Dutchess County vacation rentals

We found 1,359 vacation rentals — enter your dates for availability

Discover a selection of 227 homes, 57 apartments, and other vacation rentals in Dutchess County that are perfect for your trip. Whether you're staying in a vacation rental with friends, family, or even just your pets, you'll find the best amenities for hanging out with the people that matter most, which might include WiFi and a washer and dryer. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.

Popular cities in Dutchess County

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Find out more about Dutchess County

Find out more about Dutchess County

Why visit Dutchess County

  1. Breathtaking landscapes: Dutchess County features stunning scenery, particularly in the picturesque Hudson Valley.
  2. Rich history: Explore historic towns like Poughkeepsie and Beacon, filled with charming architecture and cultural landmarks.
  3. Outdoor adventures: Enjoy a range of family-friendly activities, from hiking to local beaches amid beautiful natural settings.
  4. Unique accommodations: Choose from private homes, apartments, and rustic cabins for a cozy stay.
  5. Welcoming atmosphere: Experience the friendly vibe and community spirit that Dutchess County has to offer.

Popular types of accommodation in Dutchess County

If you’re wondering what types of accommodations await you in Dutchess County, worry not—we’ve got you covered! Our most sought-after vacation rentals include houses, apartments, and charming cabins. Whether you're looking for Dutchess County house rentals, townhouse rentals, or delightful holiday cottages, you’ll find the perfect spot to unwind and enjoy your getaway. Experience the best of Dutchess County with our transparent and reassuring vacation rental options!

  • Houses: The top choice for visitors seeking spacious and comfortable stays, ideal for families or groups in Dutchess County.
  • Apartments: A popular option for couples or solo travellers, offering convenience and a local feel in the heart of the county.
  • Cabins: A charming retreat amidst nature, perfect for those looking to unwind in a rustic setting.
  • Cottages: Quaint and cozy, these rentals provide a picturesque escape with a homey atmosphere.
  • Condos: Modern and well-equipped, condos cater to those who appreciate contemporary comforts during their stay.**

Top attractions in Dutchess County

Dutchess County, New York, offers a fantastic blend of outdoor adventures, stunning scenery, and rich history for Canadian tourists. Explore a variety of attractions, from modern and historic colleges to charming historic buildings. Whether you're seeking cultural experiences, family-friendly activities, or simply a chance to bask in nature, Dutchess County has something for everyone to enjoy during your vacation.

  1. Culinary Institute of America: A renowned culinary school offering a unique blend of education and culture. Experience world-class dining at its restaurants and explore the art of cooking in a historic setting.
  2. Vassar College: A beautiful liberal arts college with stunning architecture and vibrant city vibes. Enjoy leisurely strolls through its picturesque campus, rich in history and culture.
  3. Omega Institute: A holistic retreat focused on personal growth and wellness. Engage in workshops and classes in a tranquil environment that merges nature with urban inspiration.

Things to do recommended for couples

For a romantic getaway in Dutchess County, explore the charming Millbrook Vineyards and Winery or the scenic Oak Summit Vineyard for outdoor vibes. Don't miss the delightful Clinton Vineyards, where entertainment and romance blend seamlessly, creating unforgettable moments for couples.

Things to do recommended for families

Your family will have a blast at SplashDown Beach, a thrilling waterpark perfect for adventure seekers. Enjoy the serene atmosphere of Bowdoin Park for relaxation, and catch an exciting game at Dutchess Stadium, where sports enthusiasts can cheer for their favourite teams.

Things to do recommended for groups

Groups visiting Dutchess County can explore the vibrant Stormville Airport Antique Show & Flea Market, enjoy shopping and entertainment at Poughkeepsie Galleria, and experience culture and romance at the Center for Performing Arts at Rhinebeck. Each offers a unique local vibe perfect for group adventures.

What do I need to keep in mind when booking a vacation in Dutchess County

If you're travelling with a group, family, pets, or planning for an extended stay, it's important to refine your search based on your specific needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Dutchess County with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Dutchess County with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Dutchess County: For many, a family vacation wouldn't be the same without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Dutchess County: If you're in search of vacation rentals with special offers for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Dutchess County

Discover the charm of Dutchess County, New York, where outdoor adventures and stunning scenery await. From the historic towns of Poughkeepsie and Beacon to the picturesque landscapes of the Hudson Valley, there’s something for everyone. Enjoy family-friendly attractions, explore local beaches, and immerse yourself in the friendly atmosphere. With nearby neighbourhoods offering unique experiences, your vacation in Dutchess County promises unforgettable memories amidst its rich history and natural beauty.

  • Poughkeepsie: Nestled in the heart of Dutchess County, Poughkeepsie offers a vibrant city experience with a blend of outdoor and family-friendly activities. The Hudson River Valley provides a stunning backdrop for exploring local landmarks such as the Walkway Over the Hudson, a scenic pedestrian bridge that offers panoramic views. Poughkeepsie is also home to several educational institutions, parks, and shopping areas that cater to all ages. Visitors can enjoy a leisurely day at the nearby lakes or take in the beauty of the surrounding mountains, making it an ideal destination for those seeking both adventure and relaxation.
  • Beacon: Beacon is a charming city that attracts visitors with its artistic vibe and outdoor adventures. Situated along the Hudson River, it offers stunning views and opportunities for hiking and skiing in the nearby mountains. Beacon is known for its vibrant arts scene, featuring galleries and theaters that showcase local talent. The city's proximity to parks and recreational areas makes it ideal for families seeking adventure. Whether you're skiing at a local field or exploring the art exhibits, Beacon promises a memorable experience filled with culture and outdoor fun.
  • Rhinebeck: Rhinebeck is a picturesque town that embodies the beauty of the Hudson Valley, attracting outdoor enthusiasts and those seeking scenic views. Known for its charming Main Street lined with boutique shops and eateries, Rhinebeck also features educational institutes and outdoor recreational areas. The nearby mountains and lakes offer ample opportunities for skiing and exploring nature. With its rich history and vibrant community, Rhinebeck is perfect for a leisurely getaway filled with adventure and breathtaking scenery.

Booking with Vrbo is simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can lead to significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your journeys, pick up from where you last left off, or manage your travel arrangements. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Choose a vacation rental for your Dutchess County getaway

Experience the unique character of Dutchess County with a stay in a vacation home rental. There's no shortage of things to see and do in the area.If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Dutchess County

Do you want to discover top things to see and do in the area? Venture out of your vacation home and experience everything that makes Dutchess County a fun place to get away. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Millbrook Vineyards and Winery (5.3 mi / 8.6 km)
  • Casperkill Golf Club (12.9 mi / 20.7 km)
  • Beekman Golf Course (12.9 mi / 20.8 km)
  • Benmarl Vineyards and Winery (17.6 mi / 28.4 km)
  • SplashDown Beach (17.9 mi / 28.8 km)
  • Mohonk Golf Course (20 mi / 32.1 km)

Exploring the natural features in Dutchess County

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Dutchess County is a great place to get outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Innisfree Garden (1.1 mi / 1.7 km)
  • Vanderbilt Mansion National Historic Site (10.1 mi / 16.2 km)
  • Walkway Over the Hudson State Historic Park (11.4 mi / 18.4 km)
  • Kingston Point Beach (15.3 mi / 24.6 km)
  • Kent Falls State Park (17 mi / 27.4 km)
  • Harlem Valley Rail Trail (17.2 mi / 27.7 km)

How to get to and around Dutchess County

If you're traveling by train, Poughkeepsie Station, Rhinecliff Station and Appalachian Trail are the main stations in the city.

Frequently asked questions

What is the best area to stay in Dutchess County when booking a vacation rental?
Among the more in-demand destinations to choose a vacation property in Dutchess County is Rhinebeck. Base yourself here and discover some must-see attractions, including Dutchess County Fairgrounds and Old Rhinebeck Aerodrome.
What is the most popular type of vacation rental accommodation in Dutchess County?
Based on our research, houses are the most in-demand property type in Dutchess County. But as you might expect, everyone’s idea of the perfect stay differs. Vrbo has vacation rentals of all sizes, shapes and budgets, and we’ll help you locate the perfect fit for you.
How much does it cost to rent a vacation rental in Dutchess County?
A number of factors affect the price of a vacation rental in Dutchess County, including the type of property, season and length of stay. Still, all Vrbo homes have something in common — amazing value. Simply add your travel dates to find your dream escape.
How much does it cost to rent a beach house in Dutchess County?
When you travel and the style and size of the property will influence the cost of your beachside stay. Click on your Dutchess County travel dates to see your options on Vrbo. Did someone just say “private pool”? Use the filters to choose the features and amenities you need.
What are popular rental amenities in Dutchess County?
A stovetop, off-street parking options and a fridge head the list of most popular rental amenities in Dutchess County. Whether you’re taking a trip on your own, with your other half or a group of family members, Vrbo can help you find a vacation home that fits your tastes with all the conveniences you’re looking for.
Are there large group vacation rentals in Dutchess County?
Choose from 44 properties in Dutchess County that can host a group of 10 or more people. Whether you’re planning a trip with extended family or a special event, there’s plenty of room to get your favorite people together under one roof.
What are the top attractions for families in Dutchess County?
Keeping the kids happy during your stay in Dutchess County is a snap with these leading family-friendly attractions:

  • Vanderbilt Mansion National Historic Site
  • Dia Beacon
  • Stormville Airport Antique Show & Flea Market

Can I find two-bedroom vacation rentals in Dutchess County?
Dutchess County has 44 two-bedroom vacation rentals to choose from. Enjoy a vacation home with all the space and privacy you want at a price that’s hard to resist on Vrbo.
Are there vacation rentals with WiFi in Dutchess County?
Dutchess County has 108 vacation rentals with WiFi, so you’ll be able to stay connected while you’re away. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming movies with the family to checking emails, these Vrbo homes make it a breeze to go online.
How old do you have to be to rent a vacation rental in Dutchess County?
The age limit can differ across properties on Vrbo, so be sure to check the rules of the vacation rental in Dutchess County you’re considering. But typically, it’s 16, 18 or 21.
How long can I rent a vacation rental in Dutchess County for?
It’s up to the Dutchess County property. To view all available options offering extended stays, just type your dates and number of guests into Vrbo. You can enjoy having the place to yourself, along with home comforts like air conditioning, a kitchen and a backyard where your little ones can play. Keep your eyes open for any long-term stays that offer weekly or monthly discounts.

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