Vacation rentals near Castlewood
We found 658 vacation rentals — enter your dates for availability
Select the perfect private vacation rental within easy reach of Castlewood. Vacation rentals offer the amenities you expect for your stay with friends, family, or just your pet, like WiFi and cable TV. You'll be sure to find a rental to meet everyone's needs, including options that are accessible or non-smoking.
Vacation rentals with weekly discounts - Castlewood
Showing deals for:Nov 7 - Nov 14
Image gallery for Luxurious 1-bedroom riverfront Cottage with AC and WiFi in charming Midlothian.
1010 out of 10 rating
Exceptional
(5 reviews)
Luxurious 1-bedroom riverfront Cottage with AC and WiFi in charming Midlothian.
Midlothian, VA
10% off
Price is CA $619
CA $619
CA $5,845 total
CA $5,845 total
includes taxes & fees
Image gallery for Cozy three bedroom fully furnish house
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Cozy three bedroom fully furnish house
Petersburg, VA
10% off
Price is CA $190
CA $190
CA $1,885 total
CA $1,885 total
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
20% off
Price is CA $400
CA $400
CA $3,899 total
CA $3,899 total
includes taxes & fees
Image gallery for Beautiful and Spacious home w/Outdoor Kitchen
1010 out of 10 rating
Exceptional
(32 reviews)
Beautiful and Spacious home w/Outdoor Kitchen
Midlothian, VA
10% off
Price is CA $495
CA $495
CA $4,925 total
CA $4,925 total
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
10% off
Price is CA $208
CA $208
CA $2,204 total
CA $2,204 total
includes taxes & fees
Image gallery for Cozy 4 bed 2 bath house located less than 4 minutes from the Richmond Airport.
9.29.2 out of 10 rating
Wonderful
(19 reviews)
Cozy 4 bed 2 bath house located less than 4 minutes from the Richmond Airport.
Highland Springs, VA
10% off
Price is CA $389
CA $389
CA $4,469 total
CA $4,469 total
includes taxes & fees
Image gallery for Welcome to King George Manor your family-friendly getaway!
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Welcome to King George Manor your family-friendly getaway!
Charles City, VA
15% off
Price is CA $401
CA $401
CA $3,810 total
CA $3,810 total
includes taxes & fees
Image gallery for Charming Cul-de-sac Retreat | Double Master + Garage + Home Office
9.69.6 out of 10 rating
Exceptional
(27 reviews)
Charming Cul-de-sac Retreat | Double Master + Garage + Home Office
Chesterfield, VA
10% off
Price is CA $469
CA $469
CA $4,556 total
CA $4,556 total
includes taxes & fees
Image gallery for Cozy Suburban Nest Guest Suite separate from main home with hottub
8.88.8 out of 10 rating
Excellent
(11 reviews)
Cozy Suburban Nest Guest Suite separate from main home with hottub
Hopewell, VA
5% off
Price is CA $121
CA $121
CA $1,146 total
CA $1,146 total
includes taxes & fees
Image gallery for Spacious 2900 SQ Feet House In Ginter Park, 10 min to Everywhere
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Spacious 2900 SQ Feet House In Ginter Park, 10 min to Everywhere
Richmond, VA
15% off
Price is CA $468
CA $468
CA $4,787 total
CA $4,787 total
includes taxes & fees
Image gallery for Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown
9.09.0 out of 10 rating
Wonderful
(8 reviews)
Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown
Richmond, VA
15% off
Price is CA $267
CA $267
CA $3,013 total
CA $3,013 total
includes taxes & fees
Image gallery for Large Home, 2 Blocks from Lake/ Park, Outdoor Dining + Parking
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Large Home, 2 Blocks from Lake/ Park, Outdoor Dining + Parking
Richmond, VA
10% off
Price is CA $308
CA $308
CA $3,288 total
CA $3,288 total
includes taxes & fees
Image gallery for The Cozy Rancher | Petersburg | King Bed
1010 out of 10 rating
Exceptional
(31 reviews)
The Cozy Rancher | Petersburg | King Bed
Petersburg, VA
10% off
Price is CA $192
CA $192
CA $1,919 total
CA $1,919 total
includes taxes & fees
Image gallery for Grand Retreat with VMFA Views + Large Groups
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Grand Retreat with VMFA Views + Large Groups
Richmond, VA
10% off
Price is CA $903
CA $903
CA $9,238 total
CA $9,238 total
includes taxes & fees
Image gallery for Church Hill • Fenced • Pet Friendly • One Level • King Suite + 2 Queen Bedrooms
1010 out of 10 rating
Exceptional
(12 reviews)
Church Hill • Fenced • Pet Friendly • One Level • King Suite + 2 Queen Bedrooms
Richmond, VA
10% off
Price is CA $259
CA $259
CA $2,877 total
CA $2,877 total
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
10% off
Price is CA $130
CA $130
CA $1,270 total
CA $1,270 total
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
10% off
Price is CA $359
CA $359
CA $3,492 total
CA $3,492 total
includes taxes & fees
Image gallery for Spacious 4-bedroom house in charming Richmond with WiFi and AC
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Spacious 4-bedroom house in charming Richmond with WiFi and AC
Richmond, VA
10% off
Price is CA $495
CA $495
CA $5,312 total
CA $5,312 total
includes taxes & fees
Image gallery for Historic Marshall house w/3 King sized beds, 11 total beds & saltwater Pool
1010 out of 10 rating
Exceptional
(36 reviews)
Historic Marshall house w/3 King sized beds, 11 total beds & saltwater Pool
Richmond, VA
10% off
Price is CA $1,256
CA $1,256
CA $12,205 total
CA $12,205 total
includes taxes & fees
Image gallery for Cozy Cape Cod Home!
9.89.8 out of 10 rating
Exceptional
(49 reviews)
Cozy Cape Cod Home!
Richmond, VA
10% off
Price is CA $279
CA $279
CA $2,918 total
CA $2,918 total
includes taxes & fees
Image gallery for Stylish retreat in charming Richmond with Private Sauna and other modern touches
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Stylish retreat in charming Richmond with Private Sauna and other modern touches
Richmond, VA
10% off
Price is CA $622
CA $622
CA $6,505 total
CA $6,505 total
includes taxes & fees
Image gallery for Private Romantic Bungalow for Artists & Writers, 7 Mins to Downtown Richmond,
1010 out of 10 rating
Exceptional
(11 reviews)
Private Romantic Bungalow for Artists & Writers, 7 Mins to Downtown Richmond,
Richmond, VA
20% off
Price is CA $182
CA $182
CA $1,890 total
CA $1,890 total
includes taxes & fees
Image gallery for Spectacular, two-bedroom apartment near downtown RVA.
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Spectacular, two-bedroom apartment near downtown RVA.
Richmond, VA
10% off
Price is CA $209
CA $209
CA $2,203 total
CA $2,203 total
includes taxes & fees
Image gallery for Recline at Timberline! Family friendly!
9.29.2 out of 10 rating
Wonderful
(46 reviews)
Recline at Timberline! Family friendly!
Colonial Heights, VA
10% off
Price is CA $233
CA $233
CA $2,349 total
CA $2,349 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Castlewood
No Fees 2BR Cabin Tucked Away on Private Lake
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
14 reviews(14 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, yards and more
More for lessMore space, more privacy, more amenities — more value