House vacation rentals in Dutchess County
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Top-rated house rentals in Dutchess County
Guests agree: these houses 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 house rentals
House rentals with a pool
Home in Pine Plains
4.95 out of 5 average rating, 131 reviewsStylish, Secluded Getaway with Pool & Fireplace
May 27 – Jun 3
Home in Rhinebeck
4.96 out of 5 average rating, 164 reviewsOn The Hill in Rhinebeck
Nov 22 – 29
Home in Lagrangeville
4.84 out of 5 average rating, 120 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
Sep 27 – Oct 4
Home in Staatsburg
4.98 out of 5 average rating, 105 reviewsHilltop Escape ~ 25 acre private retreat
Home in Saugerties
4.81 out of 5 average rating, 123 reviewsHillside Escape: HITS Home w/ Pool & Hot Tub
Mar 23 – 30
Home in Saugerties
4.93 out of 5 average rating, 106 reviewsView Top Farmhouse-comfy, cozy get togethers.
Jan 29 – Feb 5
Home in Millbrook
5.0 out of 5 average rating, 7 reviewsMillbrook serenity and privacy
Dec 29 – Jan 5
Home in Stanfordville
4.98 out of 5 average rating, 40 reviewsCharming lakeside cabin with private heated pool
Sep 12 – 19
Weekly house rentals
Home in Rhinebeck
4.97 out of 5 average rating, 120 reviewsHoneybug Snug near Omega Institute!
Jan 29 – Feb 5
Home in Pawling
4.9 out of 5 average rating, 275 reviewsAppalachian Trail House! Easy access to NYC trains
Oct 4 – 11
Home in Rhinebeck
4.98 out of 5 average rating, 142 reviewsLong Pond Cottage, Country Retreat in Rhinebeck
Dec 31 – Jan 7
Home in Poughkeepsie
4.97 out of 5 average rating, 175 reviews4BR|2Bath|King Beds|Walk to Marist|CIA|Pet|Parking
Oct 11 – 18
Home in Rhinebeck
4.83 out of 5 average rating, 239 reviewsPrivate Lakefront Bungalow
Sep 22 – 29
Home in Millbrook
4.9 out of 5 average rating, 139 reviewsSerene Waterfront Mill House, Stroll to Village
Mar 3 – 10
Home in Pine Plains
4.98 out of 5 average rating, 110 reviewsTwin Island Lake House • Hot Tub
Feb 10 – 17
Home in Beacon
4.96 out of 5 average rating, 310 reviewsRiver & Mtn Views - Jacuzzi - near Metro North
Nov 6 – 13
Private house rentals
Home in Milan
5.0 out of 5 average rating, 21 reviewsModernist Wooded Retreat Rhinebeck on 75 acres
Apr 22 – 29
Home in Hyde Park
5.0 out of 5 average rating, 65 reviewsThe Gatehouse in Historic Hyde Park
Oct 9 – 16
Home in Pawling
4.97 out of 5 average rating, 76 reviewsFarmhouse Oasis in the Hudson Valley, Stream Views
May 17 – 24
Home in West Park
4.95 out of 5 average rating, 42 reviewsRustic Hudson R. home with firepit/bar/billiard
Aug 8 – 15
Home in Dover Plains
5.0 out of 5 average rating, 52 reviewsMillstone Manor with East Mountain View
May 12 – 19
Home in Staatsburg
5.0 out of 5 average rating, 29 reviewsThe Daydream: Hudson River Views, 4 bedrooms & Gym
Oct 14 – 21
Home in Hyde Park
4.96 out of 5 average rating, 76 reviewsCozy Historic Piersaull House - Charming & Quirky!
Dec 31 – Jan 7
Home in Clinton Corners
5.0 out of 5 average rating, 35 reviewsEnjoy the Hudson Valley at our quiet Farmhouse!
May 7 – 14
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