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Aug 22 - Aug 24
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Aug 29 - Aug 31
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Sep 12 - Sep 14
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Featured Cottages in Old Saybrook

Guilford Carriage House at Granite Lodge!
Interior

Guilford Carriage House at Granite Lodge!

3.0 star property
9.0 out of 10, Wonderful, (2)
"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!
New Haven Gem w/ Private Pool, Walk to Beach!
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!
Private Guest House w/ Deck + Spectacular Views!
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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!
Dreamy Waterfront Westbrook Home on Private Beach
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Dreamy Waterfront Westbrook Home on Private Beach

3.0 star property
Dreamy Waterfront Westbrook Home on Private Beach
3 Mi to Dtwn: Mystic Getaway w/ Deck & Grill!
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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!
Elegant Middlefield Getaway w/ Game Room!
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Elegant Middlefield Getaway w/ Game Room!

3.0 star property
Elegant Middlefield Getaway w/ Game Room!
Charming Old Lyme Cottage, Steps to Private Beach!
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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!
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Lovely Westerley Home w/ Yard & Grill!

3.0 star property
Lovely Westerley Home w/ Yard & Grill!
Cozy Westbrook Vacation Rental - Walk to Beach!
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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!
Deluxe Waterford Home w/ Views, Outdoor Bar & More
Private kitchen

Deluxe Waterford Home w/ Views, Outdoor Bar & More

3.0 star property
Deluxe Waterford Home w/ Views, Outdoor Bar & More
Westbrook Home w/ Ocean Views - Walk to Beach
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Westbrook Home w/ Ocean Views - Walk to Beach

3.0 star property
Westbrook Home w/ Ocean Views - Walk to Beach
Remodeled Farmhouse in Waterford Near 2 Beaches!
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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!
Pet-friendly Lebanon House w/ Lake Access!
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Pet-friendly Lebanon House w/ Lake Access!

3.0 star property
Pet-friendly Lebanon House w/ Lake Access!
French Château Near Beaches, Mystic & Casinos!
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French Château Near Beaches, Mystic & Casinos!

3.0 star property
French Château Near Beaches, Mystic & Casinos!
Walk to Beach: Long Island Wine Country Home!
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Walk to Beach: Long Island Wine Country Home!

3.0 star property
Walk to Beach: Long Island Wine Country Home!
Waterfront Cottage w/ Sunroom + Patio & Grill
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Waterfront Cottage w/ Sunroom + Patio & Grill

3.0 star property
Waterfront Cottage w/ Sunroom + Patio & Grill
Walkable New Haven Retreat w/ Ocean Views!
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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!
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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!
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Shelter Island Retreat w/ Outdoor Pool!

3.0 star property
Shelter Island Retreat w/ Outdoor Pool!
Elegant Norwich House w/ Billiards Room & Ballroom
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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
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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Top Old Saybrook Hotel Reviews

Mohegan Sun

Mohegan Sun

10/10 Excellent
"Resturant were amazing and accesible "
Jose 1-night trip
Posted 17 hours ago
Mohegan Sun

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 61 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.