
Cottage vacation rentals in Orange County
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Top-rated cottage rentals in Orange County
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Orange County cottage rentals
Cottage rentals with a hot tub

Hideaway Haven
Beautiful hideaway in the middle of the snowy woods and only a quick drive to the grocery store, restaurants and wineries! Loved relaxing by the fire and enjoying the scenery. This place is the perfect weekend getaway to decompress and enjoy nature. Also spotlessly clean, especially given it’s dog friendly! Cant recommend enough!

Our Happy Place
Sarah's place was perfect for a quick weekend getaway! It was rainy and cold during our stay, so we didn't get to use the outdoor space as much as we'd like. However, the inside was perfectly cozy and beautifully decorated! It was a great spot to relax, turn off our phones, and just enjoy being together. We will definitely be back, and hopefully have warmer weather next time!

THE PERFECT HIKING & WINERY COUNTRY RETREAT
I had a wonderful stay at Chris and Sandy’s farm guesthouse. It was very easy to find and exceeded my expectations. They were the best hosts and I would definitely return. I especially loved feeding the donkey, Jasper. Sandy and Chris went out of their way to make it feel like home for us. Thanks again for the Yoder’s icecream recommendation, we loved seeing the free petting zoo.

Quaint Cottage - Wolftrap Farm (Horse neighbors)

'Pond House' on Huge Horse/Cattle Farm

Milker's Cottage at Wolftrap Farm (Horses in back)
Pet-friendly cottage rentals

Willie's Place Country Cottage Pets Allowed
Our family enjoyed our time at Patti’s place. The place is comfortable and easy to navigate. The outdoor seating areas are relaxing and great for star gazing.

Private Fenced Yard for Dogs/Horses - 2BR Cottage
Very peaceful and lots of nature and animals to see

THE PERFECT HIKING & WINERY COUNTRY RETREAT
I had a wonderful stay at Chris and Sandy’s farm guesthouse. It was very easy to find and exceeded my expectations. They were the best hosts and I would definitely return. I especially loved feeding the donkey, Jasper. Sandy and Chris went out of their way to make it feel like home for us. Thanks again for the Yoder’s icecream recommendation, we loved seeing the free petting zoo.

Country Cottage with Modern Amenities
The Shade Tree cottage was super comfortable. We felt right at home! We loved the little extras like charging stations, spices in the kitchen, laundry detergent, soap and shampoo in the bathroom. The large kitchen table was great for having friends join us for dinner. We greatly appreciated Matt providing the shower chair we requested. If we are ever in the area again, we will surely stay at the Shade Tree cottage!

Hideaway Haven
Beautiful hideaway in the middle of the snowy woods and only a quick drive to the grocery store, restaurants and wineries! Loved relaxing by the fire and enjoying the scenery. This place is the perfect weekend getaway to decompress and enjoy nature. Also spotlessly clean, especially given it’s dog friendly! Cant recommend enough!

Quaint & Cozy LakeView Cottage - Lake of the Woods
Everything was absolutely perfect from the moment we arrived! The house is beautifully decorated, so clean, and so well stocked. There was everything you could ever need in the kitchen, plus laundry detergent and cleaning supplies, shampoo and conditioner in both bathrooms, and even snacks and coffee, etc.! You can literally just show up with your clothes and bathing suit!! We would 100% stay here again, and recommend it to anyone!

A Charming Cottage on a Country Estate
Morgan was extremely responsive. We loved the cottage experience, esp since we also had full use of the outdoor space, inc around the main house. True serenity. My mom didn’t want to leave her room behind. Gordonsville is a great location and we barely made a dent in all the things we wanted to do. Drove to Lake Anna one day which wasn’t bad at all. Only con is that the price seemed similar to lakefront properties and/or full houses (I.e. full kitchen). Since it was neither, felt the price could have come down.

Our Happy Place
Sarah's place was perfect for a quick weekend getaway! It was rainy and cold during our stay, so we didn't get to use the outdoor space as much as we'd like. However, the inside was perfectly cozy and beautifully decorated! It was a great spot to relax, turn off our phones, and just enjoy being together. We will definitely be back, and hopefully have warmer weather next time!
Private cottage rentals

Willie's Place Country Cottage Pets Allowed
Our family enjoyed our time at Patti’s place. The place is comfortable and easy to navigate. The outdoor seating areas are relaxing and great for star gazing.

Merry View Cottage
My husband and I had a thoroughly enjoyable stay at Merryview Cottage. Everything is as pictured and described, right down to the room-darkening shades for the bedrooms, the makings for s’mores around the fire pit, and the hammock-with-a-view. For us, this Airbnb is our new favorite. Nothing can match the incredible views of the rolling hills from the porch, the soul-restoring quiet, and the sweet sounds of birds. Julie has thought of absolutely everything; I felt right at home. We had the delightful pleasure of meeting Julie and Rodney, and felt immediately like we found friends. Hope to return in the future.

Private Fenced Yard for Dogs/Horses - 2BR Cottage
Very peaceful and lots of nature and animals to see

Bond House: Historic Retreat at Walnut Grove
A lovely & quaint place to stay that's well kept and clean. We loved the historic element of it. We stayed one night but this is on our list to return for a longer stay! Close to Lake Anna and a short drive to Orange.

THE PERFECT HIKING & WINERY COUNTRY RETREAT
I had a wonderful stay at Chris and Sandy’s farm guesthouse. It was very easy to find and exceeded my expectations. They were the best hosts and I would definitely return. I especially loved feeding the donkey, Jasper. Sandy and Chris went out of their way to make it feel like home for us. Thanks again for the Yoder’s icecream recommendation, we loved seeing the free petting zoo.

French Cottage
We had an awesome 1 night stay. The location was perfect for hiking and wineries. The place was as described with the amenities like coffee and waters. The beds were very comfortable. Highly recommend:)

Hideaway Haven
Beautiful hideaway in the middle of the snowy woods and only a quick drive to the grocery store, restaurants and wineries! Loved relaxing by the fire and enjoying the scenery. This place is the perfect weekend getaway to decompress and enjoy nature. Also spotlessly clean, especially given it’s dog friendly! Cant recommend enough!

Lake Haven Cottage
Very enjoyable stay! The cottage was very clean and well maintained. Alicia was very responsive and accommodating. The peaceful surroundings made for a very good night's sleep. Thank you, Alicia, for your hospitality.
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