Chesapeake Holiday Rentals

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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Chesapeake holiday rentals

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, (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 HK$1,192
HK$2,234 total
includes taxes & fees
14 Apr - 15 Apr
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$1,018
HK$1,351 total
includes taxes & fees
5 Apr - 6 Apr
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$1,164
HK$1,528 total
includes taxes & fees
26 Apr - 27 Apr
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$1,089
HK$1,439 total
includes taxes & fees
5 Apr - 6 Apr
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$915
HK$1,233 total
includes taxes & fees
26 Apr - 27 Apr
Great Studio | Pool & Hot Tub. Your Next Vacation
Indoor pool

Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
The price is HK$1,018
HK$1,351 total
includes taxes & fees
26 Apr - 27 Apr
Studio | Free Breakfast. Indoor Pool & Hot Tub.
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$1,091
HK$1,435 total
includes taxes & fees
26 Apr - 27 Apr
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.
The price is HK$978
HK$1,304 total
includes taxes & fees
26 Apr - 27 Apr
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$1,164
HK$1,519 total
includes taxes & fees
5 Apr - 6 Apr
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Marina

Your Tropical Oasis awaits in Hampton Roads Virginia

Your Tropical Oasis awaits in Hampton Roads Virginia
Portsmouth
The price is HK$1,568
HK$2,565 total
includes taxes & fees
6 Apr - 7 Apr
Your Tropical Oasis awaits in Hampton Roads Virginia
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$1,568
HK$3,148 total
includes taxes & fees
5 Apr - 6 Apr
Luxurious RV
Interior

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.4 out of 10, Exceptional, (18 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
The price is HK$776
HK$2,277 total
includes taxes & fees
6 Apr - 7 Apr
Comfortable & Private 2 Bedrm Cottage w/ King bed.
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$827
HK$1,817 total
includes taxes & fees
14 Apr - 15 Apr
Knot Three- Balcony View of ICW- Dog Friendly!
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$698
HK$2,088 total
includes taxes & fees
25 Apr - 26 Apr
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
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$635
HK$1,457 total
includes taxes & fees
6 Apr - 7 Apr
Private 1 Bed Apt - Historic Olde Towne Portsmouth
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, (109 reviews)
"Many restaurants and shopping nearby. Excellent place to stay."
United States
Daniel A.
The price is HK$783
HK$1,772 total
includes taxes & fees
15 Apr - 16 Apr
The Art Door Duplex only minutes from beach
Interior

Walk to Dtwn & Campus! Spacious Hampton Home

Walk to Dtwn & Campus! Spacious Hampton Home
3.0 star property
Hampton
Walk to Dtwn & Campus! Spacious Hampton Home
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, (26 reviews)
"Great stay, host is very responsive to issues and concerns "
United States
Jackson H.
The price is HK$784
HK$2,223 total
includes taxes & fees
22 Apr - 23 Apr
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Fridge, microwave, oven, stovetop

2 king beds -2nd fl walk 2 beach apt3

2 king beds -2nd fl walk 2 beach apt3
East Ocean View
10.0 out of 10, Exceptional, (2 reviews)
"Clean and perfect for our family stay. The apartment had everything we needed to be comfortable. "
United States
Kelly D.
The price is HK$686
HK$2,296 total
includes taxes & fees
6 Apr - 7 Apr
2 king beds -2nd fl walk 2 beach apt3
Property grounds

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Portsmouth
9.2 out of 10, Wonderful, (40 reviews)
"Beautiful place, beautiful location "
United States
rocco m.
The price is HK$941
HK$2,115 total
includes taxes & fees
8 Apr - 9 Apr
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
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 it was a great place"
rita 2-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
  • Use the map to find apartments and other holiday homes in the Chesapeake neighbourhood you prefer
  • 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?

The Art Door Duplex only minutes from beach: 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 40 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 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 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.