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Compare 77 Vacation Homes in Orlean with updated reviews, rates, and availability.

Big Sunny Family House
A large dining room table comfortably seats 10 people for large gatherings,
Big Sunny Family House
10.0 out of 10, Exceptional, (22)
"This was a girls’ trip for a homesteaders conference. We enjoyed the spacious living spaces; the pictures just don’t give them justice. We had meals around the large dining table, then moved into the large living room for further conversation and fellowship. The bedrooms were great also. The neighborhood hosts several restaurants and coffee shops. Just a great experience! "
Big Sunny Family House
Surrounded by majestic trees Hilltop Hideaway is located within the woodlands.
Hilltop Hideaway Manor
Surrounded by majestic trees Hilltop Hideaway is located within the woodlands.
9.8 out of 10, Exceptional, (80)
"We had a wonderful stay! The house was clean and comfortable. The deck is fantastic with lots of privacy and surrounding woods. The location was great for hiking in Shenandoah National Park and we visited nearby restaurants, wineries and a distillery. The host was very responsive with questions I had before we arrived and the property was as described. "
The price is AED 753
AED 1,563 total
includes taxes & fees
10 Nov - 11 Nov
Surrounded by majestic trees Hilltop Hideaway is located within the woodlands.
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
Outdoor spa tub
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
10.0 out of 10, Exceptional, (29)
"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
Sunny Front Royal Vacation Rental w/ Hot Tub!
Front Royal Vacation Rental | 1BR | 2BA | 900 Sq Ft | Stairs Required
Sunny Front Royal Vacation Rental w/ Hot Tub!
9.8 out of 10, Exceptional, (7)
"A great property, beautifully decorated and furnished, located in a bucolic setting with a magnificent view of the mountains and skyline. Can't say enough how nice!"
Sunny Front Royal Vacation Rental w/ Hot Tub!
Linden Family Home w/ Yard < 5 Mi to Wineries!
Linden Vacation Rental | 3BR | 2BA | Stairs Required | 3,000 Sq Ft
Linden Family Home w/ Yard < 5 Mi to Wineries!
2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and quaint property. Beautiful sunset skies. Dogs have plenty of space to stretch their legs on the gorgeous grass."
Linden Family Home w/ Yard < 5 Mi to Wineries!
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
3 Penny Acres was built in 1916 on the foundations of an 1800's cabin.
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
9.8 out of 10, Exceptional, (25)
"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
River Front Retreat
Good morning view
River Front Retreat
8.8 out of 10, Excellent, (34)
"We had another vacation for the books! Had a great time with family. Justin was very quick to respond to any needs. Some improvements from last year which was great. Dock still a little challenging. Downstairs mattresses could use an upgrade. Overall the location and space of the home is perfect! We really enjoyed vacation 2024 and hope to plan another for 2025!"
River Front Retreat
Hot tub w/ Sunset Views! Secluded mountain chalet
Bright, light chalet
Hot tub w/ Sunset Views! Secluded mountain chalet
10.0 out of 10, Exceptional, (31)
"The Chalet is a diamond on the mountain and has plenty of room for two families, was also great that we could take our fur babies with us. We did not go anywhere, just enjoyed the comfort and well stocked kitchen. It was very nice to have all of the extras provided by David who is a wonderful host and quickly responds to communication. The views are wonderful from the morning mist off of the river to the stunning sunsets. We just relaxed, enjoyed the Chalet and fire pit for our smores nights. We...
The price is AED 1,164
AED 2,343 total
includes taxes & fees
25 Nov - 26 Nov
Hot tub w/ Sunset Views! Secluded mountain chalet
Home w/ Hot Tub Near Shenandoah Nat'l Park!
Browntown Vacation Rental | 3BR | 2BA | 1,516 Sq Ft | Step-Free Access
Home w/ Hot Tub Near Shenandoah Nat'l Park!
9.8 out of 10, Exceptional, (18)
"We had a wonderful anniversary weekend. This was the perfect place to be out in nature and yet only a 15 minute drive into town. Place was clean. Screened in porch was great and so was the hot tub. Took a minute to figure out how to work the range and coffee pot but after we figured that out it was all good. Thoroughly enjoyed our stay. "
Home w/ Hot Tub Near Shenandoah Nat'l Park!
Modern Mountain Retreat w/ Deck + Hot Tub!
Chester Gap Vacation Rental | 3BR | 2.5BA | 2 Stories | 1,400 Sq Ft
Modern Mountain Retreat w/ Deck + Hot Tub!
10.0 out of 10, Exceptional, (63)
"Quiet peaceful neighborhood. House is clean and spacious. Enjoyed relaxing on the deck, birdwatching, and admiring the Mountain View."
Modern Mountain Retreat w/ Deck + Hot Tub!
Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!
Welcome to Sweet Pea Cottage! We can't wait to host your stay:)
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 558
AED 1,106 total
includes taxes & fees
19 Nov - 20 Nov
Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!
The Nest at Chester Gap
The Nest Landscape
The Nest at Chester Gap
10.0 out of 10, Exceptional, (95)
"The pictures don’t do it justice. Can’t wait to go back!!"
The Nest at Chester Gap
6-Person House with private hot tub and screen porch
Terrace/patio
6-Person House with private hot tub and screen porch
10.0 out of 10, Exceptional, (3)
"Gorgeous views from the back patio - we had a great time! I do wish we'd known that the Donkey was going to be in the field right out back, this was a huge plus - our kids would have loved it."
6-Person House with private hot tub and screen porch
10 Person House with Private Hot tub on Spectacular Rural Estate
Exterior
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!
Front Royal Vacation Rental | 2BR | 1BA | 908 Sq Ft | Stairs Required
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!
Historic Warrenton Home w/ Patio & Hot Tub!
Warrenton Vacation Rental | 5BR | 3.5BA | Stairs Required | 3,500 Sq Ft
Historic Warrenton Home w/ Patio & Hot Tub!
10.0 out of 10, Exceptional, (1)
"We had an awesome stay here! The location is super close to downtown Warrenton and the pricing is very reasonable for a group! I would definitely recommend this place and stay here again! "
Historic Warrenton Home w/ Patio & Hot Tub!
NEW LISTING! Contemporary Architectural Gem: Modern Retreat by RedAwning
Grass,Outdoors,House,Hotel,Nature
NEW LISTING! Contemporary Architectural Gem: Modern Retreat by RedAwning
10.0 out of 10, Exceptional, (1)
"Host responded to my questions in a timely manner. Beautiful house."
NEW LISTING! Contemporary Architectural Gem: Modern Retreat by RedAwning
Rolling River Farm: Exquisite Riverfront Paradise
Farmhouse Front Yard
Rolling River Farm: Exquisite Riverfront Paradise
10.0 out of 10, Exceptional, (109)
"House very well equipped. Only negative thing I can say is mattresses were not very comfortable."
Rolling River Farm: Exquisite Riverfront Paradise
Warrenton Gem: Walk to Dtwn, Dogs Welcome
Warrenton Vacation Rental | 4BR | 2.5BA | 1,800 Sq Ft | 4 Steps to Enter
Warrenton Gem: Walk to Dtwn, Dogs Welcome
2.0 star property
10.0 out of 10, Exceptional, (1)
Warrenton Gem: Walk to Dtwn, Dogs Welcome
⭐️Lunar Lookout ⭐️ NEW Build Geodesic Dome situated on 8 acres!
Living area
⭐️Lunar Lookout ⭐️ NEW Build Geodesic Dome situated on 8 acres!
10.0 out of 10, Exceptional, (2)
"The property is beautiful and just outside of Front Royal. We visited local vineyards and hit the skyline drive on the way home. We loved relaxing in the GeoDome home!"
The price is AED 1,469
AED 2,641 total
includes taxes & fees
13 Nov - 14 Nov
⭐️Lunar Lookout ⭐️ NEW Build Geodesic Dome situated on 8 acres!
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.
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Other property types in Orlean

Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
Sunset on the porch
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
9.6 out of 10, Exceptional, (287)
"I was surprised about how on top of the river you feel while viewing it from the porch. I had great weather for my stay and was able to watch two amazing sunsets over the river and mountains in the background. The location is awesome if you want to feel secluded and to enjoy the outdoors. And the cabin itself feels very welcoming and cozy overall."
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Riverview from covered deck area
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
9.6 out of 10, Exceptional, (324)
"True log cabin with a beautiful new addition, great view of the mountains and the Shenandoah River from a beautiful deck and a wood and gas burning fireplace!"
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!
Exterior from the deck
Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!
10.0 out of 10, Exceptional, (73)
"Fabulous and absolutely beautiful cabin. Everything in the cabin had great details to the cutting board and wine opener. The owners were spectacular with communicating. My girlfriends and I were celebrating our birthdays as Libras an annual trip. We had an amazing time!"
Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!
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.