Holiday rentals near Castlewood
We found 663 holiday rentals — enter your dates for availability
Choose the perfect holiday home that's near Castlewood. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as parking and a TV. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Castlewood
Showing deals for:3 Oct - 10 Oct
Image gallery for Charming Cul-de-sac Retreat | Double Master + Garage + Home Office
9.69.6 out of 10 rating
Exceptional
(25 reviews)
Charming Cul-de-sac Retreat | Double Master + Garage + Home Office
Chesterfield, VA
7% off
Price is NZ$5,446
NZ$5,446
NZ$778 per night
includes taxes & fees
Image gallery for No Fees 2BR Cabin Tucked Away on Private Lake
1010 out of 10 rating
Exceptional
(12 reviews)
No Fees 2BR Cabin Tucked Away on Private Lake
Dinwiddie, VA
12% off
Price is NZ$2,675
NZ$2,675
NZ$382 per night
includes taxes & fees
Image gallery for Experience the "Lincoln Home" --#1 Historic Mansion Old Town; & Luxury Bathrooms
9.09.0 out of 10 rating
Wonderful
(8 reviews)
Experience the "Lincoln Home" --#1 Historic Mansion Old Town; & Luxury Bathrooms
Petersburg, VA
15% off
Price is NZ$4,666
NZ$4,666
NZ$667 per night
includes taxes & fees
Image gallery for Hidden Gem in the City!!!
8.08.0 out of 10 rating
Very good
(6 reviews)
Hidden Gem in the City!!!
Richmond, VA
7% off
Price is NZ$2,648
NZ$2,648
NZ$378 per night
includes taxes & fees
Image gallery for Pet-friendly spacious home with parking! Large deck & close to major attractions
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Pet-friendly spacious home with parking! Large deck & close to major attractions
Richmond, VA
7% off
Price is NZ$2,976
NZ$2,976
NZ$425 per night
includes taxes & fees
Image gallery for The Studio@ Eanes Drug
1010 out of 10 rating
Exceptional
(11 reviews)
The Studio@ Eanes Drug
Richmond, VA
7% off
Price is NZ$1,659
NZ$1,659
NZ$237 per night
includes taxes & fees
Image gallery for 1830's House in Historic Old Towne Petersburg, VA
9.69.6 out of 10 rating
Exceptional
(10 reviews)
1830's House in Historic Old Towne Petersburg, VA
Petersburg, VA
7% off
Price is NZ$1,657
NZ$1,657
NZ$237 per night
includes taxes & fees
Image gallery for Stylish RVA Rooftop Retreat - 3BR, 3BA, King Bed, Sleeps 6 & Free Parking!
1010 out of 10 rating
Exceptional
(6 reviews)
Stylish RVA Rooftop Retreat - 3BR, 3BA, King Bed, Sleeps 6 & Free Parking!
Richmond, VA
7% off
Price is NZ$3,325
NZ$3,325
NZ$475 per night
includes taxes & fees
Image gallery for The "Blissful Bungalow” your home away from home.
1010 out of 10 rating
Exceptional
(6 reviews)
The "Blissful Bungalow” your home away from home.
Petersburg, VA
7% off
Price is NZ$2,190
NZ$2,190
NZ$313 per night
includes taxes & fees
Image gallery for Unique Modern Farmhouse Comfort in the Heart of Richmond VA
1010 out of 10 rating
Exceptional
(5 reviews)
Unique Modern Farmhouse Comfort in the Heart of Richmond VA
Richmond, VA
7% off
Price is NZ$6,563
NZ$6,563
NZ$938 per night
includes taxes & fees
Image gallery for Convenient & Luxe Designer Apt w/ King Sized Bed
1010 out of 10 rating
Exceptional
(10 reviews)
Convenient & Luxe Designer Apt w/ King Sized Bed
Richmond, VA
10% off
Price is NZ$2,430
NZ$2,430
NZ$347 per night
includes taxes & fees
Image gallery for Near West End off Libby Avenue
1010 out of 10 rating
Exceptional
(6 reviews)
Near West End off Libby Avenue
Richmond, VA
7% off
Price is NZ$4,201
NZ$4,201
NZ$600 per night
includes taxes & fees
Image gallery for Retreat Zen/3br ranch house/private parking/FIRE-PIT/RF
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Retreat Zen/3br ranch house/private parking/FIRE-PIT/RF
Richmond, Virginia
8% off
Price is NZ$4,749
NZ$4,749
NZ$678 per night
includes taxes & fees
Image gallery for Superb 3BR W/Balcony Near Capitol Center
9.49.4 out of 10 rating
Exceptional
(13 reviews)
Superb 3BR W/Balcony Near Capitol Center
Richmond, VA
7% off
Price is NZ$4,402
NZ$4,402
NZ$629 per night
includes taxes & fees
Image gallery for Gorgeous Home with Office, Bonus Room & Large Deck
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Gorgeous Home with Office, Bonus Room & Large Deck
Richmond, VA
5% off
Price is NZ$3,946
NZ$3,946
NZ$564 per night
includes taxes & fees
Image gallery for Private Romantic Bungalow for Artists & Writers, 7 Mins to Downtown Richmond,
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Private Romantic Bungalow for Artists & Writers, 7 Mins to Downtown Richmond,
Richmond, VA
14% off
Price is NZ$2,358
NZ$2,358
NZ$337 per night
includes taxes & fees
Image gallery for Newly Renovated, Spacious Suite with Every Luxury
1010 out of 10 rating
Exceptional
(38 reviews)
Newly Renovated, Spacious Suite with Every Luxury
Richmond, VA
10% off
Price is NZ$2,398
NZ$2,398
NZ$343 per night
includes taxes & fees
Image gallery for Renovated Modern Stylish “Vibrant” 4bdrm Home
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Renovated Modern Stylish “Vibrant” 4bdrm Home
Richmond, VA
7% off
Price is NZ$6,373
NZ$6,373
NZ$910 per night
includes taxes & fees
Image gallery for Great Location. Close to about everywhere .Can't beat the value. Check reviews!
1010 out of 10 rating
Exceptional
(210 reviews)
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
Richmond, VA
6% off
Price is NZ$3,586
NZ$3,586
NZ$512 per night
includes taxes & fees
Image gallery for VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms
9.89.8 out of 10 rating
Exceptional
(118 reviews)
VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms
Richmond, VA
6% off
Price is NZ$3,154
NZ$3,154
NZ$451 per night
includes taxes & fees
Image gallery for Prime location! Minutes to RVA downtown, UVA, and top hospitals. Act now!
1010 out of 10 rating
Exceptional
(12 reviews)
Prime location! Minutes to RVA downtown, UVA, and top hospitals. Act now!
Richmond, VA
11% off
Price is NZ$2,351
NZ$2,351
NZ$336 per night
includes taxes & fees
Image gallery for Perfect Holiday Retreat Steps from Downtown RVA
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Perfect Holiday Retreat Steps from Downtown RVA
Richmond, VA
7% off
Price is NZ$3,372
NZ$3,372
NZ$482 per night
includes taxes & fees
Image gallery for VMFA • Carytown • Keyless • Coffee & Treats • Queen Bedrooms • Generous Deck
1010 out of 10 rating
Exceptional
(116 reviews)
VMFA • Carytown • Keyless • Coffee & Treats • Queen Bedrooms • Generous Deck
Richmond, VA
7% off
Price is NZ$3,553
NZ$3,553
NZ$508 per night
includes taxes & fees
Image gallery for Downtown, 2 Parking spaces, Historic Beauty
1010 out of 10 rating
Exceptional
(7 reviews)
Downtown, 2 Parking spaces, Historic Beauty
Richmond, VA
7% off
Price is NZ$3,815
NZ$3,815
NZ$545 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Castlewood
Amazing Private House Rental w/ pool! Richmond, VA
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
63 reviews(63 reviews)
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Sleeps 4 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
213 reviews(213 reviews)
VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms
Sleeps 6 · 3 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
118 reviews(118 reviews)
Charming 1-bedroom suite with WiFi and AC in Bon Air
Sleeps 7 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Lovely 2 Bedroom in the Heart of The Fan
Sleeps 4 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
59 reviews(59 reviews)
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
65 reviews(65 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value