Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Chesapeake vacation rentals

Pool

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 ￥26,525
￥34,152 total
includes taxes & fees
Apr 19 - Apr 20
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Indoor pool

Studio | Free Breakfast. Indoor Pool & Hot Tub

Studio | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is ￥29,983
￥38,494 total
includes taxes & fees
May 18 - May 19
Studio | Free Breakfast. Indoor Pool & Hot Tub
Indoor pool

Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
The price is ￥23,375
￥30,542 total
includes taxes & fees
Apr 19 - Apr 20
Studio | Free Breakfast. Indoor Pool & Hot Tub.
Indoor pool

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is ￥25,043
￥32,448 total
includes taxes & fees
Apr 26 - Apr 27
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Pool

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 ￥25,487
￥32,959 total
includes taxes & fees
May 17 - May 18
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Terrace/patio

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, (45 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 ￥25,842
￥47,914 total
includes taxes & fees
Apr 22 - Apr 23
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Indoor pool

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 ￥24,770
￥32,134 total
includes taxes & fees
Apr 26 - Apr 27
Great Studio | Pool & Hot Tub. Your Next Vacation
Indoor pool

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 ￥25,487
￥32,959 total
includes taxes & fees
May 17 - May 18
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Indoor pool

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 ￥23,744
￥30,954 total
includes taxes & fees
May 17 - May 18
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Dining

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 ￥31,728
￥63,710 total
includes taxes & fees
Apr 19 - Apr 20
Luxurious RV
Indoor pool

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, (1,496 reviews)
"Very easy check in, pool was nice and convenient for kids, great location to beach"
United States
Porsch
The price is ￥12,252
￥23,528 total
includes taxes & fees
May 3 - May 4
The Ocean Key Virginia Beach Resort
Terrace/patio

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
4.0 star property
Northeast Virginia Beach
8.2 out of 10, Very Good, (1,240 reviews)
"Great location. Staff was friendly. Room was clean and cute with spacious bathroom and nice size kitchenette. "
United States
Jennifer
The price is ￥16,546
￥28,468 total
includes taxes & fees
Apr 27 - Apr 28
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
2.5 star property
Suffolk
9.4 out of 10, Exceptional, (70 reviews)
"perfect stay. would definitely stay again "
United States
berry
The price is ￥18,878
￥21,680 total
includes taxes & fees
Apr 27 - Apr 28
stayAPT Suites Suffolk-Chesapeake
Smart TV, fireplace

Comfort near the water and University

Comfort near the water and University
Elizabeth city
7.6 out of 10, Good, (5 reviews)
"The host was welcoming, very clean, and quiet area. Ty"
United States
Hector S.
The price is ￥11,898
￥45,174 total
includes taxes & fees
Apr 20 - Apr 21
Comfort near the water and University
Interior

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is ￥15,812
￥42,291 total
includes taxes & fees
Apr 19 - Apr 20
The Speakeasy Downtown Newport News
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, (110 reviews)
"Many restaurants and shopping nearby. Excellent place to stay."
United States
Daniel A.
The price is ￥15,848
￥36,056 total
includes taxes & fees
Apr 20 - Apr 21
The Art Door Duplex only minutes from beach
Fridge, microwave, oven, stovetop

Duplex w/fast Wi‑Fi & kitchen near shipyard

Duplex w/fast Wi‑Fi & kitchen near shipyard
Portsmouth
10.0 out of 10, Exceptional, (1 review)
"The owners were very quick to answers any questions and able to assist with our needs.Amazing costumer service."
United States
Stephanie T.
The price is ￥10,312
￥38,867 total
includes taxes & fees
Apr 20 - Apr 21
Duplex w/fast Wi‑Fi & kitchen near shipyard
2 bedrooms, iron/ironing board, WiFi, bed sheets

Sojourn's Harborage 9549 unit 1

Sojourn's Harborage 9549 unit 1
East Ocean View
9.2 out of 10, Wonderful, (10 reviews)
"Our stay was amazing! We felt safe in the area and the property was clean and felt very comfortable. There was a lot to do around the area and we are looking forward to staying here when we visit in the future. "
United States
Adriana
The price is ￥10,788
￥53,032 total
includes taxes & fees
Apr 20 - Apr 21
Sojourn's Harborage 9549 unit 1
Terrace/patio

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 ￥13,627
￥33,843 total
includes taxes & fees
Apr 26 - Apr 27
Knot One- Balcony View of ICW- Dog Friendly!
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

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

10/10 Excellent
"yes, great place Infront of the ocean and the breakfast was excellent very clean environment. "
Sidar 3-night trip
Posted 2 hours ago
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Find out more about Chesapeake

Search for holiday rentals in Chesapeake on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesapeake using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chesapeake!

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 Chesapeake City Park and Oak Grove Lake 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.