Vacation rentals in Dover

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Top-rated vacation rentals in Dover

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Guest favorite

Guest suite in Dover Plains

4.91 out of 5 average rating, 262 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. Plenty of quaint towns near-by: Kent, Millbrook, Amenia, Wassaic for great food, coffee shops, antiques, parks, breweries and vineries. Inside, you will feel right at home in this comfortable one bedroom apartment.

Guest favorite

Apartment 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.*

Guest favorite

Apartment in Amenia

5.0 out of 5 average rating, 28 reviews

Amenia Main St Cozy Studio

Cozy studio in well maintained house from 1900. 150 sq ft with full size bed. Right in small town of Amenia. Front porch with seats/table. Walking distance to food, shops, drive-in movie theatre, and rail trail. Rail trail is 1/4 mile from house, paved and maintained and only allows walking/biking. On trail: Arts village Wassaic (3 miles south) Town of Millerton (8 miles north). Train to NYC is 2.5m south. Tons to do in area: wineries, distillery, lakes, hiking, theatre & quaint towns.

Guest favorite

Cabin in New Milford

4.95 out of 5 average rating, 152 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.

Superhost

Home in Dover Plains

4.91 out of 5 average rating, 35 reviews

5 Harts Rd - Newly built home in Dover, NY

5 Harts Rd is a multi-purpose venue and communal living space in Dover, NY, built on 7.2 acres of old farmland still in the early development stages. Enjoy our newly built 2-bedroom, 1-loft, 1-bath home. High ceilings, all new appliances, a workspace in the loft, a beautiful place to escape the city and relax. The house is built about 125 feet away from our main house. The blue trailer is empty across our private road. THE HOUSE HAS A 40" TV + FIRESTICK NOT SHOWN IN PHOTOS.

Guest favorite

Home in Pawling

4.9 out of 5 average rating, 277 reviews

Appalachian Trail House! Easy access to NYC trains

Hike the Appalachian Trail! This is a cozy 3 bedroom, 1 bath, full basement and 3 acres of land. Located in town of Pawling, NY, about 90 minutes from NYC. Walking distance from Appalachian Trail train stop. Enjoy mother nature at it's finest with a short hike up historic Quaker Hill section of the Appalachian Trail. We accept up to 2 well behaved pets under 40 lbs. There is a $50 fee per pet. For companion and service dogs/pets, paperwork must be submitted before stay.

Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 188 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Guest favorite

Apartment in Stanfordville

4.95 out of 5 average rating, 155 reviews

Country Apartment great for a romantic getaway

Second story apartment above garage with private entrance has everything you need for a comfortable getaway. Located on quiet rural neighborhood road with off street parking. Enjoy nature right out your door walking to the beaver pond in the back woods or on the many nearby hiking and biking trails. Relax in the backyard. An easy drive from the Taconic Parkway or 20 minutes from the Metro-North Wassiac train station.

Guest favorite

Apartment in Millbrook

4.93 out of 5 average rating, 207 reviews

Red Tail Ridge

One BR with bath, full kitchen, eating area and living room. Separate entrance and sliding glass door in rear with country views. Located on 12 acre parcel. Close to village of Millbrook (less than 4 miles). We are located in center of Dutchess County. There is great antique shopping, historic sites and some of the finest restaurants and chefs with tastes to suit most everyone. .

Guest favorite

Guest suite in Morris

4.99 out of 5 average rating, 348 reviews

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own private lounging/dining area. Separate entrance and parking space. Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing and just 10 minutes to Washington Depot.

Guest favorite

Apartment in Dover Plains

4.95 out of 5 average rating, 138 reviews

*The Ridge House*

Escape to a quiet, pleasant and serene getaway at The Ridge House. A lovely attached apartment with private entrance and covered deck to enjoy the sights and sounds of nature. Stop by the stream down the hill with a drink or enjoy the sunrise while reading outside. Roast marshmallows in the fire after dinner on the grill and finish the day relaxing in the comfortable queen bed.

Guest favorite

Home in Dover Plains

5.0 out of 5 average rating, 13 reviews

Blue Heron - Scenic Oasis on Working Farm

Plan your ideal upstate getaway to our working farm stay oasis at Brookby Farm. Embrace the adventures of the Hudson Valley in any season. Design meets modest tranquility, the home features a bright, airy open concept with a fully stocked kitchen, reading nook, outdoor deck with stream views, and plenty of space to make this the perfect choice for your family and friends.