Chesapeake Vacation Rentals

Our Favorite Vacation Rentals in Chesapeake

  • Sunny Miami-Style Villa
  • Quay Caribe (Island Vibes 365)
     3br Townhouse
  • The Streets of Greenbrier
  • 3 bedroom bungalow 25 min to the beach w/ king bed, cable, WiFi, Keurig machine
    Excellent3br Home/Apartment
  • King Guest Suite
  • Beautiful Waterfront Cottage Near Downtown Norfolk with Private Dock and Sunroom
  • The Water Lily
  • *NEW* Beautiful Virginia Beach House (Taxes included In Nightly Rate)
     4br Home/Apartment

Check prices for these upcoming dates

Chesapeake Vacation Rentals with a Pool

  • Private room, Virginia Beach, Several amenites
  • Virginia Beach Home with a Pool
    Good3br Home/Apartment
  • Beautiful contemporary HOME w/pool, 22m away.
     5br Home/Apartment
  • Babe Cave 2.0
     2br Home/Apartment

Chesapeake Vacation Rentals with Wi-Fi

  • SureStay Hotel by Best Western Norfolk Little Creek
     70br 2-star Home/Apartment
  • *NEW* Beautiful Chesapeake Townhome
    Excellent3br Home/Apartment
  • Welcome to this cozy home in Chesapeake, VA
    Excellent3br Home/Apartment
  • One bedroom townhouse in Greenbrier Chesapeake

Chesapeake Pet-Friendly Vacation Rentals

  • Great Location: Near Airport & Downtown and Beach. Clean and Organized!
  • Downtown Norfolk
  • Virginia Beach Getaway perfect for families
    Excellent3br Home/Apartment
  • Your home in Vabeach-Chesapeake-Norfolk
    Excellent2br Home/Apartment

Chesapeake Travel Guide

Located in the Commonwealth of Virginia, Chesapeake is an independent city close to Virginia Beach, Newport, and Norfolk. Chesapeake is a very popular travel destination due to the great parks, wildlife reserves, hills, creeks, and beaches. Chesapeake is a diverse city because it has plenty of green space, but it is also populated with protected farmlands, swamps and miles of industrial waterfronts. The city has a long history having been settled in the late 1600s. Chesapeake started out as a small, farming community but it has since grown to be one of the economic backbones of Virginia.

Things to Do in Chesapeake

Chesapeake is a much beloved city, as it has plenty of amazing things to do. This historical town features many buildings and historical districts. However, the city is also an excellent place for an adventure or two. Outdoor lovers can spend time in the mother nature while exploring Oak Grove Lake Park. The park features places to fish, observation decks, picnic benches, hiking trails, and a few excellent birdwatching tours.

One of the most visited places in Chesapeake is the Dismal Swamp Canal Trail in the Dismal Swamp Wildlife Area. Despite the name, it is a beautiful place where visitors can see wildlife, go hiking, biking, play soccer, tennis, or fish in the pond. There has even been a number of black bear sitings in the area, but they are usually harmless.

For some beach fun travel to Virginia Beach, which is only a few miles northeast of Chesapeake. Beautiful sandy beach parks and lovely, iconic Virginia shores await visitors.

For those eager to spend some time in museums, visit the MacArthur Memorial Museum, which is dedicated to the US Army General, Douglas MacArthur, who served in three major wars and was considered a strategic mastermind. For a great maritime museum check out Nauticus Museum, where visitors can learn all about the naval and nautical history. The museum also has a number of interactive exhibits to keep kids entertained.

Best Places to Stay in Chesapeake

Chesapeake is located between a few state parks and bays, so those who want to be closer to downtown should look for places to stay in the northern portion of Chesapeake but to have more access to the great nature surrounding the city then try a place south of the city. Greenbrier East is also a good location because there are many restaurants, bars, clubs, stores, and shops within walking distance. The eastern shore also presents the distinct advantage of offering vacation rentals and hotels with ocean views.

Best Time to Visit Chesapeake

The most popular time to visit Chesapeake is September when the temperature warm, there is a lot of sunshine, and very little rain. The winter months are definitely cold for a beach destination but the month of August is actually the rainiest.

Price and Availability in Chesapeake

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The cheapest day to stay at a vacation rental in Chesapeake tends to be Tuesday, while the most expensive day tends to be Sunday. Vacation homes in Chesapeake tend to be busiest on Saturdays, while it tends to be much quieter on Mondays.
The most expensive month to stay in a vacation rental in Chesapeake is in August, while the cheapest month is in January. The most popular time to book a vacation rental in Chesapeake is in the high season in August. Chesapeake has its low season in December, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Chesapeake

Rainy days
83° 31°
70° 28°
74° 10°
81° 25°
83° 28°
83° 38°
93° 48°
101° 62°
95° 60°
95° 66°
91° 62°
91° 40°
Rainy days

This climate histogram shows you the weather patterns in Chesapeake. The hottest month in Chesapeake is July, when temperatures peak at 101 ˚F. The coolest month is December, when temperatures drop to 10 ˚F. The wettest month in Chesapeake is June with 9.21 inches of rain, while the driest month is November with 1.73 inches of rain.

What Expert Travelers Think

  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

    Whitney Wear
    Whitney WearTravel Better Guide
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School
  • — makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from


Vacation Rentals in Chesapeake

At we have rentals from all of the best providers - Airbnb, Priceline, Agoda and others. We have 390 vacation rentals, hotels and other places to stay in Chesapeake ranging from inexpensive options to luxury places to stay. A vacation in Chesapeake can be affordable - the cheapest price vacation rental is available at $13 a night. The average price of a vacation rental is $98 per night.

If you need to stay connected during your trip, then you can choose from over 64 accommodations in Chesapeake that have WiFi. 24 of our accommodations include a breakfast in the price. Choose from 18 accommodations that provide gym facilities, so you won't miss a single workout. Driving to Chesapeake? Then choose one of the 66 places to stay that comes with a parking spot included. We track 27 vacation rentals that have a pool or jacuzzi.

AllTheRooms has 16 pet-friendly places to stay in Chesapeake, so if you're traveling with your cat or dog you won't have any trouble.

We combine a wide variety of Chesapeake accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 3 providers, including 51 places to stay from Airbnb, 13 accommodations from Priceline and 11 places to stay from Agoda.

183 of our rentals in Chesapeake have been rated by previous guests. They rated 78% as excellent or good. 51 accommodations allow instant booking.

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