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.

Guest favourite

Flat in Kent

4.93 out of 5 average rating, 127 reviews

Loft 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

€ 154 per night
Guest favourite

Cabin in New Milford

4.95 out of 5 average rating, 143 reviews

The 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

€ 269 per night
Guest favourite

Guest suite in Dover Plains

4.91 out of 5 average rating, 261 reviews

Hoppy 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

€ 148 per night

Popular amenities for Dover Plains holiday rentals

Other great holiday rentals in Dover Plains

Guest favourite

Home in Pawling

4.9 out of 5 average rating, 269 reviews

Appalachian Trail House! Easy access to NYC trains

14–21 Jan

€ 207 per night
Guest favourite

Cottage in Sharon

4.9 out of 5 average rating, 120 reviews

Foxfire Hill: A Bit of Luxury in the Countryside

21–28 Apr

€ 195 per night
Guest favourite

Flat in Millbrook

4.98 out of 5 average rating, 278 reviews

Blue Cottage Apartment in Village of Millbrook

18–25 Jul

€ 199 per night
Guest favourite

Home in Millerton

4.95 out of 5 average rating, 110 reviews

Vacation Home In Millerton

17–24 Nov

€ 187 per night
Guest favourite

Flat in Copake Falls

4.93 out of 5 average rating, 250 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

14–21 Sep

€ 122 per night
Superhost

Guest house in Dover Plains

4.88 out of 5 average rating, 82 reviews

Spilt Milk Cottage - Hudson Valley, NY

9–16 Dec

€ 115 per night
Guest favourite

Flat in Amenia

5.0 out of 5 average rating, 18 reviews

Amenia Main St Cozy Studio

11–18 Sep

€ 79 per night
Guest favourite

Home in Dover Plains

5.0 out of 5 average rating, 52 reviews

Millstone Manor with East Mountain View

21–28 Jul

€ 233 per night
Guest favourite

Guest suite in Kent

5.0 out of 5 average rating, 52 reviews

Bright 1-bedroom in walking distance to town

8–15 Feb

€ 133 per night
Superhost

Home in Dover Plains

4.91 out of 5 average rating, 33 reviews

5 Harts Rd - Newly built home in Dover, NY

2–9 Jun

€ 143 per night
Guest favourite

Home in Dover Plains

4.88 out of 5 average rating, 32 reviews

Pastoral Country Retreat

21–28 Oct

€ 298 per night
Guest favourite

Guest house in Sharon

5.0 out of 5 average rating, 59 reviews

Cottage with a Waterfall View

19–26 Aug

€ 124 per night

Destinations to explore

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