Search Cottages in Old Saybrook

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Cottages in Old Saybrook

New Haven Gem w/ Private Pool, Walk to Beach!
House (3 Bedrooms) | Front of property

New Haven Gem w/ Private Pool, Walk to Beach!

3.0 star property
New Haven Gem w/ Private Pool, Walk to Beach!
Guilford Carriage House at Granite Lodge!
Relax in this spacious living area with a high ceiling and exposed beams, featuring a large sofa and armchair, wooden coffee table, and dining area.

Guilford Carriage House at Granite Lodge!

3.0 star property
10.0 out of 10, Exceptional, (1)
"I’m normally not one to leave reviews but I had to for The Carriage House! Everything from the homey, relaxing feel to the great views was amazing! My friends and I wanted to extend our stay lol. We’re already planning another stay here for a summer trip! Also appreciated the host’s friendliness and ensuring we had an enjoyable experience. 10/10"
Guilford Carriage House at Granite Lodge!
3 Mi to Dtwn: Mystic Getaway w/ Deck & Grill!
Enjoy meals in this dining area with a wooden table and four chairs, a unique chandelier, and a large window.

3 Mi to Dtwn: Mystic Getaway w/ Deck & Grill!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Perfect for our family get together. Great location. Very clean"
3 Mi to Dtwn: Mystic Getaway w/ Deck & Grill!
Remodeled Farmhouse in Waterford Near 2 Beaches!
Relax in the serene backyard with a dining table, comfortable seating, and lush greenery.

Remodeled Farmhouse in Waterford Near 2 Beaches!

3.0 star property
10.0 out of 10, Exceptional, (2)
"This is a beautiful home and comfortable for our family of 4 to spend a long weekend. All the amenities were perfect in this cute farmhouse. There were toiletries and kitchen essentials to make our stay easier. Communication was great with the host. Highly recommend! "
Remodeled Farmhouse in Waterford Near 2 Beaches!
Charming Old Lyme Cottage, Steps to Private Beach!
Enjoy cooking in this well-lit kitchen with a microwave, stove, and sink.

Charming Old Lyme Cottage, Steps to Private Beach!

2.0 star property
10.0 out of 10, Exceptional, (1)
Charming Old Lyme Cottage, Steps to Private Beach!
Lovely Westerley Home w/ Yard & Grill!
Stunning two-story home with a central entrance, flanked by windows and a charming porch area.

Lovely Westerley Home w/ Yard & Grill!

3.0 star property
Lovely Westerley Home w/ Yard & Grill!
Walk to Beach: Long Island Wine Country Home!
Walk along the pier and enjoy the serene atmosphere.

Walk to Beach: Long Island Wine Country Home!

3.0 star property
Walk to Beach: Long Island Wine Country Home!
Pet-friendly Lebanon House w/ Lake Access!
House (3 Bedrooms) | Interior

Pet-friendly Lebanon House w/ Lake Access!

3.0 star property
Pet-friendly Lebanon House w/ Lake Access!
Deluxe Waterford Home w/ Views, Outdoor Bar & More
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and ample counter space.

Deluxe Waterford Home w/ Views, Outdoor Bar & More

3.0 star property
Deluxe Waterford Home w/ Views, Outdoor Bar & More
Elegant Middlefield Getaway w/ Game Room!
Relax in a serene garden setting with a circular table and Adirondack chairs.

Elegant Middlefield Getaway w/ Game Room!

3.0 star property
Elegant Middlefield Getaway w/ Game Room!
Cozy Westbrook Vacation Rental - Walk to Beach!
Guests can enjoy stunning sea views from this property, with kayaks available for use.

Cozy Westbrook Vacation Rental - Walk to Beach!

3.0 star property
4.0 out of 10, (1)
"The property was clean. The pictures in the ads made it clear that it was supposed to be a waterfront property. It was not. The pictures were taken on a neighbors private property that actually does sit on the water. The fireplace did not work. The only beach access was through a public park which was immediately next to the house. There were several slats missing from the blinds in the bedroom facing the parking lot which was about 8 feet away. Very disappointing for what was supposed to be a...
Cozy Westbrook Vacation Rental - Walk to Beach!
Private Guest House w/ Deck + Spectacular Views!
Cottage (1 Bedroom) | Interior

Private Guest House w/ Deck + Spectacular Views!

3.0 star property
10.0 out of 10, Exceptional, (2)
"The pool was amazing, the host was great, very accessible and the property was prisine. The views alone made us immediately want to come back. Very clean and well stocked. "
Private Guest House w/ Deck + Spectacular Views!
Walkable New Haven Retreat w/ Ocean Views!
Enjoy a scenic waterfront view from the paved walkway at Pardee Seawall Park.

Walkable New Haven Retreat w/ Ocean Views!

3.0 star property
Walkable New Haven Retreat w/ Ocean Views!
Historic Essex Home w/ Large Yard Near Downtown!
Relax in a cozy living space with a comfortable sofa, round coffee table, and warm rug.

Historic Essex Home w/ Large Yard Near Downtown!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Amazing Host. Fantastic trip "
Historic Essex Home w/ Large Yard Near Downtown!
Shelter Island Retreat w/ Outdoor Pool!
Sleep comfortably in this well-organized space with a bunk bed system and a bean bag chair.

Shelter Island Retreat w/ Outdoor Pool!

3.0 star property
Shelter Island Retreat w/ Outdoor Pool!
Elegant Norwich House w/ Billiards Room & Ballroom
Stunning grand hallway with polished floors, elegant artwork, and classic lamps.

Elegant Norwich House w/ Billiards Room & Ballroom

3.0 star property
10.0 out of 10, Exceptional, (1)
Elegant Norwich House w/ Billiards Room & Ballroom
Waterfront Cottage w/ Sunroom + Patio & Grill
Enjoy a serene view of the water and lush surroundings from this room's large window.

Waterfront Cottage w/ Sunroom + Patio & Grill

3.0 star property
Waterfront Cottage w/ Sunroom + Patio & Grill
Westbrook Home w/ Ocean Views - Walk to Beach
Enjoy cooking in this well-equipped kitchen with a central island, dishwasher, and sink.

Westbrook Home w/ Ocean Views - Walk to Beach

3.0 star property
Westbrook Home w/ Ocean Views - Walk to Beach
Mattituck Home w/ Fireplaces - Near Wineries
House (3 Bedrooms) | Interior

Mattituck Home w/ Fireplaces - Near Wineries

3.0 star property
Mattituck Home w/ Fireplaces - Near Wineries
Dreamy Waterfront Westbrook Home on Private Beach
House (3 Bedrooms) | Interior

Dreamy Waterfront Westbrook Home on Private Beach

3.0 star property
Dreamy Waterfront Westbrook Home on Private Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

How much do cottages in Old Saybrook cost?
Expect to pay between and per night for cottages in Old Saybrook. No matter your budget, a terrific stay is only clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Old Saybrook?
Claim your vacation time and pick from 58 cottages in Old Saybrook. Yearning for a place where you can get in touch with nature? Expedia will help you find your ideal stay in only a click or two.
Why book your cottage in Old Saybrook with Expedia?
Expedia has some terrific cottages in Old Saybrook, so start planning for an unforgettable vacation on nature's doorstep. If you have a fixed budget, click on how much you're willing to spend and your preferred property star rating. Or, use our filters to search for cottages with a pool or free WiFi. We'll help you find the perfect pad whatever your getaway looks like.