A golf course, a large building complex, and a marina by a river.

Chesapeake Holiday Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Chesapeake holiday rentals

TV

Nyakio Suite - Chesapeake

Nyakio Suite - Chesapeake
Greenbrier
The price is HK$1,654
HK$3,159 total
includes taxes & fees
7 Jul - 8 Jul
Nyakio Suite - Chesapeake
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$1,259
HK$1,656 total
includes taxes & fees
6 Jul - 7 Jul
Great Studio | Pool & Hot Tub. Your Next Vacation
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, (48 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is HK$1,710
HK$2,920 total
includes taxes & fees
29 Jul - 30 Jul
3-bedroom home away from home in fabulous Chesapeake, Virginia.
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$1,333
HK$1,759 total
includes taxes & fees
9 Jul - 10 Jul
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Living area

Nyakio Suite

Nyakio Suite
2.0 star property
Greenbrier
The price is HK$2,578
HK$4,712 total
includes taxes & fees
15 Jul - 16 Jul
Nyakio Suite
Indoor pool

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is HK$1,273
HK$1,654 total
includes taxes & fees
12 Jul - 13 Jul
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Indoor pool

Studio | Free Breakfast. Indoor Pool & Hot Tub

Studio | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,259
HK$1,656 total
includes taxes & fees
7 Jul - 8 Jul
Studio | Free Breakfast. Indoor Pool & Hot Tub
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$1,513
HK$1,992 total
includes taxes & fees
7 Jul - 8 Jul
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 HK$1,333
HK$1,750 total
includes taxes & fees
12 Jul - 13 Jul
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Indoor pool

Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!

Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
Chesapeake
9.4 out of 10, Exceptional, (8 reviews)
"The condo is nice, clean and very roomy. We love the stay and very convenient. The hotel provides breakfast it’s great!!"
United States
Linh T.
Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
Terrace/patio

Comfortable Beach Trailer Home

Comfortable Beach Trailer Home
Sandbridge
9.2 out of 10, Wonderful, (82 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$1,569
HK$3,113 total
includes taxes & fees
4 Aug - 5 Aug
Comfortable Beach Trailer Home
Dining

Luxurious RV

Luxurious RV
Sandbridge
8.6 out of 10, Excellent, (20 reviews)
"Excellent accommodation close to beach I would stay here again !!! "
United States
Scott E.
The price is HK$1,569
HK$3,150 total
includes taxes & fees
10 Jul - 11 Jul
Luxurious RV
Outdoor dining

Knot Three- Balcony View of ICW- Dog Friendly!

Knot Three- Balcony View of ICW- Dog Friendly!
Coinjock
8.4 out of 10, Very good, (6 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$1,171
HK$2,329 total
includes taxes & fees
6 Jul - 7 Jul
Knot Three- Balcony View of ICW- Dog Friendly!
Smart TV, DVD player

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.6 out of 10, Exceptional, (22 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
The price is HK$918
HK$2,666 total
includes taxes & fees
7 Jul - 8 Jul
Comfortable & Private 2 Bedrm Cottage w/ King bed.
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$1,025
HK$2,146 total
includes taxes & fees
6 Jul - 7 Jul
Knot One- Balcony View of ICW- Dog Friendly!
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)
"Everything was wonderful"
United States
Marc
The price is HK$706
HK$2,331 total
includes taxes & fees
3 Aug - 4 Aug
Comfort near the water and University
Smart TV

Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC

Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC
Portsmouth
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay,host was very hospital.love to enjoy it again in December "
United States
earnest d.
The price is HK$1,235
HK$3,176 total
includes taxes & fees
7 Jul - 8 Jul
Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC
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
9.8 out of 10, Exceptional, (6 reviews)
"Quiet comfortable"
United States
Rebecca K
The price is HK$628
HK$2,063 total
includes taxes & fees
11 Jul - 12 Jul
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
2 bedrooms

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is HK$1,148
HK$2,380 total
includes taxes & fees
6 Jul - 7 Jul
The Speakeasy Downtown Newport News
Fridge, microwave, stovetop, coffee/tea maker

Guesthouse in ideal location with private entrance

Guesthouse in ideal location with private entrance
Suffolk
10.0 out of 10, Exceptional, (6 reviews)
"The property was clean, quiet and had everything we needed for a few days in town to see our grandbabies and daughter. Easy to find, park and just a few blocks from the highway, many food options and Kroger."
United States
Audrey J.
The price is HK$761
HK$1,546 total
includes taxes & fees
12 Jul - 13 Jul
Guesthouse in ideal location with private entrance
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

Schooner Inn

Schooner Inn

10/10 Excellent
"Muy buena atención"
Yesica 2-night trip
Posted 1 hour ago
Schooner Inn

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 Chesapeake Arboretum, 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 is equipped with a selection of games, air conditioning and a Smart TV to help you feel comfortable during your stay.

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 Crestwood Park are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places such as Sandbridge Beach and Naval Station Norfolk.

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.