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Chesapeake Holiday Rentals

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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 NZ$290
includes taxes & fees
11 Jan - 12 Jan 2026
Great Studio | Pool & Hot Tub. Your Next Vacation

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 NZ$317
includes taxes & fees
13 Jan - 14 Jan 2026
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

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 NZ$283
includes taxes & fees
6 Jan - 7 Jan 2026
King Suite. 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 NZ$265
includes taxes & fees
20 Jan - 21 Jan 2026
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 NZ$279
includes taxes & fees
11 Jan - 12 Jan 2026
Studio | Free Breakfast. Indoor Pool & Hot Tub

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 NZ$281
includes taxes & fees
6 Jan - 7 Jan 2026
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
The price is NZ$302
includes taxes & fees
20 Jan - 21 Jan 2026
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 NZ$317
includes taxes & fees
13 Jan - 14 Jan 2026
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Comfortable Beach Trailer Home

Comfortable Beach Trailer Home
Sandbridge
9.2 out of 10, Wonderful, (80)
"There were three of us staying there, and we couldn't have been more comfortable and enjoyed the stay more. Loved the space! Loved the area! A great place for a vacation!"
United States
Joseph V.
Comfortable Beach Trailer Home

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 NZ$692
includes taxes & fees
1 Jan - 2 Jan 2026
Luxurious RV

Sojourn's Harborage Jellyfish Suite Near Beach

Sojourn's Harborage Jellyfish Suite Near Beach
2.0 star property
East Ocean View
10.0 out of 10, Exceptional, (1)
"The apartment was excellent! It was clean and well stocked with everything we need. The staff communicated very well. We were very satisfied and enjoyed our stay. Thank you so much for making our trip so good!"
United States
Jerrie W.
The price is NZ$579
includes taxes & fees
4 Jan - 5 Jan 2026
Sojourn's Harborage Jellyfish Suite Near Beach

OV Mosaic - Topaz Suite

OV Mosaic - Topaz Suite
East Ocean View
10.0 out of 10, Exceptional, (2)
"We had a wonderful stay in Norfolk, Virginia, at OV. The room was very clean, exactly as described, and just a very short walk to the beach. We brought our dog, and the area was perfect for walks and relaxing. Communication with the property manager was excellent, and the location couldn’t have been better. Would definitely stay again!"
United States
Jose V.
The price is NZ$465
includes taxes & fees
13 Jan - 14 Jan 2026
OV Mosaic - Topaz Suite

Cozy 1-bedroom only in shared apartment with AC, WiFi in welcoming Norfolk

Cozy 1-bedroom only in shared apartment with AC, WiFi in welcoming Norfolk
Willoughby Spit
10.0 out of 10, Exceptional, (2)
"very friendly host! very patient with me on day of check in, made sure we had everything we needed & more !"
United States
Shydymond B.
Cozy 1-bedroom only in shared apartment with AC, WiFi in welcoming Norfolk

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 NZ$376
includes taxes & fees
9 Jan - 10 Jan 2026
The Art Door Duplex only minutes from beach

OV Mosaic - River Suite

OV Mosaic - River Suite
East Ocean View
9.2 out of 10, Wonderful, (7)
"Great place and cool area"
United States
Matt W.
The price is NZ$558
includes taxes & fees
11 Jan - 12 Jan 2026
OV Mosaic - River Suite

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is NZ$416
includes taxes & fees
10 Jan - 11 Jan 2026
The Speakeasy Downtown Newport News

Knot Three- Balcony View of ICW- Dog Friendly!

Knot Three- Balcony View of ICW- Dog Friendly!
Coinjock
9.6 out of 10, Exceptional, (4)
"The whole process was very easy and smooth. The property was clean and comfortable. I would definitely stay here again in the future!"
United States
Pam P.
The price is NZ$384
includes taxes & fees
1 Jan - 2 Jan 2026
Knot Three- Balcony View of ICW- Dog Friendly!

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
10.0 out of 10, Exceptional, (16)
"It was a great stay. Was there for work. Close for work and close to the beach. "
United States
Clayton M.
The price is NZ$562
includes taxes & fees
4 Jan - 5 Jan 2026
Comfortable & Private 2 Bedrm Cottage w/ King bed.

Knot Four- Balcony View of ICW- Dog Friendly!

Knot Four- Balcony View of ICW- Dog Friendly!
Coinjock
10.0 out of 10, Exceptional, (1)
"This place is always perfect for us. Thank you!"
United States
David S.
The price is NZ$383
includes taxes & fees
3 Jan - 4 Jan 2026
Knot Four- Balcony View of ICW- Dog Friendly!

900. B Seaside 2 Br Cottage with Bay Views, Veranda, High Ceilings, Hot Tub, Private Beach, Beachfront Grilling, & Kayaks

900. B Seaside 2 Br Cottage with Bay Views, Veranda, High Ceilings, Hot Tub, Private Beach, Beachfront Grilling, & Kayaks
2.0 star property
Willoughby Spit
The price is NZ$1,844
includes taxes & fees
4 Jan - 5 Jan 2026
900. B Seaside 2 Br Cottage with Bay Views, Veranda, High Ceilings, Hot Tub, Private Beach, Beachfront Grilling, & Kayaks
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, 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 NZ$177 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 Bryant Farms Park, 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 39 holiday rentals for your stay in Chesapeake.

What’s there to see and do in Chesapeake?

Family-friendly attractions include Bryant Farms Park and Broadmoor 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.