738+ Private Villas and Holiday Rentals in Dutchess County |
  1. USA
  2. New York
  3. Dutchess County

Dutchess County Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Dutchess County

Discover more than 738 vacation rentals available in Dutchess County. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Dutchess County.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Dutchess County, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Dutchess County. On average, places to stay near Dutchess County offer 1139.19 ft², with nightly prices averaging US $512.

With Casai, finding and comparing holiday rentals in Dutchess County is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Show more
Show less

Top Accommodation Types in Dutchess County

Type Count
Vacation Homes 405
Holiday Apartments 105
Cottages 34
Villas 8

Use these Quick Filters to Find a Holiday Rental in Dutchess County

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Dutchess County.

Weather in Dutchess County, NY

View the weather forecast for Dutchess County before booking your Dutchess County Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Dutchess County, NY

Casai offers a large selection of top attractions around Dutchess County . Research things to do on your vacation before you visit Dutchess County.


Marist College
Train Station
Vassar College
Culinary Institute of America
Dia Beacon
Bard College
SplashDown Beach
Mid-Hudson Civic Center
Omega Institute
Chance Theater
Franklin D. Roosevelt Presidential Library and Museum
Stormville Airport Antique Show & Flea Market
Dutchess County Fairgrounds
Millbrook Vineyards and Winery
Vanderbilt Mansion National Historic Site
Home of Franklin D. Roosevelt National Historic Site
Poughkeepsie Galleria
Vassar Brothers Medical Center
Locust Grove
Old Rhinebeck Aerodrome
Poughkeepsie Bridge
Innisfree Garden
Springwood
Mid-Hudson Children's Museum
Harlem Valley Rail Trail
Mid-Hudson Bridge
Eleanor Roosevelt National Historic Site
Bardavon 1869 Opera House
Hudson Valley Research Park
Center for Performing Arts at Rhinebeck

Other Places to Stay in Dutchess County, NY


Lower Hudson Valley 3,325 Properties
Poughkeepsie 871 Properties
Fishkill 64 Properties
Beacon 52 Properties
Rhinebeck 50 Properties
Pine Plains 44 Properties
Town of Stanford 38 Properties
Town of East Fishkill 34 Properties
Hopewell Junction 33 Properties
Red Hook 28 Properties
Staatsburg 27 Properties
Clinton Corners 27 Properties

Frequently Asked Questions About Dutchess County?

What are the top holiday rentals in Dutchess County?

With numerous options available in Dutchess County, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Dutchess County:

How many holiday rentals have private pools in Dutchess County?

Discover a selection of holiday rentals with private pools near Dutchess County with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Dutchess County are best for families?

If you're searching for a family-friendly holiday home in Dutchess County, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Dutchess County:

How many Casai.nz holiday rentals are available in Dutchess County?

As of 2025, Casai boasts over 738 properties listed in the Dutchess County area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Dutchess County.


People Also Ask

There are 738 Dutchess County, NY Holiday Rentals

Recently Booked Holiday Rentals in Dutchess County