Chesapeake City County Holiday Rentals

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Top Holiday Rentals Destinations in Chesapeake City County

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1434)
"Check in was very easy and staff super friendly and helpful. Location was great. Rooms are a bit dated but clean and bed was comfortable. Loved having a kitchen area in the little suite. "
The price is AU$252
includes taxes & fees
14 Oct - 15 Oct
The Ocean Key Virginia Beach Resort

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.2 out of 10, Very good, (1151)
"We love staying here everyone is very helpful and it’s right in the middle of the boardwalk "
The price is AU$323
includes taxes & fees
9 Oct - 10 Oct
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very good, (1469)
"My stay at the atrium was well, very nice staff and helpful with all my needs. "
The price is AU$232
includes taxes & fees
12 Oct - 13 Oct
The Atrium Resort, Virginia Beach by Vacatia

Four Sails Resort

4.0 star property
7.6 out of 10, Good, (43)
"It was peaceful"
The price is AU$243
includes taxes & fees
5 Oct - 6 Oct
Four Sails Resort

Angie's Guest Cottage

2.0 star property
8.6 out of 10, Excellent, (224)
"Central location to boardwalk music venues. Friendly staff, clean, quiet. "
The price is AU$149
includes taxes & fees
28 Sept - 29 Sept
Angie's Guest Cottage

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

9.8 out of 10, Exceptional, (107)
"We really enjoyed the area, the property, & the ease of communication with the host. Would highly recommend! "
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

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

9.8 out of 10, Exceptional, (182)
"This house was perfect for my family. The location was beautiful "
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

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, (123)
"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

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.

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

10.0 out of 10, Exceptional, (81)
"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

Oceanfront House on the beach at Croatan

8.0 out of 10, Very good, (117)
"Wonderful location with uncrowded beach! House is large enough to meet the needs of multiple families with plenty of space to hang out too! Host responds quickly to solve problems. Many parts of the house are beautiful and others need some cosmetic updates, but it was perfect for us!"
Oceanfront House on the beach at Croatan

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

9.4 out of 10, Exceptional, (104)
"We had 18 people ranging in age 7-68 years old staying and you could not tell. The house was so big and was able to accommodate everyone. Less than 5 min walk to the beach and 5 min drive to amusement/ water park. The host was great communicating and answering questions. Oh I forgot to mention one elevator!!!!"
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach

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

9.8 out of 10, Exceptional, (50)
"The house was what we needed for our family. Even though on busy street, great location with easy beach access and great pool. House had everything we needed."
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony

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."
Loft Space Minutes from Beach

OceanFront Row,Private Pool,New Hottub,Sleeps 16,PetFriendly,Beachfront&Updates!

9.4 out of 10, Exceptional, (34)
"The ocean views from this house are breathtaking. Each morning began with sipping coffee and overlooking the ocean view complete with dolphin sightings daily. We had 3 families of 4 with us so it was nice that each bedroom came with its own bathroom. The kiddos LOVED the pool and hot tub. The adults loved walking the beach. The host was very friendly and answered my messages quickly. We had a wonderful vacation."
OceanFront Row,Private Pool,New Hottub,Sleeps 16,PetFriendly,Beachfront&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$229
includes taxes & fees
5 Oct - 6 Oct
Cozy Room • Near Dam Neck Base & Beach Access

Luxurious RV

8.6 out of 10, Excellent, (13)
"Upon arriving it was dark & I was having a hard time finding the residence. I gave the host a call & he was very friendly and helpful, was able to find it right after speaking with him. The RV is super cute, very relaxing view in the back."
The price is AU$616
includes taxes & fees
27 Sept - 28 Sept
Luxurious RV

Wildhorse Beachfront 12 bedroom Pool Estate

8.4 out of 10, Very good, (5)
"The house was beautiful and the experience with our family was perfect for the holidays. "
Wildhorse Beachfront 12 bedroom Pool Estate

Nautical Dream, redecorated oceanfront home with incredible views and decks

10.0 out of 10, Exceptional, (12)
"Wonderful location, generous floor plan."
Nautical Dream, redecorated oceanfront home with incredible views and decks
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 City County Hotel Reviews

Find out more about Chesapeake City County

Find out more about Chesapeake City County

Everything you need to know about Chesapeake City County 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 City County 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 City County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesapeake City County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake City County. 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 City County 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 City County holiday rentals we have chosen for you start as low as AU$149 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Chesapeake City County rentals

At Expedia, we put the best Chesapeake City County 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 City County 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 City County 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 City County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.