Choose from 536 vacation rentals located in Chesapeake, Virginia. Top filters in Chesapeake include Air conditioner, Kitchen or Kitchenette, and Internet / Wifi. Prices range from $66 to $5,846 per night. Our most popular vacation rental types near Chesapeake are Apartment and Hotel.

Top vacation rentals in Chesapeake

Fridge, microwave, oven, stovetop
4.8
Outstanding(63 Reviews)
Lakefront Oasis Centrally Located. Elegant, spacious and you're going to love it
House
 in Virginia Beach
12 guests · 4 bedrooms · 3 baths
Garden · Pool · Kitchen or Kitchenette

This House for $511 in Chesapeake, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Beach towels
5.0
Outstanding(88 Reviews)
Beautiful Waterfront Cottage near Downtown Norfolk- A Peaceful Secluded Paradise
Cottage
 in Norfolk
2 guests · 1 bedroom · 1 bath
Garden · Kitchen or 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 $261 for your next trip.

$$$$
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Property building
4.1
Excellent(585 Reviews)
Norfolk Waterside Marriott
Hotel
 in Norfolk
3star
1 king bed
Pool · Kitchen or 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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Motel 6-Norfolk, VA
Hotel
 in Norfolk
2star
1 king bed
Pets allowed · Kitchen or Kitchenette · Air conditioner
Most favorited

Experience the best of Chesapeake with this Hotel available for $106. This property is equipped with amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Vacation rentals with air conditioning in Chesapeake

Property building
3.8
Good(543 Reviews)
Comfort Suites Chesapeake - Norfolk
Hotel
 in Chesapeake
3star
1 sofa bed, 2 full beds
Garden · Pool · Kitchen or Kitchenette

Discover the beauty of Chesapeake with a stay at Comfort Suites Chesapeake - Norfolk, a top rated Hotel with amenities such as Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Motel 6-Portsmouth, VA
Hotel
 in Portsmouth
2star
1 king bed
Pets allowed · Kitchen or Kitchenette · Air conditioner

Are you ready to indulge in a relaxing getaway? Our Hotel in Chesapeake has everything you need for a rejuvenating stay. Treat yourself to Motel 6-Portsmouth, VA's exceptional amenities, such as Air conditioner, Internet / Wifi and Laundry.

$$$$
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Extended Stay America Suites - Chesapeake - Greenbrier Circle
Hotel
 in Chesapeake
2star
2 full beds
Pets allowed · Kitchen or Kitchenette · Air conditioner

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

$$$$
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Property building
4.1
Excellent(859 Reviews)
Hyatt Place Chesapeake
Hotel
 in Chesapeake
4star
1 king bed, 1 sofa bed
Pool · Pets allowed · Kitchen or Kitchenette
Most favorited

This attractive Hotel in Chesapeake, $95 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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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 or Kitchenette
  • Internet / Wifi

What is the price range for rentals in Chesapeake?

Vacation rentals in Chesapeake have a price range between $66-$5,846. The average price for rentals in Chesapeake is $130 per night.

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