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Chesapeake Holiday Rentals

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Check prices for these dates

Tonight
2 Jan - 3 Jan
Tomorrow
3 Jan - 4 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Chesapeake holiday rentals

Indoor pool
Great Studio | Pool & Hot Tub. Your Next Vacation

Apartment in Chesapeake

Great Studio | Pool & Hot Tub. Your Next Vacation
10.0 out of 10, Exceptional, (3)
"Impressed with the whole experience. "
United States
Patricia M.
The price is HK$852
HK$1,159 total
includes taxes & fees
4 Jan - 5 Jan
Great Studio | Pool & Hot Tub. Your Next Vacation
Indoor pool
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

Condo in Chesapeake

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
2.5 star property
8.0 out of 10, Very good, (4)
"Perfect for what we needed for one day layover before outer Banks"
Canada
Michael L.
The price is HK$1,023
HK$1,355 total
includes taxes & fees
20 Jan - 21 Jan
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!

Condo in Chesapeake

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
10.0 out of 10, Exceptional, (1)
"Very clean , great location. Will stay there again!!!"
United States
Tony H.
The price is HK$899
HK$1,213 total
includes taxes & fees
4 Jan - 5 Jan
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Indoor pool
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

Apartment in Chesapeake

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Indoor pool
Studio | Free Breakfast. Indoor Pool & Hot Tub

Apartment in Chesapeake

Studio | Free Breakfast. Indoor Pool & Hot Tub
The price is HK$815
HK$1,116 total
includes taxes & fees
4 Jan - 5 Jan
Studio | Free Breakfast. Indoor Pool & Hot Tub
Dining
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

Condo in Chesapeake

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
The price is HK$948
HK$1,270 total
includes taxes & fees
20 Jan - 21 Jan
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Indoor pool
Studio | Free Breakfast. Indoor Pool & Hot Tub.

Apartment in Chesapeake

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Studio | Free Breakfast. Indoor Pool & Hot Tub.
Dining
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Condo in Chesapeake

Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
The price is HK$963
HK$1,286 total
includes taxes & fees
4 Jan - 5 Jan
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Outdoor dining
Comfortable Beach Trailer Home

Mobile Home in Sandbridge

Comfortable Beach Trailer Home
9.2 out of 10, Wonderful, (80)
"There were three of us staying there, and we couldn't have been more comfortable and enjoyed the stay more. Loved the space! Loved the area! A great place for a vacation!"
United States
Joseph V.
The price is HK$1,557
HK$3,127 total
includes taxes & fees
31 Jan - 1 Feb
Comfortable Beach Trailer Home
Private kitchen
Luxurious RV

Mobile Home in Sandbridge

Luxurious RV
8.4 out of 10, Very good, (17)
"Excellent accommodation close to beach I would stay here again !!! "
United States
Scott E.
The price is HK$1,557
HK$3,126 total
includes taxes & fees
2 Feb - 3 Feb
Luxurious RV
Fridge, microwave, oven, stovetop
Sojourn's Harborage Jellyfish Suite Near Beach

Apartment in East Ocean View

Sojourn's Harborage Jellyfish Suite Near Beach
2.0 star property
10.0 out of 10, Exceptional, (1)
"The apartment was excellent! It was clean and well stocked with everything we need. The staff communicated very well. We were very satisfied and enjoyed our stay. Thank you so much for making our trip so good!"
United States
Jerrie W.
The price is HK$560
HK$2,652 total
includes taxes & fees
18 Jan - 19 Jan
Sojourn's Harborage Jellyfish Suite Near Beach
Fridge, microwave, oven, stovetop
OV Mosaic - Topaz Suite

Apartment in East Ocean View

OV Mosaic - Topaz Suite
10.0 out of 10, Exceptional, (2)
"We had a wonderful stay in Norfolk, Virginia, at OV. The room was very clean, exactly as described, and just a very short walk to the beach. We brought our dog, and the area was perfect for walks and relaxing. Communication with the property manager was excellent, and the location couldn’t have been better. Would definitely stay again!"
United States
Jose V.
The price is HK$475
HK$2,050 total
includes taxes & fees
2 Feb - 3 Feb
OV Mosaic - Topaz Suite
Beach
Cozy 1-bedroom only in shared apartment with AC, WiFi in welcoming Norfolk

Apartment in Willoughby Spit

Cozy 1-bedroom only in shared apartment with AC, WiFi in welcoming Norfolk
10.0 out of 10, Exceptional, (2)
"very friendly host! very patient with me on day of check in, made sure we had everything we needed & more !"
United States
Shydymond B.
The price is HK$467
HK$740 total
includes taxes & fees
31 Jan - 1 Feb
Cozy 1-bedroom only in shared apartment with AC, WiFi in welcoming Norfolk
Property grounds
The Art Door Duplex only minutes from beach

Holiday Home in Northeast Virginia Beach

The Art Door Duplex only minutes from beach
9.6 out of 10, Exceptional, (104)
"This was just as advertised and perfect for our overnight stay. Easy drive to the beach."
United States
Laura K.
The price is HK$701
HK$1,681 total
includes taxes & fees
6 Jan - 7 Jan
The Art Door Duplex only minutes from beach
Interior
OV Mosaic - River Suite

Apartment in East Ocean View

OV Mosaic - River Suite
9.2 out of 10, Wonderful, (7)
"Great place and cool area"
United States
Matt W.
The price is HK$475
HK$2,522 total
includes taxes & fees
1 Feb - 2 Feb
OV Mosaic - River Suite
2 bedrooms
The Speakeasy Downtown Newport News

Apartment in Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
The price is HK$694
HK$1,868 total
includes taxes & fees
10 Jan - 11 Jan
The Speakeasy Downtown Newport News
Property grounds
Knot Three- Balcony View of ICW- Dog Friendly!

Holiday Home in Coinjock

Knot Three- Balcony View of ICW- Dog Friendly!
9.6 out of 10, Exceptional, (4)
"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$740
HK$1,747 total
includes taxes & fees
8 Jan - 9 Jan
Knot Three- Balcony View of ICW- Dog Friendly!
Fridge, microwave, oven, stovetop
Comfortable & Private 2 Bedrm Cottage w/ King bed.

Cottage in Portsmouth

Comfortable & Private 2 Bedrm Cottage w/ King bed.
10.0 out of 10, Exceptional, (16)
"It was a great stay. Was there for work. Close for work and close to the beach. "
United States
Clayton M.
The price is HK$771
HK$2,261 total
includes taxes & fees
4 Jan - 5 Jan
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Property grounds
Knot Four- Balcony View of ICW- Dog Friendly!

Apartment in Coinjock

Knot Four- Balcony View of ICW- Dog Friendly!
10.0 out of 10, Exceptional, (1)
"This place is always perfect for us. Thank you!"
United States
David S.
The price is HK$740
HK$1,730 total
includes taxes & fees
3 Jan - 4 Jan
Knot Four- Balcony View of ICW- Dog Friendly!
Beach nearby
900. B Seaside 2 Br Cottage with Bay Views, Veranda, High Ceilings, Hot Tub, Private Beach, Beachfront Grilling, & Kayaks

Cottage in Willoughby Spit

900. B Seaside 2 Br Cottage with Bay Views, Veranda, High Ceilings, Hot Tub, Private Beach, Beachfront Grilling, & Kayaks
2.0 star property
The price is HK$856
HK$8,334 total
includes taxes & fees
4 Jan - 5 Jan
900. B Seaside 2 Br Cottage with Bay Views, Veranda, High Ceilings, Hot Tub, Private Beach, Beachfront Grilling, & Kayaks
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

Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

10/10 Excellent
"Staff and room "
Duane 1-night trip
Posted 16 hours ago
Hyatt Place 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 Bryant Farms Park, 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?

Oceanfront home “Sea Watch” ~~brand new pool: This holiday home rental outside of Chesapeake is located on the beach, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of an arcade/games room in this rental home to help you unwind.

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 Bryant Farms Park and Broadmoor Play Area, whereas Oak Grove Lake Park and Chesapeake Arboretum are a couple of great spots to enjoy the outdoors. Greenbrier Mall and Chesapeake Conference Center are other places to visit while you're in town.

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.