We use cookies to provide you with the best browsing experience. The data collected by cookies is used to optimise the website for our users and deliver an appropriate service and relevant information to you. By using our site we assume you’re aware and agree to use the cookies for this purpose.

Destination Photo

Chesapeake Vacation Rentals

Our Favorite Vacation Rentals in Chesapeake

See all 387 vacation rentals in Chesapeake

Chesapeake Vacation Rentals with a Pool

See all vacation rentals in Chesapeake with a pool

Chesapeake Vacation Rentals with Wi-Fi

See all vacation rentals in Chesapeake with WiFis

Chesapeake Pet-Friendly Vacation Rentals

See all vacation rentals in Chesapeake that allow pets

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

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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 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 Weather in Chesapeake

93º 48º
7.68
101º 62º
4.96
95º 60º
9.21
95º 66º
8.13
91º 62º
3.88
91º 40º
2.27
83º 31º
4.13
70º 28º
3.89
74º 10º
3.51
81º 25º
1.73
83º 28º
3.88
83º 38º
3.41
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
Rainy days
This climate histogram shows you the weather patterns in Chesapeake. The warmest months in Chesapeake are July and June, when temperatures reach 101 ˚F. The coolest month is January, when temperatures drop to 10 ˚F. The wettest month in Chesapeake is July with 9.21 inches of rain, while the driest month is February with 1.73 inches of rain.

What Expert Travelers Think

Vacation Rentals in Chesapeake

Browse accommodations from all the best providers including Airbnb, priceline, Agoda and many more at AllTheRooms.com. Chesapeake has 387 hotels, vacation rentals and other special places to stay, with prices to suit budget travelers, extravagant travelers and everything in between. When traveling on a budget, the cheapest place to stay in Chesapeake is available at $15 per night. The average price of an accommodation is $95 per night.

If you need to stay connected during your trip, then you can choose from over 49 accommodations in Chesapeake that have WiFi. We have 19 accommodations that include a breakfast included. Fitness addicts can get a workout in during their stay by choosing from 17 accommodations that have gym facilities. If you are driving to Chesapeake, you'll want to pick from 50 places to stay that provide parking. We have 22 hotels and vacation rentals that have a pool or jacuzzi.

AllTheRooms has 15 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 4 providers, including 35 places to stay from Airbnb, 13 accommodations from priceline and 11 places to stay from Agoda.

189 of the accommodations in Chesapeake have been reviewed and rated. 69% are rated excellent or good. You can instantly book any of 44 places to stay right now.