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Dutchess County, NY vacation rentals
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Best Vacation rentals and Airbnb offers in Dutchess County, NY

Best family friendly Dutchess County, NY vacation rentals

Among the 1839 accommodations in Dutchess County, NY, here are the 4 best family friendly rentals

Clover Mountain House  A Historic Retreat Near Hunter Mountain - Dutchess County, NY
10 25 reviews

Clover Mountain House A Historic Retreat Near Hunter Mountain

apartment, Tannersville
This renovated schoolhouse in Elka Park, Catskills, offers easy access to local hiking trails and is a short drive from skiing in the Catskill Mountains and attractions like Opus 40 and Bethel Woods.
The 2,000-square-foot home features four bedrooms, two bathrooms, sleeps eight, and includes a full kitchen with a fridge, microwave, and dishwasher, plus air conditioning, a garden, parking, and concierge service.
Litchfield County Getaway - Dutchess County, NY
9.9 166 reviews

Litchfield County Getaway

apartment, Warren
This family-friendly vacation home is located in a peaceful rural setting near Warren, Connecticut, just 6 miles from Above All State Park, Lake Waramaug State Park, and the Housatonic River, perfect for nature lovers. The house consistently receives excellent ratings for location, cleanliness, and overall experience.
The 1860-square-foot house has three bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a well-equipped kitchen, a spacious garden, a relaxing spa, and a private terrace, making it ideal for families and groups seeking a comfortable and enjoyable stay.
Cardinal Cottage - Dutchess County, NY
10 17 reviews

Cardinal Cottage

apartment, Haviland
Cardinal Cottage, a four-bedroom Haviland house rental in Hyde Park, offers easy access to local attractions and is a two-hour drive or train ride from New York City.
This pet-friendly vacation home sleeps seven, features two bathrooms, a full kitchen with a refrigerator and microwave, air conditioning, internet access, a garden, and parking.
1875 School House Near Hv Rail Trail - Dutchess County, NY
9.9 84 reviews

1875 School House Near Hv Rail Trail

apartment, New Paltz
This renovated 1875 schoolhouse in New Paltz is a quarter-mile from New York State Thruway Exit 18 and 500 feet from the Hudson Valley Rail Trail.
The two-bedroom, one-bathroom home sleeps six, features a full kitchen with gas range, washer/dryer, a large deck with fire pit, and offers easy access to local restaurants and the Hudson Valley Rail Trail for walking and biking.

Top cities

Best pet friendly Dutchess County, NY vacation rentals

Among the 1839 accommodations in Dutchess County, NY, here are the 4 best pet friendly rentals

Spacious 4-bedroom Estate In Adorable Carmel Hamlet With Ac - Dutchess County, NY
No reviews

Spacious 4-bedroom Estate In Adorable Carmel Hamlet With Ac

apartment, Lake Carmel
This 4-bedroom estate is located in Carmel Hamlet, offering proximity to Wonder Lake State Park and Clarence Fahnestock State Park, as well as historical sites like the John Kane House and Van Wyck Homestead Museum.
This pet-friendly house accommodates up to 8 guests with 4 bedrooms and 1 bathroom, featuring air conditioning, internet, and is conveniently situated near family-friendly attractions such as Stonecrop Gardens and SplashDown Beach.
Lakefront Escape W/ Dock! Hudson Valley Home - Dutchess County, NY
No reviews

Lakefront Escape W/ Dock! Hudson Valley Home

apartment, Copake Lake
This Hillsdale vacation rental offers direct access to Copake Lake, the county's largest motorized lake, and is within a short drive of Bash Bish Falls and hiking in the Taconic Range.
This family-friendly apartment sleeps up to 6 guests, featuring 2 bedrooms, 1 bathroom, air conditioning, a full kitchen with a dishwasher, internet, a deck overlooking the lake, and a fire pit.
Gatherwild Ranch - Dutchess County, NY
8.5 4 reviews

Gatherwild Ranch

farm, Germantown
The Gatherwild Ranch luxury tent in Germantown is located 10 miles from Hudson Athens Lighthouse and 31 miles from Holley Williams House Museum.
This 200-square-foot accommodation features one bedroom and one bathroom, air conditioning, free WiFi, and on-site amenities including a swimming pool, spa, bar, and bicycle rentals.
Catskills Retro Retreat- Upstate Home W Hot Tub - Dutchess County, NY
9.4 8 reviews

Catskills Retro Retreat- Upstate Home W Hot Tub

house, Saugerties
This Saugerties Catskills retreat is located approximately 28-30 miles from Catskill State Park, Historic Huguenot Street, and SUNY New Paltz, offering easy access to area attractions.
This 1500-square-foot house features three bedrooms, two bathrooms, sleeps twelve guests, and includes a fully equipped kitchen, jacuzzi, bar, and free Wi-Fi and parking.

Frequently Asked Questions about vacation rentals in Dutchess County, NY

  • What are the must-see sights in Dutchess County, New York?

    In Dutchess County, you absolutely have to visit the Vanderbilt Mansion National Historic Site in Hyde Park, a stunning Gilded Age mansion. Another must-see is the Home of Franklin D. Roosevelt National Historic Site, also in Hyde Park, offering a glimpse into the life of a president. Walk the grounds of the breathtaking Lyndhurst Mansion in Tarrytown, a Gothic Revival masterpiece. For art lovers, the Dia Beacon is a world-renowned contemporary art museum housed in a former Nabisco box printing factory.
  • What are the best Airbnb and vacation rentals in Dutchess County, NY?

    Cozy New Paltz Apartment (No Cleaning Fee), Modern Cottage With Hudson River View and Vintage-inspired Revitalized Historical Bau Guesthaus - A are the most popular Airbnb and vacation rentals in Dutchess County, NY among travelers.

  • Are there unique natural phenomena in Dutchess County, New York?

    While not a unique geological formation in the sense of a single landmark, the Hudson River Valley itself is a remarkable natural phenomenon, shaping the landscape and history of Dutchess County. The dramatic cliffs and rolling hills offer stunning views and excellent hiking opportunities. Many areas boast diverse plant and wildlife, adding to the natural beauty.
  • What are the most popular Airbnbs in Dutchess County, NY?

  • What essentials should you bring along for a trip to Dutchess County, New York?

    Comfortable walking shoes are a must, as you'll likely be doing a lot of exploring on foot. Pack layers of clothing, as the weather can change quickly, especially during shoulder seasons. Sunscreen, a hat, and sunglasses are essential, even on cloudy days. Don't forget insect repellent, especially if you plan on hiking or spending time outdoors.
  • What are the best vacation rentals with a pool in Dutchess County, NY?

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Dutchess County, New York?

    A daily budget will vary greatly depending on your travel style. For a mid-range experience, expect to spend around $200-$300 per day per person. This includes moderate accommodation, meals at local restaurants, some paid activities, and local transportation costs. Budget travelers could likely manage on less, while luxury travelers would spend considerably more.
  • What are the best rentals for families and kids in Dutchess County, NY?

  • Where can you find the best restaurants serving local dishes in Dutchess County, New York, and what are the must-try specialties?

    Dutchess County boasts a thriving culinary scene. The Culinary Institute of America in Hyde Park is a major draw, with student-run restaurants offering excellent meals. Many farm-to-table restaurants feature locally sourced ingredients. Look for restaurants specializing in Hudson Valley specialties like wild mushrooms, locally grown produce, and fresh-caught fish from the Hudson River. Apple picking and cider donuts are seasonal favorites.
  • What are the best rentals or Airbnbs with a jacuzzi in Dutchess County, NY?

  • What are some less-famous attractions in Dutchess County, New York that are worth the visit?

    The Walkway Over the Hudson State Historic Park offers incredible views of the Hudson River and surrounding area. Explore the charming towns of Beacon and Cold Spring, each with unique shops, restaurants, and historical sites. Consider a visit to the Vanderbilt Estate's Carriage House, a less-visited but equally interesting part of the property.
  • What are the best activities for engaging with locals and understanding their culture in Dutchess County, New York?

    Visiting local farmers' markets is a great way to interact with residents and sample local produce. Attend a community event or festival in a smaller town. Consider visiting a local brewery or winery for a tasting and conversation with the owners. Exploring the many antique shops and browsing local art galleries offers opportunities to meet people and learn about the area's creative side.
  • What unique natural landscapes and terrain features can travelers explore in Dutchess County, New York?

    The Hudson River Valley's dramatic cliffs and rolling hills offer diverse hiking trails. The region is known for its forests, offering opportunities for birdwatching and nature walks. Many parks and preserves provide access to these natural landscapes, including the Shawangunk Ridge, offering stunning views and challenging hikes.
  • How many days are ideal for visiting Dutchess County, New York, and what are some itinerary suggestions?

    Three to four days allows for a good balance of exploring major attractions and experiencing the smaller towns. A possible itinerary could include: Day 1: Vanderbilt Mansion and Home of Franklin D. Roosevelt; Day 2: Dia Beacon and Beacon town exploration; Day 3: Walkway Over the Hudson and Cold Spring; Day 4: Hiking or exploring a local farm.

Nearby regions

Best Dutchess County, NY vacation rentals with a pool

Among the 1839 accommodations in Dutchess County, NY, here are the 4 best rentals with a pool

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House In The Gunks - Dutchess County, NY
9.6 35 reviews

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House In The Gunks

apartment, New Paltz
This waterfront New Paltz vacation home, located within three miles of attractions like the Testimonial Gateway and Huguenot Street Historic District, offers scenic views and easy access to local landmarks.
This 2,000-square-foot house features four bedrooms, three bathrooms, sleeps twelve guests, and includes a pool, spa, and fully equipped kitchen; enjoy free Wi-Fi, a terrace, and a garden with barbecue grills.
7 Mi To The Walkway: Hudson Valley Adventure Base - Dutchess County, NY
9.5 2 reviews

7 Mi To The Walkway: Hudson Valley Adventure Base

house, Clintondale
This Milton vacation home is located 7 miles from The Walkway, 7.5 miles from The State University of New York at New Paltz, and 7.8 miles from Historic Huguenot Street.
This 2500 square foot house offers 4 bedrooms, 2 bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, a garden, and parking for up to 15 guests.
7-acre Horse Farm - Pool, Mountain View, Hot Tub, Sauna, Game Room - Sleeps 10 - Dutchess County, NY
10 1 review

7-acre Horse Farm - Pool, Mountain View, Hot Tub, Sauna, Game Room - Sleeps 10

manor house, Palenville
This private 7+ acre estate in the Catskill Valley House, located in Saugerties, offers sweeping Catskill Mountain views and is 8 miles from Saugerties, 12 miles from Woodstock and Catskill, and 18 miles from Kingston.
This family-friendly farm stay accommodates up to 10 guests with 4 bedrooms, 3 bathrooms, a hot tub, barrel sauna, fire pit, and a game room, and is 20 miles from Hunter Mountain Skiing.
The Scenic Mansion With Breathtaking View - Dutchess County, NY
8.4 20 reviews

The Scenic Mansion With Breathtaking View

house, Highland
This luxurious Milton mountain villa boasts stunning views, situated 1.1 miles from Franny Reese State Park and within 3 miles of the Hudson River and Walkway Over the Hudson State Historic Park.
The 4-bedroom, 6-bathroom house comfortably sleeps 10 guests and features a private pool, Jacuzzi, tennis court, and fully equipped kitchen with modern appliances, including a dishwasher; enjoy nearby hiking and explore the Hudson Valley.

Neighborhoods and points of interest in Dutchess County, NY

Best Dutchess County, NY vacation rentals with parking

Cheerful 3 Bedroom Cottage By Rail Trail - Dutchess County, NY
9.9 147 reviews

Cheerful 3 Bedroom Cottage By Rail Trail

apartment, New Paltz
This charming cottage-style apartment is located in a quiet neighborhood on the outskirts of New Paltz, just a short walk from the bus station, Main Street, and a bike rental shop. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience.
The apartment offers a variety of sleeping arrangements, including a loft-style master bedroom, a smaller bedroom with a sleeper-couch, and a downstairs bedroom, accommodating up to 5 guests. Enjoy the fully-equipped kitchen, outdoor space with a deck and fire pit, and the quiet setting perfect for relaxation.
Cozy Hudson Valley House - Dutchess County, NY
9.9 90 reviews

Cozy Hudson Valley House

cabin, Amenia
This three-bedroom A-frame cottage in Amenia, New York, is located one mile from Wassaic, home to The Lantern restaurant and the Wassaic Project arts space, and within a 20-minute drive of Millbrook, Millerton, Kent, and Lakeville.
The 2-acre property features a fully equipped kitchen, two wood-burning stoves, wrap-around decks with a German beer hall table, and accommodates up to six guests with two bathrooms, internet access, and pet-friendly options.
Farmhouse Oasis In The Hudson Valley, Stream Views - Dutchess County, NY
9.9 105 reviews

Farmhouse Oasis In The Hudson Valley, Stream Views

apartment, Pawling
Wicked Finch Farm, a Hudson Valley farmhouse near Pawling, New York, is steps from Dykeman Farm and a short drive from the "A Quiet Place" filming location.
This 7-acre property offers a recently renovated 4-bedroom, 3-bathroom house sleeping up to 10 guests, boasting a gourmet kitchen, multiple gathering spaces, and access to bicycles, cornhole, snowshoes, and other amenities.
Somewhere Thats Green, Gameroom/bar, Fenced Yard - Dutchess County, NY
10 46 reviews

Somewhere Thats Green, Gameroom/bar, Fenced Yard

apartment, Dover Plains
This three-bedroom Dover Plains rental home, situated on five private acres near the Metro-North Railroad and Appalachian Trail hiking trails, offers easy access to New York City and outdoor recreation.
The 3-bedroom, 2-bathroom residence boasts a full kitchen with double oven, a game room with pool table and foosball, three TVs with streaming services, a fenced yard, and accommodates up to six guests.
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