Best Vacation Homes in Dutchess County
New
House
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
1364 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
CA $841/Night
7 Nights - CA $5,885
Apartment
10.0(7 Reviews)
1 Bedroom
1 Bath
2 Guests
398.26 ft²
- Parking
- Balcony/Terrace
Internet
Bar
CA $351/Night
7 Nights - CA $2,459
Bed & Breakfast
9.8(307 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
- Balcony/Terrace
- Kitchen
CA $406/Night
7 Nights - CA $2,842
Other
9.8(16 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Parking
Pool- Balcony/Terrace
- Kitchen
CA $356/Night
7 Nights - CA $2,495
House
10.0(7 Reviews)
1 Bedroom
1 Bath
2 Guests
904.17 ft²
- Parking
- Internet
Child Friendly
Sports/Activities
CA $320/Night
7 Nights - CA $2,237
House
10.0(71 Reviews)
4 Bedrooms
4 Baths
10 Guests
Private Pool- Parking
- Pool
Ocean View
CA $1,449/Night
7 Nights - CA $10,140
House
10.0(26 Reviews)
3 Bedrooms
2 Baths
6 Guests
2661 ft²
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
CA $846/Night
7 Nights - CA $5,919
Cottage
10.0(2 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $546/Night
7 Nights - CA $3,824
Dutchess County Luxury Rentals
CA $7,377/Night
7 Nights - CA $51,636
House
9.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
11840.3 ft²
- Parking
- Balcony/Terrace
View- Air Conditioner
CA $7,010/Night
7 Nights - CA $49,068
House
10.0(30 Reviews)
8 Bedrooms
5 Baths
12 Guests
10000 ft²
- Private Pool
- Hot Tub
- Breakfast
- Parking
CA $5,153/Night
7 Nights - CA $36,069
New
House
10.0(1 Review)
8 Bedrooms
3 Baths
22 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $3,865/Night
7 Nights - CA $27,055
House
9.6(59 Reviews)
7 Bedrooms
7 Baths
20 Guests
8000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
CA $3,860/Night
7 Nights - CA $27,019
House
6 Bedrooms
4 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $3,244/Night
7 Nights - CA $22,707
House
3 Bedrooms
2 Baths
6 Guests
10763.91 ft²
- Hot Tub
- View
- Air Conditioner
- Internet
CA $3,049/Night
7 Nights - CA $21,342
Villa
9.6(19 Reviews)
8 Bedrooms
8 Baths
20 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $3,029/Night
7 Nights - CA $21,200
Dutchess County Pet Friendly Vacation Rentals
House
9.8(7 Reviews)
4 Bedrooms
2 Baths
8 Guests
4000 ft²
- Private Pool
- Parking
- Pool
- Ocean View
CA $2,263/Night
7 Nights - CA $15,843
House
10.0(3 Reviews)
4 Bedrooms
2 Baths
8 Guests
2497.23 ft²
- Parking
- Balcony/Terrace
- Internet
Pet Friendly
CA $534/Night
7 Nights - CA $3,739
Cottage
1 Bedroom
1 Bath
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $1,383/Night
7 Nights - CA $9,679
House
3 Bedrooms
2 Baths
6 Guests
3229 ft²
- Private Pool
- Hot Tub
- Breakfast
- Parking
CA $1,510/Night
7 Nights - CA $10,568
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Parking
- Internet
- Pet Friendly
- Child Friendly
CA $713/Night
7 Nights - CA $4,988
House
3 Bedrooms
1 Bath
6 Guests
18299 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $803/Night
7 Nights - CA $5,625
New
House
10.0(25 Reviews)
5 Bedrooms
3 Baths
13 Guests
4000 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $1,270/Night
7 Nights - CA $8,892
New
House
10.0(5 Reviews)
4 Bedrooms
2 Baths
8 Guests
2550 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $994/Night
7 Nights - CA $6,959
Dutchess County Large Vacation Homes
Villa
8.4(20 Reviews)
4 Bedrooms
6 Baths
10 Guests
4427 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
CA $1,830/Night
7 Nights - CA $12,811
House
9.0(5 Reviews)
5 Bedrooms
3 Baths
13 Guests
4004.17 ft²
- Parking
- Pool
Spa- Internet
CA $1,113/Night
7 Nights - CA $7,792
Other
9.8(59 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $1,153/Night
7 Nights - CA $8,074
Bed & Breakfast
8.6(39 Reviews)
4 Bedrooms
4 Baths
12 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
CA $301/Night
7 Nights - CA $2,110
House
10.0(129 Reviews)
5 Bedrooms
3 Baths
14 Guests
3400 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
CA $1,313/Night
7 Nights - CA $9,188
House
10.0(46 Reviews)
6 Bedrooms
3 Baths
12 Guests
4550 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
CA $2,854/Night
7 Nights - CA $19,978
House
10.0(32 Reviews)
4 Bedrooms
3 Baths
11 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $983/Night
7 Nights - CA $6,883
House
10.0(26 Reviews)
5 Bedrooms
2 Baths
8 Guests
2018 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $863/Night
7 Nights - CA $6,040
Why Choose Rent By Owner for your Dutchess County Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Dutchess County
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here allows you to fully enjoy the natural beauty and local events, making your stay in this destination even more memorable.
Peak Season Highlights
Spring (April to June)
During spring, the area comes alive with blooming flowers and lush landscapes, making it an ideal time for exploring nature and enjoying mild weather in your vacation rentals.
Average Temperature Daytime: 60-75°F - Nighttime: 40-55°F
Fall (September to November)
Autumn offers stunning foliage against a backdrop of comfortable temperatures, perfect for sightseeing and outdoor activities in your rental accommodations here.
Average Temperature Daytime: 65-70°F - Nighttime: 45-50°F
Off-Season Highlights
Summer (July to August)
The hot summer months bring warmer temperatures, providing ample opportunities for outdoor recreation, although this is the busiest season for visitors in the region.
Average Temperature Daytime: 80-85°F - Nighttime: 60-65°F
Winter (December to February)
During winter, the serene landscape takes on a snowy charm, offering a peaceful retreat and cozy stays in your preferred vacation rentals away from peak crowds.
Average Temperature Daytime: 30-40°F - Nighttime: 20-25°F
Weekly Weather Forecast for Dutchess County
How to Book Your Dutchess County Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor space with a spacious patio or deck for relaxing or entertaining.
- Take advantage of access to a lush garden or landscaped yard perfect for outdoor activities.
- Unwind around a crackling fire pit during cool summer evenings under the stars.
- Make the most of scenic views by choosing properties with panoramic balconies or verandas.
- Spend sunny afternoons near a swimming pool or in-ground hot tub if available.
- Explore walking trails or nature paths directly accessible from your rental for outdoor adventures.
- Utilize outdoor dining areas equipped with grills for al fresco meals in the fresh air.
Top Attractions Around Dutchess County
What attractions are nearby?
While staying here, you can explore a variety of outdoor activities, cultural sites, and scenic parks that are easily accessible in Dutchess County, New York, offering an enriching experience just moments from your vacation rental.
Family Activities
- Vanderbilt Mansion National Historic Site: Explore this historic estate to enjoy scenic views and engaging tours that captivate the entire family in the area.
- Embark on a family-friendly biking or walking adventure along this picturesque trail through the region's beautiful landscapes.
- Let the kids' imaginations run wild at this local theater featuring interactive performances perfect for children visiting here.
- Discover hiking trails with breathtaking vistas, offering an outdoor escape suitable for all ages in the surrounding region.
Adult Activities
- Wine Tasting Tours: Experience the region’s renowned vineyards and indulge in tasting sessions at some of the area's most celebrated wineries.
- Hiking and Nature Walks: Discover scenic trails through lush landscapes in nearby parks, offering a peaceful escape into nature.
- Historic Site Visits: Explore cultural landmarks and historical attractions that reveal the rich heritage of this destination.
Other Places to Stay in Dutchess County, NY
Lower Hudson Valley
Poughkeepsie
Hopewell Junction
Town of East Fishkill
Staatsburg
Fishkill
Hyde Park
Clinton Corners
Beacon
Town of Stanford
Rhinebeck
Pine Plains
Dutchess County Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take advantage of the region's renowned cultural sites and outdoor activities to immerse yourself fully in the area's unique charm.
- Plan Ahead for Seasons: Consider the best time to visit, whether for vibrant festivals or serene winter landscapes, to make the most of your stay throughout the year.
- Choose the Right Accommodation: Select a vacation rental that offers comfort and convenience near major points of interest within this destination for a seamless experience.
- Discover Culinary Gems: Sample local cuisine at various eateries around the area to enjoy authentic flavors and enhance your overall visit here.
Transportation Options
- Train Services: You can access regional train lines that connect the area with major cities, offering a convenient way to explore the region without needing a car.
- Bus Transit: Local bus routes provide affordable and reliable transportation options throughout the destination, making it easy to get around this area’s key attractions.
- Rental Cars: Car rental services are widely available here, giving you the flexibility to explore the region at your own pace and visit more remote attractions comfortably.
- Taxi and Rideshare: Taxis and rideshare services ensure quick and convenient transportation for short trips within the area or to nearby destinations, ideal for hassle-free travel.
Local Customs Options
- Welcoming Community Events: Local festivals and fairs are a cherished tradition, offering you a genuine taste of the area's friendly spirit and communal pride.
- Historical Preservation: Respect for this destination's rich history is evident through the preservation of landmarks and traditions that connect the past with the present.
- Farmers' Markets and Local Produce: Engaging with farmers' markets allows you to experience the region's agricultural roots and savor fresh, locally sourced goods.
- Respect for Nature and Outdoor Etiquette: Emphasizing environmental stewardship, residents and visitors alike value responsible outdoor recreation that protects the area's scenic beauty.
Frequently Asked Questions About Dutchess County?
1. What are the top vacation rentals in Dutchess County?
There are a lot of options in Dutchess County. If you plan on staying in the Dutchess County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Dutchess County:
- WELCOME TO THE COUNTRY - LAKE FRONT PROPERTY - THE FOX DEN STUDIO
- Quiet Lakefront Retreat only 80 minutes from NYC- with Private Dock
- Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!
- Romantic Log Cabin on Privately-Owned Lake with Fireplace
- Charming Brick House -Hudson Valley
- Bluebird Valley Farmhouse
- Peaceful & Quiet Lakeside Home with Hot Tub, Pool Table, Fire Pit
- PRIVATE 65 ACRE ESTATE - POOL, TENNIS, PICKLEBALL, 4BR BOOK JULY OR AUG 2026 NOW
- Hudson Valley Horse Farm Retreat in Salt Point
- Mid-Century DJ’s Dream
2. How many vacation rentals have private pools in Dutchess County?
There are 95 vacation rentals with private pools near Dutchess County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Dutchess County are best for families?
If you are looking for a family-friendly vacation home in Dutchess County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Dutchess County:
4. How many Rentbyowner vacation rentals are available in Dutchess County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 805 in the Dutchess County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Dutchess County.
5. What is the cancellation policy for vacation rentals in Dutchess County, New York?
Cancellation policies vary by listing, so it’s important to review the specific terms on the property page or contact the owner directly to understand any fees or restrictions related to cancellations.
6. How do I confirm the availability of a vacation rental in this destination?
Availability is listed on each property page, but it's recommended to reach out to the host to verify current availability and any potential booking restrictions before finalizing your reservation.
7. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning, service charges, or taxes are typically outlined in the listing details. Be sure to read the full description or contact the owner for clarification on any extra costs.
8. What amenities are usually included with vacation rentals in this region?
Most properties offer essential amenities like Wi-Fi, kitchen facilities, and parking, but specific features vary. Check the listing details for the complete list of included amenities.
9. How do I secure my reservation at a vacation rental in this area?
Reservations are secured through the booking platform once you select your dates and complete the payment process. For any special requests or questions, contacting the owner directly can help ensure your needs are met.
Dutchess County Top Rated Vacation Rentals
Apartment
10.0(23 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Parking
- Pool
- Ocean View
CA $465/Night
7 Nights - CA $3,258
House
10.0(12 Reviews)
4 Bedrooms
2 Baths
7 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $1,105/Night
7 Nights - CA $7,732
House
10.0(10 Reviews)
5 Bedrooms
3 Baths
13 Guests
4800 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
CA $2,124/Night
7 Nights - CA $14,870
House
10.0(10 Reviews)
5 Bedrooms
3 Baths
10 Guests
5005 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
CA $1,433/Night
7 Nights - CA $10,034
House
10.0(10 Reviews)
4 Bedrooms
2 Baths
7 Guests
3800 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
CA $596/Night
7 Nights - CA $4,171
House
10.0(7 Reviews)
4 Bedrooms
3 Baths
10 Guests
3662 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
CA $2,105/Night
7 Nights - CA $14,734
House
10.0(6 Reviews)
3 Bedrooms
3 Baths
8 Guests
2400 ft²
- Private Pool
- Parking
- Pool
- Ocean View
CA $1,198/Night
7 Nights - CA $8,388
House
10.0(5 Reviews)
5 Bedrooms
3 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $2,415/Night
7 Nights - CA $16,907
