Cottages in Dutchess County

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Dutchess County

Pet-friendly Hopewell Junction Home w/ Pool
Enjoy a meal or relax on the deck with a table and six chairs, surrounded by a grassy area with trees.

Pet-friendly Hopewell Junction Home w/ Pool

3.0 star property
10.0 out of 10, Exceptional, (1)
"This house was so incredible. Not only was it in a quiet nice neighborhood the inside was incredible too. Pool table as well as a pool it was perfect for my stay to have fun and enjoy our time. They were very communicative and welcoming to their house. Everything was comfortable and clean. Can’t say any bad things about this place. Definitely going to book again. I already miss it. "
Pet-friendly Hopewell Junction Home w/ Pool
Fire Pit + On-site Pond: Hudson Valley Home!
House (4 Bedrooms) | Interior

Fire Pit + On-site Pond: Hudson Valley Home!

3.0 star property
Fire Pit + On-site Pond: Hudson Valley Home!
Stylish Pine Plains Home Near Parks & Hiking!
House (1 Bedroom) | Interior

Stylish Pine Plains Home Near Parks & Hiking!

3.0 star property
10.0 out of 10, Exceptional, (1)
Stylish Pine Plains Home Near Parks & Hiking!
Hudson Valley Horse Farm Retreat in Salt Point
House (3 Bedrooms) | Front of property

Hudson Valley Horse Farm Retreat in Salt Point

3.0 star property
8.0 out of 10, Very good, (1)
Hudson Valley Horse Farm Retreat in Salt Point
Modern NY Home w/ Views By Hudson Valley Hiking!
House (3 Bedrooms) | Interior

Modern NY Home w/ Views By Hudson Valley Hiking!

3.0 star property
Modern NY Home w/ Views By Hudson Valley Hiking!
Pet-friendly Beacon Area Vacation Rental: 6 Acres
House (5 Bedrooms) | Interior

Pet-friendly Beacon Area Vacation Rental: 6 Acres

3.0 star property
Pet-friendly Beacon Area Vacation Rental: 6 Acres
Hudson Valley Vacation Rental: Near Hiking
Enjoy al fresco dining on this deck, surrounded by a natural backdrop and a charming white picket fence.

Hudson Valley Vacation Rental: Near Hiking

3.0 star property
Hudson Valley Vacation Rental: Near Hiking
Working Goat Farm - Updated Clinton Corners Home!
House (3 Bedrooms) | Interior

Working Goat Farm - Updated Clinton Corners Home!

3.0 star property
Working Goat Farm - Updated Clinton Corners Home!
Stunning Pawling Retreat w/ Ponds & Waterfall
Welcome to a charming home with a covered porch and garden, perfect for relaxation and socializing.

Stunning Pawling Retreat w/ Ponds & Waterfall

3.0 star property
Stunning Pawling Retreat w/ Ponds & Waterfall
Walk to Downtown: Pet-friendly Millerton Home!
Traditional home with a charming garden and a spacious porch.

Walk to Downtown: Pet-friendly Millerton Home!

3.0 star property
Walk to Downtown: Pet-friendly Millerton Home!
Historic Barn Retreat w/ Pool & Pond Views Longview Pond Lodge by Avantstay
House (3 Bedrooms) | Interior

Historic Barn Retreat w/ Pool & Pond Views Longview Pond Lodge by Avantstay

3.0 star property
Historic Barn Retreat w/ Pool & Pond Views Longview Pond Lodge by Avantstay
Hudson Valley Vacation Rental Near Rhinebeck!
Exterior

Hudson Valley Vacation Rental Near Rhinebeck!

3.0 star property
Hudson Valley Vacation Rental Near Rhinebeck!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Dutchess County Hotel Reviews

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

10/10 Excellent
"Stayed for one night while visiting local historical sites. Place was exceptionally clean and quiet. Poughkeepsie is a nice town with plenty of places to shop or eat. Really liked my room."
Robert 1-night trip
Posted 18 hours ago
Hampton Inn & Suites Poughkeepsie