Choose from 576 vacation rentals located in Chesapeake, Virginia. Top filters in Chesapeake include Air conditioner, Kitchen / Kitchenette, and TV. Prices range from $39 to $3,500 per night. Our most popular vacation rental types near Chesapeake are Condo and Hotel.

Top vacation rentals in Chesapeake

Beach | Beach towels
5.0
Outstanding(82 Reviews)
Cottage
 in Norfolk
Beautiful Waterfront Cottage near Downtown Norfolk- A Peaceful Secluded Paradise
2 guests · 1 bedroom · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake at Beautiful Waterfront Cottage near Downtown Norfolk- A Peaceful Secluded Paradise for $209 for your next trip.

$$$$
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Fridge, microwave, oven, stovetop
4.3
Excellent(34 Reviews)
House
 in Virginia Beach
Beach Family Time Enjoy The Backyard Pool And Sunroom
10 guests · 3 bedrooms · 3 baths
Garden · Pool · Kitchen / Kitchenette

Experience the best of Chesapeake with this House available for $519. This property is equipped with amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Property view
3.8
Good(370 Reviews)
Hotel
 in Norfolk
3star
Courtyard by Marriott Norfolk Downtown
Pool · Kitchen / Kitchenette · Air conditioner

Looking for a memorable stay in Chesapeake? Our Hotel might just be what you're looking for. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more during your stay.

$$$$
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4.1
Excellent(218 Reviews)
Hotel
 in Norfolk
3star
Residence Inn Norfolk Downtown
Pets allowed · Kitchen / Kitchenette · Air conditioner

Experience the best of Chesapeake with this Hotel available for $107. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Search by amenity

Explore vacation rentals with the most popular amenities in Chesapeake

Vacation rentals with air conditioning in Chesapeake

Property view
4.0
Good(505 Reviews)
Hotel
 in Virginia Beach
3star
Hilton Garden Inn Virginia Beach Town Center
Pool · Pets allowed · Kitchen / Kitchenette

This Hotel for $80 in Chesapeake, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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4.0
Good(333 Reviews)
Hotel
 in Chesapeake
3star
Hampton Inn Norfolk/Chesapeake - Greenbrier Area
Pool · Pets allowed · Kitchen / Kitchenette

This inviting Hotel in Chesapeake can fit your needs for many types of vacations, at $68 per night.

$$$$
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Property view
3.7
Good(500 Reviews)
Hotel
 in Virginia Beach
3star
SpringHill Suites by Marriott Norfolk Virginia Beach
Pool · Kitchen / Kitchenette · Air conditioner

Soak up the beauty of Chesapeake in our Hotel, SpringHill Suites by Marriott Norfolk Virginia Beach. With a range of amenities such as Air conditioner, Internet / Wifi and Laundry, you'll feel right at home.

$$$$
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Motel
 in Virginia Beach
Red Roof Inn Virginia Beach
Pool · Pets allowed · Kitchen / Kitchenette

Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake at Red Roof Inn Virginia Beach for $59 for your next trip.

$$$$
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Chesapeake

Chesapeake travel guide

Let us help you plan your perfect Chesapeake vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Chesapeake, and more.

Frequently asked questions

What are the most popular vacation rental amenities in Chesapeake?

  • Air conditioner
  • Kitchen / Kitchenette
  • TV

What is the price range for rentals in Chesapeake?

Vacation rentals in Chesapeake have a price range between $39-$3,500. The average price for rentals in Chesapeake is $120 per night.

Explore near Chesapeake

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