Holiday rentals in Dover Plains
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Top-rated holiday rentals in Dover Plains
Guests agree: these stays are highly rated for location, cleanliness and more.
Flat in Kent
4.93 out of 5 average rating, 127 reviewsLoft 22
Apartment/loft located above the garage in a private home. Set in the rolling hills of Kent, this 2 bedroom loft is cozy enough for anyone looking to explore this quaint little town. Sleeps 3 comfortably. Centrally located to all three private schools. 11 minute drive to Harlem Valley/Wingdale (NY) train station. *Pool is not solely for the use of the Air BNB. *Dogs on property. All friendly. *IF STAYING IN WINTER MONTHS. You must have 4 Wheel drive vehicle. Driveway/Road is long dirt road.*
11–18 Mar
Cabin in New Milford
4.95 out of 5 average rating, 143 reviewsThe Cottage on Babbling Brook
Cozy, rustic cottage. Beautifully overlooking Wimsink Brook, with custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.
30 Nov – 7 Dec
Guest suite in Dover Plains
4.91 out of 5 average rating, 261 reviewsHoppy Hill Farm House
Enjoy the simple country life in this historic farmhouse. Watch the sun rise over the breathtaking mountain views from the front porch while sipping a cup of coffee/tea. For the more adventurous, there are lots of Appalachian Trail hiking opportunities, and nature preserves to enjoy. Thunder Ridge ski mountain and Daryl Hall’s bar only 15 mins away. Take a ride to near-by towns (Kent, Millbrook, Amenia, Wassaic) for great food, coffee shops, antiques, parks, breweries and vineries.
4–11 Jun
Holiday rentals for every style
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Popular amenities for Dover Plains holiday rentals
Other great holiday rentals in Dover Plains
Home in Pawling
4.9 out of 5 average rating, 269 reviewsAppalachian Trail House! Easy access to NYC trains
14–21 Jan
Cottage in Sharon
4.9 out of 5 average rating, 120 reviewsFoxfire Hill: A Bit of Luxury in the Countryside
21–28 Apr
Flat in Millbrook
4.98 out of 5 average rating, 278 reviewsBlue Cottage Apartment in Village of Millbrook
18–25 Jul
Home in Millerton
4.95 out of 5 average rating, 110 reviewsVacation Home In Millerton
17–24 Nov
Flat in Copake Falls
4.93 out of 5 average rating, 250 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
14–21 Sep
Guest house in Dover Plains
4.88 out of 5 average rating, 82 reviewsSpilt Milk Cottage - Hudson Valley, NY
9–16 Dec
Flat in Amenia
5.0 out of 5 average rating, 18 reviewsAmenia Main St Cozy Studio
11–18 Sep
Home in Dover Plains
5.0 out of 5 average rating, 52 reviewsMillstone Manor with East Mountain View
21–28 Jul
Guest suite in Kent
5.0 out of 5 average rating, 52 reviewsBright 1-bedroom in walking distance to town
8–15 Feb
Home in Dover Plains
4.91 out of 5 average rating, 33 reviews5 Harts Rd - Newly built home in Dover, NY
2–9 Jun
Home in Dover Plains
4.88 out of 5 average rating, 32 reviewsPastoral Country Retreat
21–28 Oct
Guest house in Sharon
5.0 out of 5 average rating, 59 reviewsCottage with a Waterfall View
19–26 Aug
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