Chesapeake Vacation Rentals

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Our top choices for Chesapeake vacation rentals

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 CA $205
CA $268 total
includes taxes & fees
Apr 26 - Apr 27
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 CA $180
CA $239 total
includes taxes & fees
Apr 26 - Apr 27
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

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, (43 reviews)
"This was a wonderful place that was perfect for girls trip! I would definitely recommend and stay again!!"
United States
Tabitha P.
The price is CA $216
CA $410 total
includes taxes & fees
Apr 21 - Apr 22
3-bedroom home away from home in fabulous Chesapeake, Virginia.

Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
The price is CA $171
CA $228 total
includes taxes & fees
Apr 26 - Apr 27
Studio | Free Breakfast. Indoor Pool & Hot Tub.

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 CA $194
CA $255 total
includes taxes & fees
Apr 26 - Apr 27
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near 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 CA $180
CA $239 total
includes taxes & fees
Apr 26 - Apr 27
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!
Chesapeake
8.0 out of 10, Very good, (4 reviews)
"Good location and spacious rooms. Good stay!"
United States
Ariel G.
The price is CA $216
CA $282 total
includes taxes & fees
Apr 26 - Apr 27
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

Your Tropical Oasis awaits in Hampton Roads Virginia

Your Tropical Oasis awaits in Hampton Roads Virginia
Portsmouth
The price is CA $276
CA $457 total
includes taxes & fees
Apr 12 - Apr 13
Your Tropical Oasis awaits in Hampton Roads Virginia

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 CA $276
CA $553 total
includes taxes & fees
Apr 11 - Apr 12
Luxurious RV

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is CA $147
CA $359 total
includes taxes & fees
Apr 12 - Apr 13
The Speakeasy Downtown Newport News

Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
The price is CA $363
CA $855 total
includes taxes & fees
May 7 - May 8
Centrally Located Hampton Roads Home w/ Game Room!

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
2.5 star property
Suffolk
9.4 out of 10, Exceptional, (69 reviews)
"perfect stay. would definitely stay again "
United States
berry
The price is CA $164
CA $189 total
includes taxes & fees
Apr 30 - May 1
stayAPT Suites Suffolk-Chesapeake

Cozy 3-bedroom condo with AC and WiFi in charming Virginia Beach

Cozy 3-bedroom condo with AC and WiFi in charming Virginia Beach
Northwest
10.0 out of 10, Exceptional, (4 reviews)
"Great location , with restaurant across the street Amy family and I enjoyed our stay "
United States
shantielle T.
The price is CA $622
CA $1,183 total
includes taxes & fees
Apr 13 - Apr 14
Cozy 3-bedroom condo with AC and WiFi in charming Virginia Beach

Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental
East Ocean View
9.0 out of 10, Wonderful, (282 reviews)
"Great location. Very close to the beach and a park. Great place for families. Large dining table worked great for us for Thanksgiving. "
United States
Cody H.
The price is CA $228
CA $553 total
includes taxes & fees
Apr 16 - Apr 17
Norfolk Beach Cottage Rental

Family friendly 5 bedroom home within Walking distance To CNU

Family friendly 5 bedroom home within Walking distance To CNU
Central Newport News
10.0 out of 10, Exceptional, (51 reviews)
"Was an absolute great stay! "
United States
Melanie E.
The price is CA $895
CA $1,302 total
includes taxes & fees
Apr 12 - Apr 13
Family friendly 5 bedroom home within Walking distance To CNU

NEW! Boat Ramp, Pool, Hot Tub

NEW! Boat Ramp, Pool, Hot Tub
Sandbridge
10.0 out of 10, Exceptional, (1 review)
The price is CA $931
CA $2,478 total
includes taxes & fees
Apr 14 - Apr 15
NEW! Boat Ramp, Pool, Hot Tub

Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
Coliseum Central
9.6 out of 10, Exceptional, (42 reviews)
"Another amazing stay at Jackie's place!"
United States
Sherri J.
The price is CA $369
CA $753 total
includes taxes & fees
Apr 12 - Apr 13
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

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, (71 reviews)
"We love this little quiet beach house "
United States
Annie N.
The price is CA $206
CA $398 total
includes taxes & fees
Apr 12 - Apr 13
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

New Beach Home on the Chesapeake Bay

New Beach Home on the Chesapeake Bay
East Ocean View
8.8 out of 10, Excellent, (3 reviews)
"Excellent Host! The check in process an eaze! The house is as described super clean! The host provided more than enough accommodations and even leaves a nice treat for their guest! The location is excellent right by the stairs to the beach! Will definitely book again. "
United States
Shardae F.
The price is CA $621
CA $1,137 total
includes taxes & fees
Apr 13 - Apr 14
New Beach Home on the Chesapeake Bay

Buckroe Bungalow Buckroe Bungalow Escape to the Beach 2mins Away

Buckroe Bungalow Buckroe Bungalow Escape to the Beach 2mins Away
2.0 star property
Hampton
The price is CA $217
CA $588 total
includes taxes & fees
Apr 13 - Apr 14
Buckroe Bungalow Buckroe Bungalow Escape to the Beach 2mins Away
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chesapeake. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Chesapeake?

Yes, there are vacation rentals in Chesapeake close to Broadmoor Play Area, or you can go with a more remote 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 vacation home rentals in Chesapeake?

The Art Door Duplex only minutes from beach: This vacation home rental outside of Chesapeake comes with air-conditioning so you can feel at home during your trip.

How many vacation rentals are there in Chesapeake?

Expedia has 42 vacation 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 City Park are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places like Naval Station Norfolk and Sandbridge Beach.

What’s a vacation rental in Chesapeake like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Chesapeake. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips.