
Photo by Crystal Davidson
Holiday rentals near Uptown Alley
We found 625 holiday rentals — enter your dates for availability
Take a look at holiday rentals close to Uptown Alley that provide the perfect home base for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the amenities that you need and want for your stay, which might include parking and a garden. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Uptown Alley
Showing deals for:14 Nov - 21 Nov
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
8% off
Price is S$5,389
S$5,389
S$770 per night
includes taxes & fees
Image gallery for Steel Magnolias Cozy Main Home in Amelia County

9.89.8 out of 10 rating
Exceptional
(9 reviews)
Steel Magnolias Cozy Main Home in Amelia County
Amelia Court House, VA
8% off
Price is S$1,525
S$1,525
S$218 per night
includes taxes & fees
Image gallery for EXPERIENCES, connection, nature & luxury await you on 50 acres!

1010 out of 10 rating
Exceptional
(6 reviews)
EXPERIENCES, connection, nature & luxury await you on 50 acres!
Powhatan, VA
8% off
Price is S$12,623
S$12,623
S$1,803 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 S$3,628
S$3,628
S$518 per night
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
6% off
Price is S$4,161
S$4,161
S$594 per night
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
7% off
Price is S$1,762
S$1,762
S$252 per night
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
7% off
Price is S$4,581
S$4,581
S$654 per night
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
7% off
Price is S$4,242
S$4,242
S$606 per night
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
7% off
Price is S$10,762
S$10,762
S$1,537 per night
includes taxes & fees
Image gallery for Upscale Country Cottage on 22 acres and a Pond

1010 out of 10 rating
Exceptional
(33 reviews)
Upscale Country Cottage on 22 acres and a Pond
Powhatan, VA
8% off
Price is S$3,904
S$3,904
S$558 per night
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
11% off
Price is S$4,456
S$4,456
S$637 per night
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
7% off
Price is S$7,427
S$7,427
S$1,061 per night
includes taxes & fees
Image gallery for In the Village Of Powhatan- walking distance to owners restaurant

1010 out of 10 rating
Exceptional
(42 reviews)
In the Village Of Powhatan- walking distance to owners restaurant
Powhatan, VA
16% off
Price is S$2,548
S$2,548
S$364 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 S$1,188
S$1,188
S$170 per night
includes taxes & fees
Image gallery for Cozy Barndominium Guest Home

1010 out of 10 rating
Exceptional
(11 reviews)
Cozy Barndominium Guest Home
Amelia Court House, VA
20% off
Price is S$1,162
S$1,162
S$166 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 S$6,338
S$6,338
S$905 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 S$3,065
S$3,065
S$438 per night
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
7% off
Price is S$2,241
S$2,241
S$320 per night
includes taxes & fees
Image gallery for Perfect Holiday Retreat Steps from Downtown RVA

9.29.2 out of 10 rating
Wonderful
(9 reviews)
Perfect Holiday Retreat Steps from Downtown RVA
Richmond, VA
7% off
Price is S$3,928
S$3,928
S$561 per night
includes taxes & fees
Image gallery for Historic Apartment in the Heart of Old Towne with Bird's Eye views

9.89.8 out of 10 rating
Exceptional
(27 reviews)
Historic Apartment in the Heart of Old Towne with Bird's Eye views
Petersburg, VA
8% off
Price is S$2,633
S$2,633
S$376 per night
includes taxes & fees
Image gallery for The Fan:Short term all Sept '25 and long-term March '26-'27. Short stays 5+ days

9.89.8 out of 10 rating
Exceptional
(12 reviews)
The Fan:Short term all Sept '25 and long-term March '26-'27. Short stays 5+ days
Richmond, VA
13% off
Price is S$3,185
S$3,185
S$455 per night
includes taxes & fees
Image gallery for Peaceful & Cozy 2 Bedroom Unit with Large Fenced Backyard-Family & Pet Friendly

8.88.8 out of 10 rating
Excellent
(5 reviews)
Peaceful & Cozy 2 Bedroom Unit with Large Fenced Backyard-Family & Pet Friendly
Glen Allen, VA
7% off
Price is S$2,357
S$2,357
S$337 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 S$2,042
S$2,042
S$292 per night
includes taxes & fees
Image gallery for City Life Richmond, Escape and Relax, Free Parking

9.89.8 out of 10 rating
Exceptional
(31 reviews)
City Life Richmond, Escape and Relax, Free Parking
Richmond, VA
7% off
Price is S$7,784
S$7,784
S$1,112 per night
includes taxes & fees
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Find the best place to stay - Uptown Alley
Amazing Private House Rental w/ pool! Richmond, VA
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
64 reviews(64 reviews)
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Sleeps 4 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
218 reviews(218 reviews)
VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms
Sleeps 6 · 3 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
122 reviews(122 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)
Historic Marshall house w/3 King sized beds, 11 total beds & saltwater Pool
Sleeps 16 · 5 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
Historic Haven in Church Hill
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
24 reviews(24 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