Chesapeake Vacation Rentals

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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
73° 27°
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78° 26°
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73° 20°
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79° 27°
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81° 27°
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88° 35°
3
96° 55°
4
96° 56°
4
100° 67°
5
96° 66°
8
92° 55°
4
93° 46°
4
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Rainy days

This climate histogram shows you the weather patterns in Chesapeake. The warmest months in Chesapeake are June and May, when temperatures reach 100 ˚F. The coolest month is December, when temperatures drop to 20 ˚F. The wettest month in Chesapeake is May with 7.57 inches of rain, while the driest month is January with 2.03 inches of rain.

What Expert Travelers Think

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  • — I use and I recommend AllTheRooms because it is a complete platform. It helps to save a lot of time, it gives all the main information about price, location, and features. In a few steps, I can easily find the best place to stay according to my criteria.

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Vacation Rentals in Chesapeake

At AllTheRooms.com we have rentals from all of the leading providers - Airbnb, Priceline, Agoda and others. We have 352 vacation rentals, hotels and other places to stay in Chesapeake ranging from budget options to luxury places to stay. For those wanting to keep costs down, the cheapest place to stay in Chesapeake is just $13 a night. On average, an accommodation in Chesapeake will cost you $99 per night.

If you would like to stay connected during your vacation, then you can choose from over 64 accommodations in Chesapeake that have WiFi. 10 of our accommodations include a breakfast in the price. Choose from 22 places to stay that provide gym facilities, so you won't miss a single workout. If you're planning on arriving in Chesapeake by car, be sure to choose from 65 accommodations that provide parking. We have 28 accommodations that have a pool or jacuzzi.

AllTheRooms has 17 pet-friendly places to stay in Chesapeake, so if you're traveling with your pet you won't have any problems.

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 50 places to stay from Airbnb, 16 accommodations from Priceline and 11 places to stay from Agoda.

172 accommodations in Chesapeake have been reviewed; 66% are rated highly. 46 accommodations allow instant booking.

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