Chesapeake Holiday Rentals

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Holiday Rentals in Chesapeake

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very good, (1464)
"Very helpful staff. Location is perfect."
The price is AU$232
includes taxes & fees
1 Oct - 2 Oct
The Atrium Resort, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.2 out of 10, Very good, (1142)
"Every room has an ocean front view"
The price is AU$316
includes taxes & fees
1 Oct - 2 Oct
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1430)
"10/10 staying here again "
The price is AU$261
includes taxes & fees
5 Oct - 6 Oct
The Ocean Key Virginia Beach Resort

Four Sails Resort

3.5 star property
7.6 out of 10, Good, (42)
"Parking was tiny but can be navigated carefully "
The price is AU$237
includes taxes & fees
28 Sept - 29 Sept
Four Sails Resort

Angie's Guest Cottage

2.0 star property
8.6 out of 10, Excellent, (223)
"Central location to boardwalk music venues. Friendly staff, clean, quiet. "
The price is AU$146
includes taxes & fees
21 Sept - 22 Sept
Angie's Guest Cottage

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.4 out of 10, Exceptional, (44)
"Nice cozy place to go with your family "
The price is AU$204
includes taxes & fees
22 Sept - 23 Sept
stayAPT Suites Suffolk-Chesapeake

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

9.8 out of 10, Exceptional, (181)
"This house was perfect for my family. The location was beautiful "
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

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

9.8 out of 10, Exceptional, (107)
"fantastic stay. Phil is a great host. can not beat the location. "
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

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

9.6 out of 10, Exceptional, (63)
"Beautiful home!!! Very well kept and clean. The location was everything you can dream of! Wild horses seen daily, gorgeous beach, great pool!!! Thank you for sharing your home with us!"
Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom

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

9.6 out of 10, Exceptional, (121)
"We stayed at Lightly Salted last week; my family of five [2 adults, 3 kids (11, 5, 1)]and out close friends family of three [2 adults, 1 kid (3)]. "
Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach

Oceanfront House on the beach at Croatan

8.0 out of 10, Very good, (117)
"Fantastic location with direct beach access. A very quirky and cool house in need of some Maintenace. The house had lots of room for my large family to be comfortable."
Oceanfront House on the beach at Croatan

Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.

8.4 out of 10, Very good, (21)
"I visited the Outer Banks with my daughters and honestly the stay was amazing, the views, house, location this place had it all. "
Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.

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

9.4 out of 10, Exceptional, (104)
"This large house was perfect for our big family gathering. We loved the huge dining table, and the 2 kitchen areas were great for meal prep. There was plenty of dishes, utensils, and food storage spaces. We noticed that some furnishings had been nicely updated since the online photos. We enjoyed the beach, just a short walk from the house. The indoor pool, hot tub, & pool table kept our group entertained in the evenings. Location is just a short drive from the VA Beach boardwalk for those who...
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach

Loft Space Minutes from Beach

5.2 out of 10, (5)
"Location was good in terms of what we needed and property provided all necessary household things you would need to clean the place. However, owner was not and still is not responsive. Refrigerator did not work. A/C did not work. Lock on door was loose. Backyard had massive camping trailer through it. Save your money."
The price is AU$282
includes taxes & fees
19 Sept - 20 Sept
Loft Space Minutes from Beach

OceanFront Row,on Beach,PrivatePool,Hottub,Sleeps 16,Pet Friendly, Plus Updates!

9.4 out of 10, Exceptional, (34)
"This house was perfect for our family vacation. We loved that we had a pool and a hot tub with the beach right there. It gave our big group many options for entertainment. We enjoyed our week and the host was very responsive and helpful. "
OceanFront Row,on Beach,PrivatePool,Hottub,Sleeps 16,Pet Friendly, Plus Updates!

Cozy Room • Near Dam Neck Base & Beach Access

9.4 out of 10, Exceptional, (3)
"The room was cozy and despite other guests staying in the other rooms everything felt secure, quiet, and comfortable. "
The price is AU$214
includes taxes & fees
18 Sept - 19 Sept
Cozy Room • Near Dam Neck Base & Beach Access

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

8.0 out of 10, Very good, (8)
"Property is perfect for several college students on a shoe string budget."
The price is AU$298
includes taxes & fees
2 Oct - 3 Oct
Cozy Frog on the Beach! 2-bedroom Efficiency w/ Beach Access, WiFi, Smart TV

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

9.8 out of 10, Exceptional, (50)
"this was such a beautiful home. everything was updated and very pretty and homey. tons of room for our large family with extra room with the pool house. easy walking distance to the beach and local market. loved the kitchen with the large table for the whole family with the high chair included. kitchen was well stocked with everything you would need. loved the extra fridge for more space. Beds were super comfortable and everyone had their own bathroom ensuite. would highly recommend this...
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony

Sandbridge... Beautiful Beach Home With Direct Beach Access and Ocean Views

10.0 out of 10, Exceptional, (80)
"Great place to stay with family. Was very clean and well kept. We didn't have much sunshine, but we had a great stay! Host was great and house was like advertised."
Sandbridge... Beautiful Beach Home With Direct Beach Access and Ocean Views

The Art Door only minutes from beach

9.6 out of 10, Exceptional, (94)
"The stay was perfect for our needs, close to the beach and as described. "
The price is AU$347
includes taxes & fees
30 Sept - 1 Oct
The Art Door only minutes from beach
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

Find out more about Chesapeake

Find out more about Chesapeake

Everything you need to know about Chesapeake holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesapeake holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake holiday rentals we have selected for you start as low as AU$146 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesapeake rentals

At Expedia, we put the best Chesapeake holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesapeake rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom: 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 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with an arcade/games room and 1 hot tub.

How many holiday rentals are there in Chesapeake?

Expedia has 35 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.