Vacation rentals in Chester

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Top-rated vacation rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite
Guesthouse in Church Road
Heron Rock: Lakefront Cottage on Lake Chesdin
Enjoy peaceful lakefront living at Heron Rock Cottage, where you can stroll through the woods, swim or fish off the dock, paddle the lake in kayaks, or simply relax and enjoy the wildlife and beautiful sunsets. Situated on 6 acres in Dinwiddie County, this newly renovated cottage includes 2 bedrooms, full bath, full kitchen, living room with fireplace and private patio with dining area. Your stay includes full access to the grounds and dock and you are welcome to tie up a boat if you bring one.
Jul 16 – 23
$116 per night
5.0 out of 5 average rating, 129 reviews
Guest favorite
Home in Richmond
Luxury BOHO upper unit
Relax in this calm, stylish 3 bedroom/2 full bath upper level unit. Another Airbnb is in the finished basement unit. The space is completely yours and no access to the other basement unit. Only shared area is the back deck. Unit has a completely updated kitchen with stainless steal and granite. Master bedroom has a super comfy queen bed and a master bath that has a beautiful walk in shower. Guest room has another queen bed and office area has a futon. Elegance and romantic boho style throughout!
Sep 17 – 24
$133 per night
4.93 out of 5 average rating, 111 reviews
Guest favorite
Apartment in Chesterfield
Private guest apt on creek w/ patio & fire feature
“The Nest” is a completely private, ground level “basement” apartment. 15 minutes from downtown Richmond & 18 minutes to Pocahontas State Park, this space offers a peaceful, conveniently located, retreat. Private entrance, cozy patio, & large yard- all creek side and professionally designed. Laundry in unit, high speed internet, Smart TV. Yard is wooded and private. Many restaurants and tons of shopping within 5 min of the house, and 2.5 miles from highway access. Not pet friendly at this time.
Apr 19 – 26
$68 per night
4.86 out of 5 average rating, 237 reviews

Popular amenities for Chester vacation rentals

Stay near Chester's top sights

Kohl's Chester3 locals recommend
Half-Way House Restaurant3 locals recommend
Ashton Creek Vineyard6 locals recommend

Other great vacation rentals in Chester

Guest favorite
Guesthouse in Petersburg
"Lofty Cottage" Adorable 1-Bedroom Guest House
Mar 26 – Apr 2
$101 per night
4.93 out of 5 average rating, 132 reviews
Guest favorite
Home in Colonial Heights
Home Oasis/Fort Gregg-Adams/VSU/ 95/FirePit/PacMan
Mar 27 – Apr 3
$135 per night
4.92 out of 5 average rating, 104 reviews
Guest favorite
Barn in Richmond
Cozy Carriage House Conversion
Mar 24 – 31
$104 per night
4.92 out of 5 average rating, 208 reviews
Guest favorite
Home in Colonial Heights
Quiet Haven Near I-95 & Ft Gregg-Adams/ Petersburg
May 13 – 20
$90 per night
4.94 out of 5 average rating, 105 reviews
Guest favorite
Home in Henrico
Enjoy Breezes on the James River
Dec 21 – 28
$158 per night
4.95 out of 5 average rating, 103 reviews
Guest favorite
Cottage in Powhatan
Farm One Nights/ Pets ($65 Sun-Thur, $95 Fri/Sat)
May 17 – 24
$114 per night
4.93 out of 5 average rating, 198 reviews
Guest favorite
Farm stay in New Kent
Charming Willow Haven Modern Farmhouse Bungalow
Mar 9 – 16
$100 per night
4.99 out of 5 average rating, 114 reviews
Superhost
Boat in Richmond
Warm, Cozy and Comfortable Houseboat, Gated Marina
Dec 1 – 8
$103 per night
4.88 out of 5 average rating, 435 reviews
Superhost
Apartment in Hopewell
The Cozy Cove$ Ft Gregg Adams
Oct 31 – Nov 7
$72 per night
4.88 out of 5 average rating, 8 reviews
Guest favorite
Home in Chesterfield
Luxury Townhouse in Chesterfield
Jul 5 – 12
$99 per night
4.93 out of 5 average rating, 14 reviews
Guest favorite
Townhouse in Petersburg
Historic Mill Workers Cottage
Mar 2 – 9
$72 per night
4.93 out of 5 average rating, 41 reviews
Guest favorite
Home in Chester
Bohemian Bungalow
Jun 27 – Jul 4
$135 per night
4.88 out of 5 average rating, 8 reviews

Quick stats about vacation rentals in Chester

Total rentals

10 properties

Popular amenities

Gym, BBQ grill, and Laptop-friendly workspace

Wifi availability

10 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Total number of reviews

1.2K reviews

Nightly prices starting at

$40 before taxes and fees

Destinations to explore

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  2. United States
  3. Virginia
  4. Chesterfield County
  5. Chester