Chesapeake Vacation Rentals

Our Favorite Vacation Rentals in Chesapeake

  • Quay Villa
     Country House
    Booking.com
    From
    $154
  • Beautiful Waterfront Cottage Near Downtown Norfolk with Private Dock and Sunroom
    ExcellentCottage
    HolidayLettings
    From
    $163
  • Studios and Suites 4 Less Western Branch
     Studio
    NextTrip
    From
    $75
  • Sunny Miami-Style Villa
     Villa
    Booking.com
    From
    $499
  • *NEW* Beautiful Virginia Beach House (Taxes included In Nightly Rate)
     4br Home/Apartment
    HolidayLettings
    From
    $640
  • King Guest Suite
     Home/Apartment
    Booking.com
    From
    $63
  • Great Location: Near Airport & Downtown and Beach. Clean and Organized!
     Home/Apartment
    HolidayLettings
    From
    $218
  • Waterfront Townhouse, close to beach and shopping - Water Lily
     Home/Apartment
    Booking.com
    From
    $85

Check prices for these upcoming dates

Chesapeake Vacation Rentals with a Pool

  • Sweet Suite!
    ExcellentHome/Apartment
    Airbnb
    From
    $115
  • Virginia Beach Home with a Pool
    Good3br Home/Apartment
    Airbnb
    From
    $243
  • Beautiful contemporary HOME w/pool, 22m away.
     5br Home/Apartment
    Airbnb
    From
    $1,243
  • Babe Cave 2.0
     2br Home/Apartment
    Airbnb
    From
    $186

Chesapeake Vacation Rentals with Wi-Fi

  • SureStay Hotel by Best Western Norfolk Little Creek
     70br 2-star Home/Apartment
    Booking.com
    From
    $54
  • Welcome to this cozy home in Chesapeake, VA
    Excellent3br Home/Apartment
    Airbnb
    From
    $267
  • The Finesse Home
    Excellent3br Home/Apartment
    Airbnb
    From
    $185
  • Big Home 1Story ★Love & Laugh ★ 2KingBeds★ Wifi
    Good4br Home/Apartment
    Airbnb
    From
    $194

Chesapeake Pet-Friendly Vacation Rentals

  • Waterfront Oasis
    ExcellentHome/Apartment
    Airbnb
    From
    $146
  • ★Studio Apt CLOSE TO EVMS★
    GoodHome/Apartment
    Airbnb
    From
    $58
  • 20x20ftTENTCampsite. INDOOR Bathroom.Sleeps10
    Good3br Home/Apartment
    Airbnb
    From
    $84
  • Cozy updated home w/ huge comfy couch/sleep # bed
     2br Home/Apartment
    Airbnb
    From
    $130

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
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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
91 º62
4
91 º40
2
83 º31
4
70 º28
4
74 º10
4
81 º25
2
83 º28
4
83 º38
3
93 º48
8
101 º62
5
95 º60
9
95 º66
8
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
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
  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen
  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit

Vacation Rentals in Chesapeake

Pick the perfect accommodation for your trip at AllTheRooms.com. We aggregate Airbnb, Priceline, Agoda and many more. We have 377 vacation rentals, hotels and other accommodation types in Chesapeake ranging from cheap options to luxury places to stay. A vacation in Chesapeake can be affordable - the lowest price accommodation is available at $13 a night. A typical accommodation in Chesapeake costs on average $99 a night.

If you have to have an internet connection during your stay in Chesapeake, then you can choose from over 63 accommodations that have WiFi internet. We have 24 accommodations that come with breakfast included. You can maintain your workout regime by staying at one of 17 accommodations that provide gym facilities. Driving to Chesapeake? Then choose one of the 64 places to stay that comes with a parking spot included. We track 26 hotels and vacation rentals that have a pool or jacuzzi.

If you're traveling with a furry friend, then make sure to select one of the 15 pet-friendly accommodations available.

AllTheRooms compares vacation rentals, hotels and other bespoke accommodation types from loads of providers in Chesapeake, including 49 places to stay from Airbnb, 13 accommodations from Priceline and 11 places to stay from Agoda

208 of our rentals in Chesapeake have been rated by previous guests. They rated 78% as great. 50 accommodations allow instant booking.

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