House holiday rentals in Chesterfield County
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Top-rated house rentals in Chesterfield County
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for house rentals in Chesterfield County
House rentals with a pool
Home in Richmond
4.84 out of 5 average rating, 349 reviewsNo cleaning fee/Hot tub/Entire House 2100 Sq ft
6–13 Oct
Home in Sandston
4.71 out of 5 average rating, 7 reviewsCharming Sandston Home ~ 9 Mi to Richmond!
25 Feb – 4 Mar
Home in Midlothian
5.0 out of 5 average rating, 7 reviewsA house you wish you called home
4–11 Oct
Home in Midlothian
5.0 out of 5 average rating, 8 reviewsSpacious Peaceful Getaway
1–8 Dec
Home in Chesterfield
5.0 out of 5 average rating, 9 reviewsLakefront Resort
14–21 Nov
Weekly house rentals
Home in Midlothian
5.0 out of 5 average rating, 124 reviewsThe Cottage on Bernard's Creek
29 Aug – 5 Sep
Home in Midlothian
4.99 out of 5 average rating, 185 reviewsSheffield Cottage -Charming and Cozy 4BR Cottage
26 Dec – 2 Jan
Home in Midlothian
4.95 out of 5 average rating, 133 reviewsGinger's House.
25 Jun – 2 Jul
Home in Richmond
4.94 out of 5 average rating, 105 reviewsThe Cottage in the City -Private Yard and Fire Pit
25 Feb – 4 Mar
Home in Richmond
4.87 out of 5 average rating, 150 reviewsThe Van Life House
21–28 Oct
Home in Richmond
4.87 out of 5 average rating, 147 reviewsChurch Hill house with view of river and park
24 Sep – 1 Oct
Home in Richmond
4.89 out of 5 average rating, 102 reviews💎Bright 3BR Hidden Gem - 5 mins from Downtown RVA💎
4–11 Jul
Home in Colonial Heights
4.82 out of 5 average rating, 117 reviews3 bedroom Charm with flowing creek Getaway Trip
21–28 Jul
Private house rentals
Home in Richmond
4.85 out of 5 average rating, 41 reviewsCozy Cape Close to the City!
17–24 Sep
Home in Petersburg
4.95 out of 5 average rating, 38 reviewsHistoric Home Near Old Town
7–14 Dec
Home in Prince George
4.93 out of 5 average rating, 29 reviewsLuxury stay in Prince George
14–21 Oct
Home in Petersburg
4.93 out of 5 average rating, 72 reviewsThe historic John Baird House
25 Mar – 1 Apr
Home in Chesterfield
4.94 out of 5 average rating, 96 reviewsCharming Cul-de-sac Retreat|Double Master + Garage
8–15 Apr
Home in Richmond
5.0 out of 5 average rating, 21 reviewsPrivate 2 acres minutes from Airport & Downtown
14–21 Aug
Home in Richmond
5.0 out of 5 average rating, 33 reviewsRVA Retreat
3–10 Aug
Home in Hopewell
5.0 out of 5 average rating, 8 reviewsCity Point Cottage
4–11 Jun
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