Holiday houses in Stockport

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Top-rated holiday rentals in Stockport

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Guest favourite

A historic two-story stone building is complemented by a smaller adjoining structure. Lush green lawns surround the buildings, and trees provide shade. The background showcases the Hudson River, reflecting a soft evening light with the moon rising above. Outdoor seating areas are visible along the shore.

Loft in Athens

4.93 out of 5 average rating, 166 reviews

1860's Hudson River Carriage House Loft

Carriage house apartment on grounds of historic 1600's Dutch bouwerij (farm), yet with all of the modern amenities. Our Hudson river side apartment features original exposed beams, wood floors, tasteful decor, and a complete country kitchen. On-Hudson river edge setting with beach access allows watching eagles & herons, or kayaking. Walk-in to marshland wildlife refuge. 19th century lighthouse on property. Leaf peeping or apple picking during the fall. Hunter and Windham ski areas nearby.

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Top Guest favourite

An aerial view captures the serene landscape surrounding the red barn, nestled among lush green fields. Pastures and trees create a tranquil setting, with distant farmland visible in the background, providing a sense of seclusion in the countryside.

Farm stay in Kinderhook

4.87 out of 5 average rating, 272 reviews

Barn House: open layout isolated farm Hudson area

April lambing, October leaf peeping, summer swimming, winter by the stove: A century-old brick barn, eclectic style, much art, 10 miles from Hudson, near Kinderhook, secluded, unique residence. Gardens, sheep, and ponies are set off a country road, with a converted jungle shower, loft, and woodstove. Waterfall swimming area nearby. Empire bike path, e-bikes by request. Hudson Valley. The farm shares space with nature as it is - country life. Pony rides for children by prior arrangement.

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Top Guest favourite

The living room showcases a retro-style sofa reupholstered in warm orange wool, complemented by wooden beams and large windows allowing natural light. Various seating options are arranged around a central coffee table, enhancing the room's spacious feel.

Home in Hudson

4.96 out of 5 average rating, 413 reviews

Rushing Rapids Cottage – a birdwatcher's paradise

Complete renovation with privacy. Rural mill worker's cottage is upgraded with midcentury touches while leaving antique finishes. Overlooking the Kinderhook Creek rapids on a rural paved road and AHET Rail Trail. Minutes to Hudson and Kinderhook. You may see Carolina Wrens, Cardinals, Chickadees, Woodpeckers, Goldfinches and Hummingbirds. The creek to the front attracts Bald and Golden Eagles, Osprey, Blue Herons, Red Tail Hawks, Ducks and Geese. ABSOLUTELY NO PETS ALLOWED.

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Top Guest favourite

A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.

Apartment in Coxsackie

4.99 out of 5 average rating, 165 reviews

Hudson River Beach House

Explore all the activities the Hudson Valley has to offer and then relax in a room full of windows overlooking the Hudson River. Make a meal in the full kitchen or hang out by the beach, build a fire, play lawn games, read a book or float in the river. For you early risers, the sunrises are spectacular. This 1860 river house is 1/2 mile from the charming Village of Coxsackie NY and a central location to many great destinations such as Hudson, Woodstock, Athens, and Catskill.

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Guest favourite

A tranquil outdoor scene showcases several wooden Adirondack chairs arranged around a fire pit, facing a calm body of water. The surrounding trees exhibit vibrant autumn colors, reflecting beautifully in the water, creating a serene natural atmosphere.

Cottage in Hudson

4.84 out of 5 average rating, 154 reviews

Hudson area waterfront-fish, kayak, farm visits!

Love nature? Enjoy your own entire home on the Stockport Creek with private kayak/boat launch to the Hudson River. Hiking and bike trails nearby. You are immersed in Columbia County’s rural beauty between the Berkshires and the Catskills with Hudson’s hopping food and art scene minutes away. OMI sculpture park, Olana, farm markets, and Warren Street are a short drive. Ski Hunter or Catamount. Cozy wood burning stove as well as outdoor fire pit. Ask about a farm visit!

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Top Guest favourite

A charming red cottage is framed by lush greenery, with vibrant plants surrounding the entrance. A gravel driveway leads up to the home, inviting guests to explore the surrounding natural beauty. The structure features multiple windows, allowing light to brighten the interior.

Barn in Stuyvesant

5.0 out of 5 average rating, 137 reviews

Pond Side R & R

Our home is a close drive from Hudson, Kinderhook or Chatham, NY and a ten minute walk to the Hudson River and a boat launch. Enjoy miles of country roads for walking and biking and our nine acres through meadows and woods on mowed paths. Guests have access to an Adirondack style cottage overlooking a pond. Close to numerous restaurants, galleries, antique shops and cultural activities. This property is good for couples, a group of friends and families.

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Guest favourite

A peaceful front deck features two black chairs and a glass table, offering a view of the green landscape and Hudson River. The sun shines brightly in the background, illuminating the surroundings and creating a serene outdoor space.

Cottage in Stuyvesant

4.94 out of 5 average rating, 179 reviews

Perfect Cottage On A Hill With A View

A peaceful cottage with views of the Hudson River and Sunsets over the Catskill Mountain Range. Personal, private and all inclusive this little cottage is an incredible place to unwind relax and soak in the beauty of the Hudson Valley. With easy access many local hikes, swimming holes, towns and shopping you’ll find This little cottage to be the perfect place to relax with nature & indulge in all of the luxuries that the Hudson Valley has to offer.

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Top Guest favourite

Home in Athens

4.96 out of 5 average rating, 112 reviews

Lake House close to Skiing & Indoor Hot Tub

Sleepy Hollow is a small community with lots to offer inside . This home offers so much entertainment you won't even have to leave the driveway . From a pool table, and video games to outside on a luxurious lawn overlooking this private lake. Sit down have a fire , cookout and watch the sun go down. Hunter and Windham mountain are both approx 40 minutes. Hudson is a skip away at 20-25 minutes putting you right on Main Street where all the action is.

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Guest favourite

A charming country home is presented with a welcoming red front door. A pergola covers the entryway, surrounded by well-maintained landscaping that includes shrubs and a stone path. The exterior features light yellow siding, providing a warm, inviting appearance.

Home in Hudson

4.83 out of 5 average rating, 302 reviews

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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Guest favourite

Townhouse in Hudson

4.94 out of 5 average rating, 112 reviews

Chic Hot Tub Escape | PetFriendly | Hudson, NY

Step into The Still — a moody, pet-friendly speakeasy-inspired retreat in Hudson, NY. Soak in your private hot tub in a fully fenced backyard, mix cocktails at the dedicated bar, and settle into decor guests say is even better in person. Hudson is the birthplace of the word "cocktail" — and this space celebrates that with style. Minutes from downtown, wineries, distilleries, and trails. Bring your pets — they'll love the yard.

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Guest favourite

A well-lit studio space features a spacious bed dressed in white linens with decorative pillows. Light wooden cabinets and a dining table with four chairs are visible in the background, complemented by a full kitchen equipped with essential appliances.

Guest suite in Hudson

4.94 out of 5 average rating, 231 reviews

Harmony Valley Home, bright & inviting studio

You and your guests will be close to it all when you stay at our centrally-located home. The space is nestled perfectly between the Berkshire and Catskill Mountains, which provides countless opportunities for adventure! Whether a romantic getaway or a family vacation- you are an idea away from an unforgetable experience! Wineries & breweries Museums & art Hiking trails Empire State Rail Trail Conservation Areas Shopping

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Superhost

Home in Hudson

4.91 out of 5 average rating, 148 reviews

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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