Search Old Saybrook Cottage Rentals from CA $169

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Browse Select Old Saybrook Cottages

Stroll along the garden pathway to a charming home with a cozy porch and lush surroundings.

"Cute cottage, newly refurbished, quiet, nice neighborhood, well stocked."

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."

Cozy attic retreat with a bunk bed, bedside table, and dormer window.

"We visited here for a weekend in the Mystic area. Our daughter joined us for an evening and the home was cozy and comfortable for 3 adults. The check in process was seamless and communication with the host was always timely. They thought of everything to make our stay enjoyable and everything was within arms reach. The home is located in a great spot and enabled us to enjoy many surrounding areas. Pawcatuck/Westerly, Mystic, Watch Hill... all were very close so this was a perfect base of...

CA $535 total

includes taxes & fees

Sep 2 - Sep 3

Enjoy a serene lake view from the comfort of your room, which features a deck with a table and chairs.

"Great cottage right on the water! Cute swings on the deck! The hot tub was great! "

CA $783 total

includes taxes & fees

Aug 25 - Aug 26

Situated in a wooded area, this cozy shed features a simple design with a front door and two windows.

"Spent Christmas at the cottage with my family and we had an amazing time!! I highly recommend! Beautiful place, beautiful area! The host was fantastic and very responsive! 10/10! "

Enjoy outdoor dining or relaxation on the covered patio with comfortable seating and tables.

"Perfect stay in Madison. Beautiful location. Clean and comfy house. Will be back!"

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!"

Relax in this serene outdoor seating area with a bird-patterned cushion and a vase of fresh flowers.

"Joel was terrific, very responsive. The “cozy cottage” was everything we were expecting and hoping for. We plan to return."

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 "

Escape to a serene outdoor oasis surrounded by lush greenery and a tranquil atmosphere.

"We had a great time. Our new puppy loved walking the grounds (on leash inside and out). Very private and close to all we wanted to see...seaport, restaurants, casinos. Loved our stay there. Thanks for everything."

Compact kitchen with a stainless steel refrigerator, double sink, and oven, complete with white cabinetry and a countertop.

"My wife and I, and our little dog, had a great experience staying at the Yellow Cottage. For our needs, it was perfectly located. It's on a busy street, but the traffic noises wound down at night. Much nicer than the hotels in the area."

Cozy cabin with a covered outdoor area featuring a grill and picnic tables.

"Enjoyable and comfortable, great spot to chill."

CA $872 total

includes taxes & fees

Aug 31 - Sep 1

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."

Relax on the patio with a clear view of the water, surrounded by a low wall for added seclusion.

"This rental was perfect. Super clean and comfy with the most amazing views. Loved that it’s right on the water with a private beach. We will definitely book this property again."