Search Vacation Homes in Orlean

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 73 Vacation Homes in Orlean with updated reviews, rates, and availability.

1800s Family Farmhouse with Huge Yard- PRIVATE TRAIL WALK TO WINE!

10.0 out of 10, Exceptional, (46)
"With grandparents and 2 families with children, not only was the house perfect but the fenced yard was huge and spectacular. We didn’t use the hot tub, but there was plenty of good space for adults, too. We gathered for a family wedding, but the space enabled us to spend a few wonderful relaxing days with family we rarely see. Communication with Leora was prompt and accommodating. 5 stars all around! Thank you!"
1800s Family Farmhouse with Huge Yard- PRIVATE TRAIL WALK TO WINE!

Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly

10.0 out of 10, Exceptional, (30)
"Beautiful cozy home with a fantast view. Fenced in deck (our dog loved it as well as the fenced in yard)! Great location for day hikes! "
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly

Cozy Country Getaway in the Heart of Upperville

10.0 out of 10, Exceptional, (7)
"Highly recommend this place."
Cozy Country Getaway in the Heart of Upperville

River Front Retreat

8.8 out of 10, Excellent, (36)
"The home is in a very cool location. We loved the drive to the house. There were great views of the river. The home had everything needed to enjoy the river, but our stay was too cold to enjoy the river. Overall, the home was just what we were looking for!"
River Front Retreat

Where Charming Local History Meets Modern Comfort ~ Historic Fauquier County, VA

10.0 out of 10, Exceptional, (67)
"Thanksgiving week with family and friends at the Cottage was perfect. This home is extremely comfortable, relaxing, well stocked with needed kitchen supplies. Was so fun being in the middle of town but felt like you were in the middle of nowhere. Thank you so much for making such a wonderful home available for rent."
Where Charming Local History Meets Modern Comfort ~ Historic Fauquier County, VA

Big Sunny Family House

10.0 out of 10, Exceptional, (27)
"The house was exactly what we needed. We go away every year and this house was big enought for all of us. Lived the comfortable beds and living room. Will hopefully be back. "
Big Sunny Family House

10 Person House with Private Hot tub on Spectacular Rural Estate

9.8 out of 10, Exceptional, (66)
"The property was perfect for our large group and the hosts at Castleton Meadows were extremely kind, helpful and communicative. Would definitely return!!!"
10 Person House with Private Hot tub on Spectacular Rural Estate

Chic Front Royal Retreat Near Shenandoah River!

9.4 out of 10, Exceptional, (13)
"Fit all our needs. Enjoyed the area. "
Chic Front Royal Retreat Near Shenandoah River!

Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country

9.6 out of 10, Exceptional, (13)
"We had a small family gathering here around Christmas and we absolutely loved it! We immediately felt right at home. It is a gorgeous property, well appointed, and very comfortable. The game room was a huge hit with everyone. We're hoping to make it an annual tradition, hopefully for longer than one night next time!"
The price is AED 1,723
AED 2,064 total
includes taxes & fees
28 Jan - 29 Jan
Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country

Excellent location across the Inn Entire 3 beds Colonial House with fast Wi-Fi

10.0 out of 10, Exceptional, (113)
"The house was very clean, well stocked and an easy walk to the area businesses. Owners very friendly and informative. We greatly enjoyed our stay! "
The price is AED 735
AED 1,140 total
includes taxes & fees
22 Jan - 23 Jan
Excellent location across the Inn Entire 3 beds Colonial House with fast Wi-Fi

Historic spacious home in the heart of Upperville, VA

10.0 out of 10, Exceptional, (3)
"We loved staying here, by far our favorite part was the gardens. We sat outside as much as we could and it made the whole setting so lovely. A well appointed kitchen and nice linens made our stay so comfortable. Our kids found soccer balls and things to play with. I can't recommend it enough for a big family group!"
Historic spacious home in the heart of Upperville, VA

New - Modern Mountain Retreat w/ Hot tub and view!

10.0 out of 10, Exceptional, (11)
"The house is beautiful. It is nicely decorated, spacious, very clean and super comfortable. The kitchen is huge and well stocked. The mountain views are lovely. The location is peaceful and close to hiking trails. All in all, a great place for a getaway."
New - Modern Mountain Retreat w/ Hot tub and view!

Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

9.8 out of 10, Exceptional, (26)
"Hiking, playing in the creek, S'mores by the fire pit, enjoying meals on the porch all add up to fun memories. We enjoyed our stay. "
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

Hot tub w/ Sunset Views! Secluded mountain chalet

10.0 out of 10, Exceptional, (33)
"Our family had a wonderful time celebrating Thanksgiving in this most spacious cabin. Main floor living was perfect for our older family member. The cabin meet all our needs and then some. Our family enjoyed the old-school record player and pool/ping-pong table. David’s communication was clear and he responded in a timely manner (helping us in a bind on check out day). The extensive valley and river views are indescribable and most enjoyable from the hot tub! We enjoyed watching the birds and...
Hot tub w/ Sunset Views! Secluded mountain chalet

Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

10.0 out of 10, Exceptional, (63)
"We were looking for the perfect place to stay during our week in hunt country- convenient to the farm where we kept our horses and the restaurants in Middleburg. This exceeded our expectations. This house has been lovingly restored and is beautifully decorated. Its cozy, traditional vibe meshes perfectly with its modern updates. There are thoughtful touches everywhere- from a large selection of coffees, to the working fireplace, and many more. The beds and bedding are super comfortable. We...
Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

Home w/ Hot Tub Near Shenandoah Nat'l Park!

10.0 out of 10, Exceptional, (22)
"Loved our stay here and loved the views! Such great house with everything we needed and Jim was a great host! We had a wonderful time in the hot tub and in the cabin and it was close to everything! Highly recommend!"
Home w/ Hot Tub Near Shenandoah Nat'l Park!

Modern Mountain Retreat w/ Deck + Hot Tub!

10.0 out of 10, Exceptional, (65)
"This place is wonderful. The hot tub, wood burning stove, fire pits are all just as stated and shown in pictures. Everything is clean. Beds are comfy and kitchen is well stocked. Bathrooms are updated. Master Bath is beautiful. The location is great for winery tours and hiking. If you enjoy shopping or nightlife, this would not be a good choice. We thought it was heaven. Just a warning that if you are older or have mobility issues, the stairs are narrow and all bedrooms are upstairs. We didn’t...
Modern Mountain Retreat w/ Deck + Hot Tub!

1900s farmhouse with yard games, firepit, & renovated interior - dog-friendly

9.6 out of 10, Exceptional, (8)
"Delightfully warm home with all you could want for a comfortable stay. The farmhouse provided plenty of space and very comfortable beds for a good night sleep. The kitchen is well stocked and the wi-fi is reliable and strong. We highly recommend staying at this lovely home."
1900s farmhouse with yard games, firepit, & renovated interior - dog-friendly

Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!

9.0 out of 10, Wonderful, (24)
"The property was ok. There wasn't much of a view from the cottage. It was clean but kind of small. The gas grill on the deck was nice to have. The only major problem was that there was no hot water on our last day there. We notified the owner, but he could not get anyone out there until the next day, when we left. So that was kind of a bummer. No showers or hot water to properly do the dishes."
The price is AED 622
AED 1,124 total
includes taxes & fees
12 Jan - 13 Jan
Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!

The Nest at Chester Gap

10.0 out of 10, Exceptional, (96)
"The pictures don’t do it justice. Can’t wait to go back!!"
The Nest at Chester Gap
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.
Don't see what you're looking for?
See all available properties in Orlean
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Orlean

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

9.4 out of 10, Exceptional, (333)
"Amazing!!!"
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

9.6 out of 10, Exceptional, (296)
"The cabin is a very cozy getaway location, with a great view just out the window."
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (34)
"Nice place! Clean, beautiful, and located just two miles from town. "
The price is AED 1,010
AED 1,458 total
includes taxes & fees
12 Jan - 13 Jan
18th Century Stone Cottage minutes from historic Middleburg
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.