Chester, VA Vacation Rentals

Our Favorite Vacation Rentals in Chester

  • Cozy Luxury Condo
     Home/Apartment
    Booking.com
    From
    $234
  • NEW! Petersburg Apt. w/ WiFi - Walk to Old Towne!
     Home/Apartment
    HolidayLettings
    From
    $183
  • Luxury Downtown Condo (HGTV AWARD WINNING CONDO)
     Home/Apartment
    Booking.com
    From
    $249
  • NEW! Petersburg Apt. w/Balcony, Walk to Old Towne!
     2br Home/Apartment
    HolidayLettings
    From
    $207
  • Luxury Downtown Condo (HGTV AWARD WINNING CONDO)
     Home/Apartment
    Booking.com
    From
    $249
  • Chic 2BR condo on Richmond’s downtown riverfront.
    Nice2br Home/Apartment
    HolidayLettings
    From
    $160
  • Not Available
     Home/Apartment
    Booking.com
    From
    $234
  • **Apt w/kit, Lvrm, and Bd, bath; Mins to Ft. Lee
    ExcellentHome/Apartment
    Airbnb
    From
    $67

Check prices for these upcoming dates

Chester Vacation Rentals with a Pool

  • Cozy Luxury Condo
     Home/Apartment
    Airbnb
    From
    $322
  • Luxury Downtown Condo (HGTV AWARD WINNING CONDO)
     2br Home/Apartment
    Airbnb
    From
    $431

Chester Vacation Rentals with Wi-Fi

  • Private Basement Apartment
    ExcellentHome/Apartment
    Airbnb
    From
    $77
  • Warm, Cozy and Comfortable Houseboat Gated Marina
    ExcellentBoat
    Airbnb
    From
    $133
  • Cozy, Fully Equipped RV - Cedar Crest on The James
    Excellent2br Home/Apartment
    Airbnb
    From
    $166
  • Remodeled studio basement unit, near Ft. Lee & VSU
    Excellent3br Home/Apartment
    Airbnb
    From
    $90

Chester Pet-Friendly Vacation Rentals

  • Cute Bungalow Near Ft Lee Base
    Nice2br Home/Apartment
    Airbnb
    From
    $192
  • Luxury Bungalow walking distance to Virginia State
    Good2br Home/Apartment
    Airbnb
    From
    $147
  • The "Cookie B", Private, Cozy and One of a Kind
    ExcellentHome/Apartment
    Airbnb
    From
    $133

Chester VA Travel Guide

Situated between the James and Appomattox Rivers, Chester, Virginia is both rich in history and experiences in the great outdoors.

Things to Do in Chester VA

Top things to do include hiking and picnicking at R. Garland Dodd Park at Point of Rocks, taking a step back in time at the interactive Henricus Historical Park, and exploring nature at the Dutch Gap Conservation Area.

Best Time to Visit Chester VA

The best tim eto visit Chester is from late May to late June and from early August to early October.

Price and Availability in Chester

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in Chester tends to be Monday, while the most expensive day tends to be Saturday. Vacation homes in Chester tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Chester is in November, while the cheapest month is in May. The most popular time to book a vacation rental in Chester is in the high season in April. Chester has its low season in September, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Chester

Rainy days
72° 21°
6
68° 16°
3
71° -1°
3
80° 14°
2
82° 23°
2
84° 27°
3
92° 39°
6
96° 58°
8
95° 53°
5
94° 54°
4
93° 57°
4
90° 28°
5
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Chester. The hottest month in Chester is July, when temperatures peak at 96 ˚F. The coolest month is December, when temperatures drop to -1 ˚F. The wettest month in Chester is July with 7.52 inches of rain, while the driest month is November with 2.24 inches of rain.

What Expert Travelers Think

  • — 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
  • — 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
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School

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