Holiday houses in Troy

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Top-rated holiday rentals in Troy

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Orange

5.0 out of 5 average rating, 182 reviews

Taj Garage Guesthouse

Newly constructed (2021) above garage guesthouse with private, self check-in entrance, off-street parking, located among historic homes just 4 blocks to restaurants, shops, park and art galleries in downtown Orange. Guesthouse includes a fully equipped kitchen, queen bed, full bath, seating area, TV, wifi and balcony. Handcrafted heart pine furniture. Level 2 EV Charger. Kitchen includes refrig, stove, microwave, toaster and Keurig. Close to superb wineries, breweries and historic sites.

9–16 Oct

$223 NZD per night

Guest favourite

Cottage in Palmyra

4.97 out of 5 average rating, 131 reviews

Bluebird Cottage B: Quiet, Firepit, Patio, Games

You’ll enjoy the simple charms of this home for up to 4 guests conveniently located near Lake Monticello, Charlottesville, the Rivanna River, and wineries. Relax in peace in a quiet neighborhood. Enjoy your private patio with outdoor dining table. Play board games, cornhole, and horseshoes. Make memories around the firepit. You’ll have everything you need, including fully equipped kitchen, washer-dryer, electric fireplace, fast Wi-Fi, 2 smart TVs for streaming services w/antenna for local fare.

2–9 Oct

$280 NZD per night

Guest favourite

Guest suite in Goochland

4.98 out of 5 average rating, 144 reviews

Relax at Pop & Nana’s Place at Nothin’ Flat

If you’re looking for a peaceful, country style getaway on a wooded 2.5 acre lot, look no further. This 2-bedroom, 2 bath unit offers all the comforts of home including a full kitchen, dining area, game room, laundry room, covered patio and single-car garage. Outdoor parking is also available. Hang out indoors and play on our pool table, dart board, foosball table, games, puzzles, or enjoy the great outdoors making s’mores over the fire pit or enjoy the hammock. Check out our Guidebook!

8–15 Aug

$189 NZD per night

Guest favourite

Guesthouse in Troy

4.99 out of 5 average rating, 116 reviews

Beaver Pond Farm - Near Charlottesville

Relax at this unique and tranquil getaway. Sit on the screened in porch and enjoy the sights and sounds of nature while you enjoy a beverage. Take a walk on miles of trails that are adjacent to the property. Visit the Downtown Mall, Monticello, a Winery, a Brewery, or UVA (20 min). Enjoy a dip in the pool (JUN-AUG) or relax by the firepit - perhaps joined by the horses for cocktails. Feel like staying in - SmartTVs and Gig-speed Internet await. Easy checkout. No cleaning fee.

2–9 Oct

$260 NZD per night

Guest favourite

Apartment in Gordonsville

4.99 out of 5 average rating, 369 reviews

A private apartment with Self Check-in.

This newly renovated one bedroom apartment is in the heart of historic downtown Gordonsville. No box stores here, just quaint shops and restaurants. The apartment is right on Main Street nestled in the middle of boutique shops and brick sidewalks with Monticello, Montpelier, the University of Virginia, Shenandoah National Park, local vineyards and many historic sites near by. This is a private second story apartment above a local business with a separate entrance and key-less entry.

4–11 Nov

$172 NZD per night

Superhost

Treehouse in Palmyra

4.89 out of 5 average rating, 283 reviews

Luxury Treehouse with hot tub on the Rivanna River

Gorgeous Treehouse soaring 15 feet above ground! Enjoy the sounds of nature when you stay in this unique space. Built by hand, every inch is meticulously curated by the owner himself. Nestled on the banks of the Rivanna River, this is a TRUE treehouse, suspended in a grove of Sycamore and Poplar trees. Panoramic windows, high end furnishings and every comfort you're looking for. Sit outside on the wrap-around porch, surrounded by leaves. We're sure you'll have an incredible stay!

9–16 Sep

$594 NZD per night

Guest favourite

Cabin in Gordonsville

4.87 out of 5 average rating, 306 reviews

18th Century Charming Bungalow# 127 pool & wifi

Escape & unwind from city life on a beautiful historic, 250 acre estate 20 minutes from Charlottesville! Our historic bungalow comfortably fits 2-4 people and is perfect for those who just want to take a step back in history and enjoy the wonder nature has to offer! For outings we are only 20 min away from Jefferson's "Monticello" & 35 min from James Madison " Montpelier". Play golf 5 min away at Spring Creek Golf. Treat yourself to an onsite certified massage wellness therapist.

26 Aug – 2 Sep

$275 NZD per night

Guest favourite

Guest suite in Louisa

4.92 out of 5 average rating, 241 reviews

The Crystal Peony (WIFI INCLUDED)

Welcome and thank you for considering The Crystal Peony in Louisa, VA as you search for your next stay! For those travelling East and West through VA, we are conveniently located JUST off I-64; and for those travelling North and South, we are only one exit from Rt-15. Our ideal location sits 30 minutes from Charlottesville and 40 minutes from Richmond. This room has its own private entrance with ample parking, a private attached bathroom and shower with a gorgeous double sink.

10–17 Sep

$150 NZD per night

Guest favourite

Home in Keswick

4.99 out of 5 average rating, 163 reviews

Country Living - 18 min to Downtown C'Ville

Located on a dead-end road with only local traffic, enjoy the peace and tranquility our home has to offer with an easy drive to Charlottesville or Richmond as well as DC. With approximately 2100 square feet, you will be able to spread out comfortably! Three bedrooms, 2.5 bathrooms await your stay! We are an easy 20-21 minutes to UVA Grounds/"The Corner" and 18 minutes to Downtown Charlottesville. Please reach out to me with any questions! We look forward to hosting you.

17–24 Aug

$472 NZD per night

Guest favourite

Tiny home in Scottsville

4.99 out of 5 average rating, 344 reviews

Rare Find: Private Animal Sanctuary & Tiny Cottage

Voted one of the coolest Airbnbs in Virginia by Trips to Discover! Voted one of the top 12 tiny houses in Virginia by Trip101! Peaceful, safe, and magical are just a few words guests use to describe our farm. It's the perfect retreat to relax and reconnect with yourself and nature. Enjoy exploring the farm, spending time with our animals, and stargazing by the firepit. We invite you to soak in all the richness the farm and animals have to offer. We’re also 420 friendly.

7–14 Mar

$228 NZD per night

Guest favourite

Tiny home in Charlottesville

4.94 out of 5 average rating, 668 reviews

Oxford Cottage: Cville’s favorite tiny home!

This 350 sq ft cottage is a tiny home concept space, boasting an airy entry, living area, storage landing, kitchenette, bathroom and sleeping loft. Perfect for a romantic getaway, a work retreat, a stop through town on the way to another location, a small family, or a group of friends participating in the many events held in Charlottesville- weddings, concerts, triathlons. Accommodates 1-4 people looking for a relaxed, stylish, modern and comfortable place to stay.

14–21 Dec

$214 NZD per night

Guest favourite

Tiny home in Scottsville

4.9 out of 5 average rating, 193 reviews

Convenient Rustic Cabin near Wineries

I’m located 6 miles from Scottsville, 15 miles from Charlottesville, 25-30 minute drive. A pasture of cattle is not too far away you can hear the mooing at times and see sightings of deer quite often. It’s a private and quiet location. Two large rivers, James and Rivanna offer recreational activities. Rustic cabin, country located. Clean and cozy with a well stocked kitchen with all your cooking needs. If not, leave suggestions on what is missed. Thank you.

26 Aug – 2 Sep

$181 NZD per night