
Dutchess County vacation rentals
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Top-rated vacation rentals in Dutchess County
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Dutchess County vacation rentals
Other great vacation rentals in Dutchess County
Top guest favorite

Home in Millerton
4.96 out of 5 average rating, 189 reviewsVacation Home In Millerton
Top guest favorite

Home in Saugerties
5 out of 5 average rating, 115 reviewsSaugerties Log Home W/ Game Room
Superhost

Home in Millerton
4.88 out of 5 average rating, 25 reviewsFarmhouse with a view, hot tub, pool, and fire pit
Guest favorite

Home in Beacon
4.91 out of 5 average rating, 98 reviewsBeacon 2BR house w/ backyard, easy walk to main st
Superhost

Home in Lake Katrine
4.79 out of 5 average rating, 24 reviewsStylish Retro Escape!3 Bed 2 bath/2 decks
Superhost

Apartment in Beacon
4.85 out of 5 average rating, 107 reviewsLovely 2 bed, 2 full bath. & private yard getaway
Superhost

Tiny home in Poughkeepsie
4.85 out of 5 average rating, 115 reviewsLake Side Tiny House
Superhost

Home in Holmes
4.83 out of 5 average rating, 18 reviewsCountry outside the city
Destinations to explore
- Waterfront rentals Dutchess County
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- Rentals with a fire pit Dutchess County
- Kid-friendly rentals Dutchess County
- Rentals with lake access Dutchess County
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- Rentals with a hot tub Dutchess County
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Windham Mountain
- Minnewaska State Park Preserve
- Catamount Mountain Ski Resort
- The Kartrite Resort & Indoor Waterpark
- Resorts World Catskills
- Rockland Lake State Park
- Taconic State Park
- Thunder Ridge Ski Area
- Walkway Over the Hudson State Historic Park
- Brotherhood, America's Oldest Winery
- The Connecticut Golf Club
- Zoom Flume
- Hudson Highlands State Park
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Sterling Forest State Park
- Mount Peter Ski Area
- Hook Mountain State Park
- Tamarack Country Club
- Opus 40
- Bash Bish Falls State Park
- Kent Falls State Park
- Things to do Dutchess County
- Nature and outdoors Dutchess County
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- Things to do United States
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- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes