Chesapeake Holiday Rentals

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Our top choices for Chesapeake holiday rentals

3-bedroom home away from home in fabulous Chesapeake, Virginia.

3-bedroom home away from home in fabulous Chesapeake, Virginia.
Chesapeake
10.0 out of 10, Exceptional, (47 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is AU$473
includes taxes & fees
8 June - 9 June
3-bedroom home away from home in fabulous Chesapeake, Virginia.

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

Central Chesapeake Stay Near Mall, Trails & parks

Central Chesapeake Stay Near Mall, Trails & parks
Greenbrier
The price is AU$683
includes taxes & fees
3 July - 4 July
Central Chesapeake Stay Near Mall, Trails & parks

Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
The price is AU$350
includes taxes & fees
30 June - 1 July
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 AU$380
includes taxes & fees
9 June - 10 June
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is AU$346
includes taxes & fees
30 June - 1 July
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 AU$355
includes taxes & fees
30 June - 1 July
Studio | Free Breakfast. Indoor Pool & Hot Tub

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!
Chesapeake
8.0 out of 10, Very good, (4 reviews)
"Good location and spacious rooms. Good stay!"
United States
Ariel G.
The price is AU$397
includes taxes & fees
7 June - 8 June
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

Great Studio | Pool & Hot Tub. Your Next Vacation

Great Studio | Pool & Hot Tub. Your Next Vacation
Chesapeake
10.0 out of 10, Exceptional, (3 reviews)
"Impressed with the whole experience. "
United States
Patricia M.
The price is AU$328
includes taxes & fees
30 June - 1 July
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
9.0 out of 10, Wonderful, (2 reviews)
"Very clean , great location. Will stay there again!!!"
United States
Tony H.
The price is AU$384
includes taxes & fees
7 June - 8 June
King Suite. 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 reviews)
"The stay was great. We loved walking around the neighborhood at sunset to see the view over the water. We would definitely stay here again. "
United States
Maddi S.
The price is AU$555
includes taxes & fees
12 June - 13 June
Comfortable Beach Trailer Home

Luxurious RV

Luxurious RV
Sandbridge
8.4 out of 10, Very good, (18 reviews)
"Excellent accommodation close to beach I would stay here again !!! "
United States
Scott E.
The price is AU$555
includes taxes & fees
8 June - 9 June
Luxurious RV

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is AU$466
includes taxes & fees
8 June - 9 June
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, (5 reviews)
"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 AU$400
includes taxes & fees
7 June - 8 June
Knot Three- Balcony View of ICW- Dog Friendly!

Comfort near the water and University

Comfort near the water and University
Elizabeth city
8.0 out of 10, Very good, (7 reviews)
"Everything was wonderful"
United States
Marc
The price is AU$424
includes taxes & fees
8 June - 9 June
Comfort near the water and University

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.6 out of 10, Exceptional, (22 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
The price is AU$473
includes taxes & fees
10 June - 11 June
Comfortable & Private 2 Bedrm Cottage w/ King bed.

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Portsmouth
9.6 out of 10, Exceptional, (4 reviews)
"Property is well maintained. Great AC. Perfect for a couple to get away for a week. Central location was perfect for everything we planned to do for the week. "
United States
Paige M.
The price is AU$367
includes taxes & fees
16 June - 17 June
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
10.0 out of 10, Exceptional, (4 reviews)
"What an awesome place! A perfect location. Close to tons of activities. We would definitely stay again. "
United States
bethany h.
The price is AU$263
includes taxes & fees
9 June - 10 June
Private 1 Bed Apt - Historic Olde Towne Portsmouth

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
2.5 star property
Suffolk
9.4 out of 10, Exceptional, (82 reviews)
"Very clean and modern room at a very reasonable price. We will definitely stay there again if we are in that area."
United States
Scott
The price is AU$192
includes taxes & fees
18 June - 19 June
stayAPT Suites Suffolk-Chesapeake
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 favourite 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 depend 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 AU$174 per night. Entering your travel dates in the search wizard might find you 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 Riverwalk Parkway Park and Playground, 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?

Spacious 4-bedroom house in beautiful 4x4 area of Corolla with ocean views!: This holiday home rental outside of Chesapeake is located by the ocean, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Riverwalk Parkway Park and Playground and Broadmoor Play Area, whereas Chesapeake City Park and Lake Drummond are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places such as Naval Station Norfolk and Veterans United Home Loans Amphitheater at Virginia Beach.

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.