Holiday houses in Troy

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Top-rated holiday rentals in Troy

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Guest favourite
A light-filled living room features a comfortable sofa adorned with decorative cushions. A coffee table sits in front, and two lamps illuminate the space. Large windows overlook the backyard, allowing natural light to enhance the inviting atmosphere.
Cottage in Palmyra
4.95 out of 5 average rating, 166 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.

Top Guest favourite
Houseboat in Louisa
4.98 out of 5 average rating, 321 reviews

Tugboat/Private Lake - Farm Animals - Fish, Swim,

Get swept away to a Magical Tug/Houseboat! Newly renovated with all modern conveniences, incl. fully stocked kitchen, full bathroom, AC, heat, & WiFi. Tug floats on an 8 acre private Lake w/ Island on 142 Wooded Acres, with 5+miles of hiking/biking trails. Enjoy Swimming, Kayaking, SUP, Fishing, Hiking, Biking, Exploring, or just relax on your own beach by the fire pit. Visit farm animals just a short walk around the lake...Theo the Cow, Sheep, goats, turkey, ducks, chickens, and rabbits.

Top Guest favourite
The dark wooden cabin, framed by lush greenery, sits at a hillside location with panoramic mountain views. A deck extends from the cabin, featuring a hanging basket chair. A warm sunset casts a golden hue across the sky, enhancing the serene atmosphere.
Cabin in Free Union
4.99 out of 5 average rating, 213 reviews

Shenandoah Stargazer with Sauna

Stargazer is the perfect place to get away from it all! The stillness and serenity of being nestled in a bird and wildlife sanctuary is so good for your soul. Watch the sunrise from a hanging basket chair at 2700 feet of elevation, or wait for moonrise and toast spectacular star views! Relax in the sauna after a day filled with hiking and an al fresco meal on the deck. Roast s’mores at the deck fire table or over the side yard fire pit. There's magic in the air at this mountaintop retreat!

Superhost
The exterior of the cottage is shown, featuring a light-colored wood facade and a brown roof. A spacious wooden deck extends from the side, and a firepit is visible nearby within a grassy area. Lush trees form a natural backdrop.
Cottage in Troy
4.75 out of 5 average rating, 194 reviews

Pine Grove Cottage: Visit Monticello & Wineries

The Pine Grove Cottage is just 3 miles from the bustling Zion Crossroads retail and business area (and from Interstate 64), but is in a secluded, quiet rural spot. Professionally decorated and luxuriously furnished, the Cottage can accommodate up to 7 people if the sofa bed is included. It is great to be so near to Charlottesville, on the Monticello side of town, with quick access to all Charlottesville has to offer. So many wineries close by. Beautiful countryside. Yet affordable.

Top Guest favourite
The treehouse structure is framed by lush greenery, featuring a combination of wood and metal elements. A spacious deck surrounds the entrance, leading to steps that connect to the ground. Large windows offer views of the forest, enhancing the connection to nature.
Treehouse in Palmyra
4.97 out of 5 average rating, 191 reviews

Delightful one bedroom treehouse with king bed

You'll love this unique and romantic escape. Come and disconnect from the world and reconnect with each other in the Treehouse at Backabit Farm. You can enjoy the indoor fireplace or outside propane fire pit! Private deck for gazing at the stars or watching the wildlife. Two person hammock tucked under the trees! Inside you will find king bed with a view out of the three large windows, loveseat, tv, microwave, small fridge, coffee station and quaint bathroom with tiled shower.

Top Guest favourite
Cabin in Vesuvius
4.99 out of 5 average rating, 368 reviews

The Sanctuary

Nature lovers paradise! Named "The Sanctuary" for the place you can UNPLUG, unwind & find your peace! Perched up high on nearly 60 acres- you are sure to get fresh air & the rest you are searching for! Only 4 miles to Wintergreen, 6 miles to Sherando lake and backs up to the Blue Ridge Parkway there are plenty of things to do OR just relax and enjoy the crickets & stars! With crazy careers, growing kids & constant hustle- everyone needs a hide out like this every now and then!

Top Guest favourite
An aerial view captures a spacious guest house nestled among trees displaying vibrant autumn foliage. The surrounding landscape features a mix of green and colorful leaves, with an open area visible beside the property. Outdoor amenities are discernible, blending harmoniously with the natural setting.
Guesthouse in Troy
5 out of 5 average rating, 219 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. 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 a Great Pyrenees for cocktails. Feel like staying in - SmartTVs with YouTubeTV (which includes local channels) and Gig-speed Internet await. Easy checkout. No cleaning fee.

Guest favourite
A cozy living space features a queen bed with a light-colored coverlet, accompanied by a small sofa adorned with red cushions. A wooden coffee table and a black chair enhance the inviting atmosphere, while natural light filters through two windows, illuminating the room.
Apartment in Troy
4.89 out of 5 average rating, 121 reviews

Black Cat Retreat

Private entrance. upstairs, Lots of light, Wrap around deck! Full private bath in room. Large room with a small kitchenette. Refrigerator, microwave and coffeemaker a kitchen sink and induction burner to cook on. Also washer and dryer in the room. Upon your arrival there will be Banana Nut Bread, fruit & filtered water. All cotton sheets on the queen size bed (plus for the full size air mattress in room.) Cotton towels, shampoo, blow dryer, iron and ironing board.

Top Guest favourite
The cabin exterior features a wooden facade complemented by metal accents. A screened-in porch with a white door opens into the entryway, surrounded by potted plants and greenery. Stone steps lead to the porch, creating an inviting entrance.
Tiny home in Scottsville
4.92 out of 5 average rating, 277 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.

Top Guest favourite
The cottage is set in a spacious yard, surrounded by greenery. A large tree with bare branches is visible to one side. Bright pink flowers bloom nearby, complementing the exterior's muted tones. The home features a welcoming porch with white railings.
Farm stay in Palmyra
4.97 out of 5 average rating, 175 reviews

Cottage at Fruit Hill Orchard

The Cottage at Fruit Hill is nestled between our peach and apple orchards on my family’s 12 acre farm. Take a stroll through the peach blossoms, pick from our sunflower patch, enjoy some private time in the orchards during the fall, and gaze at our Christmas lights display in December. This charming cottage was originally built in the 1940’s and has recently been updated to be as comfortable for our guests as possible. Come enjoy a peaceful getaway at the orchard!

Top Guest favourite
The exterior of the house is framed by vibrant autumn foliage, showcasing a mix of reds, oranges, and yellows. Stone steps lead to a welcoming porch, illuminated by soft interior lights. A gravel pathway is bordered by lush greenery, enhancing the natural setting.
Cottage in Palmyra
4.96 out of 5 average rating, 168 reviews

Hawkwood House King Bedroom

Hawkwood House is close to Charlottesville, VA. It is in a 100-acre wood. Two guests share downstairs bedroom. Guests may use upper floor only with prior arrangements. It is a very quiet, peaceful setting. It is located near historic sites from colonial times of the United States and the Civil War and near Charlottesville VA and homes to three early US presidents (Monticello, Ash Lawn and Montpelier).

Top Guest favourite
A tranquil pond reflects the grassy landscape and the farmhouse, which features a welcoming front porch. A small boat rests on the water's edge, surrounded by greenery, creating a serene outdoor setting.
Farm stay in Louisa
4.99 out of 5 average rating, 168 reviews

Golden Meadows a Pet-Friendly Country Farm House

Pet-Friendly Country Farm House on Pond Farm stay hosted by Julie and Rick Bring your dogs. We have a huge fenced yard for them to play in. Come and enjoy the peace and quiet. We have 40 acres of fields and woods to help you relax a little. With over a mile of maintained trails you can take your pet for a long walk.  Have a corn hole match or barbecue and just relax. Wineries and breweries are nearby.

Popular amenities for Troy holiday rentals

  1. Airbnb
  2. United States
  3. Virginia
  4. Fluvanna County
  5. Troy