Holiday Homes in Chesapeake City County

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Check prices for these dates

Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul
In one month
25 Jul - 27 Jul
In two months
22 Aug - 24 Aug

Featured Holiday Homes in Chesapeake City County

The Hide Away Beach on the Bay
House

The Hide Away Beach on the Bay

2.0 star property
The Hide Away Beach on the Bay
Rustic Rooftop Delight - Bay Front 2 Bedroom Apts by RedAwning
Apartment, 2 Bedrooms | Balcony

Rustic Rooftop Delight - Bay Front 2 Bedroom Apts by RedAwning

3.5 star property
Rustic Rooftop Delight - Bay Front 2 Bedroom Apts by RedAwning
Bay View Bungalow By The Pier 4 Bedroom Home by RedAwning
House, 4 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker

Bay View Bungalow By The Pier 4 Bedroom Home by RedAwning

3.0 star property
The price is Rp7.140.875
Rp12.797.330 total
includes taxes & fees
23 Jul - 24 Jul
Bay View Bungalow By The Pier 4 Bedroom Home by RedAwning
Tri - Level Residential Home; Pet Friendly, Wifi, Off Street Parking 4 Bedroom Home by RedAwning
House, 5 Bedrooms | 5 bedrooms, free WiFi

Tri - Level Residential Home; Pet Friendly, Wifi, Off Street Parking 4 Bedroom Home by RedAwning

3.0 star property
2.0 out of 10, (1)
"Absolutely Horrible – Do Not Stay Here This property should not be listed for rent. When we arrived, it looked abandoned—broken windows on the ground floor, no exterior lighting (very unsafe at night), and the key was difficult to retrieve from the lockbox. As soon as we entered, we were hit with a musty, stale odor that made the entire place feel like a haunted house. The ground-floor bathroom door literally fell off the hinges when opened. That bathroom also flooded, making it unusable....
Tri - Level Residential Home; Pet Friendly, Wifi, Off Street Parking 4 Bedroom Home by RedAwning
Harbor Delight On The Bay - Private Sandy Beach! 4 Bedroom Home by RedAwning
House, 4 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster

Harbor Delight On The Bay - Private Sandy Beach! 4 Bedroom Home by RedAwning

3.5 star property
Harbor Delight On The Bay - Private Sandy Beach! 4 Bedroom Home by RedAwning
Luxury Beach Side Home 2 Bedroom Home by RedAwning
House, 2 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker

Luxury Beach Side Home 2 Bedroom Home by RedAwning

3.0 star property
Luxury Beach Side Home 2 Bedroom Home by RedAwning
Mermaids & Mutts 3 Bedroom Bungalow by RedAwning
Bungalow, 3 Bedrooms | Property grounds

Mermaids & Mutts 3 Bedroom Bungalow by RedAwning

3.0 star property
The price is Rp7.303.135
Rp13.230.991 total
includes taxes & fees
10 Jul - 11 Jul
Mermaids & Mutts 3 Bedroom Bungalow by RedAwning
Beach Front On The Bay 3 Bedroom Bungalow
Bungalow, 3 Bedrooms | Exterior

Beach Front On The Bay 3 Bedroom Bungalow

3.0 star property
10.0 out of 10, Exceptional, (1)
"This was excellent for my plans. The location was amazing and the beach access top tier. I would definitely rent this property again!"
Beach Front On The Bay 3 Bedroom Bungalow
Captains Quarters By The Bay 3 Bedroom Cottage by RedAwning
Cottage, 4 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster

Captains Quarters By The Bay 3 Bedroom Cottage by RedAwning

3.5 star property
Captains Quarters By The Bay 3 Bedroom Cottage by RedAwning
Charming Family Retreat With Spacious Yard 3 Bedroom Home
House, 3 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster

Charming Family Retreat With Spacious Yard 3 Bedroom Home

3.0 star property
10.0 out of 10, Exceptional, (1)
"This place was ideal and I'd stay here over and over again."
Charming Family Retreat With Spacious Yard 3 Bedroom Home
Beach Front On The Bay In Our Rustic, Pet Friendly Cottage 4 Bedroom Cottage by RedAwning
House, 4 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster

Beach Front On The Bay In Our Rustic, Pet Friendly Cottage 4 Bedroom Cottage by RedAwning

3.0 star property
Beach Front On The Bay In Our Rustic, Pet Friendly Cottage 4 Bedroom Cottage by RedAwning
The Boat House - Water Front, Wifi, Pet Friendly 1 Bedroom Home by RedAwning
House, 1 Bedroom | Property grounds

The Boat House - Water Front, Wifi, Pet Friendly 1 Bedroom Home by RedAwning

3.0 star property
The Boat House - Water Front, Wifi, Pet Friendly 1 Bedroom Home by RedAwning
Beach Front On The Bay In Our Rustic Beach 4 Bedroom Cottage by RedAwning
Cottage, 4 Bedrooms | 4 bedrooms, free WiFi

Beach Front On The Bay In Our Rustic Beach 4 Bedroom Cottage by RedAwning

3.5 star property
8.0 out of 10, Very good, (1)
Beach Front On The Bay In Our Rustic Beach 4 Bedroom Cottage by RedAwning
Buckroe Getaway- Walk to Beach dog Friendly
House

Buckroe Getaway- Walk to Beach dog Friendly

2.0 star property
Buckroe Getaway- Walk to Beach dog Friendly
Bay Oak Beach Cottage
House

Bay Oak Beach Cottage

2.0 star property
2.0 out of 10, (1)
"The property was lovely and as described BUT there were what sounded like raccoons in the attic that kept us awake every night scurrying around and fighting which made the stay unenjoyable. Attempts to reach out to rental company via email and through the app were unsuccessful. Even left a note on the kitchen table and there has been no response."
Bay Oak Beach Cottage
Luxury Beach Side Home Ii 2 Bedroom Home
House, 2 Bedrooms | Interior

Luxury Beach Side Home Ii 2 Bedroom Home

3.0 star property
Luxury Beach Side Home Ii 2 Bedroom Home
Nestled in Norfolk in Norfolk
House

Nestled in Norfolk in Norfolk

2.0 star property
Nestled in Norfolk in Norfolk
Ocean View Bay Beach Beauty
House

Ocean View Bay Beach Beauty

2.0 star property
Ocean View Bay Beach Beauty
Kosmos Rentals
Family Townhome | In-room dining

Kosmos Rentals

3.5 star property
10.0 out of 10, Exceptional, (1)
"The staff was immensely professional; clear and concise communication provided directions and instructions. The property was quiet and peaceful, the interior was immaculately clean, and amenities were laid out thoughtfully and in abundance. The bed was comfortable, and the view was incredible. I felt safe and relaxed. Wish I had more days to enjoy the property. Kosmos is elite, and I recommend for anyone traveling for any reason. "
Kosmos Rentals
Water Front Oasis 4 Bedroom Home by RedAwning
House, 4 Bedrooms | Property grounds

Water Front Oasis 4 Bedroom Home by RedAwning

3.0 star property
Water Front Oasis 4 Bedroom Home by RedAwning
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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