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Chester, VA Vacation Rentals

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Our Favorite Vacation Rentals in Chester

  • Private apt just off I-95 near Fort Lee & VSU
    Private apt just off I-95 near Fort Lee & VSU
     1br Home/Apartment
    HolidayLettingsFrom $79
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  • NEW! Petersburg Apt. w/ WiFi - Walk to Old Towne!
    NEW! Petersburg Apt. w/ WiFi - Walk to Old Towne!
     1br Home/Apartment
    HolidayLettingsFrom $214
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  • Chic 2BR condo on Richmond’s downtown riverfront.
    Chic 2BR condo on Richmond’s downtown riverfront.
     2br Home/Apartment
    HolidayLettingsFrom $160
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  • NEW! Petersburg Apt. w/Balcony, Walk to Old Towne!
    NEW! Petersburg Apt. w/Balcony, Walk to Old Towne!
     2br Home/Apartment
    HolidayLettingsFrom $220
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  • Welcome to RVA, Comfy Chester home, +FREE WiFi
    Welcome to RVA, Comfy Chester home, +FREE WiFi
    Good2br Bedroom
    AirbnbFrom $215
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  • Bea's Place
    Bea's Place
    Good1br Home/Apartment
    AirbnbFrom $85
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  • Cozy, Fully Equipped RV - Cedar Crest on The James
    Cozy, Fully Equipped RV - Cedar Crest on The James
    Excellent2br Home/Apartment
    AirbnbFrom $133
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  • Lucy Long Lane
    Lucy Long Lane
     4br Home/Apartment
    AirbnbFrom $142
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See all 88 deals in Chester

Chester Vacation Rentals with a Pool

  • River Ridge on the James
    River Ridge on the James
    Excellent5br Other
    AirbnbFrom $1413
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  • 3 Story Townhouse with amazing Community Amenities
    3 Story Townhouse with amazing Community Amenities
     3br Home/Apartment
    AirbnbFrom $339
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See all deals in Chester with a pool

Chester Vacation Rentals with Wi-Fi

  • Enjoy Breezes on the James River
    Enjoy Breezes on the James River
    Excellent2br Home/Apartment
    AirbnbFrom $291
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  • Welcoming Hopewell Unit by Fort Lee/ Richmond I-95
    Welcoming Hopewell Unit by Fort Lee/ Richmond I-95
    Good1br Home/Apartment
    AirbnbFrom $63
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  • "Staccato" Entire home, minutes to downtown!
    "Staccato" Entire home, minutes to downtown!
    Excellent3br Other
    AirbnbFrom $209
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  • Bird's-Eye View in the Heart of Historic Old Towne
    Bird's-Eye View in the Heart of Historic Old Towne
    Excellent3br Home/Apartment
    AirbnbFrom $201
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See all deals in Chester with WiFis

Chester Pet-Friendly Vacation Rentals

  • Cute Bungalow Near Ft Lee Base
    Cute Bungalow Near Ft Lee Base
     2br Home/Apartment
    AirbnbFrom $133
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  • Fulton house for outdoor lovers and dogs, 3 bdrm
    Fulton house for outdoor lovers and dogs, 3 bdrm
    Excellent3br Home/Apartment
    AirbnbFrom $130
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  • COZY BUNGALOW DOWNTOWN RICHMOND
    COZY BUNGALOW DOWNTOWN RICHMOND
    Good3br Home/Apartment
    AirbnbFrom $99
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  • Cedar Crest on The James, Riverfront Campsite
    Cedar Crest on The James, Riverfront Campsite
    ExcellentCampsite
    AirbnbFrom $51
    View Deal
See all deals in Chester that allow pets

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
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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 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 Weather in Chester

95º 53º
5.12
94º 54º
4
93º 57º
4.47
90º 28º
5.16
72º 21º
5.54
68º 16º
2.58
71º -1º
3.39
80º 14º
2.24
82º 23º
2.3
84º 27º
3.46
92º 39º
6.38
96º 58º
7.52
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Rainy days
This climate histogram shows you the weather patterns in Chester. The warmest months in Chester are July and June, when temperatures reach 96 ˚F. The coolest month is January, when temperatures drop to -1 ˚F. The wettest month in Chester is June with 7.52 inches of rain, while the driest month is February with 2.24 inches of rain.

What Expert Travelers Think

Destinations near Chester