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Vacation rentals in Dover Plains

Vacation rentals in Dover Plains

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Dover Plains

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

Cottage at Furnace Brook
SUPERHOSTEntire guesthouse · 2 guests · 1 bed · 1 bath
Cottage at Furnace Brook

Come enjoy our cozy, clean, newly renovated semi-detached cottage in the Litchfield Hills. Stay in, cook dinner, and relax on the large porch and listen to the sound of our brook and the Housatonic River just steps away. An ideal writer or artist retreat. Or enjoy the surrounding area - there are lots of restaurants, galleries, day hikes, and outdoor activities within a short drive. 8 miles to Kent, voted the prettiest small town in CT, 5 miles to Mohawk Ski Area and 20 minutes to Metro North.

What guests are saying:

“This cottage surpassed all my expectations, from the incredible setting next to a babbling brook to the lovely decor to the thoughtful supplies provided. It was truly one of my most favorite airbnb experiences given the surrounding natural landscape and kindness of the hosts. Watching the fireflies light up the summer nights, the multitude of birds flitting about in the early mornings, and the trout jump in the protected pool of the river across the street were just a few highlights of a too-short stay. Will definitely be back to enjoy this idyllic spot again. Thanks Pam and Walt for sharing your little slice of heaven!”

Hoppy Hill
SUPERHOSTEntire guest suite · 4 guests · 2 beds · 1 bath
Hoppy Hill

Newly renovated, comfortable and neat. Private apartment in the Harlem Valley with one queen bedroom, full bathroom, kitchenette/living room combo with pull out queen sofa. Watch the sun rising over the mountains and enjoy the quiet life settings. Located only 10 minutes from the Appalachian Trail, 5 mins. from Old Dovers Inn and Harlem Valley Homestead, 15 mins. to Thunder Ridge Mt ski, 8 mins. from Metro North Train Station, 15 mins. from Kent. Close to all private schools and wedding venues.

What guests are saying:

“Space was exactly as pictured. Very comfortable. Easy to find. Spotlessly clean. Friendly, accommodating, and super responsive to messages. Wonderful getaway, would have stayed longer if it were possible. Thank you!”

Cedarhurst 2
SUPERHOSTPrivate room · 2 guests · 1 bed · 1 shared bath
Cedarhurst 2

Our home was built in 1872 and is used to welcoming guests. In the early 1900's it was a bed&breakfast called Cedarhurst Farm. We are situated at the center of Dutchess County, about one and a half hour north of New York City. This puts you within easy reach of many places of interest in all directions. Beautiful rural towns like Rhinebeck, Hudson, New Paltz at the foothills of the mountainous Catskill area and the artist community of Beacon, to name a few.

What guests are saying:

“Thank you to Rob and Yoko for a magnificent stay. I felt welcomed into the most fascinating warm home throughout my stay. You will NOT meet any other couple like Rob and Yoko. Wonderful people, very knowledgeable and extremely easy to talk to and ask questions. The house is big and sits on a beautiful scenic view of fields and extra land. The walk into the house as you walk up the original wooden steps dates back years ago in out of this world. As you enter the house it’s overwhelming and special. You find yourself eager to ask questions about this warm mansion. The walk up to the room is breathtaking and unique. The rooms are spacious, old but modern at the same time. Old radiator heaters that heat the whole house, the original windows and beams help your stay feel more at home and back in time. The bed was very comfy and if you leave the door agar, you may find Kepa at the bottom of your bed in the middle of the night. Yes that’s their cat. Very cute and easy to talk to 😄. Breakfast is served each morning with extra care and Rob and Yoko are always asking if you need anything else. I’m extremely grateful that I found a place like this but I’m even more grateful that I made 2 wonderful friends for life. Thank you so much for making my stay the most amazing stay I could have wished for. Worth every $. Thank you again. Jamie”

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Popular amenities for Dover Plains vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Dover Plains

The Getaway! Pool, Spa in Scenic Litchfield Hills
SUPERHOSTEntire house
The Getaway! Pool, Spa in Scenic Litchfield Hills
Price:€348 / night
Lakeside Private Guest Suite
SUPERHOSTEntire guest suite
Lakeside Private Guest Suite
Price:€61 / night
The Spirit Horse Farm in Kent, Ct.
SUPERHOSTFarm stay
The Spirit Horse Farm in Kent, Ct.
Price:€297 / night
Hudson Valley Hideout – w/Pool & Gorgeous Grounds
SUPERHOSTEntire guesthouse
Hudson Valley Hideout – w/Pool & Gorgeous Grounds
Price:€180 / night
Red Tail Ridge
SUPERHOSTEntire apartment
Red Tail Ridge
Price:€78 / night
The Beech House - Light and Open, Stunning Views
SUPERHOSTEntire house
The Beech House - Light and Open, Stunning Views
Price:€175 / night
Serene, Peaceful Cabin by the Lake
SUPERHOSTEntire cabin
Serene, Peaceful Cabin by the Lake
Price:€167 / night
Quiet, lakefront cabin
SUPERHOSTEntire cabin
Quiet, lakefront cabin
Price:€276 / night
A retreat rich with history yet made to relax!
SUPERHOSTEntire guesthouse
A retreat rich with history yet made to relax!
Price:€153 / night
Appalachian Trail House! Easy access to NYC trains
SUPERHOSTEntire house
Appalachian Trail House! Easy access to NYC trains
Price:€123 / night
The Perch: Pvt Hiking, A/C, Deck, Garden, Pool Tbl
SUPERHOSTEntire chalet
The Perch: Pvt Hiking, A/C, Deck, Garden, Pool Tbl
Price:€355 / night
Tranquil Private Guest Room in a Charming Home
SUPERHOSTPrivate room
Tranquil Private Guest Room in a Charming Home
Price:€59 / night
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