Cottage holiday rentals in Sleepy Hollow
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Top-rated cottage rentals in Sleepy Hollow
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Holiday rentals for every style
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Popular amenities for cottage rentals in Sleepy Hollow
Cottage rentals with a hot tub
Cottage in Greenwood Lake
4.86 out of 5 average rating, 138 reviewsCozy Cottage | HotTub & Family Rm | 1H fr NYC
2–9 Jan
Cottage in Kerhonkson
4.84 out of 5 average rating, 141 reviewsGunks Cottage|Fire Pit|Pool|Near Minnewaska Park
9–16 Dec
Cottage in Highland Lakes
4.97 out of 5 average rating, 268 reviewsThe Mountaintop Lakehouse that Time Forgot.
17–24 Oct
Cottage in Kent
4.88 out of 5 average rating, 153 reviewsNEW - Hot Tub - Mohawk Mtn - Appalachian Trl
11–18 Mar
Cottage in Kerhonkson
4.84 out of 5 average rating, 252 reviewsStony Kill Ranch - Hot Tub and Waterfall Access
10–17 Jun
Cottage in Monticello
4.98 out of 5 average rating, 108 reviewsRustic Chic hidden Gem in the southern Catskills.
29 Aug – 5 Sep
Cottage in Kerhonkson
5.0 out of 5 average rating, 87 reviewsYe Little Wood | Cozy Forest Cottage with Hot Tub
4–11 Feb
Cottage in Danbury
4.92 out of 5 average rating, 71 reviewsThe Nugget: Sunlit Cottage with Hot Tub & Fire Pit
2–9 Dec
Pet-friendly cottage rentals
Cottage in Newtown
4.92 out of 5 average rating, 164 reviewsPrivate and Serene home close to I-84 and shopping
14–21 Aug
Cottage in Kerhonkson
4.86 out of 5 average rating, 160 reviewsKerhonkson cottage in the woods with stream
30 May – 6 Jun
Cottage in Redding
4.93 out of 5 average rating, 232 reviewsCozy Cottage by the pond
15–22 Jun
Cottage in Kerhonkson
4.91 out of 5 average rating, 379 reviewsHome Alone Woods
23–30 Jul
Cottage in Rhinebeck
4.95 out of 5 average rating, 232 reviewsRidgetop 2 Br Cabin- Views, 130acre forest & falls
21–28 Sep
Cottage in Bloomington
4.98 out of 5 average rating, 468 reviews'The Blue Jay Cottage' - Privacy With A View!
24 Jun – 1 Jul
Cottage in Philipstown
4.99 out of 5 average rating, 178 reviewsModern Country Cottage by Bear Mountain
8–15 Sep
Cottage in Poughkeepsie
4.91 out of 5 average rating, 301 reviewsBe in Nature at this Gorgeous Riverfront Cabin
20–27 Mar
Private cottage rentals
Cottage in Rosendale
4.99 out of 5 average rating, 123 reviewsSweet Green Rosendale Cottage
19–26 Sep
Cottage in South Salem
4.96 out of 5 average rating, 113 reviewsSerene lake front cottage 1 hour from NYC
2–9 Oct
Cottage in Clintondale
4.93 out of 5 average rating, 167 reviewsThe cottage at Maple Ave - upstate mountain view
9–16 Jul
Cottage in Parksville
4.97 out of 5 average rating, 240 reviewsRolling River Guest House ~ Cozy & Fun
16–23 Sep
Cottage in West Park
4.84 out of 5 average rating, 195 reviewsRustic, Sunny, Little Red Cottage in the Woods
19–26 Aug
Cottage in Matamoras
4.98 out of 5 average rating, 141 reviewsThe Cottage at Bluestone Falls
7–14 Nov
Cottage in Ulster Park
4.94 out of 5 average rating, 186 reviewsHidden Gem Cottage — cozy escape to play or WFH
21–28 Mar
Cottage in Vernon Township
4.86 out of 5 average rating, 125 reviewsDream Lakefront Home + Skiing near NYC
23–30 Oct
Destinations to explore
- New City Holiday rentals
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