Choose from 593 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

Property view
4.8
Outstanding(47 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 $452 in Chesapeake, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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Beautiful Winter Sunrise!
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 $199 for your next trip.

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Property view
3.6
Good(488 Reviews)
Hotel
 in Portsmouth
3star
Quality Inn & Suites Olde Town
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

When traveling to Chesapeake, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $53 per night.

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Property view
3.1
Average(486 Reviews)
Motel
 in Chesapeake
Red Roof Inn Chesapeake Conference Center
Pets allowed · Kitchen / Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Chesapeake? This Motel offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Pets allowed, and more.

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Search by amenity

Vacation rentals with air conditioning in Chesapeake

Room
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 $175 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

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Property view
4.1
Excellent(158 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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Hotel
 in Virginia Beach
3star
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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Property view
3.6
Good(456 Reviews)
Hotel
 in Suffolk
3star
Comfort Suites Suffolk – Chesapeake
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Nestled in Chesapeake, this Hotel is perfect for your next vacation. Enjoy Comfort Suites Suffolk – Chesapeake's top-rated amenities, including Air conditioner, Internet / Wifi and Laundry, 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.

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.

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