
Guesthouse vacation rentals in Dutchess County
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Top-rated guesthouse rentals in Dutchess County
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Vacation rentals for every style
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Popular amenities for Dutchess County guesthouse rentals
Family-friendly guest house rentals
Guest favorite

Guesthouse in Tivoli
4.94 out of 5 average rating, 255 reviewsLight-filled guest cottage
Top guest favorite

Guesthouse in Pine Plains
4.97 out of 5 average rating, 79 reviewsCozy Cottage by the Pond

Guesthouse in Red Hook
4.88 out of 5 average rating, 114 reviewsCharming country cottage near Rhinebeck
Superhost

Guesthouse in Stormville
4.97 out of 5 average rating, 174 reviewsHudson Valley Cottage with Pond Access
Guest favorite

Guesthouse in Beacon
4.94 out of 5 average rating, 400 reviewsCozy Mountainside Suite - Minutes from Beacon
Superhost

Guesthouse in Pine Plains
4.57 out of 5 average rating, 30 reviewsRustic 2 bedroom Stissing Lake Guest Cabin
Guest house rentals with a patio
Top guest favorite

Guesthouse in Cold Spring
5 out of 5 average rating, 11 reviewsCold Spring Woodland Retreat 5 Bed 2.5 Bath
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Guesthouse in Staatsburg
5 out of 5 average rating, 12 reviewsAberdeen Farm
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Guesthouse in Wingdale
5 out of 5 average rating, 5 reviewsMountain Creek Getaway
Guest favorite

Guesthouse in Beacon
5 out of 5 average rating, 8 reviewsThe Beacon Woods
Guest favorite

Guesthouse in Saugerties
4.97 out of 5 average rating, 65 reviewsLittle Bliss Pond House
Top guest favorite

Guesthouse in Beacon
4.97 out of 5 average rating, 34 reviewsSpacious Trailside Studio
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Guesthouse in Kingston
5 out of 5 average rating, 132 reviewsChic, Private Cabin with Stunning River Views
Top guest favorite

Guesthouse in Millerton
4.96 out of 5 average rating, 23 reviewsThree Corner Farm
Guest house rentals with a washer and dryer
Top guest favorite

Guesthouse in Millbrook
5 out of 5 average rating, 42 reviewsCottage on Coddington Lane
Guest favorite

Guesthouse in Red Hook
4.94 out of 5 average rating, 93 reviewsPrivate Cottage, Walk to Restaurants and Shops
Guest favorite

Guesthouse in Marlboro Township
4.87 out of 5 average rating, 45 reviewsCharming 1850's Guest House in Nature

Guesthouse in Brewster
5 out of 5 average rating, 4 reviewsHidden Hope Cottage
Guest favorite

Guesthouse in Wappingers Falls
4.91 out of 5 average rating, 11 reviews1723 Guesthouse
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- Taconic State Park
- Resorts World Catskills
- Catamount Mountain Ski Resort
- Zoom Flume
- Windham Mountain
- Kent Falls State Park
- Rockland Lake State Park
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- Sterling Forest State Park
- The Stanwich Club
- The Connecticut Golf Club
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Beartown State Forest
- Hancock Shaker Village
- Hunter Mountain Resort
- Things to do Dutchess County
- Nature and outdoors Dutchess County
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