
Cottage holiday rentals in Orange County
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Top-rated cottage rentals in Orange County
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Holiday rentals for every style
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Popular amenities for cottage rentals in Orange County
Cottage rentals with a hot tub

Quaint Cottage - Wolftrap Farm (Horse neighbors)
My husband and I had a wonderful time celebrating our honeymoon at Wolftrap farm! The hosts were incredibly welcoming , professional, and responsive! They were available and willing to answer any questions we had! The view was breathtaking. Our pups enjoyed seeing the horses and the daily walks around the farm. Thank you for a wonderful experience!

'Pond House' on Huge Horse/Cattle Farm
The house was well kept and had everything we needed. We loved the amount of space for our family of 5! The patio, deck with grill and fire pit were wonderful additions. The area and yard were beautiful. Such a wonderful getaway!

Hideaway Haven
Tracy was a fantastic host who made us right at home. We loved being back in the woods and had a relaxing stay. Definitely appreciated a host who had some really delicious restaurant recommendations. We hope to be back soon.

Our Happy Place
20/10 — can’t recommend enough. Sarah thought of everything in every aspect, from a well equipped kitchen to the extra hair ties in the restroom. Truly was our happy place for the weekend!

Milker's Cottage at Wolftrap Farm (Horses in back)
My siblings and I had a great stay visiting family in the area. This magical horse farm was very friendly and th house was beautifully comfortable for work and plày.

THE PERFECT HIKING & WINERY COUNTRY RETREAT
We had a wonderful stay at Majestic Meadows. Sandy & Chris were wonderful hosts and the property was a great home away from home, with a beautiful courtyard full of colorful birds, a private pool, and a ton of flowering plants. Close enough to town to not feel like you’re in the middle of nowhere, but far away enough to feel secluded. I wouldn’t hesitate to book here again. Highly recommend.
Pet-friendly cottage rentals

Willie's Place Country Cottage Pets Allowed
Patti’s place provides a peaceful getaway in a beautiful area. Everything was as described!

Cheerful 4Br Water View Lakehouse with Dock & More
The house was great and so was Leonid! He was extremely responsive and so helpful. We will definitely come back

Private Fenced Yard for Dogs/Horses - 2BR Cottage
This was our second stay here. Second time was just as good as the first. The fenced yard for the dog was what originally made us book here, but the beautiful location and well-appointed house will keep us coming back. This trip was the first time we were able to use the walk on access to Montpelier and that was a nice added bonus.

THE PERFECT HIKING & WINERY COUNTRY RETREAT
We had a wonderful stay at Majestic Meadows. Sandy & Chris were wonderful hosts and the property was a great home away from home, with a beautiful courtyard full of colorful birds, a private pool, and a ton of flowering plants. Close enough to town to not feel like you’re in the middle of nowhere, but far away enough to feel secluded. I wouldn’t hesitate to book here again. Highly recommend.

Quaint Cottage - Wolftrap Farm (Horse neighbors)
My husband and I had a wonderful time celebrating our honeymoon at Wolftrap farm! The hosts were incredibly welcoming , professional, and responsive! They were available and willing to answer any questions we had! The view was breathtaking. Our pups enjoyed seeing the horses and the daily walks around the farm. Thank you for a wonderful experience!

Country Cottage with Modern Amenities
When my husband and I travel to Virginia to visit our daughter and her family, we prefer Shade Tree Cottage to any other B&B we have tried. It is such a pleasant place with plenty of space for family visits and meals. It is located between Charlottesville and Richmond allowing great day trips with our granddaughters. We have always been warmly welcomed and every need we could possibly have has been thoughtfully provided for. We think of Shade Tree as our home away. The Hastings

Scenic VA Wine & Horse Country Cottage, Near UVA
Everything was great. The place was exactly as described. There were great touches such as baked treats and farm fresh eggs. The place was well cared for and met all our expectations. It was quiet and peaceful and a perfect place for our long weekend

'Pond House' on Huge Horse/Cattle Farm
The house was well kept and had everything we needed. We loved the amount of space for our family of 5! The patio, deck with grill and fire pit were wonderful additions. The area and yard were beautiful. Such a wonderful getaway!
Private cottage rentals

Willie's Place Country Cottage Pets Allowed
Patti’s place provides a peaceful getaway in a beautiful area. Everything was as described!

Merry View Cottage
We enjoyed every moment of our stay. The location was secluded enough for us but also not far from town. The view was beautiful and the house had so many amenities and surprising details that enhanced our time there! Communication was great and we didn’t struggle with checking in or getting to the house. We would 100% come back and recommend anyone to stay here.

Private Fenced Yard for Dogs/Horses - 2BR Cottage
This was our second stay here. Second time was just as good as the first. The fenced yard for the dog was what originally made us book here, but the beautiful location and well-appointed house will keep us coming back. This trip was the first time we were able to use the walk on access to Montpelier and that was a nice added bonus.

Bond House: Historic Retreat at Walnut Grove
We enjoyed a wonderful overnight stay at this amazing cottage and are already checking our calendars for when we can return. Karina was friendly and very responsive. The home was perfect for our needs as we were a family of four adults attending a nearby wedding. The added bonus was the spectacular sunrise over the trees/distant mountains across the street this morning! As a photographer, I was thrilled to awaken to such a beautiful view! We had a relaxing, lovely time and look forward to our next visit in this peaceful home, where you truly feel like you’ve stepped back in time (but with modern conveniences like A/C and a dishwasher!).

THE PERFECT HIKING & WINERY COUNTRY RETREAT
We had a wonderful stay at Majestic Meadows. Sandy & Chris were wonderful hosts and the property was a great home away from home, with a beautiful courtyard full of colorful birds, a private pool, and a ton of flowering plants. Close enough to town to not feel like you’re in the middle of nowhere, but far away enough to feel secluded. I wouldn’t hesitate to book here again. Highly recommend.

Country Cottage with Modern Amenities
When my husband and I travel to Virginia to visit our daughter and her family, we prefer Shade Tree Cottage to any other B&B we have tried. It is such a pleasant place with plenty of space for family visits and meals. It is located between Charlottesville and Richmond allowing great day trips with our granddaughters. We have always been warmly welcomed and every need we could possibly have has been thoughtfully provided for. We think of Shade Tree as our home away. The Hastings

Hideaway Haven
Tracy was a fantastic host who made us right at home. We loved being back in the woods and had a relaxing stay. Definitely appreciated a host who had some really delicious restaurant recommendations. We hope to be back soon.

Lake Haven Cottage
The stay was wonderful! It had gorgeous surroundings and is a great stay if you’re looking for a peaceful private place to relax. The area had good stores and markets! The hosts were amenable and responded quickly when messaged. We had some unexpected events when it rained and we were provided with alternate accommodations. Overall it was a great place and we had a fun relaxing time!
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- Massanutten Resort
- Kings Dominion
- Luray Caverns
- Ash Lawn-Highland
- Early Mountain Winery
- Robert Trent Jones Golf Club
- Lee's Hill Golfers' Club
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- Chisholm Vineyards at Adventure Farm
- Lake Anna State Park
- Hermitage Country Club
- Prince Michel Winery
- Spring Creek Golf Club
- The Foundry Golf Club
- Massanutten Ski Resort
- Kinloch Golf Club
- Car and Carriage Caravan Museum
- Grand Prix Raceway