Dutchess County holiday rentals

We found 1,382 holiday rentals — enter your dates for availability

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August 2025

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Discover a selection of 233 homes, 58 apartments and other holiday rentals in Dutchess County that are perfect for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a pool. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Popular Dutchess County destinations on Stayz

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Find the best place to stay - Dutchess County

Showing deals for: 28 Oct - 31 Oct

Stunning, 8 Bedroom Estate & Retreat. Historic Elegance with Designer Interiors

Sleeps 12 · 8 bedrooms · 5+ bathrooms

for 3 nights, 1 home

AU$5,979 per night

includes taxes & fees

Hidden Charm in Hudson Valley In Dutchess County

Sleeps 10 · 4 bedrooms · 3 bathrooms

for 3 nights, 1 home

AU$1,049 per night

includes taxes & fees

Aerial View Private-Luxury 31 Acre Estate.
Catskills Mountains in background.

NEW! Gated 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.

Sleeps 20 · 7 bedrooms · 7 bathrooms

for 3 nights, 1 home

AU$4,273 per night

includes taxes & fees

Spacious Country Farmhouse on 8 Lush Acres, Five Minutes to Rhinebeck Village

Sleeps 10 · 4 bedrooms · 3+ bathrooms

for 3 nights, 1 room

AU$1,076 per night

includes taxes & fees

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Sleeps 8 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$527 per night

includes taxes & fees

Spacious New Luxurious holiday house in lovely Hudson Valley

Sleeps 8 · 4 bedrooms · 4 bathrooms

for 3 nights, 1 home

AU$1,028 per night

includes taxes & fees

Choose a holiday rental for your Dutchess County getaway

Learn about the unique charm of Dutchess County with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Dutchess County

Are you looking for attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Dutchess County a fun place to get away to. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

Millbrook Vineyards and Winery (5.3 mi / 8.6 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)
Thunder Ridge Ski Resort (20.6 mi / 33.1 km)

Exploring the natural features in Dutchess County

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Dutchess County. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

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 travelling by train, Poughkeepsie Station, Rhinecliff Station and Appalachian Trail are the main stations in the area.

Frequently asked questions

What is the best area to stay in Dutchess County when booking a holiday home?

Among the more in-demand destinations to choose a holiday 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 holiday home 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. Stayz has holiday homes 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 holiday home in Dutchess County?

A number of factors affect the price of a holiday home in Dutchess County, including the type of property, season and length of stay. Still, all Stayz 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 Stayz. Did someone just say "private pool"? Use the filters to choose the features and amenities you need.

What are popular home amenities in Dutchess County?

A stovetop, off-street parking options and a fridge head the list of most popular home amenities in Dutchess County. Whether you're taking a trip on your own, with your other half or a group of family members, Stayz can help you find a holiday home that fits your tastes with all the conveniences you're looking for.

Are there large group holiday homes 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 favourite 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 holiday homes in Dutchess County?

Dutchess County has 44 two-bedroom holiday homes to choose from. Enjoy a holiday home with all the space and privacy you want at a price that's hard to resist on Stayz.

Are there holiday homes with WiFi in Dutchess County?

Dutchess County has 108 holiday homes 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 Stayz homes make it a breeze to go online.

How old do you have to be to rent a holiday home in Dutchess County?

The age limit can differ across properties on Stayz, so be sure to check the rules of the holiday home in Dutchess County you're considering. But typically, it's 16, 18 or 21.

How long can I rent a holiday home 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 Stayz. 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.