Guesthouse vacation rentals in Orange County

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Top-rated guesthouse rentals in Orange County

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A spacious loft area features high ceilings accented by exposed wooden beams. A queen size bed is fitted with a soft blanket, while a colorful area rug complements the white furniture. A dining table with chairs and a cozy sitting area are visible in the background.

Guesthouse in Warwick

4.94 out of 5 average rating, 437 reviews

Rustic Loft Space with Distinctive Artistic Charm

Beautiful spacious and bright artist loft on the second floor of a newly renovated Warwick barn behind our 1893 Warwick Village home. More information The space We offer our furnished live and work artist loft on a daily or weekly basis. The loft : -is 400 sqf -is located on the second floor -has nicely designed bathroom -has a very comfortable queen size bed -has high speed internet access -is very tidy and clean The neighborhood: -one blocks from the NJ Transit bus to Manhattan. -great restaurants and cafés nearby This loft is wonderful is perfect for 2-4 visitors. You are in the middle of lovely village neighborhood, but get the comfort of a cozy retreat. Guests will have access to the entire SECOND FLOOR space. Situated in the lower Hudson Valley, the town of Warwick is just over an hour’s bus ride New York City. Explore its numerous orchards and wineries, head to the drive-in movie theater, or grab a bite from one of the village restaurants. The loft is just one block from the NJ Transit bus that leaves from Port Authority.

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Guest favorite

A two-story house is presented in a well-maintained exterior, featuring a stone chimney and a welcoming entry with steps leading to the front door. Lush greenery surrounds the property, with a well-kept lawn and clear blue sky overhead.

Guesthouse in Greenwood Lake

4.96 out of 5 average rating, 82 reviews

Spacious, two bedroom apartment with parking

"Located in the village of Greenwood Lake, the apartment is the entire second floor of the house, it is clean and bright. Easy walk to all Greenwood Lake has to offer - lake beach, restaurants, hiking trails, and the NJ Transit bus stop is close. Easy 7 min drive to skiing at Mt Peter, 26 min to ski Mountain Creek, 25 min to Legoland, 20min to Warwick NY, 40 min to West Point. Each bedroom offers a queen sized bed, apt has full bath and kitchen. Parking, central air and WiFi. Permit # 21-07639

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Guest favorite

A winding pathway leads towards a modern, dark-colored barn-style structure surrounded by greenery, with a panoramic view of the mountains in the background. The cloudy sky adds a soft, diffused light to the scene, highlighting the natural landscape.

Guesthouse in Beacon

4.94 out of 5 average rating, 93 reviews

A modern barn on the Hudson River

Welcome to your perfect getaway in the heart of picturesque Beacon, NY! Nestled amidst the tranquil beauty of HV, this newly renovated one-bedroom offers a unique blend of historic charm and modern comfort. The barn is conveniently located close to downtown Beacon. Step into your own private oasis, where you'll be greeted by the breathtaking views of the majestic Hudson River and be transported to world of peace and tranquility. Immerse yourself in the serene beauty this barn oasis offers!

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Top guest favorite

An open-concept area features warm wood flooring and soft lighting from hanging lamps. A kitchen space is visible with a small island equipped with seating. A spacious bed is situated in the corner, dressed in patterned linens. Large windows allow natural light to brighten the room.

Guesthouse in Wallkill

5 out of 5 average rating, 85 reviews

Millie's Inn

Private retreat immersed in nature. Enjoy a one-bedroom open concept area, with full kitchen. Secluded personal deck and fire pit area to relax. Two miles from Angry Orchard. Local to Mohonk Mountain, Minnewaska Preserve, wineries and walking trails. Gardner and New Paltz are a short driving distance away. Enjoy the quiet warmth of your place and all the local attractions that the area has to offer. Your host Jackie and Lenny are on the premises and are available to make your stay memorable.

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Top guest favorite

Guesthouse in Woodbury

5 out of 5 average rating, 20 reviews

The Simplicity of the Experience.

This space was created to be experienced. Tiny House inspired with a Maximist interpretation. I created something that offers much for its size. Oversized granite fireplace, vaulted ceiling and exposed beams. A modern cottage interpretation. Loft platform beds for restful sleep. Lighting beautifully customized to the space. Full-size washer/ dryer. Small bathroom with all the convenience. 3-stage whole house carbon filtration system (Chlorine free water). Modern shower and a kitchenette.

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Top guest favorite

A sunlit open space features a light-colored wooden floor and white walls. Two large windows invite natural light, while a patterned area rug adds warmth. A small table and chairs are arranged nearby, creating a versatile area for dining or work.

Guesthouse in Cold Spring

4.99 out of 5 average rating, 233 reviews

Modern Bright Forest Escape : Near Village & Train

Modern, efficient, and elegant private flexible garden apt. Guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station to NYC and beyond. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens and forest surround. Solar orientation brings in natural light.

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Superhost

A cozy dining area features a round table and four chairs, with a colorful plant centerpiece. Natural light enters through a nearby window adorned with red curtains, illuminating the adjacent living space, where a red sofa is positioned.

Guesthouse in Bloomingburg

4.85 out of 5 average rating, 53 reviews

Mondrian Manor

Welcome to the Mondrian Manor in the lower Catskill mountains. This stylish, quiet getaway is a freestanding cottage that includes a private deck and separate bedroom. Just 1.5 hours from New York City it has access to many hiking trails, Sam's Point/Ice Caves, Blue Cliff Monastery, unique eateries, and concert venues including Bethel Woods. With a comfortable workspace it will work for someone needing to finish a project or anyone wanting a peaceful respite.

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Top guest favorite

A navy blue sofa with bright yellow accent pillows is centered in the image. Behind the sofa, a well-organized shelving unit displays various books, decorative items, and plants. The light-colored walls and patterned rug contribute to a cozy living area.

Guesthouse in Beacon

4.98 out of 5 average rating, 225 reviews

Beacon Modern victorian+garden—steps to mainstreet

Hey there! Welcome to style and ease at our GUESTHOUSE in the heart of the creative and vibrant Beacon NY. Central air and heat (new!). Retreat to your 1000 square foot GH with your own private entrance, 2 bedrooms, (King sized bed!), queen bed, and plush queen pull out sofa in the living room (with door for privacy), and microwave, toasteroven, kettle, mini fridge, glasses, plates/utensils (no stove or kitchen sink). Streaming tv, WiFi, workstation, garden!

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Guest favorite

The exterior of a renovated farm cottage features a two-story structure with a red umbrella over a wooden deck. The landscaped surroundings include a stone wall and various greenery, creating an inviting atmosphere. A pathway leads to the entrance, immersed in a natural setting.

Guesthouse in Chester

4.95 out of 5 average rating, 21 reviews

1786 Farm Cottage "Honeymoon Suite" Renovated 2022

Beautifully renovated original farm cottage with 700 cozy square feet. Downstairs gas fireplace living room, kitchenette with custom sink and cabinet, and all in one bathroom. Upstairs master bedroom with King sized bed work area and walkout full sized French door deck looking over a gorgeous view. This space can fit up to 3 (we recommend 2!) and allows access to the entire 36 acre farm for walking and hiking. Conveniently located in the Warwick Valley!

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Top guest favorite

A spacious loft area features a queen-size bed with decorative pillows and a comfortable futon sofa positioned against a wooden wall. Natural light enters through large windows, illuminating a colorful area rug that spans the floor. A fan is mounted on the ceiling.

Guesthouse in Wurtsboro

4.92 out of 5 average rating, 134 reviews

Hiker’s Haven, a Cozy Cabin above Bashakill Refuge

Just 90 minutes from NYC, Wurtsboro is a charming and tranquil Catskills retreat. Hiker’s Haven is a cozy, detached Loft on the same property as our log cabin home, set above the Bashakill Wildlife Refuge. While trees block direct water views, you’ll hear birdsong and may spot bald eagles or red-tailed hawks. In fall, glimpses of the Bashakill emerge through colorful foliage. Enjoy hiking, fishing, glider rides, and local shops and galleries.

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Top guest favorite

A cozy sitting room features exposed wooden beams and a brick fireplace. Two comfortable leather chairs are arranged around a wooden coffee table. Natural light enters through multiple windows adorned with sheer curtains, illuminating the space, which is enhanced by decorative touches like artwork and plants.

Guesthouse in Philipstown

4.99 out of 5 average rating, 155 reviews

Historic 1 bedroom home in Cold Spring, NY

This lovingly restored home, built in 1826,is located within the hamlet of Nelsonville within walking distance of the village of Cold Spring. This home has its own entrance and private courtyard and is attached to the owners main residence. Space is curated with antiques and is intended for a couple. This is cozy any time of the year. This home is near trailheads of spectacular hikes in the Hudson Highlands and at the base of Bull Hill.

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Guest favorite

An aerial view of the spacious living and dining area showcases a modular pit sofa arranged with decorative pillows, a wooden dining table for six, and a cozy area rug. Large windows allow natural light to fill the room, providing a view of the outdoor deck.

Guesthouse in Vernon

4.9 out of 5 average rating, 127 reviews

New! Super Cozy, Slope-Side Loft, Family Friendly

Welcome!! The Black Bear Loft is a new, renovated townhome located right on the slopes of Mountain Creek. Experience all of the comforts of home, as well as 4 seasons of adventure. The Loft features a Queen Bedroom on the bottom floor and 2 Queen Beds in the Loft. There is a modular oversized pit sofa perfect for family movie nights or an extra sleeping space. Come and enjoy all that this slopeside townhome has to offer.

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