House holiday 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.
Holiday 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
22–29 Dec
Home in Pine Plains
4.95 out of 5 average rating, 131 reviewsStylish, Secluded Getaway with Pool & Fireplace
21–28 Aug
Home in Lagrangeville
4.84 out of 5 average rating, 120 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
27 Sep – 4 Oct
Home in Saugerties
4.81 out of 5 average rating, 123 reviewsHillside Escape: HITS Home w/ Pool & Hot Tub
6–13 Oct
Home in Saugerties
4.93 out of 5 average rating, 106 reviewsView Top Farmhouse-comfy, cozy get togethers.
4–11 Apr
Home in Millbrook
5.0 out of 5 average rating, 7 reviewsMillbrook serenity and privacy
30 Dec – 6 Jan
Home in Wappingers Falls
5.0 out of 5 average rating, 39 reviewsLuxe Modern Retreat with Outdoor Spa
3–10 May
Home in Stanfordville
4.98 out of 5 average rating, 40 reviewsCharming lakeside cabin with private heated pool
7–14 Sep
Weekly house rentals
Home in Carmel Hamlet
4.92 out of 5 average rating, 129 reviewsLux Bungalow on the Lake
29 Sep – 6 Oct
Home in Poughkeepsie
4.97 out of 5 average rating, 164 reviews3 BR|CIA|Marist|King Beds|Pets|Cable| Wifi
11–18 Oct
Home in Pawling
4.9 out of 5 average rating, 275 reviewsAppalachian Trail House! Easy access to NYC trains
18–25 Feb
Home in Rhinebeck
4.83 out of 5 average rating, 239 reviewsPrivate Lakefront Bungalow
13–20 Jun
Home in Rhinebeck
4.98 out of 5 average rating, 141 reviewsLong Pond Cottage, Country Retreat in Rhinebeck
9–16 Nov
Home in Beacon
4.96 out of 5 average rating, 310 reviewsRiver & Mtn Views - Jacuzzi - near Metro North
10–17 Sep
Home in Pine Plains
4.98 out of 5 average rating, 110 reviewsTwin Island Lake House • Hot Tub
3–10 Mar
Home in Poughkeepsie
5.0 out of 5 average rating, 10 reviewsNewly Renovated Studio - In Heart of Poughkeepsie
2–9 Nov
Private house rentals
Home in Hyde Park
5.0 out of 5 average rating, 65 reviewsThe Gatehouse in Historic Hyde Park
5–12 Jul
Home in Milan
5.0 out of 5 average rating, 21 reviewsModernist Wooded Retreat Rhinebeck on 75 acres
16–23 Jul
Home in Hyde Park
4.93 out of 5 average rating, 76 reviewsHyde Parks Hideaway
5–12 Jan
Home in Pawling
4.97 out of 5 average rating, 76 reviewsFarmhouse Oasis in the Hudson Valley, Stream Views
18–25 Oct
Home in Pleasant Valley
4.97 out of 5 average rating, 35 reviewsCosmic Hollow
22–29 Jun
Home in Staatsburg
5.0 out of 5 average rating, 29 reviewsThe Daydream: Hudson River Views, 4 bedrooms & Gym
21–28 Sep
Home in Dover Plains
5.0 out of 5 average rating, 52 reviewsMillstone Manor with East Mountain View
27 Oct – 3 Nov
Home in Stanfordville
4.91 out of 5 average rating, 43 reviewsTwin Cedar Pond: Farmhouse w/ Pool House + Hot Tub
1–8 Mar
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