Search Wainscott Woods Cottage Rentals from CA $307

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Browse Select Wainscott Woods Cottages

Stroll through the serene garden, surrounded by lush greenery and a tranquil water feature.

"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!"

Enjoy a serene beachside escape with access to the ocean.

"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!"

Relax by the clear pool surrounded by lush greenery and comfortable lounge chairs.

Enjoy a serene beach experience with calm seas and sandy shores.

"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 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...

CA $847 total

includes taxes & fees

Jul 29 - Jul 30

Relax in this spacious living room with a large window offering a view of the outdoors, a glass coffee table, and a comfortable white sectional sofa.

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

Relax on the deck with a chair and table, surrounded by lush greenery.

Enjoy meals in this well-equipped kitchen with an oven and microwave, and dine at the adjacent table.

"Excellent Host, great stay, beautiful property and set up and very modern."

Relax in this stylish living space with a sofa, two chairs, and a small table, leading to an outdoor area through a large sliding door.

"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...

Relax on the porch with a view of lush greenery, featuring a wicker sofa and a small table.

"We were pleased with our stay. The house was very clean. My contact with the property manager were great. Would stay again."

Enjoy a serene beach experience with access to the calm sea.

"A lovely beach cottage with bay views and easy walking access to the Atlantic beaches.The place was cozy and clean with expansive open views across reserve land to the bay.A bit tricky to find off the highway at night but we eventually got our bearings!"

Relax in a comfortable living area with a flat-screen TV, sofa, and dining table.

"Stay was relaxing, space was very cozy. we enjoyed our stay. "

CA $981 total

includes taxes & fees

Jul 31 - Aug 1

Relax in a serene outdoor space with a shaded deck, lounge chairs, and a nearby fire pit.

Walk along the serene beach pathway to the ocean's edge.

"Walking distance to Bridgehampton and a short drive to sag harbor. Great for 2 couples."

CA $1,410 total

includes taxes & fees

Jul 30 - Jul 31

Cozy retreat with vaulted ceiling, table, and a view of lush surroundings.

"My wife and I stayed for the weekend for our Anniversary and this was the perfect location. Quaint and quite hideout with tons to do nearby."

Enjoy a serene beach experience with expansive sand and a tranquil natural landscape.

"This is great property - perfectly renovated and close to everything including a nice North Fork beach in walking distance. Our host Bill communicates well and has thought of everything - house is well appointed and tastefully renovated with AirCon and washer/dryer. Sheets and Towels are clean and high quality! A beautiful, lush and grassy yard awaits your kids and the fire pit is perfect. Bill, our host was very nice in providing suggestions on where to go and what to do - some very nice...