Chesapeake City County Holiday Rentals

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Our top choices for Chesapeake City County holiday rentals

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 NZ$348
includes taxes & fees
3 May - 4 May
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

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, (46 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is NZ$540
includes taxes & fees
6 May - 7 May
3-bedroom home away from home in fabulous Chesapeake, Virginia.

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 NZ$335
includes taxes & fees
17 May - 18 May
Great Studio | Pool & Hot Tub. Your Next Vacation

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is NZ$427
includes taxes & fees
2 May - 3 May
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$369
includes taxes & fees
25 May - 26 May
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 NZ$388
includes taxes & fees
26 Apr - 27 Apr
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

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$406
includes taxes & fees
10 May - 11 May
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Studio | Free Breakfast. Indoor Pool & Hot Tub

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

Luxurious RV

Luxurious RV
Sandbridge
8.4 out of 10, Very good, (17 reviews)
"Excellent accommodation close to beach I would stay here again !!! "
United States
Scott E.
The price is NZ$675
includes taxes & fees
2 May - 3 May
Luxurious RV

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is NZ$461
includes taxes & fees
26 Apr - 27 Apr
The Speakeasy Downtown Newport News

The Art Door Duplex only minutes from beach

The Art Door Duplex only minutes from beach
Virginia Beach
9.6 out of 10, Exceptional, (112 reviews)
"Many restaurants and shopping nearby. Excellent place to stay."
United States
Daniel A.
The price is NZ$386
includes taxes & fees
5 May - 6 May
The Art Door Duplex only minutes from beach

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Portsmouth
9.2 out of 10, Wonderful, (26 reviews)
"Pretty clean, convenient location to my daily travel, host was wonderful and very helpful when I needed help with something in the house. I would definitely stay here again."
United States
Niya w.
The price is NZ$488
includes taxes & fees
26 Apr - 27 Apr
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

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 NZ$441
includes taxes & fees
8 May - 9 May
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, (2 reviews)
"Great place. Nice area. Parking was confusing at first but host was very responsive "
United States
Ed and Laura S.
The price is NZ$316
includes taxes & fees
27 Apr - 28 Apr
Private 1 Bed Apt - Historic Olde Towne Portsmouth

Sojourn | Coastal Cottage | 3 BR

Sojourn | Coastal Cottage | 3 BR
Willoughby Spit
9.4 out of 10, Exceptional, (34 reviews)
"The house was clean and had everything you need. The neighborhood was quiet. Beach access was just a short walk away and not crowded. "
United States
Daniel P.
The price is NZ$647
includes taxes & fees
26 Apr - 27 Apr
Sojourn | Coastal Cottage | 3 BR

Knot One- Balcony View of ICW- Dog Friendly!

Knot One- Balcony View of ICW- Dog Friendly!
Coinjock
9.0 out of 10, Wonderful, (8 reviews)
"Loved watching the yachts in the ICW"
United States
susan
The price is NZ$373
includes taxes & fees
28 Apr - 29 Apr
Knot One- Balcony View of ICW- Dog Friendly!

❤️Breakfast @ Tiffany's❤️Downtown Newport News!

❤️Breakfast @ Tiffany's❤️Downtown Newport News!
Downtown Newport News
9.0 out of 10, Wonderful, (6 reviews)
"Cool little place, large bathroom and living spaces.. Near restaurants and quiet too."
United States
Nathan H.
❤️Breakfast @ Tiffany's❤️Downtown Newport News!

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
2.5 star property
Suffolk
9.4 out of 10, Exceptional, (72 reviews)
"perfect stay. would definitely stay again "
United States
berry
The price is NZ$232
includes taxes & fees
5 May - 6 May
stayAPT Suites Suffolk-Chesapeake

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Willoughby Spit
8.8 out of 10, Excellent, (72 reviews)
"We love this little quiet beach house "
United States
Annie N.
The price is NZ$600
includes taxes & fees
6 May - 7 May
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
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 City County Hotel Reviews

Find out more about Chesapeake City County

Everything you need to know about Chesapeake City County 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 City County 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 City County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesapeake City County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake City County. 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 City County 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 City County holiday rentals we have selected for you start as low as NZ$191 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesapeake City County rentals

At Expedia, we put the best Chesapeake City County 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 City County 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 City County 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 City County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.