Holiday Rentals in Chesapeake City County

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Featured Holiday Rentals in Chesapeake City County

The Atrium Resort, Virginia Beach by Vacatia
Stunning coastal views from a scenic pier overlooking a sandy beach and the ocean.

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very good, (1414)
"My family has a really great time and stay"
The Atrium Resort, Virginia Beach by Vacatia
The Ocean Key Virginia Beach Resort
Relax by the pool, surrounded by lounge chairs and a seating area.

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1397)
"Our room was clean and stocked with everything we needed. Great, convenient location. Staff was nice at the front desk."
The Ocean Key Virginia Beach Resort
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Relax in this serene outdoor seating area with a sofa and chairs, perfect for taking in the view.

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.2 out of 10, Very good, (1105)
"My family truly enjoyed our stay! Would definitely stay here again. "
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
stayAPT Suites Suffolk-Chesapeake
Relax in style around the fire pit, surrounded by a clean and minimalist design.

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.4 out of 10, Exceptional, (29)
"Great place to stay!"
The price is €116
includes taxes & fees
4 Aug - 5 Aug
stayAPT Suites Suffolk-Chesapeake
Angie's Guest Cottage
Traditional home with a charming front porch and a red door, featuring a glass panel.

Angie's Guest Cottage

2.0 star property
8.6 out of 10, Excellent, (217)
"Very Cozy and near the beach, Staff is very courteous and friendly. "
Angie's Guest Cottage
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi
Relax in this stylish living room with a sofa, armchair, and coffee table, offering a view of the ocean and beach.

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

9.8 out of 10, Exceptional, (175)
"Amazing house, great location! This house was perfect for our family vacation. The wild horses strolled by a few times and the owner was great on giving helpful tips on where to find the horses. Highly suggest this house if you want to have a once in a lifetime experience in the Outer Banks! "
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi
Four Sails Resort
Relax by the serene pool, surrounded by lounge chairs and tables, with expansive city views.

Four Sails Resort

3.5 star property
7.6 out of 10, Good, (36)
"Very nice place"
Four Sails Resort
Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.
Relax in a spacious living area with a high ceiling, ceiling fan, and expansive views of the surrounding landscape.

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

8.6 out of 10, Excellent, (19)
"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.
Loft Space Minutes from Beach
A single-story building with a sloped roof and a small window, situated next to a tree.

Loft Space Minutes from Beach

5.4 out of 10, (3)
"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
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach
Enjoy cooking in this well-equipped kitchen with a granite countertop, stainless steel appliances, and a convenient island with sink and seating.

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

9.4 out of 10, Exceptional, (101)
"Our family enjoyed the property rental at VA Beach. The owners responded "
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach
Nautical Dream, redecorated oceanfront home with incredible views and decks
Guests can enjoy access to the sandy beach.

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
Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach
Relax in this beachside retreat with a wicker sofa, armchair, and ocean views from large windows.

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

9.6 out of 10, Exceptional, (119)
"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
Newly Updated Beautiful 4BR Oceanfront Home with Pool & Hot Tub
Horses stroll along the shoreline, where the ocean meets the horizon.

Newly Updated Beautiful 4BR Oceanfront Home with Pool & Hot Tub

9.8 out of 10, Exceptional, (138)
"The house was beautiful, clean and plenty of room for all our guest! The view was amazing! "
Newly Updated Beautiful 4BR Oceanfront Home with Pool & Hot Tub
The Art Door only minutes from beach
Relax in a serene backyard oasis with a potted plant and two comfortable chairs.

The Art Door only minutes from beach

9.6 out of 10, Exceptional, (83)
"Loved the stay! Property was very clean, quiet and easy to get to everything Virginia Beach has to offer. The property manager was very quick to respond and helpful. Will stay there again"
The price is €212
includes taxes & fees
6 Aug - 7 Aug
The Art Door only minutes from beach
Lovely 2 bedroom condo walking distance to Beach Condominium - Entire home
Cozy living space with a kitchenette, dining area, and seating area, featuring a microwave, stove, and refrigerator.

Lovely 2 bedroom condo walking distance to Beach Condominium - Entire home

9.4 out of 10, Exceptional, (22)
"As listed close to everything and made our stay very easy. Communication with owner was easy and all questions we had were answered."
The price is €534
includes taxes & fees
4 Aug - 5 Aug
Lovely 2 bedroom condo walking distance to Beach Condominium - Entire home
OceanfrontOasis w/Breathtaking Views! Pool w/TikiBar.Hottub.Guesthouse
Relax in this ocean-view living room with a sofa, armchairs, and coffee table.

OceanfrontOasis w/Breathtaking Views! Pool w/TikiBar.Hottub.Guesthouse

9.8 out of 10, Exceptional, (44)
"Wonderful trip with an awesome house. Very quiet and the house is beautiful. Lots of room. Thank you so much."
OceanfrontOasis w/Breathtaking Views! Pool w/TikiBar.Hottub.Guesthouse
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.
Experience the charm of this multi-level building with a spacious upper deck and balconies.

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

9.8 out of 10, Exceptional, (103)
"We stayed as a family for our spring break. House was clean, beds were comfortable, and location was great! The kids loved seeing wild horses right off the deck and we found more by driving around. We spent one day on the beach and that was a lot of fun. Weather was a bit chilly, but nothing we could control!"
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.
OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission
On the beach, beach towels

OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission

8.0 out of 10, Very good, (15)
"Loved the location and the avtivitoes/events in the neighborhood."
The price is €435
includes taxes & fees
29 Jul - 30 Jul
OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission
Luxurious RV
Compact kitchen with microwave, stainless steel refrigerator, and modern sink.

Luxurious RV

7.8 out of 10, Good, (8)
"Great location, the rv itself was ok, spacious, does the job for a beach weekend. a little overpriced for what you get. The pull out couches were not comfortable at all and there was not much provided. One roll of toilet paper, one trash bag. It would have been nice to have a sponge to wash dishes and some basic spices. Maybe a couple K cups for coffee. I would rent again."
The price is €350
includes taxes & fees
30 Jul - 31 Jul
Luxurious RV
Home Near Towncenter | Minutes from Beaches | Central to Hamptonroads
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and sink.

Home Near Towncenter | Minutes from Beaches | Central to Hamptonroads

4.0 star property
7.4 out of 10, Good, (41)
"First want to start off by saying the house is as described actually better then the photos online led us to believe. It's an older house but was clean and decorated beautifully. For the money, description, and space you get staying in this home I would definatley recomend you staying here. It's not a 5 star luxury resort, but I gave 5 stars for the house being it was better then what we expected. Our family enjoyed our stay."
The price is €397
includes taxes & fees
29 Jul - 30 Jul
Home Near Towncenter | Minutes from Beaches | Central to Hamptonroads
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

Schooner Inn

Schooner Inn

10/10 Excellent
"It was a great stay. Would recommend getting more luggage carts! Staff did not make an effort to locate one upon checkout, just stating they must be on another floor. "
Natasha 6-night trip
Posted 10 hours ago
Schooner Inn