Estia Villas - Vacation Rentals in Dutchess County
Villa
9.6
(
19 Reviews
)
8 Bedrooms
8 Bathrooms
20 Guests
-
Private Pool -
Hot Tub -
Parking -
Pool
US $2,656
/Night
7 Nights - $18,590
New
Apartment
1 Bedroom
1 Bathroom
2 Guests
699.65 ft²
-
Parking
-
Pool
-
Balcony/Terrace -
View
US $5,262
/Night
7 Nights - $36,832
Villa
8.4
(
20 Reviews
)
4 Bedrooms
6 Bathrooms
10 Guests
4427 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,317
/Night
7 Nights - $9,216
Villa
2 Bedrooms
1 Bathroom
4 Guests
-
Pool
-
Air Conditioner -
Internet -
Child Friendly
US $765
/Night
7 Nights - $5,352
Villa
4 Bedrooms
2 Bathrooms
9 Guests
4000 ft²
-
Balcony/Terrace
-
Kitchen -
Air Conditioner
-
Internet
US $663
/Night
7 Nights - $4,641
Villa
4 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $392
/Night
7 Nights - $2,742
Villa
2.8
(
3 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $613
/Night
7 Nights - $4,294
Villa
4 Bedrooms
4 Bathrooms
8 Guests
-
Private Pool
-
Hot Tub
-
EV Charge Station -
Parking
US $1,605
/Night
7 Nights - $11,235
See More Dutchess County Vacation Rentals
Luxury Places to Stay in Dutchess County
Over 792+
Luxury Places to Stay in or Near Dutchess County
House
9.0
(
1 Review
)
4 Bedrooms
2 Bathrooms
8 Guests
11840.3 ft²
-
Parking
-
Balcony/Terrace
-
View
-
Air Conditioner
US $5,000
/Night
7 Nights - $35,000
House
10.0
(
30 Reviews
)
8 Bedrooms
5 Bathrooms
12 Guests
10000 ft²
-
Private Pool
-
Hot Tub
-
Breakfast -
Parking
US $3,619
/Night
7 Nights - $25,330
House
9.6
(
58 Reviews
)
7 Bedrooms
7 Bathrooms
20 Guests
8000 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $2,817
/Night
7 Nights - $19,721
New
House
10.0
(
1 Review
)
8 Bedrooms
3 Bathrooms
22 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $2,778
/Night
7 Nights - $19,449
House
6 Bedrooms
4 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $2,334
/Night
7 Nights - $16,335
House
3 Bedrooms
2 Bathrooms
6 Guests
10763.91 ft²
-
Hot Tub
-
View
-
Air Conditioner
-
Internet
US $2,175
/Night
7 Nights - $15,223
House
10.0
(
44 Reviews
)
6 Bedrooms
3 Bathrooms
12 Guests
4550 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $2,149
/Night
7 Nights - $15,046
House
2.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $2,056
/Night
7 Nights - $14,394
Find More Dutchess County Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Dutchess County
Over 179+
Top-Rated Vacation Rentals with a Pool in or Near Dutchess County
House
10.0
(
71 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
-
Private Pool
-
Parking
-
Pool
-
Ocean View
US $1,037
/Night
7 Nights - $7,259
New
House
10.0
(
25 Reviews
)
5 Bedrooms
3 Bathrooms
13 Guests
4000 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $882
/Night
7 Nights - $6,173
Apartment
10.0
(
23 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Private Pool
-
Parking
-
Pool
-
Ocean View
US $328
/Night
7 Nights - $2,293
House
10.0
(
12 Reviews
)
4 Bedrooms
2 Bathrooms
7 Guests
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $749
/Night
7 Nights - $5,241
House
10.0
(
10 Reviews
)
5 Bedrooms
3 Bathrooms
13 Guests
4800 ft²
-
Hot Tub
-
Parking
-
Pool
-
Ocean View
US $1,515
/Night
7 Nights - $10,607
House
10.0
(
10 Reviews
)
5 Bedrooms
3 Bathrooms
10 Guests
5005 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,099
/Night
7 Nights - $7,693
House
10.0
(
9 Reviews
)
4 Bedrooms
2 Bathrooms
7 Guests
3800 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $417
/Night
7 Nights - $2,922
House
10.0
(
7 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
3662 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,411
/Night
7 Nights - $9,875
Pet-Friendly Vacation Rentals in Dutchess County
Over 314+
Pet-Friendly Vacation Rentals in or Near Dutchess County
House
10.0
(
66 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1500 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $635
/Night
7 Nights - $4,442
Ski Chalet
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
6 Guests
1097.92 ft²
-
Breakfast
-
Parking
-
Kitchen
-
Air Conditioner
US $238
/Night
7 Nights - $1,666
Cottage
1 Bedroom
1 Bathroom
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $986
/Night
7 Nights - $6,904
House
9.8
(
63 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Private Pool
-
Parking
-
Pool
-
Ocean View
US $581
/Night
7 Nights - $4,070
House
10.0
(
14 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
2300 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $650
/Night
7 Nights - $4,549
Apartment
10.0
(
4 Reviews
)
1 Bedroom
1 Bathroom
1 Guest
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $232
/Night
7 Nights - $1,623
House
10.0
(
129 Reviews
)
5 Bedrooms
3 Bathrooms
14 Guests
3400 ft²
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $933
/Night
7 Nights - $6,533
Apartment
10.0
(
54 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $271
/Night
7 Nights - $1,897
See More Pet-Friendly Vacation Rentals in Dutchess County on PetFriendly.io
Large Vacation Homes & Villas in Dutchess County
Over 121+
Large Vacation Homes & Villas in or Near Dutchess County
House
10.0
(
10 Reviews
)
5 Bedrooms
5 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $1,266
/Night
7 Nights - $8,860
House
5 Bedrooms
3 Bathrooms
10 Guests
2497.23 ft²
-
Parking
-
Pool
-
Ocean View
-
View
US $640
/Night
7 Nights - $4,480
House
10.0
(
5 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $614
/Night
7 Nights - $4,296
House
10.0
(
2 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
4911 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $949
/Night
7 Nights - $6,641
Cabin
10.0
(
1 Review
)
6 Bedrooms
5 Bathrooms
12 Guests
5500 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $1,710
/Night
7 Nights - $11,973
House
9.6
(
7 Reviews
)
5 Bedrooms
5 Bathrooms
10 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $1,119
/Night
7 Nights - $7,832
House
9.6
(
4 Reviews
)
5 Bedrooms
2 Bathrooms
18 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $601
/Night
7 Nights - $4,205
House
9.2
(
18 Reviews
)
5 Bedrooms
2 Bathrooms
10 Guests
3000 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $686
/Night
7 Nights - $4,799
See More Family Vacation Rentals in Dutchess County on FVR
Wheelchair Accessible Vacation Homes in Dutchess County
Over 67+
Wheelchair Accessible Vacation Homes in or Near Dutchess County
Apartment
9.8
(
7 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
560 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $117
/Night
7 Nights - $816
Apartment
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
4 Guests
1001.04 ft²
-
Parking
-
Air Conditioner
-
Pet Friendly -
Child Friendly
US $184
/Night
7 Nights - $1,288
Bed & Breakfast
7.8
(
31 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Kitchen
US $225
/Night
7 Nights - $1,576
House
10.0
(
2 Reviews
)
4 Bedrooms
4 Bathrooms
6 Guests
4700 ft²
-
Private Pool
-
Hot Tub
-
Breakfast
-
Parking
US $1,250
/Night
7 Nights - $8,750
House
4.7
(
17 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Wheelchair Accessible
US $299
/Night
7 Nights - $2,093
House
10.0
(
25 Reviews
)
5 Bedrooms
2 Bathrooms
8 Guests
2018 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $575
/Night
7 Nights - $4,028
House
10.0
(
1 Review
)
3 Bedrooms
3 Bathrooms
6 Guests
-
Hot Tub
-
Parking
-
Spa -
Balcony/Terrace
US $617
/Night
7 Nights - $4,320
House
9.8
(
34 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
2000 ft²
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Kitchen
US $421
/Night
7 Nights - $2,948
Dutchess County Vacation Rentals and Airbnb Places to Stay Under $200
Over 169+
Dutchess County Vacation Rentals and Airbnb Places to Stay Under $200
House
10.0
(
7 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
904.17 ft²
-
Parking
-
Internet
-
Child Friendly
-
Sports/Activities
US $153
/Night
7 Nights - $1,071
Apartment
10.0
(
18 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
301 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $148
/Night
7 Nights - $1,036
House
9.2
(
205 Reviews
)
1 Bedroom
1 Bathroom
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $168
/Night
7 Nights - $1,178
Apartment
10.0
(
17 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
301 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $116
/Night
7 Nights - $810
Apartment
10.0
(
16 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
355 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $113
/Night
7 Nights - $792
Apartment
10.0
(
16 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
301 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $104
/Night
7 Nights - $729
New
Apartment
10.0
(
15 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
355 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $113
/Night
7 Nights - $792
Apartment
10.0
(
13 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
301 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $104
/Night
7 Nights - $729
Instantly Bookable Vacation Homes in Dutchess County
Over 309+
Instantly Bookable Vacation Homes in or Near Dutchess County
Apartment
10.0
(
190 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
600 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $288
/Night
7 Nights - $2,017
Apartment
9.4
(
9 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $243
/Night
7 Nights - $1,703
Cabin
10.0
(
92 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
480 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $352
/Night
7 Nights - $2,467
House
10.0
(
75 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $743
/Night
7 Nights - $5,203
House
10.0
(
71 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
2750 ft²
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $592
/Night
7 Nights - $4,142
New
Cottage
10.0
(
49 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $301
/Night
7 Nights - $2,110
Cottage
10.0
(
39 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1000 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $396
/Night
7 Nights - $2,770
Apartment
10.0
(
31 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $327
/Night
7 Nights - $2,289
About Dutchess County Vacation Rentals
With more than 8 Dutchess County vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Dutchess County.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Dutchess County, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Dutchess County. Places to stay near Dutchess County are 1140.83 ft² on average, with prices averaging US $1,659 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Dutchess County with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Use these Quick Filters to Find a Vacation Rental in Dutchess County
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Dutchess County.
Weather in Dutchess County
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
Estiavillas 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 Near Dutchess County, NY
Lower Hudson Valley
2,222 Properties
Poughkeepsie
587 Properties
Hopewell Junction
114 Properties
Town of East Fishkill
109 Properties
Staatsburg
51 Properties
Fishkill
46 Properties
Hyde Park
44 Properties
Clinton Corners
39 Properties
Beacon
31 Properties
Rhinebeck
28 Properties
Town of Stanford
25 Properties
Pine Plains
25 Properties
Complexes around Dutchess County, NY
Fishkill Inn
15 Properties
Quality Inn
3 Properties
Courtyard
3 Properties
Hampton Inn Poughkeepsie
3 Properties
Holiday Inn Express Poughkeepsie Ihg Hotel
3 Properties
Hyatt
3 Properties
Springhill
3 Properties
The Inn At Falls
3 Properties
The City Cottage
2 Properties
Tentrr Hudson Valley Hilltop Campsite
1 Properties
Tentrr State Park Site Mills
1 Properties
Dutchess County Vacation Rental Frequently Asked Questions
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:
- Rhinebrook Estate - 8 Bed/8Bath + Pool (Sleeps 20)
- The Scenic Mansion With Breathtaking View
- Villa Sabrina
- Charming 2-bedroom villa in serene Holmes with AC, WiFi
- Spacious 1 BR Unit w/Washer-Dryer and Parking
- Serene Mid-century Villa with a pool 1.5h from NYC
- Fabulous Designer Spa Retreat
- Hudson Valley mid century house w/stunning views
How many vacation rentals have private pools in Dutchess County?
There are 94 vacation rentals with private pools near Dutchess County. Top-rated homes that have access to a swimming pool include:
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:
How many vacation rentals are available in Dutchess County?
Currently, the total number of properties listed in 2026 is over 8 in the Dutchess County area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Dutchess County.
