Vacation rentals in Cunningham

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Top-rated vacation rentals in Cunningham

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Guest favorite

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.

Oct 2 – 9

G$29,469 GYD per night

Guest favorite

Cabin in Gordonsville

4.82 out of 5 average rating, 226 reviews

1700's Summer Kitchen Cottage #147 Pool & WIFI

Escape from city life on a beautiful historic 250-acre estate. It is close to historic attractions and wineries. You’ll love it because of the gorgeous outdoors and historic charm. This place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). There is WIFI. This is only 20 minutes away from Jefferson's Monticello, and James Madison's "Montpelier" or play golf (5 min) away. Treat yourself to an onsite certified massage wellness therapist.

Sep 9 – 16

G$28,679 GYD per night

Guest favorite

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!

Aug 9 – 16

G$21,021 GYD per night

Guest favorite

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.

Dec 14 – 21

G$30,283 GYD 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!

Jan 28 – Feb 4

G$65,426 GYD per night

Guest favorite

Treehouse in Palmyra

4.98 out of 5 average rating, 121 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.

Jun 10 – 17

G$36,670 GYD per night

Guest favorite

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.

Aug 26 – Sep 2

G$25,244 GYD per night

Guest favorite

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.

Feb 2 – 9

G$21,883 GYD per night

Guest favorite

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.

Apr 10 – 17

G$19,226 GYD per night

Guest favorite

Farm stay in Palmyra

4.97 out of 5 average rating, 128 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!

Sep 12 – 19

G$57,870 GYD per night

Guest favorite

Apartment in Palmyra

5.0 out of 5 average rating, 106 reviews

The Cottage Next Door

Private and modern in a peaceful country setting near Charlottesville, Scottsville, Palmyra, Fork Union, Lake Monticello and historical attractions. The nearby James River offers rafting, floating and fishing. Scheier Natural Area, a local hiking trail, is just next door. Wineries and distilleries are a short drive away as well. While you can prepare full meals in the kitchen, there are several wonderful restaurants within a short drive, if you choose.

Sep 26 – Oct 3

G$20,552 GYD per night

Guest favorite

Farm stay in Palmyra

4.96 out of 5 average rating, 206 reviews

The Sunflower Cottage at Chevy Chase Farm

Peaceful 350-acre cattle farm/estate in Central Virginia. Enjoy pastoral walks with over 2.5 miles of gravel trails—just 17 minutes from Scottsville and 35 minutes from Charlottesville. Visit historical sites including Jefferson's Monticello and James Monroe's Ashlawn Highland. Enjoy kayaking on the James River and multiple award-winning wineries and breweries within minutes of your stay. Equine enthusiasts welcome—a fenced yard for the pup.

Jul 2 – 9

G$36,309 GYD per night