Cottage vacation rentals in Orange County

Find and book unique cottages on Airbnb

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Popular amenities for Orange County cottage rentals

Cottage rentals with a hot tub

Guest favorite
A bright living room is showcased with large windows providing views of the wooded surroundings. A comfortable sofa and armchairs are arranged around a wooden coffee table, while a wall-mounted television and a small wood-burning stove are visible. Warm lighting is offered by two lamps.
Cottage in Gordonsville
4.97 out of 5 average rating, 32 reviews

Hideaway Haven

BrookeRating, 5 stars3 months ago
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!
Top guest favorite
A charming cabin is nestled among tall trees, featuring a blue exterior and a sloped roof. A covered porch is visible, with colorful chairs providing a cozy sitting area. A hammock hangs between two trees, inviting relaxation in the serene woodland setting.
Cottage in Orange
4.96 out of 5 average rating, 158 reviews

Our Happy Place

CaseyRating, 5 stars2 weeks ago
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!
Top guest favorite
An aerial view captures the guest house and the surrounding property, showcasing a spacious grass area and a 30,000-gallon in-ground pool. The pool area features several blue lounge chairs and is framed by mature trees and landscaped pathways.
Cottage in Madison
4.95 out of 5 average rating, 417 reviews

THE PERFECT HIKING & WINERY COUNTRY RETREAT

JennRating, 5 starstoday
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.
Guest favorite
The Servants' Cottage, built in 1856, is showcased with a classic white exterior and a metal roof. Surrounded by well-maintained grass and shrubs, it is set against a backdrop of trees and open fields. Natural light casts gentle shadows on the lawn.
Cottage in Gordonsville
4.84 out of 5 average rating, 154 reviews

Quaint Cottage - Wolftrap Farm (Horse neighbors)

Guest favorite
A charming wooden house is complemented by a blooming dogwood tree, its branches adorned with soft pink flowers. A screened porch extends across the front, offering an inviting space to enjoy the surrounding nature on a clear day.
Cottage in Gordonsville
4.85 out of 5 average rating, 101 reviews

'Pond House' on Huge Horse/Cattle Farm

Guest favorite
The exterior of the Milker's Cottage is captured against a clear blue sky. The one-story white structure features a welcoming porch with railing and a covered entryway, surrounded by green grass and trees, conveying a sense of serenity in the rural landscape.
Cottage in Gordonsville
4.81 out of 5 average rating, 81 reviews

Milker's Cottage at Wolftrap Farm (Horses in back)

Pet-friendly cottage rentals

Guest favorite
A front porch features two black rocking chairs positioned beside a small table adorned with flowers. The view beyond shows a spacious yard with a fence and horses grazing in the distance, framed by trees under a clear sky.
Cottage in Orange
4.9 out of 5 average rating, 170 reviews

Willie's Place Country Cottage Pets Allowed

JessicaRating, 5 stars1 day ago
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.
Top guest favorite
A living area features a comfortable gray sofa and armchair, set on a light area rug. A wooden coffee table is centrally located, while a TV sits on a decorative stand. Natural light enters through a window, complemented by soft lighting from a chandelier above.
Cottage in Orange
4.96 out of 5 average rating, 431 reviews

Private Fenced Yard for Dogs/Horses - 2BR Cottage

NathanRating, 5 stars1 week ago
Very peaceful and lots of nature and animals to see
Top guest favorite
An aerial view reveals the layout of a charming property featuring a guest house and main house surrounded by greenery. A large pool is visible alongside well-maintained lawns and trees, with gently rolling mountains in the background.
Cottage in Madison
4.95 out of 5 average rating, 417 reviews

THE PERFECT HIKING & WINERY COUNTRY RETREAT

JennRating, 5 starstoday
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.
Top guest favorite
The exterior of Shade Tree Cottage is highlighted by a front pathway leading to a welcoming front door, painted in red. Soft garden lighting illuminates the surrounding landscape, enhancing the cottage's rural charm against a dusky sky.
Cottage in Gordonsville
5 out of 5 average rating, 81 reviews

Country Cottage with Modern Amenities

JaniceRating, 5 stars2 weeks ago
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!
Guest favorite
A wooden cottage surrounded by tall trees showcases a combination of grey siding and brick accents. Large windows reflect the natural surroundings, and a wooden deck extends from the side, providing a peaceful retreat in a wooded environment.
Cottage in Gordonsville
4.97 out of 5 average rating, 32 reviews

Hideaway Haven

BrookeRating, 5 stars3 months ago
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!
Top guest favorite
A cozy living room features a stone gas fireplace framed by elegant wooden details. Two black reclining chairs provide comfortable seating around a patterned area rug. Ambient lighting from decorative fixtures complements large windows that invite natural light into the space.
Cottage in Locust Grove
4.99 out of 5 average rating, 136 reviews

Quaint & Cozy LakeView Cottage - Lake of the Woods

ShannonRating, 5 stars1 day ago
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!
Superhost
Lush green grass blankets the ground near a cottage, framed by a flowering shrub and a small tree. The landscape is complemented by a wooden fence in the background, enhancing the serene natural setting.
Cottage in Gordonsville
4.88 out of 5 average rating, 8 reviews

A Charming Cottage on a Country Estate

TaiRating, 5 stars20 months ago
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.
Top guest favorite
Cottage in Orange
4.96 out of 5 average rating, 158 reviews

Our Happy Place

CaseyRating, 5 stars2 weeks ago
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

Guest favorite
A front porch features two black rocking chairs positioned beside a small table adorned with flowers. The view beyond shows a spacious yard with a fence and horses grazing in the distance, framed by trees under a clear sky.
Cottage in Orange
4.9 out of 5 average rating, 170 reviews

Willie's Place Country Cottage Pets Allowed

JessicaRating, 5 stars1 day ago
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.
Top guest favorite
A front porch is showcased, featuring two white rockers positioned on a wooden deck. The scene is enhanced by a misty landscape in the background as the sun rises over rolling hills, casting a soft light on the surroundings.
Cottage in Gordonsville
5 out of 5 average rating, 166 reviews

Merry View Cottage

ShirleyRating, 5 stars1 week ago
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.
Top guest favorite
A wooden deck features a round table and two matching chairs, both in a vibrant turquoise color. The railing offers a clear view of the surrounding grassy area and trees, creating a serene outdoor space.
Cottage in Orange
4.96 out of 5 average rating, 431 reviews

Private Fenced Yard for Dogs/Horses - 2BR Cottage

NathanRating, 5 stars1 week ago
Very peaceful and lots of nature and animals to see
Guest favorite
A charming historic cottage is featured, showcasing a white exterior with a red metal roof. The front porch is framed by a small staircase and surrounded by well-maintained greenery. Tall trees provide shade on the side, set against a backdrop of an expansive blue sky.
Cottage in Spotsylvania Courthouse
4.88 out of 5 average rating, 157 reviews

Bond House: Historic Retreat at Walnut Grove

DavidRating, 5 stars3 weeks ago
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.
Top guest favorite
An aerial view highlights a spacious property surrounded by lush green fields and trees. The guesthouse is situated near a blue in-ground pool, with a winding driveway leading to the main entrance. Nearby, a small outbuilding is visible amidst the landscape.
Cottage in Madison
4.95 out of 5 average rating, 417 reviews

THE PERFECT HIKING & WINERY COUNTRY RETREAT

JennRating, 5 starstoday
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.
Top guest favorite
Cottage in Barboursville
4.96 out of 5 average rating, 28 reviews

French Cottage

BrigetteRating, 5 stars2 days ago
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:)
Guest favorite
A wooden cottage surrounded by tall trees showcases a combination of grey siding and brick accents. Large windows reflect the natural surroundings, and a wooden deck extends from the side, providing a peaceful retreat in a wooded environment.
Cottage in Gordonsville
4.97 out of 5 average rating, 32 reviews

Hideaway Haven

BrookeRating, 5 stars3 months ago
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!
Guest favorite
A charming cottage surrounded by lush greenery and trees in autumn colors. The red structure with a sloped roof sits in a serene area, offering a peaceful retreat, while a dirt path leads towards it, under a clear blue sky.
Cottage in Ruckersville
4.9 out of 5 average rating, 314 reviews

Lake Haven Cottage

TeresaRating, 5 stars1 week ago
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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