Dover Plains Vacation Rentals

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Browse Select Dover Plains Vacation Homes

Set amidst lush greenery and mature trees, this charming building features a steeply pitched roof and a brick facade.

"We were visiting the Culinary Institute highly recommend it."

Relax in this serene outdoor seating area with a covered patio overlooking a lush garden.

"Perfect for small family stay over for a wedding ! "

CA $460 total

includes taxes & fees

Aug 31 - Sep 1

Enjoy cooking in this well-equipped kitchen with a central island, stainless steel stove, and ample counter space.

"We loved our stay. It was great for a family Thanksgiving"

Enjoy a peaceful lakeside retreat with a barbecue grill and comfortable seating area.

"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."

Enjoy a serene lakeside retreat with a dining table, comfortable seating, and a thatched structure.

"Had an amazing stay. House was stocked with all of the essentials. Fantastic location. Would definitely stay again!"

Cozy living room with a fireplace, flat-screen TV, and comfortable seating area.

"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."

"This was our family's first time to Candlewood Lake/Squantz Pond. The area is picturesque and the location of this property is perfect. The porch off of the living area directly overlooks Squantz Pond and mountains. The basement was ideal for teenagers with a projector screen, air hockey/pool, and exercise equipment. The bedroom were spacious and beds comfortable. The kitchen/living area are open concept and the whole family could be together. The owner and his daughter are incredibly kind and...

Relax on the deck overlooking a lush garden with a tranquil atmosphere.

"Great property great location wonderful day"

Relax in this stylish living space with a large sofa, matching ottoman, and modern light fixture.

"Lovely home and great proximity to Taconic Parkway for all points north and south. Owner very accomodating"

Enjoy cooking in this fully equipped kitchen with a range, oven, microwave, and sink.

"Place looked great in pictures and turned out to be even better! Will definitely stay there again."

Relax by the pool surrounded by lush greenery and a serene water feature.

"Property was great and the owners thought of everything. Instructions were clear and helpful! Didn’t want for a thing, such a lovely space to spend a few days and so close to Litchfield and Bantam shops and restaurants. We loved it!! "

Spacious living area with a high ceiling, stone accent wall, and kitchen island.

"Nice, clean place out in the woods. Enjoyed our stay and had no issues. Host responded quickly and check-in/out was refreshingly simple. Our kid enjoyed the supply of children’s books. "

Enjoy outdoor dining and relaxation on the spacious deck with comfortable seating and a barbecue grill.

"We had an absolutely wonderful stay at Highland House! This beautiful property is nestled in the woods, providing a serene and peaceful environment, yet it is conveniently close to town, making it easy to access local amenities and attractions. The kitchen was a standout feature, stocked with everything you could possibly need. From a Keurig and coffee pot to a tea kettle and KitchenAid mixer, it had all the appliances and utensils necessary for cooking up a storm. The variety of pots and pans...

Relax on the covered porch with outdoor seating and grill, surrounded by a serene backyard with a brick patio and well-maintained lawn.

"Very cool place everything u need is just a short drive away "

Relax on the patio with a round table and two chairs, surrounded by a white railing and overlooking a serene grassy area with trees.

"Our stay was only a couple nights but it was what we expected. I would recommend this property. Had a great stay."

CA $861 total

includes taxes & fees

Aug 14 - Aug 15

Traditional home with a gabled roof, front porch, and stone foundation, set amidst mature trees and a well-manicured lawn.

"We loved our stay at this local and charming Red Hook property, complete with a piano for our son to play!"

Enjoy meals in this stylish dining area with a long table for four, a pendant light, and a vase with a single flower.

Cozy living space with a comfortable seating area, dining table, and fireplace.

"We had a wonderful vacation with our grandchildren and family. The children lived in the water if not kayaking or water boards they were fishing!! Rainy days puzzles were our entertainment the summer house provided everything one wanted or needed. It was a very delightful vacation"