
Holiday houses in Greenport
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Top-rated holiday rentals in Greenport
Guests agree: these stays are highly rated for location, cleanliness and more.

Charming Hudson Farmhouse
This country escape is the ideal getaway from the busy city life. Guests will experience the best of both worlds. The farmhouse is located in an idyllic acre of land with a lovely garden and huge deck to enjoy the sunsets and picturesque mountain views. This serene location is the perfect place to relax and rejuvenate. When you're ready to hit the town, the house is only a 5-minute drive to downtown, where you can enjoy its many restaurants, shops, bars, café, art, and vibrancy of Warren Street.
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Cheerful Catskill Village Cottage
Bright and airy Catskill village refuge - a wildflower and wildlife haven in the thick of things. Historic house set on a quarter acre of trees and wildflowers, but blocks from Main Street, Catskill. Walk to Foreland, The Lumberyard, the incredible village cemetery, Thomas Cole House, restaurants and shops. Olana State Historic Site is right across the bridge! Cottage has a full kitchen, clawfoot tub, penny tile shower, front porch, dining room and large living room. Truly peaceful and lovely.
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Welcome to Casa Bartolo, Your Oasis on the Hudson!
It's now wildflowers season! Why book a hotel when you can enjoy a charming, private 2-bedroom suite with breathtaking views of the Catskill Mountains, Hudson River, and stunning sunset! This tranquil retreat offers: Private Entrance, Private shared Bathroom, Kitchenette, cedar soaking tub & easy parking. Wake up to the sunrise and enjoy a cup of Nespresso or tea. Whether you want to relax, walk, jog, bike, meditate, smell the lilacs & pick eggs or simply unwind, this is the perfect escape.
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Secluded Magic Treehouse Escape
Poetic. Unique. Romantic. 25ft high. The sounds, smells, and fresh air of nature are all yours. 10mins to town. Surrounded by old oaks, maples, and pine trees. Details abound. Simple and minimal yet elegant. Rustic Luxe. Windows all around bring in nature, screens keep it outside. All the modern conveniences, and then some. Hot and cold running water, equipped kitchen, full bath, 2 bedrooms with queen beds, nice linens and details, plus outside shower, 2 decks, BBQ, fast WIFI, TV, etc.
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Studio Oasis nr Warren St w porch & yard
Oasis in midst of downtown Hudson, 2 blocks fr Warren St, short walk fr Amtrak, 1/2 block fr Empire State Trail. Spacious, sunny studio apartment w fenced in yard, park-like setting & private porch to relax, have a meal or watch the world go by. Inside this elegant 1850 home, you’ll find bedroom, living room and work areas, full kitchen w dining table, and a large bathroom w clawfoot tub and a walk in shower. Original architectural details have also been preserved with care. Come, and enjoy!
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Renovated historic home, walk to Hudson River!
Escape from the city and enjoy slowing down in upstate New York in this bright and spacious historic home! Just a short walk to the historic Town of Athens and the Hudson River where you can sit by the water, enjoy a picnic, or kayak/canoe. This home is made for cozy unwinding and is stocked with everything you need to cook a wonderful meal (cast irons, French cookware, baking supplies, spices and oils). 1 king bed with view of the river, 1 queen bed + a full air mattress available.
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Stylish Hudson Getaway
Enjoy our one bedroom home in the heart of beautiful Hudson, New York. Steps away from the best shops and restaurants Warren Street has to offer, our apartment is on a beautiful residential street with historic views. Introduce yourself to our town with the peace of mind that when you return to this Airbnb, you can relish in the delight of organic cotton sheets, lush robes and slippers, an assortment of organic teas and coffee, and some of the best products from our sweet little city.
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Hudson River Sunset Getaway
With sunset views of the Hudson River and Catskill Mountains you can relax poolside during the summer months or enjoy the changing fall colors next to a cozy back yard bonfire in the fall. Located only 5 mins to downtown Hudson where you’ll find ample dining, drinking & shopping opportunities. Or head out to explore the Catskill Mountain Range only 30 mins away for the best hiking and skiing in the area. Sunset House is the perfect place for families or a couples getaway!
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Contemporary Cabin in Catskill Mountains
Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.
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Spacious Loft on Warren Street
Live the loft life in the heart of Hudson. Gorgeous open floor plan with cozy living room, dining and kitchen areas. There are two completely private bedrooms each with ensuite bath. All of this within walking distance of great restaurants, galleries, shops and unique upstate cultural venues. Please note there are two sets of stairs. The first to the bedrooms and baths on the first floor, the second to the open dining and living room area on the second floor.
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Bright, Airy Home in Hudson w/ TONS of Character!
Welcome to 514 Route 66! Conveniently located 5 min from historic Warren St, this bright and stylish country home is just minutes from downtown Hudson, where you can enjoy fine-dining restaurants, hip cocktail bars, art galleries, antique shopping, and more. Or, just relax, stay home, and sip coffee or wine in the sun-drenched living area, beneath the vaulted ceiling. A perfect mix of town and country, for a perfect upstate weekend.
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Designer Home, Hot Tub, Private Yard, & Projector
A cozy, charming retreat just minutes from downtown Hudson—perfect for couples, families, or small groups looking to relax, unwind, and explore the Hudson Valley. + Hot tub, firepit & BBQ + Mini movie theater w/ projector + Dedicated workspace w/ views + Fast WiFi + Smart TV + Stocked kitchen + Coffee setup + Professionally designed interiors + Quick drive to Warren Street + Nature trail to Oakdale Lake
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Popular amenities for Greenport holiday rentals
Other great holiday rentals in Greenport

Spacious 2BR Flat in the Heart of Hudson
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The Catskill Equestrian Cabin
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Athens Cottage
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Mountain-View Retreat @ Hudson
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Riverstone Cottage
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Charming, Newly Renovated 3-bed Steps from Warren
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The River House at Cherry Ridge
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Stylish Home on Union St
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Destinations to explore
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Jiminy Peak Mountain Resort
- June Farms
- Windham Mountain
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Howe Caverns
- Plattekill Mountain
- Taconic State Park
- Mohonk Preserve
- Peekamoose Blue Hole
- Kent Falls State Park
- Thacher State Park
- Bash Bish Falls State Park
- Hunter Mountain Resort
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Millbrook Vineyards & Winery
- Hudson Chatham Winery
- Ski Sundown
- Rensselaer Polytechnic Institute
- Benmarl Winery





