Cottage vacation rentals in Orange County

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Popular amenities for Orange County cottage rentals

Pet-friendly cottage rentals

Top guest favorite
A warm sitting area features a modern electric fireplace with blue flames and a wall-mounted television. A cozy armchair is positioned next to wooden shelves displaying books and decorative items. Light-colored sofa cushions add comfort, while natural light illuminates the space.
Cottage in Cornwall
5 out of 5 average rating, 50 reviews

Carriage House: Romantic Hideaway near West Point

BrittanyRating, 5 stars6 days ago
My boyfriend and I recently stayed at Catherine and Jay’s property while attending funeral services for my mother nearby. I cannot express how grateful I am for how accommodating Cathrine was during an awful time in my life. She was extremely responsive and kind and the space itself was the nicest, coziest, and most well appointed rental I have had the pleasure of using. Being able to feel right at home during my stay was a huge comfort to me. The only regret is I wish I could have stayed longer. The space has everything you need to be comfortable including a large variety of kitchen appliances and menus from local eateries. I also cannot get over how absolutely clean the property was. Thank you again for allowing us to use your space and making a terrible time for me bearable. We would rent again in a heartbeat.
Top guest favorite
A sandy beach area by Beaver Lake is shown, with three colorful chairs positioned on the shore. Surrounded by trees, the calm water reflects the clear blue sky. Two individuals are seated, enjoying the view, while another person is in the water.
Cottage in Rock Hill
4.96 out of 5 average rating, 76 reviews

Catskills Cottage w/ Lake View – Near Ski BookNow!

JohnmarkRating, 5 stars4 days ago
Jelissa is an absolute professional host! She made this trip so convenient and her home is a perfect, peaceful getaway!
Superhost
Cottage in Pine Bush
4.95 out of 5 average rating, 86 reviews

Modern BoHo 3BR Cottage Near by Hiking, Winery

KateRating, 5 stars1 month ago
Had a wonderful stay at The Green House. Home was exactly as pictured and very clean. Ada and Miranda were wonderful, responsive hosts and we loved the proximity to various hiking trails. The kitchen was stocked with all of the dishes and utensils to make your meals. Truly a peaceful oasis!
Superhost
A spacious wooden deck offers ample seating options, including colorful lounge chairs and a sofa. The bright red exterior of the cabin is complemented by large windows, providing views of the surrounding greenery and lake. Sunlight illuminates the outdoor area.
Cottage in West Milford
4.8 out of 5 average rating, 61 reviews

Perfect Couple's Getaway! Stunning views of Lake!

MatthewRating, 5 stars4 months ago
loved the getaway! really cozy, beautiful view, felt right at home. would highly recommend.
Guest favorite
Cottage in Wurtsboro
4.9 out of 5 average rating, 31 reviews

Cute Upstate Cottage - 90 Minutes from NYC!

JasonRating, 5 stars1 month ago
The house is Aweosme right near the lake but there is nothing Else around. Great place but a little expensive for off season.
Superhost
Cottage in Cornwall
4.85 out of 5 average rating, 41 reviews

Cozy Cottage near Hiking and Storm King

AlexandraRating, 5 stars5 months ago
Such a cozy cabin! Super friendly host(s) who are responsive and were able to answer any question. Would stay there again and plan to! 5 stars for a peaceful quiet weekend!
Guest favorite
A spacious backyard is showcased, featuring a swingset and slide. A grill and outdoor dining area are visible under a shaded patio nearby. Lush green grass surrounds the fenced yard, with trees providing a natural backdrop and a blue shed located in the distance.
Cottage in Wurtsboro
4.91 out of 5 average rating, 23 reviews

Family&pet friendly lakeside home-renovated-fenced

MelanieRating, 5 stars4 months ago
We had the perfect stay for our Thanksgiving. Lots of toys for the kiddo, backyard for the dogs to run around, and a well-stocked kitchen for all our cooking needs (utensils, platters, etc). Sadly we didn’t get to use the play set or the fire pit due to the weather, but we hope to come back when weather is slightly warmer!
Guest favorite
A wooden home is surrounded by lush greenery and manicured gardens. Flower beds with colorful blooms are visible in the foreground, while the house features a large deck. Mature trees provide a natural backdrop, enhancing the serene outdoor atmosphere.
Cottage in Greenwood Lake
4.96 out of 5 average rating, 48 reviews

5 bedroom 7 beds Cottage Sauna, Hike, Winery & Ski

JasonRating, 5 stars6 days ago
We had a great time at Carmine's place, highly recommend.

Private cottage rentals

The cottage features a two-story exterior with a welcoming entrance flanked by multiple large windows. Lush greenery surrounds the property, and a gravel path leads to the front door, enhancing the inviting atmosphere of this tranquil countryside location.
Cottage in Huguenot
3.57 out of 5 average rating, 7 reviews

Huguenot Retreat w/ Screened Porch & Lake Access!

AmyRating, 5 stars6 months ago
As I told the host multiple times, this place is beautiful! It was exactly what we needed for a couples getaway in the Catskills! Most activities and restaurants we visited were within 20-30min away plus 40 min away for a day trip to the Kartrite Indoor Waterpark! Will definitely keep this place in mind for future bookings!
A spacious outdoor deck extends towards a lush green backyard, framed by tall trees. Sunlight filters through the branches, casting a warm glow across the wooden surface. Planters with greenery are positioned along the railing, adding a touch of nature to the setting.
Cottage in Vernon Township
4.33 out of 5 average rating, 6 reviews

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

NicoleRating, 5 stars2 weeks ago
The home was very cozy and host was very responsive and helpful. Sleeps 10 (master on the main floor, 2 beds upstairs and 2 in the basement). Main floor bathroom is in the master bedroom and then there is another one upstairs. No bathroom in the basement. Beds were very comfortable and house temperature was adjustable. Bring your own fire-wood if you want to use the fire-pit!
A wooden deck provides a view of a serene lake, framed by trees and grassy areas. A small table and chairs are arranged on the deck, while a flag is visible in the distance, gently swaying in the breeze. The scene is bright and inviting.
Cottage in Port Jervis
4.9 out of 5 average rating, 72 reviews

Lake front house

MeghnaRating, 5 stars6 months ago
Jacqueline is a perfect host. We loved the local recommendations she provided About the lake house- The pictures do not do justice to what the beauty of the view is. Right from the sunset to the sunrise.. everything about the place is beautiful. The house is pretty and very welcoming. We enjoyed every bit of our stay. Can’t wait to go back!!
Guest favorite
A quaint cottage is shown nestled among trees, overlooking Greenwood Lake. Colorful autumn foliage frames the scene, with water and distant hills visible in the background. The cottage features a dark exterior and a small path leading to a covered entrance.
Cottage in Greenwood Lake
4.93 out of 5 average rating, 87 reviews

Cottage with Picturesque Views

CalaRating, 5 stars2 months ago
This place is literally a piece of heaven! During our stay, we had a full frontal of the frozen lake, it was pure magic! Waking up to the beautiful view of the lake was magic. If you are trying to disconnect, relax, reconnect with your loved one, this is your spot! The details in this rental were to die for! From the beautiful kitchen, to the rooms, there is not a single spot in this rental that was overlooked by design!! There is also ample space outside to hang out and grill! It was a beautiful and relaxing winter stay, the host was extremely responsive, even went out his way to grab allergy medicine for me through one of the snowy days.. thank you so much for your kindness! This place is absolutely heaven! I am definitely coming back!
A peaceful scene by the pond, showing a grassy area with a small shed near the water's edge. The calm pond reflects the trees and clouds above, while a canoe is visible next to the shed, ready for use.
Cottage in Walden
4.43 out of 5 average rating, 315 reviews

Hudson Valley's own Walden Pond

TammyRating, 5 stars4 weeks ago
I had a nice time neighbors was very friendly and it was very peaceful loved it I will book it again
An outdoor pool with a wooden deck is depicted, surrounded by seasonal foliage in warm hues. A tranquil lake is visible in the background, reflecting the natural beauty of the area. The scene captures the essence of relaxation in a peaceful setting.
Cottage in New Windsor
4.58 out of 5 average rating, 220 reviews

Lake Front Property Sauna and Pool Near West Point

JodiRating, 5 stars2 months ago
Definitely would stay here again! Lovely place on a beautiful lake and nice, peaceful neighborhood. Only thing I have to say is to definitely update the pictures because the upstairs bedroom and dining room don’t look like that anymore but no biggie at all! There’s a lot of things super close to the house. Host was extremely nice and very responsive when I had to message them!
A warm outdoor space features wooden steps leading to a stone cottage with large windows. A tropical bar with a thatched roof is visible on the left, alongside a bright red umbrella and decorative plants, creating a relaxed atmosphere perfect for outdoor gatherings.
Cottage in West Milford
4 out of 5 average rating, 4 reviews

Greenwood Lake Cottage w/ Shared Dock & Hot Tub!

CassidyRating, 5 stars9 months ago
I want to start by saying that the host is beyond kind. Jack is a stand up guy and the perfect host. I do not think we could have been more fortunate to choose this house. The backyard amenities are stunning. Sitting on the dock outside was incredible. A family of swans lives close to the house and we would watch them in the mornings. The hot tub was such a nice bonus. Jack clearly takes great care to ensure that his guests feel welcomed and at home and I could not appreciate his kindness any more than I already do. I truly can not wait to come back and stay again as this weekend was really one to remember. We thank you Jack for an amazing experience and we’ll see you again real soon!
Guest favorite
The exterior of a cottage features a grassy lawn and mature trees, providing a scenic backdrop. A pathway leads to a white door, framed by vibrant green shrubs. Open fields and distant trees create a peaceful and natural setting.
Cottage in Goshen
4.93 out of 5 average rating, 250 reviews

Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND

SarahRating, 5 stars3 weeks ago
Ginny helped me fix my reservation which I had mistakenly made for the wrong day. The cottage was very cozy and i felt right at home for the few nights we stayed there. We really only slept there and were out all day but it was quiet and comfortable and I would stay here again.

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