Chester, VA Vacation Rentals

Our Favorite Vacation Rentals in Chester

  • My home
     2br Home/Apartment
    HolidayLettings
    From
    $46
  • Private apt just off I-95 near Fort Lee & VSU
     Home/Apartment
    HolidayLettings
    From
    $79
  • Petersburg Apt. w/ WiFi - Walk to Old Towne!
     Home/Apartment
    HolidayLettings
    From
    $208
  • Experience The "Lincoln Home" Overnight & Wedding
     4br Home/Apartment
    HolidayLettings
    From
    $459
  • Petersburg Apt. w/Balcony, Walk to Old Towne!
     2br Home/Apartment
    HolidayLettings
    From
    $214
  • Private Basement Apartment
    ExcellentHome/Apartment
    Airbnb
    From
    $77
  • Warm, Cozy and Comfortable Houseboat Gated Marina
    ExcellentBoat
    Airbnb
    From
    $111
  • Family House convenient to everything
    Excellent4br Home/Apartment
    Airbnb
    From
    $164

Check prices for these upcoming dates

Chester Vacation Rentals with a Pool

  • TreelyRd The Relaxing Country feel in the city
     2br Home/Apartment
    Airbnb
    From
    $186

Chester Vacation Rentals with Wi-Fi

  • Cozy, Fully Equipped RV - Cedar Crest on The James
    Excellent2br Home/Apartment
    Airbnb
    From
    $154
  • Home away from home /Fort Lee / VSU/ 95/Fire-pit!
    Excellent3br Home/Apartment
    Airbnb
    From
    $186
  • Enjoy Breezes on the James River
    Excellent2br Home/Apartment
    Airbnb
    From
    $216
  • Cute Bungalow Near Ft Lee Base
    Nice2br Home/Apartment
    Airbnb
    From
    $192

Chester Pet-Friendly Vacation Rentals

  • Enjoy Comfort At This Large 5 Bed Near VSU
    Nice5br Home/Apartment
    Airbnb
    From
    $284
  • Lovely house in historic city!
    Good2br Home/Apartment
    Airbnb
    From
    $85

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
67° 11°
3
75° 17°
4
78° 20°
4
86° 25°
3
93° 42°
4
95° 46°
5
99° 62°
1
96° 55°
2
97° 44°
1
97° 34°
2
70° 16°
1
72° 18°
3
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Chester. The warmest months in Chester are June and March, when temperatures reach 99 ˚F. The coolest month is December, when temperatures drop to 11 ˚F. The wettest month in Chester is July with 5.1 inches of rain, while the driest month is April with 0.86 inches of rain.

What Expert Travelers Think

  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    Jaz
    JazThe Life of a Social Butterfly
  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston

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