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Holiday Rentals in Chesapeake

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Our top choices for Chesapeake holiday rentals

Great Studio | Pool & Hot Tub. Your Next Vacation

Great Studio | Pool & Hot Tub. Your Next Vacation
Chesapeake
10.0 out of 10, Exceptional, (3)
"Impressed with the whole experience. "
United States
Patricia M.
The price is €132
includes taxes & fees
25 Dec - 26 Dec
Great Studio | Pool & Hot Tub. Your Next Vacation

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Chesapeake
10.0 out of 10, Exceptional, (1)
"Very clean , great location. Will stay there again!!!"
United States
Tony H.
The price is €136
includes taxes & fees
25 Dec - 26 Dec
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Chesapeake
The price is €137
includes taxes & fees
25 Dec - 26 Dec
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
2.5 star property
Chesapeake
8.0 out of 10, Very good, (4)
"Perfect for what we needed for one day layover before outer Banks"
Canada
Michael L.
The price is €146
includes taxes & fees
25 Dec - 26 Dec
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

Studio | Free Breakfast. Indoor Pool & Hot Tub

Studio | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is €128
includes taxes & fees
25 Dec - 26 Dec
Studio | Free Breakfast. Indoor Pool & Hot Tub

Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Chesapeake
The price is €146
includes taxes & fees
28 Dec - 29 Dec
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is €128
includes taxes & fees
25 Dec - 26 Dec
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
The price is €155
includes taxes & fees
20 Jan - 21 Jan 2026
Studio | Free Breakfast. Indoor Pool & Hot Tub.

Luxurious RV

Luxurious RV
Sandbridge
8.4 out of 10, Very good, (17)
"Excellent accommodation close to beach I would stay here again !!! "
United States
Scott E.
The price is €351
includes taxes & fees
24 Dec - 25 Dec
Luxurious RV

Comfortable Beach Trailer Home

Comfortable Beach Trailer Home
Sandbridge
9.2 out of 10, Wonderful, (80)
"It was the best vacation we've had so far,the place was clean, beautiful,the resort was everything they said it was. We can't wait to go back. Best host ever,thank you!!"
United States
Dawn N.
The price is €350
includes taxes & fees
31 Dec - 1 Jan 2026
Comfortable Beach Trailer Home

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, (1175)
"Staff was very attentive and welcoming! Very clean, such a great place!!"
United States
michelle
The price is €164
includes taxes & fees
24 Dec - 25 Dec
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

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, (1457)
"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

Angie's Guest Cottage

Angie's Guest Cottage
2.0 star property
Northeast Virginia Beach
8.6 out of 10, Excellent, (225)
"Will definitely stay again. Very very clean and everyone was so amazing and welcoming. "
United States
Patricia
The price is €88
includes taxes & fees
24 Dec - 25 Dec
Angie's Guest Cottage

Beach Side Studio #1 - Pet Friendly, WiFi, Off-Street Parking, Large Smart TV

Beach Side Studio #1 - Pet Friendly, WiFi, Off-Street Parking, Large Smart TV
Norfolk
7.6 out of 10, Good, (23)
"Easy and convenient location! "
United States
Erica J.
The price is €131
includes taxes & fees
5 Jan - 6 Jan 2026
Beach Side Studio #1 - Pet Friendly, WiFi, Off-Street Parking, Large Smart TV

The Art Door Duplex only minutes from beach

The Art Door Duplex only minutes from beach
Northeast Virginia Beach
9.6 out of 10, Exceptional, (104)
"Great get away stay! Close drive to the shops and the beach. Very cozy. Would definitely stay there again!"
United States
Lizy G.
The price is €191
includes taxes & fees
1 Jan - 2 Jan 2026
The Art Door Duplex only minutes from beach

Beach Side Studio #3 - Pet Friendly, WiFi, Off-Street Parking, Large Smart TV

Beach Side Studio #3 - Pet Friendly, WiFi, Off-Street Parking, Large Smart TV
Cottage Line
7.8 out of 10, Good, (16)
"Cute structure, awesome location. Not well maintained. Bugs abound. Amazing price!"
United States
Stewart S.
Beach Side Studio #3 - Pet Friendly, WiFi, Off-Street Parking, Large Smart TV

Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
Downtown Newport News
10.0 out of 10, Exceptional, (2)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
Ice Ice Baby Downtown Newport News

Cabin in the Woods, Pet Friendly

Cabin in the Woods, Pet Friendly
Shawboro
8.8 out of 10, Excellent, (24)
"quiet, remote cabin full of personality. Great if you want to be AWAY from people"
United States
Jamie F.
The price is €252
includes taxes & fees
22 Jan - 23 Jan 2026
Cabin in the Woods, Pet Friendly

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, (1479)
"Staff was very nice and attentive!"
United States
Darryl
The price is €499
includes taxes & fees
23 Jan - 24 Jan 2026
The Atrium Resort, Virginia Beach by Vacatia

Cozy Frog on the Beach! 2-bedroom Efficiency w/ Beach Access, WiFi, Smart TV

Cozy Frog on the Beach! 2-bedroom Efficiency w/ Beach Access, WiFi, Smart TV
Cottage Line
8.8 out of 10, Excellent, (14)
"The Cozy Frog was just right for our visit, it was clean and comfortable. And a very short walk to the beach! Would definitely stay here again."
United States
Sara L.
The price is €172
includes taxes & fees
14 Jan - 15 Jan 2026
Cozy Frog on the Beach! 2-bedroom Efficiency w/ Beach Access, WiFi, Smart TV
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

Find out more about Chesapeake

Everything you need to know about Chesapeake holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesapeake holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake holiday rentals we have selected for you start as low as €88 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesapeake rentals

At Expedia, we put the best Chesapeake holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesapeake rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Chesapeake?

Yes, there are holiday rentals in Chesapeake close to Chesapeake Arboretum, or you can select a more secluded 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.

What are some of the best holiday rentals that Chesapeake has to offer?

Oceanfront home “Sea Watch” ~~brand new pool: This holiday home rental outside of Chesapeake is located on the beach, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of an arcade/games room in this rental home to help you unwind.

How many holiday rentals are there in Chesapeake?

Expedia has 38 holiday 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 holiday rental in Chesapeake like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesapeake. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for small groups.