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Our top choices for Orange holiday homes
1. Newly renovated entire guest suite in Orange County.
Newly renovated entire guest suite in Orange County.Orange
9.8 out of 10, Exceptional, (46 reviews)
"The stay was great. Very close to all the nearby attractions and 30 minutes to skyline drive"
vishal k.
The price is HK$847
HK$1,221 total
includes taxes & fees
16 Nov - 17 Nov
2. The Pembroke Room in the historic Holladay House
The Pembroke Room in the historic Holladay HouseOrange
9.4 out of 10, Exceptional, (3 reviews)
"The property is in the perfect location for a visit to Montpelier! Great restaurants and events are nearby. Very cozy! Great host! Expect what you would expect from a historic home. We will return."
Robert
The price is HK$1,530
HK$2,146 total
includes taxes & fees
16 Nov - 17 Nov
3. Lake access w/hot tub, game room,boat slip, kayaks & more
Lake access w/hot tub, game room,boat slip, kayaks & moreOrange
10.0 out of 10, Exceptional, (10 reviews)
"Everything was amazing "
Jeff L.
The price is HK$1,405
HK$3,469 total
includes taxes & fees
23 Nov - 24 Nov
4. Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.Gordonsville
9.6 out of 10, Exceptional, (48 reviews)
"Beautiful property and family friendly."
Tracy
The price is HK$1,130
HK$1,313 total
includes taxes & fees
16 Nov - 17 Nov
5. 2BR Farm Stay | Hot Tub & Sunset Deck
2BR Farm Stay | Hot Tub & Sunset DeckUnionville
10.0 out of 10, Exceptional, (1 review)
"Super clean and cute little place to stay. Yasmin was super nice and very accommodating. Will definitely stay again when in the area."
Jason L.
The price is HK$1,252
HK$2,587 total
includes taxes & fees
1 Dec - 2 Dec
6. Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.
Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.Gordonsville
9.4 out of 10, Exceptional, (39 reviews)
"Beautiful place"
Berhan S.
The price is HK$1,553
HK$1,802 total
includes taxes & fees
16 Nov - 17 Nov
7. Historic Madison Eagle Inn
Historic Madison Eagle InnMadison
10.0 out of 10, Exceptional, (20 reviews)
"Great place - clean and very easy parking. The bed was comfortable too!"
Tracy
The price is HK$1,091
HK$1,882 total
includes taxes & fees
1 Dec - 2 Dec
8. Charming 3-Bed Cottage on Main Street in Historic Gordonsville
Charming 3-Bed Cottage on Main Street in Historic GordonsvilleGordonsville
9.8 out of 10, Exceptional, (21 reviews)
"Wonderful home, great location. "
Jeanna S.
The price is HK$1,603
HK$2,739 total
includes taxes & fees
17 Nov - 18 Nov
9. “The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.Gordonsville
10.0 out of 10, Exceptional, (38 reviews)
"Absolutely lovely place to stay. Stunning views and conveniently located to so many of the local attractions. Will definitely come back someday."
Kirby R.
The price is HK$1,758
HK$2,417 total
includes taxes & fees
16 Nov - 17 Nov
10. The Ranch at Wine Country - Complimentary Bottle!
The Ranch at Wine Country - Complimentary Bottle!Gordonsville
10.0 out of 10, Exceptional, (54 reviews)
"This wonderful Wine Country retreat was terrific for my family. We really enjoyed our stay. Comfortable, clean, safe, quiet, nicely remodeled, and well equipped (kitchen/dining; bathrooms; linens). Complimentary bottle of wine was a nice touch.And T's (Trevor's) thoughtful and professional communication and coordination of the rental process was much appreciated.If you are looking for a place to stay around Gordonsville or Charlottesville, we highly recommend T's Wine Country retreat."
Jeffrey W.
The price is HK$2,079
HK$3,384 total
includes taxes & fees
16 Nov - 17 Nov
11. Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle FarmGordonsville
9.6 out of 10, Exceptional, (35 reviews)
"The home was great, lots of space and sleeping areas. The farm itself was amazing. Would definitely stay again. Having a golf cart was a so fun."
B S.
The price is HK$2,824
HK$3,292 total
includes taxes & fees
16 Nov - 17 Nov
12. Dome for 2 | Private Hot Tub & Farm Views
Dome for 2 | Private Hot Tub & Farm ViewsUnionville
The price is HK$1,802
HK$3,004 total
includes taxes & fees
1 Dec - 2 Dec
13. Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+Stanardsville
10.0 out of 10, Exceptional, (36 reviews)
"Stayed here for a weekend while hiking Old Rag in Shenandoah. Cozy little place that was well equipped with all the amenities we needed! It's conveniently located close to Shenandoah as well as plenty of vineyards. Would not hesitate to stay here again the next time we're in the area!"
Jason
The price is HK$1,138
HK$1,627 total
includes taxes & fees
16 Nov - 17 Nov
14. Pine and Vine
Pine and VineGordonsville
The price is HK$3,018
HK$6,693 total
includes taxes & fees
2 Dec - 3 Dec
15. Charming 4-bedroom house in Madison centrally located!
Charming 4-bedroom house in Madison centrally located!Madison
10.0 out of 10, Exceptional, (4 reviews)
"The home met all our family’s needs during a weekend stay for a party at nearby farm. The layout and outdoor spaces were a bonus. In fact, the view of Hawksbill Mountain from the porch while enjoying our morning coffee: priceless. And importantly easy access to Rt 29 and the town but yet secluded and bucolic."
B D.
The price is HK$2,012
HK$3,637 total
includes taxes & fees
29 Nov - 30 Nov
16. Barn Apartment on Farm Near Old Rag and Shenandoah National Park
Barn Apartment on Farm Near Old Rag and Shenandoah National ParkEtlan
10.0 out of 10, Exceptional, (37 reviews)
"Kids absolutely loved the property with many kinds of animals!"
Ikuo
The price is HK$1,000
HK$1,498 total
includes taxes & fees
22 Nov - 23 Nov
17. Charming 3-bdrm house in Ruckersville offering great location for your vacation
Charming 3-bdrm house in Ruckersville offering great location for your vacationRuckersville
9.8 out of 10, Exceptional, (19 reviews)
"Nice home, we enjoyed our stay. "
Carol T.
The price is HK$1,681
HK$3,522 total
includes taxes & fees
16 Nov - 17 Nov
18. 5BR Lake Anna, Boat Slip + Kayaks, Dog Friendly
5BR Lake Anna, Boat Slip + Kayaks, Dog FriendlyLouisa
10.0 out of 10, Exceptional, (30 reviews)
"Our vacation was great! We really enjoyed everything about this property. Our interaction with our host was amazing!!!We definitely would recommend this property!"
Gloria W.
The price is HK$1,946
HK$5,242 total
includes taxes & fees
1 Dec - 2 Dec
19. Tatum's Mtn View Retreat- SAUNA-Hiking- Unit A
Tatum's Mtn View Retreat- SAUNA-Hiking- Unit AMadison
10.0 out of 10, Exceptional, (12 reviews)
"This house was perfect for our weekend stay. It was very clean and had a well stocked kitchen and bathrooms. There was plenty of space for our family of 5 to spread out and relax. The beds were all comfortable to sleep in too."
Megan F.
The price is HK$911
HK$1,905 total
includes taxes & fees
29 Nov - 30 Nov
20. Fern Cottage Summary:
Fern Cottage Summary:Gordonsville
10.0 out of 10, Exceptional, (23 reviews)
"We had a great stay. The house was clean and well furnished. Recommend for anyone staying in the area."
Gary W.
The price is HK$1,930
HK$4,229 total
includes taxes & fees
2 Dec - 3 Dec
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Learn more about Orange
Step into James Madison's world at Montpelier, where guided tours bring the Founding Father's home to life. Stroll downtown's charming Main Street, popping into antique shops and sampling local wines at the Orange County Winery.
Photo by Jerry Smith
Open Photo by Jerry Smith