFi
The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

3.5 out of 5
315 21st St Virginia Beach VA
Free Cancellation
Reserve now, pay when you stay
17.97 mi from city center
$155 nightly
The price is $180 total per night
$180 total
May 1 - May 2
Total with taxes and fees
At this aparthotel, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is available if you drive. The 24-hour front desk has staff always at the ready. Additional amenities include an arcade/game room, express check-in, and express check-out.
Pool
Kitchen
Angie's Guest Cottage

Angie's Guest Cottage

2 out of 5
302 24th Street Virginia Beach VA
18.05 mi from city center
$90 nightly
The price is $105 total per night
$105 total
Apr 13 - Apr 14
Total with taxes and fees
Guests staying at Angie's Guest Cottage enjoy free WiFi in public areas, laundry facilities, and a picnic area. If you decide to drive, there's free parking. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. This smoke-free apartment building also has a garden.
Kitchen
Parking included
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

4 out of 5
2207 Atlantic Avenue Virginia Beach VA
Free Cancellation
Reserve now, pay when you stay
18.15 mi from city center
$180 nightly
The price is $209 total per night
$209 total
Apr 26 - Apr 27
Total with taxes and fees
Guests of Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia have access to an indoor pool, a gym, and a sauna. You can take advantage of free parking if you drive. The 24-hour front desk has staff standing by to help secure valuables, and answer any questions about the accommodations. Other amenities at this beach aparthotel include free WiFi in public areas, a hot tub, and an arcade/game room.
Pool
Hot Tub
Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach

Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach

Virginia Beach VA
18.32 mi from city center
At this condo, guests have access to an outdoor pool, laundry facilities, and a garden. This beach condo building also has barbecue grills.
Pool
Kitchen
Octopus Oasis, HORSES/ Sea Turtles 4x4 a must Pets OK. Jacuzzi. Carova Beach

Octopus Oasis, HORSES/ Sea Turtles 4x4 a must Pets OK. Jacuzzi. Carova Beach

Corolla NC
28.43 mi from city center
$783 nightly
The price is $883 total per night
$883 total
Apr 13 - Apr 14
Total with taxes and fees
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and barbecue grills. Transportation is made easy with limo/town car service.
Hot Tub
Kitchen
Oceanfront with Private Beach Access & Wild Horses

Oceanfront with Private Beach Access & Wild Horses

Corolla NC
28.94 mi from city center
At this vacation home, guests have access to features like laundry facilities. This beach vacation home also has barbecue grills.
Kitchen
Washer
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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.

Chesapeake Large Group Rentals

How to Book Vacation Rentals in Chesapeake



🏠 What is the best price for Chesapeake vacation rentals?

Chesapeake vacation rentals range in price, starting at $105 per night.


🏠 What types of vacation rentals in Chesapeake can I rent?

Orbitz offers a wide range of Chesapeake rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Chesapeake condo rentals.


🏠 Is it free to cancel my Chesapeake vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Chesapeake vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Chesapeake. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Chesapeake?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Chesapeake apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Chesapeake?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Chesapeake package deals will get you even more savings.