Holiday Rentals in Chesapeake City County

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Rentals in Chesapeake City County

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1290)
"Been here 3 times now and every time the staff is always helpful and just super nice. Overall just a really good team "
The price is €145
includes taxes & fees
11 Mar - 12 Mar
The Ocean Key Virginia Beach Resort

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.0 out of 10, Very good, (1112)
"Great place but need more bigger park spaces for guess"
The price is €155
includes taxes & fees
11 Mar - 12 Mar
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

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

9.8 out of 10, Exceptional, (98)
"Our family of 4 enjoyed a quiet time in the outer banks at this lovely beach house. November isn't exactly the time most folks visit the beach, but we've spent most of our lives in the far north, so the "chilly weather" didn't prevent us from enjoying kayaking in the inner channels and viewing the sunset from the crow's nest. We found the kitchen very adequate; we were able to cook a lovely thanksgiving dinner and ate quite well the entire time. We packed all our needs/food for the weekend so...
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very good, (1296)
"Great stay at a great price."
The price is €167
includes taxes & fees
11 Mar - 12 Mar
The Atrium Resort, Virginia Beach by Vacatia

The Art Door only minutes from beach

9.6 out of 10, Exceptional, (63)
"Friendly and inviting space. Great spot for our quick overnight stay. Definitely look at using again if need to return to the area."
The price is €239
includes taxes & fees
17 Mar - 18 Mar
The Art Door only minutes from beach

OBX Gorgeous 6BR beach house, stunning views . 4WD access. Wild Horses

9.4 out of 10, Exceptional, (13)
"Great location and views. Property needs some updates and fixes. Good connectivity, TV's etc. We enjoyed our stay. "
OBX Gorgeous 6BR beach house, stunning views . 4WD access. Wild Horses

Four Sails Resort

3.5 star property
7.6 out of 10, Good, (26)
"Great location, property is good for families as it has a full kitchen. It’s basic but at the beach you just need a property that is clean and in a good location. The mattress could definitely use updating. The fresh popcorn is a nice touch. There was an issue with my unit leaking down into the unit below while I was in the bath and maintenance had entered my unit . It could have been handled better instead of pounding on the bathroom door."
Four Sails Resort

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

9.8 out of 10, Exceptional, (40)
"The house was great all the amenities we needed in the home. Clean spacious and comfortable. Would love to have them accommodate me and my friends next year "
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony

Executive Oceanfront Retreat

7.8 out of 10, Good, (79)
"It was so quiet and so relaxing. I enjoyed the views and especially the ocean during the full moon! I believe if more investments are made many more will book this 90s vibe vacation home. This is definitely a vintage treasure and should be maintained but not toy changed. Lori is very communicative and I felt safe the entire time. Thank you for the stay."
Executive Oceanfront Retreat

Great Location ! 1 Short Block To The Boardwalk.

9.6 out of 10, Exceptional, (236)
"Condo was cute and comfortable. Close to the beach. Our first visit. Frank was great to work with. "
Great Location ! 1 Short Block To The Boardwalk.

Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach

9.8 out of 10, Exceptional, (87)
"The condo is a refurbed motel room. Great location. Manager was quick to respond to questions_concerns. Cooking items were dirty and the sponge at the sink wrung out dirty water. Bathroom/shower were nicely redone. "
Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach

Dolphin Run Oceanfront Suites Virginia Beach

4.5 star property
10.0 out of 10, Exceptional, (1)
"Condo was clean and close to everything. Staff was very friendly and helpful."
Dolphin Run Oceanfront Suites Virginia Beach

Best OBX vacation!4x4 beach, private dock, hot tub, pool, Horses. Pet-Friendly

10.0 out of 10, Exceptional, (3)
"Love love loved this place it was a great get away, the kids loved every minute of it and saw horses almost everyday even a baby one! Caught some fish from the dock and made lasting memories! Loved driving on the beach and not having to haul everything to it by hand! Would def recommend this for someone who doesn’t like the crowds and loves a real getaway to nature and beach! Kids can’t wait to go back!"
Best OBX vacation!4x4 beach, private dock, hot tub, pool, Horses. Pet-Friendly

Beachside Haven Backyard and BBQ Fun in Croatan

2.0 star property
6.0 out of 10, (2)
"The location was great, and the host was very informative. This was a nice weekend gateway for a girls trip. "
Beachside Haven Backyard and BBQ Fun in Croatan

Brand NEW POOL for 2025~Oceanfront Home “Sea Watch”~REDUCED RATES APRIL AND MAY~

2.0 star property
10.0 out of 10, Exceptional, (3)
"This house was perfect for our three families to spread out but also let the kids bunk up and enjoy downstairs all to themselves! We loved going down to the park, going to the market for donuts, walking the beach and enjoying the beautiful views. We can’t wait to stay here again next year. The house was well stocked, comfortable, and the host was very responsive to any questions.we loved it! "
Brand NEW POOL for 2025~Oceanfront Home “Sea Watch”~REDUCED RATES APRIL AND MAY~

STEPS FROM THE WATER! BEAUTIFUL NEW HOME IN THE HEART OF A WILD HORSE COMMUNITY!

9.8 out of 10, Exceptional, (17)
"Property is new and clean in a great location. We could see the ocean from the kitchen/living room and saw horses from the house multiple days. The arcade games and shuffle board table were big hits too! Excellent, proactive communication from the owner. All contributed to a great stay!"
STEPS FROM THE WATER! BEAUTIFUL NEW HOME IN THE HEART OF A WILD HORSE COMMUNITY!

Resort 304C Wright 5 minute walk to boardwalk, NO DRIVING REQUIRED,

9.6 out of 10, Exceptional, (31)
"Great"
Resort 304C Wright 5 minute walk to boardwalk, NO DRIVING REQUIRED,

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

9.8 out of 10, Exceptional, (165)
"Was awesome to get back to the beach, the house was amazing, and got to see the wild horses "
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

Beach Condo 2 Min Walk From The Beach

9.4 out of 10, Exceptional, (101)
"Charming & close to my parents Apartment "
Beach Condo 2 Min Walk From The Beach

Waterview Cottage on the Currituck Sound with Private Dock & Kayaks

10.0 out of 10, Exceptional, (26)
"Quiet, great views, great property and dock, overall amazing experience for me and my family."
The price is €277
includes taxes & fees
27 Feb - 28 Feb
Waterview Cottage on the Currituck Sound with Private Dock & Kayaks
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.
Don't see what you're looking for?
See all available properties in Chesapeake City County
Save an average of 15% on thousands of hotels when you're signed in