Chesapeake Vacation Rentals

Check prices for these upcoming dates

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 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
98° 72°
8
96° 56°
8
84° 47°
3
85° 33°
8
71° 26°
4
76° 29°
4
75° 25°
4
88° 31°
5
82° 36°
5
87° 40°
3
95° 56°
4
102° 71°
2
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Rainy days

This climate histogram shows you the weather patterns in Chesapeake. The hottest month in Chesapeake is June, when temperatures peak at 102 ˚F. The coolest month is November, when temperatures drop to 25 ˚F. The wettest month in Chesapeake is May with 7.99 inches of rain, while the driest month is June with 2.2 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
  • — I travel to Boston regularly and I like to use AllTheRooms as it’s tricky to find good accommodation at a good price. The platform is easy to use and provides a complete set of features that saves me time and money on every trip

    Clwyd Probert
    Clwyd ProbertWhitehat
  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

    Samantha Wragg
    Samantha WraggCoco Travels

Vacation Rentals in Chesapeake

At AllTheRooms.com we have accommodations from all of your favorite providers - Airbnb, Priceline, Agoda and many more. Chesapeake has 352 hotels, vacation rentals and other unique places to stay, with prices to suit careful travellers, luxury travelers and everything in between. When traveling on a budget, the cheapest place to stay in Chesapeake is available at $13 per night. On average, an accommodation in Chesapeake will cost you $99 per night.

If you want an internet connection during your stay in Chesapeake, then you can choose from over 64 accommodations that provide WiFi internet. 10 of our accommodations include a breakfast in the price. You can keep up with your workout regime by staying at one of 22 accommodations that provide gym facilities. Driving to Chesapeake? Then choose one of the 65 places to stay that comes with a parking spot included. We track 28 places to stay that have a pool or jacuzzi.

Those traveling with a dog, cat or some other animal can stay in any of 17 accommodations that are designated as pet-friendly.

In Chesapeake AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 3 providers, including 50 places to stay from Airbnb, 11 accommodations from Priceline and 11 places to stay from Agoda.

172 accommodations in Chesapeake have been reviewed; 66% are rated excellent or good. You can instantly book any of 46 places to stay right now.

Destinations near Chesapeake

  • Williamsburg3,498 Properties
  • Virginia Beach2,776 Properties
  • Norfolk1,908 Properties
  • Richmond1,421 Properties
  • Charlottesville1,169 Properties
  • Arlington1,078 Properties
  • Luray759 Properties
  • Chincoteague724 Properties
  • Newport News724 Properties
  • Fredericksburg666 Properties
  • Blacksburg634 Properties
  • Roanoke593 Properties
  • Reston491 Properties
  • Lexington486 Properties
  • Harrisonburg473 Properties
  • Herndon468 Properties
  • McLean465 Properties
  • Alexandria449 Properties
  • Moneta447 Properties
  • Massanutten435 Properties
  • Glen Allen424 Properties
  • Vienna371 Properties
  • Winchester358 Properties
  • Staunton357 Properties
  • Cape Charles354 Properties
  • Portsmouth354 Properties
  • Huddleston353 Properties
  • Chantilly331 Properties
  • Abingdon326 Properties
  • Woodbridge304 Properties
  • Sterling302 Properties
  • Manassas296 Properties
  • Fairfax292 Properties
  • Springfield265 Properties
  • Hampton263 Properties
  • Stafford257 Properties
  • Petersburg254 Properties
  • Front Royal228 Properties
  • Ashburn210 Properties
  • Colonial Beach189 Properties
  • Falls Church180 Properties
  • Fancy Gap173 Properties
  • Suffolk167 Properties
  • Waynesboro150 Properties
  • Nellysford124 Properties
  • Floyd115 Properties
  • Leesburg108 Properties
  • Damascus106 Properties
  • Galax103 Properties
  • Salem98 Properties
  • Lynchburg89 Properties
  • Woodstock75 Properties
  • Wytheville74 Properties
  • Chester67 Properties
  • Lovettsville65 Properties
  • Ashland60 Properties
  • McGaheysville53 Properties
  • Reedville52 Properties
  • Deltaville33 Properties
  • Hillsville30 Properties
  • Barboursville29 Properties