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Hudson Valley, NY cottages
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997 Best cottages in Hudson Valley, NY

Popular Family-Friendly Cottages in Hudson Valley, NY

Family vacations in Hudson Valley, NY work best with extra space and fresh air trails right outside your door.

Berkshires Farm, 30+ Guests, 50 Acres - Hudson Valley, NY
10 1 review

Berkshires Farm, 30+ Guests, 50 Acres

cottage, East Nassau
This historic 18th-century farm estate in New Lebanon offers a rural escape, located under 10 miles from Hancock Shaker Village and 15 miles from Tanglewood Music Center.
This large cottage accommodates up to 36 guests across 15 bedrooms and 8.5 bathrooms, featuring a hot tub, fire pits, sport court, and lawn games on 50 acres of forested mountains, farmland, and a pond.
Guest Cottage On Country Estate - Hudson Valley, NY
9.2 42 reviews

Guest Cottage On Country Estate

cottage, Watertown
This charming cottage is located in the heart of Watertown, just a short walk from the town center and two minutes from Taft School, offering a peaceful retreat near local attractions. The cottage has received excellent user ratings, making it a popular choice for travelers seeking a comfortable and convenient stay.
The cottage features two bedrooms, one bathroom, and a spacious living area, comfortably accommodating up to six guests. The property offers a private backyard with a covered dining area, a campfire area, and modern kitchen amenities, perfect for enjoying outdoor meals and relaxing in a serene setting.
Charming Cottage In Private Lake Community (Pet-friendly!) - Hudson Valley, NY
9.8 43 reviews

Charming Cottage In Private Lake Community (Pet-friendly!)

cottage, Athens
This pet-friendly riverside home near Coxsackie, New York, is 0.4 miles from Sleepy Hollow Lake and 3 miles from Hudson River Islands State Park, offering easy access to the Hudson River.
This 1190-square-foot vacation rental boasts four bedrooms, two bathrooms, sleeps seven, and includes a fully equipped kitchen, air conditioning, a swimming pool, a tennis court, and free Wi-Fi.
Stylish Loft With Parking Near Nyc + Hospital - Hudson Valley, NY
9.6 16 reviews

Stylish Loft With Parking Near Nyc + Hospital

cottage, Stamford
This charming cottage is conveniently located in central Stamford, just a short walk from the E. Gaynor Brennan Golf Course, Stamford Hospital, and the Museum of Black World War II History. Guests rave about its excellent location and amenities, making it a popular choice for travelers.
The cottage features one bedroom and one bathroom, comfortably accommodating up to four guests. Enjoy a fully equipped kitchen, laundry facilities, and convenient amenities like a coffee maker and hair dryer, perfect for a relaxing and comfortable stay.

Check Out Cottages with Fireplaces in Hudson Valley, NY

Every cottage in the mountains around Hudson Valley, NY comes with a fireplace, setting the mood for a cozy mountain evening.

Swimspa | Sport Courts | Lake | Fishing | Firepit - Hudson Valley, NY
9.6 8 reviews

Swimspa | Sport Courts | Lake | Fishing | Firepit

cottage, Smallwood
This Smallwood Highland Lake beachfront home offers direct access to the lake, is 2.2 miles from Sidwell Lake, and within 6 miles of Mohican Lake and the Upper Delaware Scenic and Recreational Area.
This 1190-square-foot vacation rental boasts three bedrooms, two bathrooms, sleeps eight, and includes a private pool, Jacuzzi, and free Wi-Fi; onsite amenities include a playground and barbecue grills.
Cozy Cottage With Ac And Lake Access In Charming Connecticut Suburb. - Hudson Valley, NY
9.6 11 reviews

Cozy Cottage With Ac And Lake Access In Charming Connecticut Suburb.

cottage, Watertown
This pet-friendly Watertown cottage is located in a rural area near a lake, a 15-minute drive from Quassy Amusement Park and a 13-minute drive from The Christmas Shop.
The two-bedroom, one-bathroom home sleeps six guests and features a fully equipped kitchen with microwave, air conditioning, free Wi-Fi, on-site barbecue, and proximity to Flanders Nature Center & Land Trust and Black Rock State Park.
Woodstock Stone Cottage 2/1 Winter Rental Jan/feb/mar 3 Mos. - Hudson Valley, NY
10 1 review

Woodstock Stone Cottage 2/1 Winter Rental Jan/feb/mar 3 Mos.

cottage, Shokan
This Mount Tremper cottage, a short 10-minute drive from Woodstock and Phoenicia, provides easy access to skiing at Belleayre and Hunter mountains (35 minutes away) and Windham Mountain (15 minutes away).
This two-bedroom, two-bathroom house sleeps four, features a fully equipped kitchen, on-site fitness room, and proximity to a lake and hiking trails; a three-month rental (January-March) is available.
Pet-friendly Catskills Retreat: Fire Pit & Deck! - Hudson Valley, NY
10 4 reviews

Pet-friendly Catskills Retreat: Fire Pit & Deck!

cottage, Prattsville
This Prattsville cottage, located 6 miles from Mine Kill State Park and 1 mile from the Catskill Scenic Trail, offers easy access to hiking, the East Branch of the Delaware River, and Hunter Mountain.
The 960-square-foot house features four bedrooms, one bathroom, and accommodates five guests, with amenities including a fully equipped kitchen, air conditioning, a fire pit, and a deck.

Frequently Asked Questions about cottages in Hudson Valley, NY

  • What would be a good 2-days itinerary for visiting Hudson Valley, NY?

    For a two-day trip, you could spend the first day exploring the historic city of Beacon, visiting the Dia Beacon art museum, and enjoying the scenic views from the Beacon waterfront. On the second day, you could visit Cold Spring, a charming village with unique shops and restaurants, and take a scenic hike on the Breakneck Ridge trail.
  • What are the best cottages in Hudson Valley, NY?

  • What part of Hudson Valley, NY is ideal for renting a cottage?

    The towns of Cold Spring, Garrison, and New Paltz are great options for renting a cottage. These areas offer a mix of peaceful countryside, charming villages, and easy access to hiking trails and outdoor activities.
  • What are the best cottages with a pool in Hudson Valley, NY?

  • When is the best time to rent a cottage in Hudson Valley, NY?

    Spring and fall are the most popular times to rent cottages in the Hudson Valley, as the weather is mild and the foliage is spectacular. Summer is also a good time to visit for outdoor activities, but you'll need to book your cottage well in advance.
  • What are the best cottages with a jacuzzi in Hudson Valley, NY?

  • What are the can't-miss sights in Hudson Valley, NY?

    The Hudson Valley is full of amazing sights, but some can't-miss attractions include the Storm King Art Center, the Vanderbilt Mansion National Historic Site, and the Walkway Over the Hudson.
  • What are the best cottages for families and kids in Hudson Valley, NY?

    The best cottages for families and kids in Hudson Valley, NY are Cozy Catskills Lakefront Cottage, Stone House 1807 - Comfort - Peace And Nature and The Hickory Cottage - Perfect.

  • Why consider renting a cottage in Hudson Valley, NY for your stay?

    Renting a cottage in the Hudson Valley offers a unique and relaxing experience. You'll have a private space to unwind and enjoy the natural beauty of the area, and you'll be close to all the best attractions.
  • What are the best pet friendly cottages in Hudson Valley, NY?

  • Can you easily explore Hudson Valley, NY on foot or by bike?

    The Hudson Valley is perfect for exploring on foot or by bike. Many towns have dedicated bike paths, and there are miles of scenic trails to explore. Just be sure to check the weather conditions before heading out.
  • What are the best cottages with parking in Hudson Valley, NY?

  • What are the best restaurants in Hudson Valley, NY with nature views?

    The Roundhouse in Beacon has breathtaking views of the Hudson River and the city. The restaurant is known for its farm-to-table cuisine and cozy atmosphere. Another option is the Harvest Restaurant at the Garrison Inn, which offers a stunning view of the Hudson River and the surrounding hills.
  • What family-friendly activities are available in Hudson Valley, NY?

    The Hudson Valley is a great place for families. There are plenty of kid-friendly activities, such as the Franklin D. Roosevelt Presidential Library and Museum, the Walkway Over the Hudson, and the Mohonk Preserve. For a fun day out, you can visit the Dutchess County Fairgrounds, which hosts a variety of events throughout the year.

Popular destinations

Best Hudson Valley, NY cottages with a garden

A Romantic Cottage And Artist's Retreat Looking Down Over An Enchanted Lake - Hudson Valley, NY
9.4 102 reviews

A Romantic Cottage And Artist's Retreat Looking Down Over An Enchanted Lake

cottage, Greenwood Lake
This Greenwood Lake cottage is located just a short drive from Sterling Forest State Park, Continental Road Trailhead, and Wawayanda State Park, offering easy access to hiking trails and natural beauty. Guests consistently rate this property as excellent, making it a popular choice for travelers. The cottage features one bedroom, one bathroom, and a comfortable living space with 650 square feet, accommodating up to three guests. Enjoy modern amenities like air conditioning, a jacuzzi, a patio, and a fully equipped kitchen, perfect for a relaxing and enjoyable getaway.
#4 Adirondack Familyfriendly Waterfront On Loonlake. Boating,fishing,swimming! - Hudson Valley, NY
9.3 60 reviews

#4 Adirondack Familyfriendly Waterfront On Loonlake. Boating,fishing,swimming!

cottage, Chestertown
This family-friendly cottage is located in Chestertown, just steps from Adirondack Park and a short drive from Loon Lake Beach. This accommodation has received excellent user ratings.
The cottage features a fully equipped kitchen, two bathrooms, free Wi-Fi, and a TV. Guests can enjoy a garden, barbecue grills, a swimming pool, a jacuzzi, and a tennis court.
Monterey Haven < 1/2 Mi To Lake Garfield W/ Kayaks - Hudson Valley, NY
9.8 7 reviews

Monterey Haven < 1/2 Mi To Lake Garfield W/ Kayaks

cottage, Monterey
This Monterey cottage, located near the Bidwell House Museum (3 miles away), Ashintully Gardens (within 6 miles), and McLennan Reservation & Tyringham Cobble (within 9 miles), offers easy access to local attractions.
This 900-square-foot house sleeps six guests in three bedrooms and one bathroom, and includes a fully equipped kitchen, laundry facilities, a patio, and an outdoor barbecue grill.
Bluebear Cottage - Hudson Valley, NY
9.8 10 reviews

Bluebear Cottage

cottage, Hadley
This charming cottage is located in Hadley, just 2 miles from the Great Sacandaga Lake and 30 minutes from Saratoga Springs and Lake George, offering easy access to the region's attractions. The cottage has received excellent user ratings, making it a popular choice for travelers seeking a peaceful getaway.
This 3-bedroom, 2-bathroom cabin can accommodate up to 8 guests. The cottage features a fully equipped kitchen, a private garden, a tennis court, and a secluded wooded setting with hiking trails, a blueberry patch, and a meadow, perfect for enjoying nature and outdoor activities.

Top-Rated Cottages with Jacuzzi in Hudson Valley, NY

Whether you prefer a jacuzzi or a hot tub, these Hudson Valley, NY cottages are designed for a relaxing soak.

Pet Friendly  Fenced Yard  Hot Tub  Romantic - Hudson Valley, NY
10 1 review

Pet Friendly Fenced Yard Hot Tub Romantic

cottage, Ravena
This pet-friendly cottage in Ravena offers a quiet countryside escape, located minutes from local amenities and a short drive to the Martin Van Buren National Historic Site and Van Alen House.
This 1-bedroom, 1-bathroom cottage accommodates up to 4 guests and features a microwave oven, air conditioning, a Jacuzzi, and a fenced yard, with a BBQ grill and fire pit available for outdoor recreation.
Charming Cottage With A Mountain View From The Wrap-around Deck, @Upstayz - Hudson Valley, NY
10 2 reviews

Charming Cottage With A Mountain View From The Wrap-around Deck, @Upstayz

cottage, Prattsville
This Prattsville cottage, near Gilboa and the Gilboa Museum, offers a secluded 1.5-acre setting adjacent to state forest with mountain views.
This 550-square-foot vacation home features two bedrooms, one bathroom with a bidet, a full kitchen, air conditioning, a Jacuzzi, WiFi, and a wrap-around deck; it comfortably sleeps four and is pet-friendly.
Cozy, Private And Modern Cottage - Hudson Valley, NY
10 23 reviews

Cozy, Private And Modern Cottage

cottage, Hudson
This Hudson, New York apartment is conveniently located less than a mile from the Claverack Library and within six miles of attractions like Stoddard Corner, Oakdale Beach, and the Hudson Area Library.
This pet-friendly one-bedroom unit sleeps two guests and boasts a fully equipped kitchen, including a dishwasher, a Jacuzzi, free Wi-Fi, and parking.
2 Lake Cabins | Pool+hottub | Game Room & Courts - Hudson Valley, NY
10 5 reviews

2 Lake Cabins | Pool+hottub | Game Room & Courts

cottage, Smallwood
This Highland Lake beach house near Smallwood, New York, is 2.5 miles from Sidwell Lake, and within 6 miles of Mohican Lake and the Upper Delaware River.
This 2,500-square-foot vacation rental boasts eight bedrooms, four bathrooms, sleeps sixteen guests, and features a private pool, hot tub, fitness center, and fully equipped kitchen.

Best Dog-Friendly Cottages in Hudson Valley, NY

No need to leave your dog behind; each of these cottages in Hudson Valley, NY offers dog-friendly trails and plenty of space to roam.

Charming Woodstock Teahouse Cottage By The Sawkill Creek Trout Stream - Hudson Valley, NY
8.8 48 reviews

Charming Woodstock Teahouse Cottage By The Sawkill Creek Trout Stream

cottage, Woodstock
Cozy Cottage Overlooking Stream On 60 Acres - Hudson Valley, NY
10 5 reviews

Cozy Cottage Overlooking Stream On 60 Acres

cottage, Galway
Pet-friendly Cottage, 2 Mi To Saugatuck Falls - Hudson Valley, NY
8.0 3 reviews

Pet-friendly Cottage, 2 Mi To Saugatuck Falls

cottage, Redding
Lily Cottage - A  Cozy Accomodation Moments From The Beautiful Ashokan Reservoir - Hudson Valley, NY
10 60 reviews

Lily Cottage - A Cozy Accomodation Moments From The Beautiful Ashokan Reservoir

cottage, Shokan
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