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.

Guest favorite

Guesthouse in Orange

5.0 out of 5 average rating, 175 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.

Oct 23 – 30

G$24,553 GYD per night
Guest favorite

Apartment in Madison

4.9 out of 5 average rating, 228 reviews

The 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

G$17,327 GYD per night
Guest favorite

Guest suite in Brandy Station

4.95 out of 5 average rating, 116 reviews

Threlkeld 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

G$23,698 GYD per night

Popular amenities for Winfrey vacation rentals

Other great vacation rentals in Winfrey

Guest favorite

Apartment in Culpeper

4.98 out of 5 average rating, 139 reviews

Aron’s Place (on the edge of Sugar Bottom)

Jun 30 – Jul 7

G$26,383 GYD per night
Guest favorite

Cabin in Reva

4.93 out of 5 average rating, 388 reviews

Cozy Cute Cabin

Dec 6 – 13

G$41,210 GYD per night
Guest favorite

Tiny home in Reva

4.94 out of 5 average rating, 287 reviews

K-9 Heaven Dogs Run Free

May 1 – 8

G$26,498 GYD per night
Guest favorite

Chalet in Brightwood

4.98 out of 5 average rating, 103 reviews

Charming Chalet in Blue Ridge Wine Country

Apr 1 – 8

G$33,959 GYD per night
Guest favorite

Home in Brightwood

4.99 out of 5 average rating, 297 reviews

Hilltop Haven Luxury lodging in Wine country

Feb 6 – 13

G$30,050 GYD per night
Guest favorite

Cottage in Orange

4.95 out of 5 average rating, 359 reviews

Private Fenced Yard for Dogs/Horses - 2BR Cottage

Mar 8 – 15

G$25,228 GYD per night
Superhost

Guesthouse in Syria

4.88 out of 5 average rating, 554 reviews

Cozy 1 room cabin in the mountains.

Jun 8 – 15

G$13,982 GYD per night
Guest favorite

Guesthouse in Midland

4.97 out of 5 average rating, 149 reviews

Modern Farm Stay

Apr 15 – 22

G$27,796 GYD per night
Guest favorite

Cabin in Unionville

4.94 out of 5 average rating, 125 reviews

Private Couples getaway with HOT TUB.

Aug 29 – Sep 5

G$34,641 GYD per night
Guest favorite

Cabin in Culpeper

4.95 out of 5 average rating, 100 reviews

Stanley’s Cabin- Beautiful farm with private pond

Aug 27 – Sep 3

G$53,994 GYD per night
Guest favorite

Home in Culpeper

4.97 out of 5 average rating, 136 reviews

Cozy Farmhouse Getaway

Jul 5 – 12

G$36,897 GYD per night
Guest favorite

Apartment in Culpeper

5.0 out of 5 average rating, 39 reviews

Red Fox Retreat

Jun 30 – Jul 7

G$24,266 GYD per night

Destinations to explore

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  2. United States
  3. Virginia
  4. Culpeper County
  5. Winfrey