Chesapeake, VA Vacation Rentals

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 $73 to $6,427 per night. Our most popular vacation rental types near Chesapeake are Apartment and Hotel.

Top vacation rentals in Chesapeake

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 $551 in Chesapeake, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$

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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 $281 for your next trip.

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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.

$$$$

Motel 6-Norfolk, VA

1 king bed

Pets allowed · Kitchen or Kitchenette · Air conditioner

Most favorited

Experience the best of Chesapeake with this Hotel available for $114. This property is equipped with amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$

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Explore vacation rentals with the most popular amenities in Chesapeake

Vacation rentals with air conditioning in Chesapeake

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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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, $102 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.