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Troy Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Troy holiday rentals

Exterior
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries

Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries

Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
Troy
9.0 out of 10, Wonderful, (130)
"The cottage was very cute and cozy. Great place for a weekend with family."
United States
Laura M.
The price is HK$1,166
HK$1,630 total
includes taxes & fees
29 Dec - 30 Dec
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
Outdoor dining
Pine Grove Apartment: Visit Monticello, wineries, UVA

Pine Grove Apartment: Visit Monticello, wineries, UVA

Pine Grove Apartment: Visit Monticello, wineries, UVA
Troy
9.6 out of 10, Exceptional, (4)
"Nice stay"
United States
Jeff M.
The price is HK$1,400
HK$1,887 total
includes taxes & fees
4 Jan - 5 Jan 2026
Pine Grove Apartment: Visit Monticello, wineries, UVA
Outdoor dining
Visit Monticello, Wineries, UVA & More

Visit Monticello, Wineries, UVA & More

Visit Monticello, Wineries, UVA & More
Troy
9.0 out of 10, Wonderful, (8)
"Beautiful home, spacious, a surroundings "
United States
Danita C.
The price is HK$3,266
HK$4,366 total
includes taxes & fees
4 Jan - 5 Jan 2026
Visit Monticello, Wineries, UVA & More
Outdoor dining
Visit Monticello, Wineries, UVA: Room for a Crowd

Visit Monticello, Wineries, UVA: Room for a Crowd

Visit Monticello, Wineries, UVA: Room for a Crowd
Troy
9.2 out of 10, Wonderful, (18)
"We had a great trip with the family to celebrate our daughter’s graduation at UVA. This property gave us plenty of space to relax, have brunch together, and enjoy the weekend"
United States
Keri B.
The price is HK$4,277
HK$5,635 total
includes taxes & fees
4 Jan - 5 Jan 2026
Visit Monticello, Wineries, UVA: Room for a Crowd
Property grounds
Newly renovated entire guest suite in Orange County.

Newly renovated entire guest suite in Orange County.

Newly renovated entire guest suite in Orange County.
Orange
10.0 out of 10, Exceptional, (43)
"Nice piece of property for our dogs to run around. Clean and had we had a great experience. "
United States
amy c.
The price is HK$770
HK$1,201 total
includes taxes & fees
26 Dec - 27 Dec
Newly renovated entire guest suite in Orange County.
Exterior
Servants' Cottage on 600 Acre Working Horse/Cattle Estate

Servants' Cottage on 600 Acre Working Horse/Cattle Estate

Servants' Cottage on 600 Acre Working Horse/Cattle Estate
Gordonsville
9.8 out of 10, Exceptional, (137)
"Beautiful setting and very peaceful. We enjoyed the friendly horse, too. Next time we are in the area, we will certainly plan on staying here again."
United States
William H.
The price is HK$1,166
HK$1,569 total
includes taxes & fees
5 Jan - 6 Jan 2026
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
Fridge, microwave, oven, stovetop
Bluebird Cottage A: Across from Lake Monticello, Near Charlottesville, 1 Dog Ok

Bluebird Cottage A: Across from Lake Monticello, Near Charlottesville, 1 Dog Ok

Bluebird Cottage A: Across from Lake Monticello, Near Charlottesville, 1 Dog Ok
Palmyra
10.0 out of 10, Exceptional, (42)
"Very cute and clean rental in a good location to easily access activities ."
United States
Christine T.
The price is HK$1,143
HK$2,095 total
includes taxes & fees
15 Jan - 16 Jan 2026
Bluebird Cottage A: Across from Lake Monticello, Near Charlottesville, 1 Dog Ok
Outdoor dining
Lovers Lane FarmStay on a working family farm. Horses, cows, sheep, bees & more

Lovers Lane FarmStay on a working family farm. Horses, cows, sheep, bees & more

Lovers Lane FarmStay on a working family farm. Horses, cows, sheep, bees & more
Gordonsville
9.0 out of 10, Wonderful, (10)
"We attended a special dinner at Barboursville and this was a convenient place to stay. "
United States
Brett H.
The price is HK$933
HK$1,418 total
includes taxes & fees
28 Dec - 29 Dec
Lovers Lane FarmStay on a working family farm. Horses, cows, sheep, bees & more
Interior
Private Guest Suite by Wineries/Orchards/Cville

Private Guest Suite by Wineries/Orchards/Cville

Private Guest Suite by Wineries/Orchards/Cville
Palmyra
10.0 out of 10, Exceptional, (47)
"A perfect place to stay! Very clean and quiet!"
United States
Joanne
The price is HK$1,127
HK$1,775 total
includes taxes & fees
29 Dec - 30 Dec
Private Guest Suite by Wineries/Orchards/Cville
Outdoor dining
Moonfire Farm Shenandoah region cozy getaway

Moonfire Farm Shenandoah region cozy getaway

Moonfire Farm Shenandoah region cozy getaway
Barboursville
10.0 out of 10, Exceptional, (30)
"Stew was a great surprise, pleasant and very hospitable "
United States
Jeff H.
The price is HK$980
HK$1,564 total
includes taxes & fees
27 Dec - 28 Dec
Moonfire Farm Shenandoah region cozy getaway
Exterior
'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.

'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.

'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.
Gordonsville
9.8 out of 10, Exceptional, (84)
"Fifth year at Wolftrap Farm. Booked again for 2025.Thanks!"
United States
J C.
The price is HK$1,827
HK$2,345 total
includes taxes & fees
31 Dec - 1 Jan 2026
'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.
Outdoor dining
Elegant Cottage on 600 Acre Horse & Livestock Farm

Elegant Cottage on 600 Acre Horse & Livestock Farm

Elegant Cottage on 600 Acre Horse & Livestock Farm
Gordonsville
9.8 out of 10, Exceptional, (147)
"Nice little place to stay and close to downtown Orange and Gordonsville with great food and such. Would recommend if you are in the area and looking for a peaceful getaway and relaxing stay."
United States
Jason L.
The price is HK$1,711
HK$2,261 total
includes taxes & fees
30 Dec - 31 Dec
Elegant Cottage on 600 Acre Horse & Livestock Farm
Terrace/patio
Affordable Suites Charlottesville

Affordable Suites Charlottesville

Affordable Suites Charlottesville
2.0 star property
Fry's Spring
8.0 out of 10, Very good, (80)
"Simple, clean comfortable suite. Full kitchen with frig, stove and microwave. Convenient to UVA campus and football stadium. "
United States
Anonymous traveller
Affordable Suites Charlottesville
Property grounds
Glade Cottage at White Lotus Eco Spa Retreat

Glade Cottage at White Lotus Eco Spa Retreat

Glade Cottage at White Lotus Eco Spa Retreat
Stanardsville
9.4 out of 10, Exceptional, (22)
"Great stay"
United States
Caroline T.
The price is HK$886
HK$1,478 total
includes taxes & fees
4 Jan - 5 Jan 2026
Glade Cottage at White Lotus Eco Spa Retreat
Smart TV, table football, ping pong
5 BDRM Dog Friendly, Lake Access Getaway w/Playground, Fire Pit & more

5 BDRM Dog Friendly, Lake Access Getaway w/Playground, Fire Pit & more

5 BDRM Dog Friendly, Lake Access Getaway w/Playground, Fire Pit & more
Louisa
10.0 out of 10, Exceptional, (21)
"We had a wonderful stay. The house was perfect and provided everything we needed. Enjoyed our time on the water, especially the kayaking."
United States
Pat M.
The price is HK$1,664
HK$4,095 total
includes taxes & fees
5 Jan - 6 Jan 2026
5 BDRM Dog Friendly, Lake Access Getaway w/Playground, Fire Pit & more
Exterior
Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+

Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+

Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+
Stanardsville
10.0 out of 10, Exceptional, (22)
"This property was one of the best we have stayed at. It was everything we needed, the bedroom and bathroom luxurious. The kitchen area was the perfect size, stocked with a choice of coffees, teas and snacks. It’s perfectly located to go to the many wineries, restaurants and shopping in the area, It is an easy drive into Charlottesville. Our hostess was great, texting to check if we needed anything. I highly recommend a stay here."
United States
william
The price is HK$972
HK$1,753 total
includes taxes & fees
1 Jan - 2 Jan 2026
Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+
Exterior
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.

“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, (33)
"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 HK$1,743
HK$2,487 total
includes taxes & fees
31 Dec - 1 Jan 2026
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
Fridge, microwave, oven, dishwasher
Unit 5 - Cozy Lower Level Studio Suite

Unit 5 - Cozy Lower Level Studio Suite

Unit 5 - Cozy Lower Level Studio Suite
Charlottesville
10.0 out of 10, Exceptional, (28)
"Studio 5 was just as described. Everything we needed and immaculately clean. It is convenient to Charlottesville and minutes from Monticello. Our children live nearby so we will surely return. "
United States
Kate B.
The price is HK$709
HK$988 total
includes taxes & fees
7 Jan - 8 Jan 2026
Unit 5 - Cozy Lower Level Studio Suite
Interior
Pond View (Second bedroom at extra cost)

Pond View (Second bedroom at extra cost)

Pond View (Second bedroom at extra cost)
Stanardsville
9.0 out of 10, Wonderful, (17)
"We had a wonderful stay at the White"
United States
Elizabeth
The price is HK$700
HK$1,304 total
includes taxes & fees
29 Dec - 30 Dec
Pond View (Second bedroom at extra cost)
Fridge, microwave, oven, stovetop
Riverview Cabin on the James

Riverview Cabin on the James

Riverview Cabin on the James
Cumberland County
9.8 out of 10, Exceptional, (22)
"Cabin was clean and well kept. "
United States
Ricardo S.
The price is HK$1,332
HK$2,637 total
includes taxes & fees
19 Jan - 20 Jan 2026
Riverview Cabin on the James
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.
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Top Troy Hotel Reviews

The Doyle Hotel

The Doyle Hotel

10/10 Excellent
"Great location. Liked not having to have plastic card to open door. "
Will 1-night trip
Posted 3 days ago
The Doyle Hotel

Find out more about Troy

Search for holiday rentals in Troy on Expedia! You can easily find your home rentals, villas, holiday apartments in Troy using one of the methods below:

  • View our selection of featured holiday rentals in Troy
  • Use the map to find apartments and other holiday homes in the Troy neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Troy while they last

Look no further and take a look at our great range of rental properties in Troy!

Frequently asked questions

Can I find a holiday rental in Troy?

Yes, there are holiday rentals close to the most popular sights in Troy, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Troy has to offer?

Farmers' Landing - Secluded Private Waterfront Home at Lake Anna in Quiet Cove.: This holiday home rental outside of Troy is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Troy?

Choose from 5 Expedia holiday rentals in Troy for a memorable holiday.

What’s there to see and do in Troy?

While exploring the area, visit family-friendly sights like Charlottesville Ice Park, or get outside and enjoy nature at Carter Mountain Orchard. In the wider area, you’ll find Keswick Vineyards and Winery and Jefferson Vineyards.

What’s a holiday rental in Troy like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Troy. Holiday rentals feature extras like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for families.