Holiday Rentals in Chesapeake City County

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Our top choices for Chesapeake City County holiday rentals

Terrace/patio

3-bedroom home away from home in fabulous Chesapeake, Virginia.

3-bedroom home away from home in fabulous Chesapeake, Virginia.
Chesapeake
10.0 out of 10, Exceptional, (47 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Indoor pool

Great Studio | Pool & Hot Tub. Your Next Vacation

Great Studio | Pool & Hot Tub. Your Next Vacation
Chesapeake
10.0 out of 10, Exceptional, (3 reviews)
"Impressed with the whole experience. "
United States
Patricia M.
The price is €212
includes taxes & fees
2 Jun - 3 Jun
Great Studio | Pool & Hot Tub. Your Next Vacation
Indoor pool

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Chesapeake
9.0 out of 10, Wonderful, (2 reviews)
"Very clean , great location. Will stay there again!!!"
United States
Tony H.
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Indoor pool

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is €212
includes taxes & fees
2 Jun - 3 Jun
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Indoor pool

Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
The price is €173
includes taxes & fees
31 May - 1 Jun
Studio | Free Breakfast. Indoor Pool & Hot Tub.
Indoor pool

Studio | Free Breakfast. Indoor Pool & Hot Tub

Studio | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is €230
includes taxes & fees
2 Jun - 3 Jun
Studio | Free Breakfast. Indoor Pool & Hot Tub
Pool

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Chesapeake
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Pool

Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Chesapeake
The price is €224
includes taxes & fees
26 May - 27 May
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Indoor pool

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Chesapeake
8.0 out of 10, Very good, (4 reviews)
"Good location and spacious rooms. Good stay!"
United States
Ariel G.
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Terrace/patio

Comfortable Beach Trailer Home

Comfortable Beach Trailer Home
Sandbridge
9.2 out of 10, Wonderful, (80 reviews)
"The stay was great. We loved walking around the neighborhood at sunset to see the view over the water. We would definitely stay here again. "
United States
Maddi S.
The price is €340
includes taxes & fees
31 May - 1 Jun
Comfortable Beach Trailer Home
Dining

Luxurious RV

Luxurious RV
Sandbridge
8.4 out of 10, Very good, (17 reviews)
"Excellent accommodation close to beach I would stay here again !!! "
United States
Scott E.
The price is €346
includes taxes & fees
25 May - 26 May
Luxurious RV
Apartment, Smoking | Private kitchen

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is €234
includes taxes & fees
26 May - 27 May
The Speakeasy Downtown Newport News
Dining

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Portsmouth
9.6 out of 10, Exceptional, (4 reviews)
"Property is well maintained. Great AC. Perfect for a couple to get away for a week. Central location was perfect for everything we planned to do for the week. "
United States
Paige M.
The price is €241
includes taxes & fees
24 Jun - 25 Jun
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Fridge, microwave, oven, stovetop

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Portsmouth
9.2 out of 10, Wonderful, (28 reviews)
"Pretty clean, convenient location to my daily travel, host was wonderful and very helpful when I needed help with something in the house. I would definitely stay here again."
United States
Niya w.
The price is €274
includes taxes & fees
24 Jun - 25 Jun
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Outdoor dining

Knot Three- Balcony View of ICW- Dog Friendly!

Knot Three- Balcony View of ICW- Dog Friendly!
Coinjock
9.6 out of 10, Exceptional, (5 reviews)
"The whole process was very easy and smooth. The property was clean and comfortable. I would definitely stay here again in the future!"
United States
Pam P.
The price is €240
includes taxes & fees
27 May - 28 May
Knot Three- Balcony View of ICW- Dog Friendly!
Terrace/patio

Knot One- Balcony View of ICW- Dog Friendly!

Knot One- Balcony View of ICW- Dog Friendly!
Coinjock
9.0 out of 10, Wonderful, (8 reviews)
"Loved watching the yachts in the ICW"
United States
susan
The price is €223
includes taxes & fees
27 May - 28 May
Knot One- Balcony View of ICW- Dog Friendly!
Property grounds

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
10.0 out of 10, Exceptional, (3 reviews)
"Great place. Nice area. Parking was confusing at first but host was very responsive "
United States
Ed and Laura S.
The price is €164
includes taxes & fees
25 May - 26 May
Private 1 Bed Apt - Historic Olde Towne Portsmouth
Smart TV, fireplace

Comfort near the water and University

Comfort near the water and University
Elizabeth city
8.0 out of 10, Very good, (7 reviews)
"The host was welcoming, very clean, and quiet area. Ty"
United States
Hector S.
The price is €256
includes taxes & fees
1 Jun - 2 Jun
Comfort near the water and University
Fridge, microwave, stovetop, coffee/tea maker

Guesthouse in ideal location with private entrance

Guesthouse in ideal location with private entrance
Suffolk
10.0 out of 10, Exceptional, (5 reviews)
"The property was clean, quiet and had everything we needed for a few days in town to see our grandbabies and daughter. Easy to find, park and just a few blocks from the highway, many food options and Kroger."
United States
Audrey J.
Guesthouse in ideal location with private entrance
Fridge, microwave, oven, stovetop

2 king beds -2nd fl walk 2 beach apt3

2 king beds -2nd fl walk 2 beach apt3
East Ocean View
10.0 out of 10, Exceptional, (3 reviews)
"Clean and perfect for our family stay. The apartment had everything we needed to be comfortable. "
United States
Kelly D.
The price is €274
includes taxes & fees
26 May - 27 May
2 king beds -2nd fl walk 2 beach apt3
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

Marriott Virginia Beach Oceanfront Resort

Marriott Virginia Beach Oceanfront Resort

6/10 Okay
"The property was nice. Had a Caribbean vibe. However I found it no different than a Holiday Inn. It was really just another hotel. I didn't like that we were restricted from ordering certain things on the menu from one of the restaurants. Not because it was available but because it was something from the kids menu. Something that they didn't offer on the adult menu. The other restaurant would not seat you in the restaurant in the morning. You had to sit outside or at a table close to the outside. And the food was not that good. Had to send several things back. And was afraid to try anything else from the menu. And the main thing. Beach chairs amenity was not available to use. You're a beach front hotel and advertise beach chairs as an amenity but did not have them available. Staff said they wouldn't be available until starting memorial day. Does not make sense. Therefore we were unable to lounge out on the beach during our stay because we left our chairs at home because they said they had chairs. Definitely not one of our best vacations or stays."
Sherry A H 4-night trip
Posted 1 hour ago
Marriott Virginia Beach Oceanfront Resort

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Holiday Homes in Chesapeake City County

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