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
11.46 mi from city center
$109 nightly
The price is $126 total per night
$126 total
Feb 15 - Feb 16
Total with taxes and fees
Guests staying at stayAPT Suites Suffolk-Chesapeake enjoy free WiFi in public areas, laundry facilities, and barbecue grills. If you drive, take advantage of free parking. This smoke-free aparthotel also has a vending machine.
Kitchen
Parking included
Oceanfront home “Sea Watch” ~~brand new pool

Oceanfront home “Sea Watch” ~~brand new pool

2 out of 5
Virginia Beach VA
19.98 mi from city center
This vacation home offers a water park, an outdoor pool, and an arcade/game room. Other amenities at this beach vacation home include laundry facilities and barbecue grills.
Pool
Kitchen
Last minute stays available! Great deals! Ocean views 8bdrm, 6bath pool!

Last minute stays available! Great deals! Ocean views 8bdrm, 6bath pool!

Virginia Beach VA
19.51 mi from city center
This vacation home offers a water park, an arcade/game room, and laundry facilities. This beach vacation home also has barbecue grills.
Pool
Kitchen
Oceanfront 7BR Home w/ Pool, Hot Tub. Sleeps 20

Oceanfront 7BR Home w/ Pool, Hot Tub. Sleeps 20

Virginia Beach VA
19.72 mi from city center
At this vacation home, guests have access to a hot tub, an arcade/game room, and laundry facilities. This beach vacation home also has barbecue grills.
Pool
Hot Tub
Luxurious RV

Luxurious RV

Virginia Beach VA
20.45 mi from city center
$343 nightly
The price is $402 total per night
$402 total
Jan 19 - Jan 20
Total with taxes and fees
Luxurious RV features a gym and laundry facilities.
Pool
Pet friendly
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
$139 nightly
The price is $162 total per night
$162 total
Feb 1 - Feb 2
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 free newspapers.
Pool
Kitchen
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3 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
Jan 31 - Feb 1
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
Four Sails Resort

Four Sails Resort

4 out of 5
3301 Atlantic Ave Virginia Beach VA
18.24 mi from city center
At Four Sails Resort, guests enjoy an indoor pool, a gym, and a sauna. There's free parking if you drive. The 24-hour front desk has staff always at the ready. Other amenities at this beach condominium resort include free WiFi in public areas, free use of bicycles, and laundry facilities.
Pool
Kitchen
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
This condo offers a water park, an outdoor pool, and laundry facilities. Other amenities at this beach condo building include barbecue grills and a garden.
Pool
Kitchen
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

Corolla NC
28.96 mi from city center
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Wildhorse Beachfront 12 bedroom Pool Estate

Wildhorse Beachfront 12 bedroom Pool Estate

Hatteras NC
29.51 mi from city center
Guests staying at Wildhorse Beachfront 12 bedroom Pool Estate enjoy a hot tub, an arcade/game room, and barbecue grills.
Pool
Hot Tub
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

Corolla NC
29.75 mi from city center
Guests staying at this vacation home enjoy access to a water park, an outdoor pool, and a hot tub. Other amenities at this beach vacation home include an arcade/game room, laundry facilities, and barbecue grills.
Pool
Hot Tub
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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 $126 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.