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Browse Select Old Greenwich Cottages

Cozy cabin with a front porch and lush surroundings.

"This was the second time I stayed at this property and really do love it. It is close enough to my family in Ridgefield for me to fee like I am just around the corner, while being in a quiet, peaceful private property. The setup was perfect for myself and my mom, but could also accommodate a larger group. It isn’t a big space, but had everything that we needed. I would highly recommend this property and will definitely be looking to stay here again on another visit. Thank you!"

Stunning two-story building with a central entrance, flanked by windows, surrounded by lush greenery and a well-maintained tree.

"Fantastic place, location with great host. Highly recommended "

Relax on the pier with lounge chairs and enjoy the serene natural surroundings.

"Very comfortable space & accomodating host! Fantastic views of Northport Harbour and steps away from the water's edge! Would return and strongly recommend."

Walk along the weathered boardwalk to a serene body of water surrounded by lush trees and vibrant flowers.

Enjoy dining or socializing in this outdoor space with a glass table and chairs.

"Check in and check out were very easy. The owner replied quickly to my questions. The home was clean and comfortable. The location is very close to major highways with a lot of shopping and restaurants nearby. The neighborhood itself was quiet. "

Two-story house with a wooden staircase and porch, set amidst lush greenery and a paved driveway.

"This was a great property - location was perfect and the hosts were so easy to communicate with. It was exactly as pictured and was a great stay!"

Stunning two-story home with a gabled roof, front porch, and beautifully manicured lawn.

"Beautiful quiet neighborhood. Extremely clean apartment. Nice yard. Air conditioning was great. Missing some supplies like silverware etc. "

Enjoy cooking in this well-lit kitchen with a double oven, stainless steel sink, and white cabinetry.

"Loved our stay. We'll be back I am sure."

CA $413 total

includes taxes & fees

Aug 31 - Sep 1

Enjoy serene views from this deck overlooking a well-maintained lawn and trees.

"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."

Relax by the patio with a round table and six comfortable chairs, surrounded by lush greenery and a beautiful ocean view.

"I grew up here! Always fun"

Relax in this inviting living room with a comfortable sofa, flat-screen TV, and cozy rug.

"Perfect for my needs. Would stay again for sure"

Stunning traditional home surrounded by a beautifully maintained garden with lush greenery.

"Great location. Very clean modern cottage by the sea. Would love to stay again. "

Surrounded by a serene snow-covered garden, this peaceful retreat offers a tranquil escape.

"Wonderful stay!"

Enjoy dining al fresco on the patio, surrounded by a lush green view and shaded by a large umbrella.

"Gerard was very responsive and helpful and the rental was lovely and in a great location. The beach access was great as were the beach accessories we could borrow! The house stayed nice and cool in during the hot days! Would stay again."

Enjoy ocean views from this balcony with a table, chairs, and shade from a large umbrella.

"Perfect beach and outdoor life for young kids! Such a great relaxing long weekend - the house had everything we needed. Hoping for another stay soon!"

Escape to a secluded cabin surrounded by a lush forest, featuring a gabled roof and arched window.

"A cozy, well-maintained cottage, conveniently located near our son and his family who we were visiting. Modern appliances in the kitchen. Exterior and interior were as shown on VRBO. The property manager and owner were very helpful whenever we needed anything. Highly recommended. We would definitely like to stay here again whenever we visit our son."