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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 1107 accommodations in Dutchess County, NY, here are the 4 best family friendly rentals

Heart Of The Village Victorian Saugerties Ny - Dutchess County, NY
10 7 reviews
Dutchess County, NY
06/23 – 07/04
$514/nighttotal: $5654 (11 )

Heart Of The Village Victorian Saugerties Ny

4 2
apartment , Saugerties
This Saugerties vacation home offers a family-friendly stay, conveniently located within a 15-minute walk of Esopus Falls, Saugerties Village Beach, and Seamon Park, and within 2 miles of the Kiwanis Ice Arena and Saugerties Lighthouse.
This 2300-square-foot house features four bedrooms, two bathrooms, and sleeps nine, boasting a fully equipped kitchen, patio with gas grills, and a smoke-free environment.
Hudson Valley - Maison Près De Millbrook. - Dutchess County, NY
9.7 85 reviews
Dutchess County, NY
06/23 – 07/04
$326/nighttotal: $3586 (11 )

Hudson Valley - Maison Près De Millbrook.

1 2
apartment , Freedom Plains
This recently renovated two-bedroom, two-bathroom house is located near Millbrook in Freedom Plains, offering easy access to both Dutchess County and New York City, and proximity to Millbrook Village and its attractions.
The 2-bedroom home, situated on 1.5 acres, features a modern kitchen with granite countertops, a heated mudroom, a fire pit, and barbecue, accommodating up to four guests and providing ample space for outdoor recreation.
Cleos Cabin: Private Retreat With Fenced Dog Run - Dutchess County, NY
9.0 12 reviews
Dutchess County, NY
06/23 – 07/04
$552/nighttotal: $6072 (11 )

Cleos Cabin: Private Retreat With Fenced Dog Run

3 2
apartment , Glasco
This Glasco cabin is located in Saugerties, a short drive from Woodstock and Kingston, offering easy access to the region's attractions. It has received excellent user ratings, making it a popular choice for travelers.
This 3-bedroom, 2-bathroom home can accommodate up to 8 guests and offers 1600 square feet of living space. Guests can enjoy amenities such as a fully equipped kitchen, a fenced-in dog run, a garden, and multiple workspaces.
Grand Arcady - 3br/2ba Renovated Farm House - Dutchess County, NY
9.6 119 reviews
Dutchess County, NY
06/23 – 07/04
$349/nighttotal: $3839 (11 )

Grand Arcady - 3br/2ba Renovated Farm House

3 2
apartment , Salt Point
This 1860s farmhouse is located in Salt Point, a short drive from the Omega Institute and a town beach, offering a peaceful retreat amidst nature. The apartment has received excellent ratings for location, cleanliness, and user experience.
The farmhouse features three bedrooms and two bathrooms, accommodating up to seven guests. It offers a screened-in porch, a fully equipped kitchen, a dining room, a library, a living room, a garden, a private beach, a fire pit, and parking.

Top cities

Best pet friendly Dutchess County, NY vacation rentals

Among the 1107 accommodations in Dutchess County, NY, here are the 4 best pet friendly rentals

Cabin In The Heart Of The Hudson Valley, Cabin 3 - Dutchess County, NY
9.8 14 reviews
Dutchess County, NY
06/23 – 07/04
$243/nighttotal: $2673 (11 )

Cabin In The Heart Of The Hudson Valley, Cabin 3

1 2
cabin , Marlboro
This Marlboro cabin is located near the Shawangunk Wine Trail and a short drive from the Walkway Over the Hudson, offering a peaceful escape in a scenic setting. The cabin has received very good user ratings, indicating a comfortable and enjoyable stay.
This cozy retreat features a king-size bed, a full kitchen, a private bathroom, and a shared grill and picnic table. Guests can enjoy the quiet ambiance, relax by the electric fireplace, and explore the nearby attractions, local farm stands, breweries, and wineries.
Cabin On 66 Acres Of Forest - Dutchess County, NY
9.4 21 reviews
Dutchess County, NY
06/23 – 07/04
$269/nighttotal: $2959 (11 )

Cabin On 66 Acres Of Forest

1 2
cabin , Pawling
This Pawling, New York cabin rental is situated in a secluded forest setting accessible by a long gravel driveway, offering easy access to Wonder Lake State Park and Whaley Lake.
The 850-square-foot cottage features one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen with a fridge and dishwasher, plus WiFi, A/C, and a washer.
Cozy Queen Suite Non-smoking Kitchen Studio 6 Fishkill - Dutchess County, NY
9.8 18 reviews
Dutchess County, NY
06/23 – 07/04
$151/nighttotal: $1661 (11 )

Cozy Queen Suite Non-smoking Kitchen Studio 6 Fishkill

1 2
apartment , Fishkill
This 300 sq ft, 1-bedroom, 1-bathroom condo in Fishkill is located along Route 9, 7 miles from the Mid Hudson Children's Museum and 8.7 miles from Marist College.
This pet-friendly rental accommodates up to 2 guests and features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, free WiFi, and on-site parking.
A Peaceful Bucolic Retreat By The Water At The Gateway Of Hudson Valley - Dutchess County, NY
10 54 reviews
Dutchess County, NY
06/23 – 07/04
$372/nighttotal: $4092 (11 )

A Peaceful Bucolic Retreat By The Water At The Gateway Of Hudson Valley

1 2
apartment , Lake Carmel
This charming one-bedroom guesthouse sits just 60 miles north of New York City, offering a peaceful retreat in the Hudson Valley. It has received excellent ratings for location, cleanliness, and overall experience.
The guesthouse is ideal for couples seeking a tranquil getaway, with a private pond view from every room. Guests can enjoy modern amenities, a spacious garden, and access to 22 acres of land for exploring, including hiking trails and opportunities to observe local wildlife.

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 1107 accommodations in Dutchess County, NY, here are the 3 best rentals with a pool

Lucious Lagrangeville - Dutchess County, NY
Dutchess County, NY
06/23 – 07/04
$664/nighttotal: $7304 (11 )

Lucious Lagrangeville

1 2
house , Freedom Plains
This spacious vacation home is located in Lucious Lagrangeville, Lagrangeville, offering convenient access to Vassar College (9 miles) and Bardavon Opera House (10 miles).
This 10,760 square foot house accommodates up to 19 guests and features air conditioning, a kitchen, swimming pool, jacuzzi, terrace, balcony, parking, and complimentary WiFi.
Beautiful Cozy 1 Bedroom Apartment Near Farms - Dutchess County, NY
9.4 87 reviews
Dutchess County, NY
06/23 – 07/04
$147/nighttotal: $1617 (11 )

Beautiful Cozy 1 Bedroom Apartment Near Farms

1 2
apartment , Merritt Park
This one-bedroom apartment is located in a peaceful, park-like setting near Fishkill Farms, less than a quarter mile away. It's also close to the Hudson River and within a short drive of nearby towns like Patterson and Walkill. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The apartment comfortably accommodates two guests and features a well-equipped kitchen with a fridge, freezer, and microwave oven. Enjoy amenities like air conditioning, a swimming pool, a garden, and parking, making it a great choice for a relaxing getaway.
Charming 2-bedroom Villa In Serene Holmes With Ac, Wifi - Dutchess County, NY
Dutchess County, NY
06/23 – 07/04
$719/nighttotal: $7909 (11 )

Charming 2-bedroom Villa In Serene Holmes With Ac, Wifi

2 2
house , Lake Carmel
This Holmes villa offers a convenient location near Wonder Lake State Park, within 6 miles of Lake Dutchess and Thunder Ridge Ski Resort.
This two-bedroom, one-bathroom house comfortably sleeps four guests and features a private pool, essential amenities, and a smoke-free environment.

Neighborhoods and points of interest in Dutchess County, NY

Best Dutchess County, NY vacation rentals with parking

Scenic Hudson Valley Getaway  Farms & Vineyards - Dutchess County, NY
9.4 3 reviews
Dutchess County, NY
06/23 – 07/04
$341/nighttotal: $3751 (11 )

Scenic Hudson Valley Getaway Farms & Vineyards

2 2
cottage , Marlboro
This Marlboro, NY cabin rental boasts a secluded 10+ acre setting near top-rated Hudson Valley vineyards, a 90-minute drive from New York City, and close to attractions like the Walkway Over the Hudson State Historic Park and Franny Reese State Park.
This two-bedroom, one-bathroom cottage sleeps four, offering air conditioning, internet access, and pet-friendly accommodations; nearby activities include winery tours, McCann Ice Arena, and exploring Marlboro's local breweries and restaurants.
New: Chic Modern Barn Style Home In Fun Area - Dutchess County, NY
Dutchess County, NY
06/23 – 07/04
$646/nighttotal: $7106 (11 )

New: Chic Modern Barn Style Home In Fun Area

1 2
apartment , Pine Plains
This newly built barn-style apartment is located in a wooded area near Pine Plains, offering proximity to Stissing House restaurant and the weekend polo scene, with Rhinebeck just a short drive away.
This pet-friendly retreat accommodates up to 6 guests with 2 bathrooms, featuring a gas fireplace, a coffee bar, a BBQ, a fire pit, and a play-friendly garden.
Stunning 5-bedroom House With Ac / Heat In Charming Poughkeepsie Ny - Dutchess County, NY
9.6 4 reviews
Dutchess County, NY
06/23 – 07/04
$540/nighttotal: $5940 (11 )

Stunning 5-bedroom House With Ac / Heat In Charming Poughkeepsie Ny

5 2
apartment , Poughkeepsie
This Poughkeepsie residence is located near Franny Reese State Park and Vanderbilt Mansion National Historic Site, providing easy access to notable local attractions.
This spacious home accommodates up to 18 guests with five bedrooms and two bathrooms, featuring air conditioning, heating, and an iron for guest convenience.
Casa Fuego Catskills - Historic Fire House - Dutchess County, NY
10 54 reviews
Dutchess County, NY
06/23 – 07/04
$276/nighttotal: $3036 (11 )

Casa Fuego Catskills - Historic Fire House

2 2
apartment , Saugerties
This renovated firehouse in Saugerties is a short walk from Main Street and its restaurants, and less than 10 minutes from Village Beach. The accommodation has excellent user, location, and cleanliness ratings.
The home has a spacious open floor plan ideal for entertaining and can accommodate up to four guests. It features a chef's kitchen with top-of-the-line appliances, a luxurious bathroom, a level two electric car outlet, and private parking.
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