Chesapeake Holiday Rentals

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Check prices for these dates

Tonight
18 Nov - 19 Nov
Tomorrow
19 Nov - 20 Nov
This weekend
21 Nov - 23 Nov
Next weekend
28 Nov - 30 Nov

Holiday Rentals in Chesapeake

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, (1451)
"Great stay, great recovery from other ocean front places! Great room for a family or girls sleepover!!"
United States
Aja-Brianne A
The Ocean Key Virginia Beach Resort
Terrace/patio
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
Northeast Virginia Beach
8.2 out of 10, Very good, (1168)
"Staff was very attentive and welcoming! Very clean, such a great place!!"
United States
michelle
The price is HK$781
HK$1,361 total
includes taxes & fees
1 Dec - 2 Dec
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Indoor pool
Four Sails Resort

Four Sails Resort

4.0 star property
Northeast Virginia Beach
7.6 out of 10, Good, (49)
"Sweet little spot for the price. Easy parking"
United States
Jon
The price is HK$864
HK$1,094 total
includes taxes & fees
26 Nov - 27 Nov
Four Sails Resort
Terrace/patio
stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake

2.5 star property
Suffolk
9.4 out of 10, Exceptional, (52)
"Nice cozy place to go with your family "
United States
Kesha
The price is HK$925
HK$1,062 total
includes taxes & fees
30 Nov - 1 Dec
stayAPT Suites Suffolk-Chesapeake
Exterior
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

Corolla
9.8 out of 10, Exceptional, (107)
"Place was great! Highly recommend!"
United States
Scott E.
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.
Property entrance
Angie's Guest Cottage

Angie's Guest Cottage

2.0 star property
Northeast Virginia Beach
8.6 out of 10, Excellent, (225)
"Will definitely stay again. Very very clean and everyone was so amazing and welcoming. "
United States
Patricia
The price is HK$616
HK$800 total
includes taxes & fees
19 Nov - 20 Nov
Angie's Guest Cottage
Smart TV, DVD player, books
Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach

Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach

Corolla
9.6 out of 10, Exceptional, (125)
"Great place"
United States
Mike H.
Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach
Fridge, microwave, oven, stovetop
Wildhorse Beachfront 12 bedroom Pool Estate

Wildhorse Beachfront 12 bedroom Pool Estate

Hatteras
8.4 out of 10, Very good, (5)
"The house was beautiful and the experience with our family was perfect for the holidays. "
United States
Sean L.
Wildhorse Beachfront 12 bedroom Pool Estate
Smart TV, fireplace, video games, DVD player
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

Corolla
9.8 out of 10, Exceptional, (186)
"Great house and location for a beach vacation"
United States
Tony B.
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi
Private kitchen
Luxurious RV

Luxurious RV

Sandbridge
8.4 out of 10, Very good, (17)
"Had a great stay! Only wish that I would’ve booked an additional night. Would love to come back. "
United States
Heather M.
The price is HK$1,555
HK$3,122 total
includes taxes & fees
19 Nov - 20 Nov
Luxurious RV
Property grounds
Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom

Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom

Corolla
9.6 out of 10, Exceptional, (65)
"The owner was extremely friendly and responsive. The location of the house was perfect- gorgeous views of the ocean, dunes and wild horses. Having a pool was also great for the entire family. This property had the perfect layout.We will be back!"
United States
Heather K.
Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom
Pool
Last minute stays available! Great deals! Ocean views 8bdrm, 6bath pool!

Last minute stays available! Great deals! Ocean views 8bdrm, 6bath pool!

Sandbridge
10.0 out of 10, Exceptional, (157)
"Fantastic location. Exactly as described. Perfect place for our family reunion. Hosts were very helpful and responded quickly to questions."
United States
Madeleine D.
Last minute stays available! Great deals! Ocean views 8bdrm, 6bath pool!
On the beach
C9289 Sun King II. Oceanfront, Elevator, 4x4 Area, Pool, Hot Tub, Pets OK!

C9289 Sun King II. Oceanfront, Elevator, 4x4 Area, Pool, Hot Tub, Pets OK!

2.0 star property
4x4 - Carova Beach
6.0 out of 10, (2)
"The house was located on a 4 x 4 only beach, which would have been fine if we had been informed prior to our arrival about the conditions to expect and the proper way to navigate them. We arrived after dark, during high tide, with inflated tires. We should have been told to watch the tide charts because the beach becomes impassable at high tide. We were not, and barely made it to our turn off because it was a shortly after high tide. We should have been told about letting the air out of the...
United States
William A.
C9289 Sun King II. Oceanfront, Elevator, 4x4 Area, Pool, Hot Tub, Pets OK!
Fridge, microwave, oven, stovetop
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach

10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach

Dam Neck
9.4 out of 10, Exceptional, (107)
"Great location and amenities. Great access to the beach and it is in a very nice neighborhood."
United States
David H.
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach
Pool
Charming 2-bedroom apartment in fabulous Virginia Beach with WiFi, AC

Charming 2-bedroom apartment in fabulous Virginia Beach with WiFi, AC

Northeast Virginia Beach
9.0 out of 10, Wonderful, (12)
"Great spot close to the beach with parking for 2 vehicles. Host was very responsive and friendly. Will definitely stay again."
United States
David A.
Charming 2-bedroom apartment in fabulous Virginia Beach with WiFi, AC
A heated pool
C9703 12 BR 4X4 Oceanfront Luxury Retreat in Carova, Private Pool & Hot Tub - Prices Reduced!!

C9703 12 BR 4X4 Oceanfront Luxury Retreat in Carova, Private Pool & Hot Tub - Prices Reduced!!

Carova Beach
4.0 out of 10, (1)
"Home was in a great location with easy beach access and fantastic views. However, several issues included black mold on the mirrors in one bedroom, pool completely unfit for use, some bathrooms did not have any toilet paper at all, no bathrooms had any shampoo or hand soap (and this was not cautioned by the host), the couch showed visible stains (and it's on dark cloth), and the dishware was not clean. The host often took too long to respond (greater than 1-2 hours), so issues could not be...
United States
Viet N.
C9703 12 BR 4X4 Oceanfront Luxury Retreat in Carova, Private Pool & Hot Tub - Prices Reduced!!
Fridge, microwave, oven, stovetop
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony

Trendy home steps from beach access w/private outdoor pool, gas grill, balcony

Sandbridge
9.8 out of 10, Exceptional, (52)
"Great space, fab pool. Temp was excessively cold and difficult to regulate. Immaculately clean, great location. We loved Anchor Fown!!"
United States
Joyce L.
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony
Property grounds
Stunning oceanfront home with private indoor/outdoor pools, game room, theater

Stunning oceanfront home with private indoor/outdoor pools, game room, theater

Sandbridge
9.4 out of 10, Exceptional, (29)
"Had a great time at this beautiful spacious home for a family vacation. Room for everyone and the game room and pools were a huge hit. We would definitely go here again."
United States
Joyce F.
Stunning oceanfront home with private indoor/outdoor pools, game room, theater
A heated pool
Black Friday Sale: Oceanfront Mega-Estate | 14BR| Pool, Game Room, Wild Horses

Black Friday Sale: Oceanfront Mega-Estate | 14BR| Pool, Game Room, Wild Horses

Corolla
9.6 out of 10, Exceptional, (7)
"Despite there being some water issues towards the end of our trip, my family and I had a great time at this home. The space and amenities allowed everyone in the family, from the bookish to the sporty, to have an awesome time."
United States
Soraya H.
Black Friday Sale: Oceanfront Mega-Estate | 14BR| Pool, Game Room, Wild Horses
Fridge, microwave, oven, stovetop
Beachfront Condo on the Boardwalk with Ocean Views

Beachfront Condo on the Boardwalk with Ocean Views

2.0 star property
Northeast Virginia Beach
10.0 out of 10, Exceptional, (20)
"Property manager was awesome, rental unit was clean and updated, location was perfect!"
United States
Kyle J.
Beachfront Condo on the Boardwalk with Ocean Views
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

Aloft Chesapeake

Aloft Chesapeake

10/10 Excellent
"All was fantastic."
Ian 2-night trip
Posted 1 day ago
Aloft Chesapeake

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 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?

The Art Door 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 38 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 Chesapeake City Park and Oak Grove Lake Park 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.