Chesapeake Holiday Rentals

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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

Our top choices for Chesapeake holiday rentals

Living area

Central Chesapeake Stay Near Mall, Trails & parks

Central Chesapeake Stay Near Mall, Trails & parks
Greenbrier
The price is HK$1,402
HK$3,402 total
includes taxes & fees
20 May - 21 May
Central Chesapeake Stay Near Mall, Trails & parks
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, (47 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Indoor pool

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is HK$1,235
HK$1,609 total
includes taxes & fees
31 May - 1 Jun
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 HK$1,637
HK$2,152 total
includes taxes & fees
1 Jun - 2 Jun
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Indoor pool

Studio | Free Breakfast. Indoor Pool & Hot Tub

Studio | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is HK$1,495
HK$1,962 total
includes taxes & fees
25 May - 26 May
Studio | Free Breakfast. Indoor Pool & Hot Tub
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 HK$1,176
HK$1,533 total
includes taxes & fees
31 May - 1 Jun
Great Studio | Pool & Hot Tub. Your Next Vacation
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 HK$1,527
HK$1,990 total
includes taxes & fees
27 May - 28 May
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
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.
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
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 HK$1,432
HK$1,863 total
includes taxes & fees
31 May - 1 Jun
Free Breakfast. Indoor Pool & Hot Tub. Close to 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 HK$1,566
HK$3,145 total
includes taxes & fees
20 May - 21 May
Luxurious RV
Terrace/patio

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 HK$1,566
HK$3,145 total
includes taxes & fees
31 May - 1 Jun
Comfortable Beach Trailer Home
Private kitchen

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is HK$961
HK$2,193 total
includes taxes & fees
21 May - 22 May
The Speakeasy Downtown Newport News
Dining

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 HK$697
HK$2,167 total
includes taxes & fees
16 Jun - 17 Jun
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Outdoor dining

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 HK$972
HK$2,067 total
includes taxes & fees
20 May - 21 May
Knot Three- Balcony View of ICW- Dog Friendly!
Interior

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.4 out of 10, Exceptional, (20 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
The price is HK$916
HK$2,635 total
includes taxes & fees
20 May - 21 May
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Property grounds

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 HK$634
HK$1,455 total
includes taxes & fees
20 May - 21 May
Private 1 Bed Apt - Historic Olde Towne Portsmouth
Fridge, microwave, oven, stovetop

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, (27 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 HK$807
HK$2,266 total
includes taxes & fees
26 May - 27 May
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
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 HK$937
HK$2,037 total
includes taxes & fees
1 Jun - 2 Jun
Knot One- Balcony View of ICW- Dog Friendly!
Smart TV

Cozy Frog on the Beach! 2-bedroom Efficiency w/ Beach Access, WiFi, Smart TV

Cozy Frog on the Beach! 2-bedroom Efficiency w/ Beach Access, WiFi, Smart TV
Cottage Line
8.6 out of 10, Excellent, (16 reviews)
"The Cozy Frog was just right for our visit, it was clean and comfortable. And a very short walk to the beach! Would definitely stay here again."
United States
Sara L.
The price is HK$775
HK$1,545 total
includes taxes & fees
20 May - 21 May
Cozy Frog on the Beach! 2-bedroom Efficiency w/ Beach Access, WiFi, Smart TV
Smart TV, fireplace

Comfort near the water and University

Comfort near the water and University
Elizabeth city
8.0 out of 10, Very good, (7 reviews)
"The host was welcoming, very clean, and quiet area. Ty"
United States
Hector S.
The price is HK$626
HK$2,318 total
includes taxes & fees
27 May - 28 May
Comfort near the water and University
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)

8/10 Good
"A little out dated and the pool gave me a fat headache but the view was amazing, loved the parking garage attached , and the short walk to the beach "
Nadia 3-night trip
Posted 1 hour 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:

  • View our selection of featured holiday rentals in Chesapeake
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  • Enter your travel dates to view the best deals on holiday rentals in Chesapeake while they last

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

Frequently asked questions

Are there holiday rentals in Chesapeake?

Yes, there are holiday rentals in Chesapeake close to Broadmoor Play Area, 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?

Beachfront Bungalow w/ BEST Location in Ocean View!: This holiday home rental outside of Chesapeake comes with air conditioning so that you can feel at home during your trip.

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 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 such as Naval Station Norfolk and Sandbridge 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.