Holiday rentals in Dover

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Top-rated holiday rentals in Dover

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

Superhost

Cabin in Pawling

4.95 out of 5 average rating, 110 reviews

Serene, Peaceful Cabin by the Lake

Take a stroll down to the lake in the crisp morning air, then light the fire and sink into the cherry leather armchair at this rustic log cabin. Touches of soft sage add a soothing side, while patterned rugs and chunky beams keep things homey. Authentic Log cabin, private lake with swimming, kayaking --1000's acres adjacent private land, fishing, hunting-- Enjoy the harvest of the Hudson Valley-- minutes to wineries, Pawling train to NYC, Appalachian trail and hiking, Child safe. Minutes walk to Lake! Private Lake-- We are here to check you in and only if you need us. We respect your privacy and "time-away". The property sits in a private, sprawling lake community minutes from wineries for tastings, Pawling station for trains to New York City, and the Appalachian trail for scenic hiking. Explore Wallkill and Warwick within around an hour's drive. Car, Metro North (train to NYC), Uber, Lyft...

30 Apr – 7 May

€ 241 per night
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

Popular amenities for Dover holiday rentals

Stay near Dover's top sights

Dover Stone Church31 locals recommend
Big W's Roadside Bar B Que13 locals recommend
Kelly’s Creamery & Kelly's Husband's Truck12 locals recommend
Stone Church12 locals recommend
Old Drovers Inn5 locals recommend
Crown Maple Estate4 locals recommend

Other great holiday rentals in Dover

Guest favourite

Home in Danbury

4.99 out of 5 average rating, 335 reviews

BEAUTIFUL PRIVATE APARTMENT SUITE IN DANBURY CT!!

15–22 Nov

€ 159 per night
Guest favourite

Tiny home in New Paltz

4.99 out of 5 average rating, 738 reviews

Hudson Valley Tiny House

11–18 Jun

€ 112 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

Flat in Amenia

5.0 out of 5 average rating, 18 reviews

Amenia Main St Cozy Studio

11–18 Sep

€ 79 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

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 house in Sharon

5.0 out of 5 average rating, 59 reviews

Cottage with a Waterfall View

19–26 Aug

€ 124 per night
Guest favourite

Cottage in Pawling

5.0 out of 5 average rating, 59 reviews

Twin Lakes Designer A-frame Stone Cottage

15–22 Sep

€ 364 per night
Guest favourite

Home in Dover Plains

5.0 out of 5 average rating, 11 reviews

Blue Heron - Scenic Oasis on Working Farm

4–11 Jun

€ 281 per night
Guest favourite

Guest house in Gaylordsville

4.98 out of 5 average rating, 90 reviews

Adorable Cottage in Pastoral Setting

20–27 Nov

€ 164 per night
Guest favourite

Guest house in New Milford

5.0 out of 5 average rating, 41 reviews

Luxury in the Litchfield Hills

29 Sep – 6 Oct

€ 220 per night

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Dutchess County
  5. Dover