Dutchess County vacation rentals

We found 1,341 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024
Discover a selection of 235 homes, 59 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.

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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)
  • 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)
  • Thunder Ridge Ski Resort (20.6 mi / 33.1 km)
  • Robibero Winery (21.8 mi / 35.1 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:

  • Vanderbilt Mansion National Historic Site (10.1 mi / 16.2 km)
  • Walkway Over the Hudson State Historic Park (11.4 mi / 18.4 km)
  • Kent Falls State Park (17 mi / 27.4 km)
  • Esopus Creek (17.8 mi / 28.6 km)
  • Lake Waramaug State Park (19.4 mi / 31.1 km)
  • Lake Waramaug (20.7 mi / 33.3 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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