Holiday rentals in Dutchess County

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Top-rated holiday rentals in Dutchess County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Cottage in Clinton Corners
brand new (Hudson Valley) Laughing Duck Cottage
Located in the bucolic Hudson Valley, this new, gut-renovated cottage isn't far from many of the area's most loved spots. In the winter you can wander trails and get cozy by our electric fireplace. In the spring you can picnic your way through historic sites and enjoy a glass of local wine on our back deck. In the summer you can ride a horse and cook with seasonal ingredients from local farms. In the fall you can hike through the Hudson Valley's perfect colors and sip hot cider on our back deck.
25 Oct – 1 Nov
$236 SGD per night
4.94 out of 5 average rating, 155 reviews
Superhost
Cottage in West Park
Rustic, Sunny, Little Red Cottage in the Woods
Just outside of New Paltz, the cottage is 400 square feet, plus loft area, in addition to a 120-square-foot (winterized) screened-in porch with bistro table and additional relaxation spots. The main room hosts a double-size, comfortable futon couch, a dining table for four or more, a fully equipped kitchen providing all the basic amenities. The loft (up a ladder) hosts a super-comfy queen-sized bed. There is a small stone patio with an outdoor dining table with umbrella and a barbeque grill.
19–26 Aug
$141 SGD per night
4.83 out of 5 average rating, 190 reviews
Guest favourite
Home in Rhinebeck
3Br Creekside Cottage on 130 acre forest w/ trails
Creekside Cottage is an extraordinary private escape nestled against a winding creek running through the rocky gorge of an 130 acre magical historic farm. Explore miles of hiking trails through old forests, trout creeks, and a 90ft waterfall or simply relax by the fire pit while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplaces, great wifi and comfortable bedrooms with quiet workspaces- learn more on our site cascadafarm
11–18 May
$242 SGD per night
4.92 out of 5 average rating, 165 reviews

Popular amenities for Dutchess County holiday rentals

Other great holiday rentals in Dutchess County

Guest favourite
Flat in Rhinebeck
Gorgeous private apartment in Rhinebeck Village
3–10 Nov
$122 SGD per night
4.95 out of 5 average rating, 438 reviews
Guest favourite
Cottage in Rhinebeck
Refined, Intimate Cottage on Private Estate
19–26 Apr
$259 SGD per night
4.95 out of 5 average rating, 116 reviews
Guest favourite
Flat in Rhinebeck
Rhinebeck Ridge - A Woodland Studio Retreat
16–21 Jul
$180 SGD per night
4.99 out of 5 average rating, 161 reviews
Guest favourite
Tiny home in Marlboro
Orchard Views from a Light-Filled Tiny Home with a Fire Pit
8–15 Jul
$173 SGD per night
4.96 out of 5 average rating, 277 reviews
Guest favourite
Home in Stormville
Private Hudson Valley Country Retreat
15–22 May
$936 SGD per night
4.94 out of 5 average rating, 156 reviews
Guest favourite
Flat in Stanfordville
Country Apartment great for a romantic getaway
15–22 May
$161 SGD per night
4.95 out of 5 average rating, 151 reviews
Guest favourite
Flat in Staatsburg
Through the Woods Farm
1–8 Sep
$178 SGD per night
5.0 out of 5 average rating, 187 reviews
Guest favourite
Home in Hyde Park
Cozy ranch near FDR Historical Site
25 Jun – 2 Jul
$221 SGD per night
4.9 out of 5 average rating, 467 reviews
Guest favourite
Flat in Amenia
Amenia Main St Cozy Studio
1–8 Aug
$89 SGD per night
5.0 out of 5 average rating, 17 reviews
Guest favourite
Guest house in Dover Plains
Spilt Milk Cottage - Hudson Valley, NY
13–20 Nov
$133 SGD per night
4.88 out of 5 average rating, 82 reviews
Guest favourite
Cottage in Clinton Corners
Sun Bear Cottage: 3-Bdrm with Sauna
20–27 Feb
$389 SGD per night
5.0 out of 5 average rating, 13 reviews
Guest favourite
Cottage in Pawling
Twin Lakes Designer A-frame Stone Cottage
6–13 Jan
$422 SGD per night
5.0 out of 5 average rating, 59 reviews

Destinations to explore