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Check prices for these dates

In two weeks
5 Sep - 7 Sep
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Browse Select Old Saybrook Cottages

Guilford Carriage House at Granite Lodge!
Cottage (1 Bedroom) | 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!
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!
Remodeled Farmhouse in Waterford Near 2 Beaches!
House (2 Bedrooms) | Interior

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!
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!
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
Charming Old Lyme Cottage, Steps to Private Beach!
Cottage (2 Bedrooms) | Interior

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!
Shelter Island Retreat w/ Outdoor Pool!
House (5 Bedrooms) | Interior

Shelter Island Retreat w/ Outdoor Pool!

3.0 star property
Shelter Island Retreat w/ Outdoor Pool!
3 Mi to Dtwn: Mystic Getaway w/ Deck & Grill!
House (3 Bedrooms) | Interior

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!
House (4 Bedrooms) | Interior

Elegant Middlefield Getaway w/ Game Room!

3.0 star property
Elegant Middlefield Getaway w/ Game Room!
Walkable New Haven Retreat w/ Ocean Views!
Interior

Walkable New Haven Retreat w/ Ocean Views!

3.0 star property
Walkable New Haven Retreat w/ Ocean Views!
Lovely Westerley Home w/ Yard & Grill!
House (3 Bedrooms) | Interior

Lovely Westerley Home w/ Yard & Grill!

3.0 star property
Lovely Westerley Home w/ Yard & Grill!
Deluxe Waterford Home w/ Views, Outdoor Bar & More
House (5 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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
House (2 Bedrooms) | Interior

Westbrook Home w/ Ocean Views - Walk to Beach

3.0 star property
Westbrook Home w/ Ocean Views - Walk to Beach
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!
French Château Near Beaches, Mystic & Casinos!
House (3 Bedrooms) | Interior

French Château Near Beaches, Mystic & Casinos!

3.0 star property
French Château Near Beaches, Mystic & Casinos!
Cozy Westbrook Vacation Rental - Walk to Beach!
House (3 Bedrooms) | Interior

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!
Walk to Beach: Long Island Wine Country Home!
House (3 Bedrooms) | Interior

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
Cottage (2 Bedrooms) | Interior

Waterfront Cottage w/ Sunroom + Patio & Grill

3.0 star property
Waterfront Cottage w/ Sunroom + Patio & Grill
Historic Essex Home w/ Large Yard Near Downtown!
House (2 Bedrooms) | Interior

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!
Elegant Norwich House w/ Billiards Room & Ballroom
House (5 Bedrooms) | Interior

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

Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino

Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino

10/10 Excellent
"Great hotel for a great price. Clean, great management, free coffee and water."
Todd 4-night trip
Posted 10 hours ago
Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino

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 holiday 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 holiday 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.