Lodging Image

Troy Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Troy holiday rentals

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

Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
Troy
9.2 out of 10, Wonderful, (151 reviews)
"Had a great stay! Everything was as expected and the property was nice."
United States
Jules R.
The price is NZ$340
includes taxes & fees
2 Nov - 3 Nov
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries

2. Pine Grove Apartment: Visit Monticello, wineries, UVA

Pine Grove Apartment: Visit Monticello, wineries, UVA
Troy
9.6 out of 10, Exceptional, (7 reviews)
"Was a great place to lay our heads for the night while we were in town for a wedding very cozy and had everything you could need would highly recommend!"
United States
Jordan
The price is NZ$385
includes taxes & fees
26 Oct - 27 Oct
Pine Grove Apartment: Visit Monticello, wineries, UVA

3. 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.
The price is NZ$877
includes taxes & fees
25 Oct - 26 Oct
Visit Monticello, Wineries, UVA & More

4. Ranchito

Ranchito
2.0 star property
Troy
The price is NZ$1,302
includes taxes & fees
28 Oct - 29 Oct
Ranchito

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

Visit Monticello, Wineries, UVA: Room for a Crowd
Troy
9.4 out of 10, Exceptional, (25 reviews)
"Great place for us, comfortable and well-equipped."
United States
Lynn F.
The price is NZ$1,145
includes taxes & fees
1 Nov - 2 Nov
Visit Monticello, Wineries, UVA: Room for a Crowd

6. Ranchito: Near Keswick Hall & Local Vineyards

Ranchito: Near Keswick Hall & Local Vineyards
Troy
The price is NZ$1,414
includes taxes & fees
28 Oct - 29 Oct
Ranchito: Near Keswick Hall & Local Vineyards

7. Bluebird Cottage B: Quiet, Firepit, Patio, Games

Bluebird Cottage B: Quiet, Firepit, Patio, Games
Palmyra
10.0 out of 10, Exceptional, (63 reviews)
"The host was very responsive and we thoroughly enjoyed staying there. Beautiful backyard!"
United States
Kelli c.
The price is NZ$466
includes taxes & fees
26 Oct - 27 Oct
Bluebird Cottage B: Quiet, Firepit, Patio, Games

8. SONSAK - MONTICELLO

SONSAK - MONTICELLO
3.5 star property
Charlottesville
9.8 out of 10, Exceptional, (10 reviews)
"Excellent For Couples Getaways!!!"
United States
Jonathan
The price is NZ$218
includes taxes & fees
1 Nov - 2 Nov
SONSAK - MONTICELLO

9. Private Guest Suite by Wineries/Orchards/Cville

Private Guest Suite by Wineries/Orchards/Cville
Palmyra
10.0 out of 10, Exceptional, (54 reviews)
"Very nice room and suite clean and accomdating "
United States
Nick S.
The price is NZ$418
includes taxes & fees
27 Oct - 28 Oct
Private Guest Suite by Wineries/Orchards/Cville

10. Cavalier Cocoon

Cavalier Cocoon
2.0 star property
Jefferson Park Avenue
10.0 out of 10, Exceptional, (1 review)
"Love this place! It’s close to campus as well as some great food. Don’t miss Pi Napo for pizza. We stayed at the end of a long road trip so we appreciated the washer and dryer."
United States
Lisa
The price is NZ$436
includes taxes & fees
3 Nov - 4 Nov
Cavalier Cocoon

11. Charming Eastham Guesthouse

Charming Eastham Guesthouse
Charlottesville
10.0 out of 10, Exceptional, (12 reviews)
"Perfect space and location!"
United States
Samantha H.
Charming Eastham Guesthouse

12. Unit 5 - Cozy Lower Level Studio Suite

Unit 5 - Cozy Lower Level Studio Suite
Charlottesville
10.0 out of 10, Exceptional, (35 reviews)
"Perfect for a short stay."
United States
Gaye W.
The price is NZ$282
includes taxes & fees
23 Nov - 24 Nov
Unit 5 - Cozy Lower Level Studio Suite

13. Unit 4 - Luxury King Suite with Private Balcony

Unit 4 - Luxury King Suite with Private Balcony
Charlottesville
10.0 out of 10, Exceptional, (16 reviews)
"Great location, clean and organized and comfortable. Hope to stay here again. "
United States
Ellie T.
The price is NZ$451
includes taxes & fees
24 Nov - 25 Nov
Unit 4 - Luxury King Suite with Private Balcony

14. Unit 3 - Luxury King Suite with Private Balcony

Unit 3 - Luxury King Suite with Private Balcony
Charlottesville
10.0 out of 10, Exceptional, (35 reviews)
"Very nice property. Quiet, clean, efficient. Great place to stay."
United States
martha a.
The price is NZ$451
includes taxes & fees
18 Nov - 19 Nov
Unit 3 - Luxury King Suite with Private Balcony

15. 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 NZ$288
includes taxes & fees
27 Oct - 28 Oct
Newly renovated entire guest suite in Orange County.

16. Locust Garden, A North Downtown C'ville Guesthouse

Locust Garden, A North Downtown C'ville Guesthouse
Locust Grove
8.0 out of 10, Very good, (1 review)
"Very clean and sweet property. Attractively furnished. Check in was easy. Good communication.Kitchen was very easy to use. Did lots of our own cooking. Would have appreciated some quality stainless steel pots and tops as we can’t use anodized cookware for specific health reasons."
United States
Susan K.
The price is NZ$652
includes taxes & fees
16 Nov - 17 Nov
Locust Garden, A North Downtown C'ville Guesthouse

17. Bright Downtown Studio w/Full Kitchen+King Bed

Bright Downtown Studio w/Full Kitchen+King Bed
North Downtown
9.6 out of 10, Exceptional, (55 reviews)
"The kitchen was well stocked and it was a wonderful stay in Charlotteville."
United States
Tina B.
The price is NZ$397
includes taxes & fees
9 Nov - 10 Nov
Bright Downtown Studio w/Full Kitchen+King Bed

18. 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, (143 reviews)
"The cottage had everything you need."
United States
William J.
The price is NZ$320
includes taxes & fees
27 Oct - 28 Oct
Servants' Cottage on 600 Acre Working Horse/Cattle Estate

19. Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Ivy
10.0 out of 10, Exceptional, (59 reviews)
"It was a couple very cozy place for us to stay in the perfect location."
United States
Linda W.
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

20. 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 NZ$1,254
includes taxes & fees
16 Nov - 17 Nov
Fern Cottage Summary:
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Troy Hotel Reviews

Find out more about Troy

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Troy holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Troy. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Troy. Seeing all the best attractions is bound to make you fall in love with Troy. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Troy short-term rentals, that won’t be hard to do.

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?

Group Getaway ~ 15 Mi to Charlottesville!: This highly rated holiday home rental in Troy offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable 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. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Troy?

Choose from 7 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 Virginia Discovery Museum, or get outside and enjoy nature at Carter Mountain Orchard. In the wider area, you’ll find Keswick Vineyards and Winery and Castle Hill Cider.

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.