Holiday Homes in Smithtown

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Featured Holiday Homes in Smithtown

Step into this charming cabin, featuring a cozy porch and a wooden deck surrounded by lush greenery.

"Lots of space, great location, suited our extended family well."

Compact kitchen area with microwave, coffee maker, and kitchenware, featuring a herringbone-patterned backsplash.

"Everything was as pictured, and the whole place was very clean. It was a perfect stay for us, and we will come again soon!"

includes taxes & fees

17 Aug - 18 Aug

Enjoy a peaceful retreat with a view of lush greenery from the large window, surrounded by a round table and comfortable seating.

"Great home to stay. Beautiful area to explore!"

includes taxes & fees

10 Aug - 11 Aug

Enjoy a home away from home in this charming two-story house with a front yard and garden.

"Great location. Very peaceful. Great house"

Relax in this inviting room with a shuffleboard table, seating area, and large mirror.

"Love staying at this comfortable house each year for Thanksgiving and the location is perfect! "

Enjoy a room with a sliding glass door leading to a scenic outdoor area overlooking a body of water.

"Beautiful views and a comfortable stay."

Situated on a raised platform, this single-story house features a gable roof and a spacious deck with a walkway to the front door.

"Bunk beds, it was very clean and kitchen was great"

"Enjoyed our stay, property was as advertised. Quiet, comfortable neighborhood, and host was prompt with all communications."

Traditional home with a charming front porch and beautifully landscaped yard.

"We had a very nice family weekend. There was plenty of room, the furniture and beds were comfortable, and the kitchen had everything we needed. Great communication with the owner"

includes taxes & fees

3 Sept - 4 Sept

Relax by the fire pit in this inviting outdoor space, surrounded by comfortable seating and shaded by umbrellas.

"This is my second time staying here. Decorated beautifully, always clean and wonderful amenities. "

Surrounded by lush trees, this elevated deck offers a serene retreat with a small platform and steps leading up to it.

"Super enjoyable."

Prepare meals in this kitchen with a large island, stainless steel appliances, and a sink with a gold faucet.

"Great place. Total of 7 of us travelled. Will absolutely use this property again. Thank you for everything!"

Enjoy meals in this kitchen with a dining table, sink, and refrigerator.

"Thank you Great Location Would book again"

Enjoy al fresco dining and socializing on this outdoor deck with wicker chairs, a cushioned bench, and a barbecue grill.

"To quote my son, our stay at Imagine was a “top-tier week”! Everything was perfect and as described. We thoroughly enjoyed the incredible kitchen and outside deck. Fran was helpful and attentive, a wonderful host. Our family was happy and comfortable all week. Thank you to the Cintorino Family for sharing your home with our family 💙"