Chesapeake City County Holiday Rentals

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Top Holiday Rentals Destinations in Chesapeake City County

The Ocean Key Virginia Beach Resort
Indoor pool

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1437)
"The hotel and staff were excellent. Even housekeeping were friendly and professional. I love this hotel. I come every year with my family. "
The price is NZ$300
includes taxes & fees
19 Oct - 20 Oct
The Ocean Key Virginia Beach Resort
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Terrace/patio

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.2 out of 10, Very good, (1154)
"We love staying here everyone is very helpful and it’s right in the middle of the boardwalk "
The price is NZ$331
includes taxes & fees
16 Oct - 17 Oct
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
The Atrium Resort, Virginia Beach by Vacatia
Beach nearby

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very good, (1473)
"Room was clean and well appointed. Staff was friendly. Located within easy walking distance of the beach and some nice restaurants. I would stay there again."
The price is NZ$282
includes taxes & fees
21 Oct - 22 Oct
The Atrium Resort, Virginia Beach by Vacatia
Four Sails Resort
Indoor pool

Four Sails Resort

4.0 star property
7.6 out of 10, Good, (43)
"It was peaceful"
The price is NZ$272
includes taxes & fees
5 Oct - 6 Oct
Four Sails Resort
Angie's Guest Cottage
Property entrance

Angie's Guest Cottage

2.0 star property
8.6 out of 10, Excellent, (225)
"Central location to boardwalk music venues. Friendly staff, clean, quiet. "
The price is NZ$177
includes taxes & fees
5 Oct - 6 Oct
Angie's Guest Cottage
stayAPT Suites Suffolk-Chesapeake
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.4 out of 10, Exceptional, (47)
"Nice cozy place to go with your family "
The price is NZ$235
includes taxes & fees
23 Oct - 24 Oct
stayAPT Suites Suffolk-Chesapeake
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.
Exterior

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.
Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach
Smart TV, DVD player, books

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

9.6 out of 10, Exceptional, (124)
"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
Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom
Property grounds

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
Sandbridge... Beautiful Beach Home With Direct Beach Access and Ocean Views
Fridge, microwave, oven, stovetop

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
On the beach, sun-loungers

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
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi
Smart TV, fireplace, video games, DVD player

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
Loft Space Minutes from Beach
Exterior

Loft Space Minutes from Beach

6.0 out of 10, (6)
"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
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (51)
"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
OceanFront Row,Private Pool,New Hottub,Sleeps 16,PetFriendly,Beachfront&Updates!
Property grounds

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

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

10.0 out of 10, Exceptional, (155)
"Access to beach is across the street and convenient. Beautiful home and plenty of room"
Last minute stays available! Great deals! Ocean views 8bdrm, 6bath pool!
Luxurious RV
Private kitchen

Luxurious RV

8.6 out of 10, Excellent, (14)
"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 NZ$690
includes taxes & fees
5 Oct - 6 Oct
Luxurious RV
Wildhorse Beachfront 12 bedroom Pool Estate
Fridge, microwave, oven, stovetop

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
Glamping your way-close to beach in Virginia Beach with AC
1 bedroom

Glamping your way-close to beach in Virginia Beach with AC

10.0 out of 10, Exceptional, (1)
"The experience was awesome, RV was more than adequate, our host were the kindest and helpful folks...even helped us find a great campground, on a holiday weekend!!! Great people and plan to come back for a longer stay . Thanks for making our vaca a great memory for our family."
Glamping your way-close to beach in Virginia Beach with AC
C9289 Sun King II. Oceanfront, Elevator, 4x4 Area, Pool, Hot Tub, Pets OK!
On the beach

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

2.0 star property
2.0 out of 10, (1)
"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...
C9289 Sun King II. Oceanfront, Elevator, 4x4 Area, Pool, Hot Tub, Pets OK!
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

Hilton Virginia Beach Oceanfront

Hilton Virginia Beach Oceanfront

10/10 Excellent
"Great scenery, lots of shops, lots of restaurants "
Marvin 1-night trip
Posted 1 day ago
Hilton Virginia Beach Oceanfront

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 favorite 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 depends 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 selected for you start as low as NZ$177 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.