Choose from 548 vacation rentals located in Chesapeake, Virginia. Top filters in Chesapeake include Air conditioner, Kitchen / Kitchenette, and Internet / Wifi. Prices range from $39 to $3,500 per night. Our most popular vacation rental types near Chesapeake are Apartment and Hotel.

Top vacation rentals in Chesapeake

Beach | Beach towels
5.0
Outstanding(85 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 $199 for your next trip.

$$$$
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4.1
Excellent(625 Reviews)
Hotel
 in Norfolk
3star
Norfolk Waterside Marriott
Pool · Kitchen / Kitchenette · Air conditioner
Most favorited

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

$$$$
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Hotel
 in Chesapeake
2star
WoodSpring Suites Chesapeake-Norfolk Greenbrier
Pets allowed · Kitchen / Kitchenette · Air conditioner

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

$$$$
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Pool
4.7
Outstanding(58 Reviews)
House
 in Virginia Beach
Lovely Town Home
10 guests · 4 bedrooms · 2 baths
Garden · Pool · Kitchen / Kitchenette

Discover the beauty of Chesapeake with a stay at Lovely Town Home , a top rated House with amenities such as Air conditioner, Dishwasher and Fireplace, 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

Fridge, microwave, oven, stovetop
4.4
Excellent(41 Reviews)
House
 in Virginia Beach
Virginia Beach comfort stay. 9 miles from Oceanfront Free Breakfast & Starbucks
9 guests · 3 bedrooms · 3 baths
Pool · Kitchen / Kitchenette · Air conditioner

House in Chesapeake, for $239 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
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4.2
Excellent(260 Reviews)
Hotel
 in Virginia Beach
4star
The Westin Virginia Beach Town Center
Pool · Pets allowed · Air conditioner

Experience vacation in Chesapeake with our Hotel, The Westin Virginia Beach Town Center. Enjoy amenities such as Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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3.4
Average(188 Reviews)
Hotel
 in Norfolk
3star
Candlewood Suites Norfolk Airport, an IHG Hotel
Pets allowed · Kitchen / Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake at Candlewood Suites Norfolk Airport, an IHG Hotel for $75 for your next trip.

$$$$
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3.7
Good(485 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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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
  • Internet / Wifi

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 $122 per night.

Explore near Chesapeake

Rentals near top attractions

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