Chesapeake Vacation Rentals

Our Favorite Vacation Rentals in Chesapeake

  • Quay Villa
     Country House
  • 3 bedroom bungalow 25 min to the beach w/ king bed, cable, WiFi, Keurig machine
    Excellent3br Home/Apartment
  • Sunny Miami-Style Villa
  • Beautiful Waterfront Cottage Near Downtown Norfolk with Private Dock and Sunroom
  • King Guest Suite
  • Great Location: Near Airport & Downtown and Beach. Clean and Organized!
  • The Great Escape of Portsmouth! 3br king bed
     Country House
  • Quay Caribe (Island Vibes 365)
     3br Townhouse

Check prices for these upcoming dates

Chesapeake Vacation Rentals with a Pool

  • Sweet Suite!
  • Private room, Virginia Beach, Several amenites
  • Cheshire Retreat
    Excellent3br Home/Apartment
  • Virginia Beach Home with a Pool
    Good3br 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
  • One bedroom townhouse in Greenbrier Chesapeake
  • The Finesse Home
    Excellent3br Home/Apartment

Chesapeake Pet-Friendly Vacation Rentals

  • Peaceful Home
     3br Home/Apartment
  • Charming Apartment in Historic Neighborhood
  • Downtown Norfolk
  • ★Studio Apt CLOSE TO EVMS★

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

This climate histogram shows you the weather patterns in Chesapeake. The hottest month in Chesapeake is June, when temperatures peak at 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

  • — 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 love that AllTheRooms has everything in one place when I need to find accommodations that fit my family. Plus it provides all the details I need to help me make the best choice. I often recommend AllTheRooms to friends and family visiting NYC and they agree that it’s a great. Such a time saver!

  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims

Vacation Rentals in Chesapeake

Find the perfect rental for your vacation at We aggregate Airbnb, Priceline, Agoda and more. AllTheRooms has 349 rentals, hotels and other great places to stay during your time in Chesapeake, with everything from cheap hostels and homestays to extravagant Airbnbs and hotels. For those trying to save money, the lowest priced place to stay in Chesapeake comes in at $13 per night. The average price of a vacation rental is around $98 per night.

If you would like to stay connected during your trip, then you can choose from over 61 accommodations in Chesapeake that have WiFi. We have 9 accommodations that come with breakfast included. Fitness addicts can get a workout in during their stay by choosing from 21 accommodations that have gym facilities. Driving to Chesapeake? Then choose one of the 62 places to stay that comes with a parking spot included. We have 27 hotels and vacation rentals that have a pool or jacuzzi.

AllTheRooms has 18 pet-friendly places to stay in Chesapeake, so if you're traveling with your pet you won't have any problems.

In Chesapeake AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 3 providers, including 47 places to stay from Airbnb, 11 accommodations from Priceline and 11 places to stay from Agoda.

163 of the places to stay in Chesapeake have been rated by previous guests. They rated 70% as great. 44 places to stay in are instantly bookable.

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