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

1 bdrm apt in Athens on the Hudson
Come enjoy village life right in the middle of this friendly and vibrant, yet quiet community in your own charmingly appointed 3 room apartment. Explore the Great Northern Catskills with its boating and paddling opportunities, antiquing, local history, art and music. The Thomas Cole House is minutes away in Catskill. Olana is right across the Rip Van Winkle Bridge. If sculpture is your passion, Opus 40 in Saugerties is not to be missed. Winerys abound and be sure not to miss Athens own brewery.

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!

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.

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!

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.

Secluded mid-century guest house in Hudson
A newly renovated studio apartment about 7 minutes drive north of downtown Hudson. Close to everything the town has to offer, but surrounded by beautiful woods at the end of a dead end street, which makes for a nice escape from city life. The house is a short walk to a large nature preserve on the Hudson River. Scenic in any season of the year. We were featured in Architectural Digest's "High Design Airbnb Rentals We'd Love to Call Home"

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.

Welcome to Casa Bartolo, Your Oasis on the Hudson!
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 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, or simply unwind, this is the perfect escape.

Owl's Nest (Rip's Retreat)
Privately nested single-story on a sloping riverfront view. Preserved charms of a mid-century modern design. Spacious, cozy, scenic, and rustic. Large fireplace. Screened in porch. 5 minute drive to Hudson. Co-host lives in the basement level of the house, accessed by a separate entrance, and may access that area during your stay. Feel free to say hi and ask any questions about the house or area.

Modern Cozy Cabin | Outdoor Infrared Sauna | Yard
Welcome to Carol Land, a Hudson Hideaway! 🏡 Carol Land is nestled along the iconic Amtrak railway and serene Hallenbeck Creek which flows from the mighty Hudson River. You will enjoy seasonal views of the Rip Van Winkle bridge and the beautiful Catskill mountains. ⛰️ This modern retreat harmoniously blends comfort, style, and a beautiful country spot located on a quiet cul-de-sac.

Studio/Guest Suite Minutes from Warren St.
This newly renovated studio/guest suite, 2 blocks from Warren Street, is centrally located and sun-filled. The studio/guest suite comes equipped with a full-bed, a smart TV, an eat-in area, a spacious bathroom and while there is no kitchen, there is a mini-fridge, microwave, coffee maker, electric tea kettle, glasses, silverware & dishes. Coffee and tea are provided.

A Lovely Historic Apartment
A historic, Italianate Victorian located on a quiet street in downtown Hudson, two blocks away from charming Warren Street. Our property has a fenced-in backyard filled with lovely greenery, lush gardens, and meditative places to lounge. Designed with comfort and beauty in mind, our chic, peaceful nest is the perfect place to land in Hudson.
Popular amenities for Greenport holiday rentals
Other great holiday rentals in Greenport

Little House on the Hudson River

Catskills Cabin on 100 Wooded Acres, Private Lake

Charming Hudson Farmhouse

Mountain-View Retreat @ Hudson

2bed farm stay as seen in Dezeen, architects cabin

Secluded Magic Treehouse Escape

New! Gemini House 1892 Farmhouse w/ Pool - Hudson

Historic 1850s Brick Federal - Minutes to Downtown
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Hunter Mountain
- Belleayre Mountain Ski Center
- Jiminy Peak Mountain Resort
- Minnewaska State Park Preserve
- Catamount Mountain Ski Resort
- Windham Mountain
- Howe Caverns
- Butternut Ski Area and Tubing Center
- Thacher State Park
- Hunter Mountain Resort
- Bash Bish Falls State Park
- Plattekill Mountain
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Zoom Flume
- Mohawk Mountain Ski Area
- Taconic State Park
- Ski Sundown
- Norman Rockwell Museum
- June Farms
- Naumkeag
- Opus 40
- Benmarl Winery
- Berkshire Botanical Garden




