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
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Popular amenities for Dutchess County house rentals
House rentals with a pool
Home in Rhinebeck
4.96 out of 5 average rating, 164 reviewsOn The Hill in Rhinebeck
Dec. 20 – 27
Home in Pine Plains
4.95 out of 5 average rating, 131 reviewsStylish, Secluded Getaway with Pool & Fireplace
Sep. 13 – 20
Home in Lagrangeville
4.84 out of 5 average rating, 120 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
Sep. 22 – 29
Home in Staatsburg
4.98 out of 5 average rating, 105 reviewsHilltop Escape ~ 25 acre private retreat
Apr. 18 – 25
Home in Saugerties
4.93 out of 5 average rating, 106 reviewsView Top Farmhouse-comfy, cozy get togethers.
Jan. 6 – 13
Home in Saugerties
4.81 out of 5 average rating, 123 reviewsHillside Escape: HITS Home w/ Pool & Hot Tub
Dec. 22 – 29
Home in Millbrook
5.0 out of 5 average rating, 7 reviewsMillbrook serenity and privacy
Jan. 5 – 12
Home in Pleasant Valley
5.0 out of 5 average rating, 73 reviewsHuge HV Retreat: pool/spa/home theater/gym
Dec. 6 – 13
Weekly house rentals
Home in Poughkeepsie
4.97 out of 5 average rating, 164 reviews3 BR|CIA|Marist|King Beds|Pets|Cable| Wifi
Oct. 9 – 16
Home in Carmel Hamlet
4.92 out of 5 average rating, 128 reviewsLux Bungalow on the Lake
Sep. 29 – Oct. 6
Home in Kingston
4.81 out of 5 average rating, 125 reviewsGarden Studio near Waterfront
Oct. 13 – 20
Home in Pawling
4.9 out of 5 average rating, 275 reviewsAppalachian Trail House! Easy access to NYC trains
Jan. 13 – 20
Home in Rhinebeck
4.84 out of 5 average rating, 238 reviewsPrivate Lakefront Bungalow
Jun. 10 – 17
Home in Rhinebeck
4.98 out of 5 average rating, 141 reviewsLong Pond Cottage, Country Retreat in Rhinebeck
Dec. 12 – 19
Home in Beacon
4.96 out of 5 average rating, 309 reviewsRiver & Mtn Views - Jacuzzi - near Metro North
Mar. 14 – 21
Home in Pine Plains
4.98 out of 5 average rating, 110 reviewsTwin Island Lake House • Hot Tub
Oct. 4 – 11
Private house rentals
Home in Pleasant Valley
4.97 out of 5 average rating, 35 reviewsCosmic Hollow
Sep. 24 – Oct. 1
Home in Milan
5.0 out of 5 average rating, 21 reviewsModernist Wooded Retreat Rhinebeck on 75 acres
Mar. 1 – 8
Home in Hyde Park
5.0 out of 5 average rating, 65 reviewsThe Gatehouse in Historic Hyde Park
Jan. 11 – 18
Home in Clinton Corners
5.0 out of 5 average rating, 28 reviewsStylish Farmhouse in the heart of Clinton Corners
Jan. 7 – 14
Home in Pawling
4.96 out of 5 average rating, 24 reviewsCountry Village Getaway
Nov. 27 – Dec. 4
Home in Stanfordville
4.91 out of 5 average rating, 43 reviewsTwin Cedar Pond: Farmhouse w/ Pool House + Hot Tub
Apr. 10 – 17
Home in Ancram
5.0 out of 5 average rating, 35 reviewsAncram / Artist run Victorian / Bohemian
Dec. 28 – Jan. 4
Home in Staatsburg
5.0 out of 5 average rating, 29 reviewsThe Daydream: Hudson River Views, 4 bedrooms & Gym
Oct. 11 – 18
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