Vacation rentals in Winfrey
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Top-rated vacation rentals in Winfrey
Guests agree: these stays are highly rated for location, cleanliness, and more.
Guesthouse in Orange
5.0 out of 5 average rating, 175 reviewsTaj 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.
Oct 23 – 30
Apartment in Madison
4.9 out of 5 average rating, 228 reviewsThe Studio at Dark Run Retreat
Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*
Sep 17 – 24
Guest suite in Brandy Station
4.95 out of 5 average rating, 116 reviewsThrelkeld Farm,quiet, restful, fat pillows!
Romantic getaway. Large, comfortable queen bedroom/bath on Threlkeld Farm (circa 1828). Civil War buffs will enjoy being at the edge of the Brandy Station Battlefield and near the Graffiti House Museum, and St James Church. It's a great base for visiting historic sites nearby in Culpeper. This is horse country and the Warrenton Hunt sometimes hunt the farm. Wonderful resturants and history to explore in Culpeper County Virginia. We are in the foothills of the Blue Ridge Mountains. Private.
Apr 21 – 28
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winfrey vacation rentals
Other great vacation rentals in Winfrey
Apartment in Culpeper
4.98 out of 5 average rating, 139 reviewsAron’s Place (on the edge of Sugar Bottom)
Jun 30 – Jul 7
Cabin in Reva
4.93 out of 5 average rating, 388 reviewsCozy Cute Cabin
Dec 6 – 13
Tiny home in Reva
4.94 out of 5 average rating, 287 reviewsK-9 Heaven Dogs Run Free
May 1 – 8
Chalet in Brightwood
4.98 out of 5 average rating, 103 reviewsCharming Chalet in Blue Ridge Wine Country
Apr 1 – 8
Home in Brightwood
4.99 out of 5 average rating, 297 reviewsHilltop Haven Luxury lodging in Wine country
Feb 6 – 13
Cottage in Orange
4.95 out of 5 average rating, 359 reviewsPrivate Fenced Yard for Dogs/Horses - 2BR Cottage
Mar 8 – 15
Guesthouse in Syria
4.88 out of 5 average rating, 554 reviewsCozy 1 room cabin in the mountains.
Jun 8 – 15
Guesthouse in Midland
4.97 out of 5 average rating, 149 reviewsModern Farm Stay
Apr 15 – 22
Cabin in Unionville
4.94 out of 5 average rating, 125 reviewsPrivate Couples getaway with HOT TUB.
Aug 29 – Sep 5
Cabin in Culpeper
4.95 out of 5 average rating, 100 reviewsStanley’s Cabin- Beautiful farm with private pond
Aug 27 – Sep 3
Home in Culpeper
4.97 out of 5 average rating, 136 reviewsCozy Farmhouse Getaway
Jul 5 – 12
Apartment in Culpeper
5.0 out of 5 average rating, 39 reviewsRed Fox Retreat
Jun 30 – Jul 7
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