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Featured Cottages in Sag Harbor

Charming single-story house with a front entrance, porch, and well-manicured lawn.

"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"

Situated in a lush environment, this two-story house features a wooden door and windows, surrounded by trees and shrubs, with a garden in the foreground.

"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."

Situated lakeside, this charming building features a large American flag on its roof and a garage door.

"The lake house was a perfect retreat, perfectly located to town, train, trails and beach. We can’t wait to visit again !"

Relax in this stylish living room with a sofa set, coffee table, and side table, perfect for unwinding.

"What a beautiful cottage. Clean and bright. Would definitely stay again!"

Enjoy ocean views and outdoor activities in a serene backyard with a covered grill area and deck.

"We stayed at this property last year and again this year. You can’t beat the location and the house is perfect for a group of family or friends. We had a lovely time and look forward to another stay in the future!"

Stunning coastal homes surround a central driveway, offering easy access to the beach and scenic ocean views.

Cozy cabin with a front porch, surrounded by a deck and a fenced yard, perfect for outdoor dining and relaxation.

"we had such a fun weekend out in southold! Cottage was perfect for us for a cold rainy weekend. Everything was so close to the house. Will definitely be back in the summer!"

Relax and socialize in this serene outdoor space, surrounded by lush greenery and mature trees.

"Lovely location very close to Harvey's Beach and local attractions . Home is very well kept in a quiet neighborhood "

Relax on the ocean-view deck with a wooden railing, surrounded by lush greenery and a small table for dining or relaxation.

"We had a fantastic weekend at Nancy’s cottage in Flanders! The cottage is extremely comfortable - a nice sitting room, an open and well-lit kitchen, eating area, a spacious deck, and an incredible backyard (the best part). The bedrooms are comfortable as well. The backyard is set with a lovely deck We had a truly amazing time at this home! When we arrived we were greeted by Rick( the caretaker)with a helpful welcome binder and a truly beautiful house. It was clean, spacious and exactly what was...

includes taxes & fees

29 July - 30 July

Situated on a quiet street, this house features a large garage and a covered porch overlooking a serene body of water.

"Cozy cottage, good location, nice access to the Sound."

Enjoy a casual outdoor space with a front porch, potted plant, and Adirondack chairs.

"Loved the overall stay and experience. The private beach access is a bonus"

includes taxes & fees

29 July - 30 July

Stylish single-story home with a gabled roof and chimney, featuring a front entrance and wooden deck.

"Perfect little beachfront cottage right on the water ...a few steps across your own beach. We had a very relaxing, comfortable visit."

Situated in a serene backyard, this two-story house offers a patio area with a table and chairs for outdoor dining or relaxation.

"We had such a nice stay, the house was clean and had everything we needed."

Relax on the sheltered front porch, perfect for unwinding.

"Very nice and comfortable property "

Relax in a serene garden setting with a lawn, lounge chairs, and mature trees.

"We enjoyed our time in the Ritz. It’s a great cottage surrounded by waterfront activities. The host was accommodating and welcoming."

Simple, single-story building with a front window and door, set amidst a grassy lawn.

"Hard to eat indoors. Kitchen cramp. Enjoyed the comfy living room"

Situated in a lush backyard, this cabin features a cozy front porch and a gravel path leading to the entrance.

Stunning two-story home with a charming front porch and inviting entryway, set amidst a beautifully manicured lawn.

"We had a lovely stay. Everything was as described on the listing and the house had everything we needed for our family. It was great to have the grill and a kitchen with all the supplies needed. The area is lovely and quiet with two small but nice private beaches within walking distance"