Chesapeake, VA Vacation Rentals

Choose from 566 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

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 $222 for your next trip.

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Motel 6-Norfolk, VA

Pets allowed · Kitchen / Kitchenette · Air conditioner

Experience the best of Chesapeake with this Hotel available for $75. This property is equipped with amenities including Air conditioner, Internet / Wifi and Laundry, and more.

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La Quinta Inn by Wyndham Norfolk Virginia Beach

Pool · Pets allowed · Kitchen / Kitchenette

Soak up the beauty of Chesapeake in our Hotel, La Quinta Inn by Wyndham Norfolk Virginia Beach. With a range of amenities such as Air conditioner, Internet / Wifi and Pets allowed, you'll feel right at home.

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Motel 6-Portsmouth, VA

Pets allowed · Kitchen / 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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Explore vacation rentals with the most popular amenities in Chesapeake

Vacation rentals with air conditioning in Chesapeake

4.8

Outstanding(51 Reviews)

House

in Virginia Beach

Lakefront Oasis Centrally Located. Everything New. Custom Elegant Features.

12 guests · 4 bedrooms · 3 baths

Garden · Pool · Kitchen / Kitchenette

This House for $714 in Chesapeake, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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3.3

Average(531 Reviews)

Hotel

in Chesapeake

3star

Sleep Inn & Suites Chesapeake - Portsmouth

Pool · Kitchen / 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 Sleep Inn & Suites Chesapeake - Portsmouth's exceptional amenities, such as Air conditioner, Internet / Wifi and Laundry.

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4.1

Excellent(1,063 Reviews)

Hotel

in Norfolk

2star

Holiday Inn Express Hotel & Suites Norfolk Airport, an IHG Hotel

Pool · Kitchen / Kitchenette · Air conditioner

The best choice in Chesapeake for Hotel, for $75 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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4.1

Excellent(163 Reviews)

Hotel

in Chesapeake

3star

Residence Inn by Marriott Chesapeake Greenbrier

Pool · Pets allowed · Kitchen / Kitchenette

Nestled in Chesapeake, this Hotel is perfect for your next vacation. Enjoy Residence Inn by Marriott Chesapeake Greenbrier's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.

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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.