Holiday houses in Greenport

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Top-rated holiday rentals in Greenport

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Top Guest favourite
A cozy living room features floral-patterned armchairs and a sofa, complemented by a low coffee table. A lamp provides soft lighting, and artwork hangs on the walls, enhancing the warm decor. A textured rug covers the floor, adding comfort to the space.
Home in Catskill
4.97 out of 5 average rating, 194 reviews

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.

Superhost
The spacious outdoor area features a wooden deck surrounded by greenery and garden beds. A long dining table with several chairs provides a gathering space, while a cozy seating area enhances the inviting atmosphere. Trees offer shade, creating a pleasant spot for relaxation.
Townhouse in Hudson
4.86 out of 5 average rating, 116 reviews

1BR Hudson Apt, 3Min Walk To Warren St For Two

Welcome to La Maison in Hudson, a labor of love from our family! This charming townhouse is your ideal retreat for relaxation or adventure with friends. Apartment #1, our cozy ground-floor unit, features direct access to the garden, porch, and private parking. Every detail has been thoughtfully curated from our home & local thrift stores, ensuring a warm & inviting stay. Experience the charm of La Maison! Warren St: 3-min walk Train station: 15-min walk Olana: 8-min drive Art OMI: 15-min drive

Top Guest favourite
Apartment in Hudson
4.97 out of 5 average rating, 215 reviews

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!

Top Guest favourite
A two-story historic home is showcased with blue siding and white trim. The front porch features a railing and is lined with flower beds. Windows are adorned with dark frames, and an air conditioning unit is visible. A driveway leads to a parked vehicle on the side.
Home in Athens
4.94 out of 5 average rating, 117 reviews

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.

Top Guest favourite
A bright living area features a comfortable sofa adorned with decorative pillows in relaxing tones. A vibrant yellow armchair adds a pop of color, while natural light fills the space through large windows with soft curtains. A round coffee table sits at the center, accompanied by a sleek TV stand.
Apartment in Hudson
4.97 out of 5 average rating, 345 reviews

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.

Guest favourite
A cozy living area features a deep red sofa adorned with decorative pillows, surrounded by warm wood accents and an area rug. Large windows provide natural light, complemented by soft drapes. A brick accent wall adds texture, while a modern mirror reflects the inviting space.
Home in Hudson
4.96 out of 5 average rating, 192 reviews

Union Street Cottage - Built in 1900

Welcome to your Hudson getaway! This bright, open-plan retreat features a cozy living area with a double-sided fireplace, a serene bedroom overlooking the garden, and a loft with a comfy sleeper sofa. The spa-like bathroom offers a rain shower, clawfoot tub, and heated towel rack. Enjoy morning coffee on the sunny deck or cook up something special in the fully equipped kitchen. And yes—it’s just steps from shops, restaurants, parks, and the Amtrak station!

Top Guest favourite
A terrace area is seen, featuring a glass-topped dining table surrounded by metal chairs. A stone pathway leads to well-maintained gardens with various plants and neatly trimmed shrubs in the background. Bright sunlight illuminates the scene, conveying a serene outdoor setting.
Home in Hudson
5 out of 5 average rating, 213 reviews

Garden Paradise minutes from Hudson

We are just a 10 minute drive from Hudson's bustling Warren Street in the historic hamlet of Claverack. We live on the property, but our guesthouse is separate and private. It's all surrounded by our 2 1/2 acre garden, which is our passion as well as our profession. We've recently adapted a 2 year old standard poodle named Nora. She is a very shy little girl, and will win your heart. We are sorry, but we do not accept pets or children under 12.

Top Guest favourite
The exterior of the historic cottage displays a simple white façade with a brick accent wall. A covered porch is supported by decorative columns, featuring a small seating area. Lush green grass and garden beds are visible in the foreground, framed by the clear blue sky.
Cottage in Hudson
4.9 out of 5 average rating, 221 reviews

Historic Hudson Cottage

A historic hideaway built in 1737 nestled just outside the city of Hudson. Featuring a full kitchen, spacious living room and bath on the main floor and a lofted, light-filled bedroom on the second. Enjoy evenings nestled by the wood stove, or get out and explore the four acre property. The city of Hudson is an easy 5 minute drive, take in the Hudson food and drink scene and explore the dozens of antique stores. We look forward to welcoming you!

Guest favourite
A comfortable living area features a gray sofa adjacent to a wooden table and two chairs. Natural light filters through sheer curtains on the windows, highlighting the rustic wood flooring and a statement brick wall with a vintage-style light fixture above.
Apartment in Catskill
4.92 out of 5 average rating, 221 reviews

Catskill Village House - Garden Studio

A serene space inspired by the contemplative calm of the open water, our Garden Suite features a large living room, outdoor deck and shared garden, private bathroom with claw foot tub and shower, and sleeper sofa. Original artwork, a custom made kitchenette, and dining area add to this beautiful and generous space. Custom Queen Size Mattress (featured at the Four Seasons NYC), organic cotton sheets. Free WIFI (150mb/12mb) and AC.

Superhost
A spacious bedroom features a large bed dressed in white linens with a colorful woven blanket. Natural light enters through multiple windows, highlighting the wooden decor, including a rustic table and decorative mirrors.
Apartment in Hudson
4.9 out of 5 average rating, 644 reviews

Gorgeous Getaway, close to everything!

The apartment is spacious, bright, peaceful and very private. There is a coded lock, and your own front entry and spacious front porch. Located on a quiet street, just slightly off the beaten path yet within a short walk to all of the best restaurants and shopping Hudson has to offer. A full kitchen will also allow for some chill out time or a family meal if that is more your speed. A beautiful and convenient refuge.

Top Guest favourite
The exterior of a single-story home is showcased, featuring a classic mid-century modern design. A spacious screened-in porch and well-maintained grounds overlook the serene river. The backdrop includes rolling hills and a cloudy sky, hinting at the scenic beauty of the surrounding landscape.
Home in Hudson
4.87 out of 5 average rating, 106 reviews

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.

Guest favourite
The living room features a light-colored sofa adorned with assorted pillows, positioned next to large windows that invite natural light. A vibrant area rug adds warmth to the wooden floor. Decorative plants and a framed piece of art contribute to the inviting atmosphere.
Apartment in Hudson
4.98 out of 5 average rating, 274 reviews

Serving Sexy Historic Hudson Realness Steps from Warren St

Feast your eyes on the drop-dead gorgeous dining room and then get ready to have a feast because the kitchen is fully equipped for everything from cocktails to the main course. Or simply take in the dramatic pops of color and sexy decor sprinkled throughout the space. Unwind after a long day of antiquing or exploring on a cozy outdoor sectional in the backyard garden.

Popular amenities for Greenport holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Columbia County
  5. Greenport