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Our top choices for Troy vacation homes

1. Visit Monticello, Wineries, UVA & More

Visit Monticello, Wineries, UVA & More
Troy
9.4 out of 10, Exceptional, (11 reviews)
"Great place to stay! Only a 25 min ride from Charlottesville!"
United States
Camryn S.
Visit Monticello, Wineries, UVA & More

2. Visit Monticello, Wineries, UVA: Room for a Crowd

Visit Monticello, Wineries, UVA: Room for a Crowd
Troy
9.2 out of 10, Wonderful, (26 reviews)
"Great place for us, comfortable and well-equipped."
United States
Lynn F.
Visit Monticello, Wineries, UVA: Room for a Crowd

3. Ranchito: Near Keswick Hall & Local Vineyards

Ranchito: Near Keswick Hall & Local Vineyards
Troy
Ranchito: Near Keswick Hall & Local Vineyards

4. Ranchito

Ranchito
2.0 star property
Troy
Ranchito

5. Spacious 4-bedroom building in wonderful Louisa with AC

Spacious 4-bedroom building in wonderful Louisa with AC
Louisa
The price is AED 1,488
AED 2,285 total
includes taxes & fees
19 Nov - 20 Nov
Spacious 4-bedroom building in wonderful Louisa with AC

6. Fern Cottage Summary:

Fern Cottage Summary:
Gordonsville
10.0 out of 10, Exceptional, (23 reviews)
"We had a great stay. The house was clean and well furnished. Recommend for anyone staying in the area."
United States
Gary W.
The price is AED 1,763
AED 3,028 total
includes taxes & fees
19 Nov - 20 Nov
Fern Cottage Summary:

7. Newly renovated entire guest suite in Orange County.

Newly renovated entire guest suite in Orange County.
Orange
9.8 out of 10, Exceptional, (45 reviews)
"The stay was great. Very close to all the nearby attractions and 30 minutes to skyline drive"
United States
vishal k.
The price is AED 441
AED 619 total
includes taxes & fees
20 Nov - 21 Nov
Newly renovated entire guest suite in Orange County.

8. Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.

Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
Gordonsville
9.6 out of 10, Exceptional, (48 reviews)
"Beautiful property and family friendly."
United States
Tracy
The price is AED 716
AED 828 total
includes taxes & fees
20 Nov - 21 Nov
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.

9. Pine and Vine: 8 Acres + Winery & Family Retreat

Pine and Vine: 8 Acres + Winery & Family Retreat
Gordonsville
10.0 out of 10, Exceptional, (3 reviews)
"This house is fantastic and meant for small groups. The floor plan is open and the rooms are simply perfect."
United States
Lisa
Pine and Vine: 8 Acres + Winery & Family Retreat

10. Charming 3-Bed Cottage on Main Street in Historic Gordonsville

Charming 3-Bed Cottage on Main Street in Historic Gordonsville
Gordonsville
9.8 out of 10, Exceptional, (21 reviews)
"This was the cutest house! Our favorite of our weeklong roadtrip. Perfect for our 6 adults. Close to town, which was adorable also. Would love to come back and stay again!"
United States
Cheryl G.
The price is AED 750
AED 1,282 total
includes taxes & fees
9 Nov - 10 Nov
Charming 3-Bed Cottage on Main Street in Historic Gordonsville

11. The Country Retreat – Cozy Comfort Meets Peaceful Countryside

The Country Retreat – Cozy Comfort Meets Peaceful Countryside
Scottsville
9.4 out of 10, Exceptional, (6 reviews)
"Nice clean place out in the country. We were there for Memorial Day weekend and had a nice relaxing time."
United States
Michael L.
The Country Retreat – Cozy Comfort Meets Peaceful Countryside

12. “The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.

“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
Gordonsville
10.0 out of 10, Exceptional, (38 reviews)
"Absolutely lovely place to stay. Stunning views and conveniently located to so many of the local attractions. Will definitely come back someday."
United States
Kirby R.
The price is AED 915
AED 1,230 total
includes taxes & fees
20 Nov - 21 Nov
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.

13. Walk to UVA & Stadium! Close to everything! Charming renovated house

Walk to UVA & Stadium! Close to everything! Charming renovated house
Fry's Spring
10.0 out of 10, Exceptional, (4 reviews)
"Very cute house and convenient location! We enjoyed our stay!"
United States
Kristin B.
Walk to UVA & Stadium! Close to everything! Charming renovated house

14. The Ranch at Wine Country - Complimentary Bottle!

The Ranch at Wine Country - Complimentary Bottle!
Gordonsville
10.0 out of 10, Exceptional, (54 reviews)
"Had a great stay! In a perfect location close to all the wineries and downtown of Gordonsville. House was very clean and had everything we needed. "
United States
Marisa G.
The price is AED 1,065
AED 1,691 total
includes taxes & fees
20 Nov - 21 Nov
The Ranch at Wine Country - Complimentary Bottle!

15. Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.

Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.
Gordonsville
9.4 out of 10, Exceptional, (39 reviews)
"Beautiful place"
United States
Berhan S.
The price is AED 1,010
AED 1,167 total
includes taxes & fees
20 Nov - 21 Nov
Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.

16. Pine and Vine

Pine and Vine
2.0 star property
Gordonsville
The price is AED 1,413
AED 3,133 total
includes taxes & fees
8 Nov - 9 Nov
Pine and Vine

17. Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+

Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
Stanardsville
10.0 out of 10, Exceptional, (35 reviews)
"Stayed here for a weekend while hiking Old Rag in Shenandoah. Cozy little place that was well equipped with all the amenities we needed! It's conveniently located close to Shenandoah as well as plenty of vineyards. Would not hesitate to stay here again the next time we're in the area!"
United States
Jason
The price is AED 459
AED 678 total
includes taxes & fees
15 Nov - 16 Nov
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+

18. Walk to UVA, Hospital, 4 BDR, Game Room

Walk to UVA, Hospital, 4 BDR, Game Room
Fifeville
10.0 out of 10, Exceptional, (3 reviews)
"Just as described!"
United States
Cristin R.
Walk to UVA, Hospital, 4 BDR, Game Room

19. Rugby Road Residential -RRR- near UVa and downtown

Rugby Road Residential -RRR- near UVa and downtown
Barracks Rugby
10.0 out of 10, Exceptional, (61 reviews)
"Spacious, quiet and very near to everything Charlottesville has to offer!"
United States
Kate M.
The price is AED 621
AED 1,045 total
includes taxes & fees
29 Nov - 30 Nov
Rugby Road Residential -RRR- near UVa and downtown

20. Beautiful New Townhome with Mountain Views. Close to downtown!

Beautiful New Townhome with Mountain Views. Close to downtown!
Charlottesville
9.0 out of 10, Wonderful, (24 reviews)
"Great host! Excellent location and a well appointed home."
United States
Wendy J.
Beautiful New Townhome with Mountain Views. Close to downtown!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Troy

Venture to Keswick Vineyards and Winery and Castle Hill Cider—just two of the sights around Troy.

A rocky shoreline with a blue paddle, calm water reflecting clouds, and vegetation growing around.
Photo by Jason Clay
Open Photo by Jason Clay

Top reviews in Troy