Dutchess County vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Dutchess County
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Dutchess County vacation rentals
Other great vacation rentals in Dutchess County
Guest suite in Rhinebeck
4.91 out of 5 average rating, 384 reviewsContemporary Rhinebeck Private Village Retreat
Nov 5 – 10
Cottage in Pine Plains
4.98 out of 5 average rating, 120 reviewsPine Plains Cottage
Sep 10 – 17
Apartment in Millbrook
4.98 out of 5 average rating, 280 reviewsBlue Cottage Apartment in Village of Millbrook
Nov 17 – 24
Cabin in Rhinebeck
4.91 out of 5 average rating, 298 reviewsSunset Bungalow-Mt views on 130acre forest & falls
Sep 27 – Oct 4
Guest suite in Marlboro
4.96 out of 5 average rating, 397 reviewsSpacious & Private Hudson Valley Getaway
Aug 5 – 12
Cottage in Clinton Corners
4.94 out of 5 average rating, 162 reviewsbrand new (Hudson Valley) Laughing Duck Cottage
Oct 7 – 14
Guest suite in Dover Plains
4.91 out of 5 average rating, 262 reviewsHoppy Hill Farm House
Sep 18 – 25
Cottage in Ulster Park
4.94 out of 5 average rating, 186 reviewsHidden Gem Cottage — cozy escape to play or WFH
Jan 7 – 14
Other great vacation rentals in Dutchess County
Farm stay in Red Hook
4.78 out of 5 average rating, 259 reviewsFarmland Tranquility at The Greig Farm Schoolhouse
Oct 16 – 23
Cabin in Red Hook
4.96 out of 5 average rating, 306 reviewsModern Upstate Cabin, near Rhinebeck NY
Aug 22 – 29
Cottage in Red Hook
4.98 out of 5 average rating, 599 reviewsbright serene + spacious barn
Nov 6 – 13
Apartment in Hopewell Junction
4.82 out of 5 average rating, 17 reviewsCozy Gem in Hopewell
Jan 24 – 31
Apartment in Amenia
5.0 out of 5 average rating, 26 reviewsAmenia Main St Cozy Studio
Oct 28 – Nov 4
Apartment in Fishkill
5.0 out of 5 average rating, 20 reviews1 Bedroom Apartment on Main St.
Aug 28 – Sep 4
Apartment in Highland
4.97 out of 5 average rating, 36 reviewsLovely 1-bedroom loft apartment in the hamlet
Sep 26 – Oct 3
Apartment in Pawling
5.0 out of 5 average rating, 20 reviewsQuiet Studio Apartment in Pawling
Jul 16 – 23
Destinations to explore
- Bed and breakfasts Dutchess County
- Rentals with a washer and dryer Dutchess County
- House rentals Dutchess County
- Family-friendly rentals Dutchess County
- Rentals with a kayak Dutchess County
- Monthly Rentals Dutchess County
- Rentals with beach access Dutchess County
- Cottage rentals Dutchess County
- Kid-friendly rentals Dutchess County
- Rentals with pools Dutchess County
- Rentals with a patio Dutchess County
- Farmstay rentals Dutchess County
- Rentals with a fire pit Dutchess County
- Pet-friendly rentals Dutchess County
- Rentals with breakfast Dutchess County
- Rentals with outdoor seating Dutchess County
- Rentals with lake access Dutchess County
- Rentals with a hot tub Dutchess County
- Private suite rentals Dutchess County
- Waterfront rentals Dutchess County
- Apartment rentals Dutchess County
- Tiny house rentals Dutchess County
- Beachfront rentals Dutchess County
- Rentals with a fireplace Dutchess County
- Guesthouse rentals Dutchess County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom