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Search results; Over 1,000 homes in Old Saybrook

Top guest favourite
Home in Old Saybrook
Best of both worlds!
3 bedrooms, 4 beds, 2 private bathrooms
15–20 Sept
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4.92 out of 5 average rating, 118 reviews
Top guest favourite
Cottage in Old Saybrook
The Cottage
1 bedroom, 2 beds, 1 bathroom
27 Oct – 1 Nov
4.75 out of 5 average rating, 259 reviews
Top guest favourite
Cottage in Old Saybrook
Beautiful View Cottage
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.98 out of 5 average rating, 166 reviews
Superhost
Home in Old Saybrook
Steps to Beach! *Cozy Cottage* Pet Friendly
1 bedroom, 1 queen bed, 1 bathroom
2–7 Oct
4.92 out of 5 average rating, 106 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
Top guest favourite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds, 1.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 103 reviews
Guest favourite
Home in Old Saybrook
Adorable home walk to Saybrook Point !
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Cottage in Old Saybrook
Osprey Cozy Cottage | Near Downtown & Beaches
1 bedroom, 1 queen bed, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
3 bedrooms, 3 beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Old Saybrook
Year Round Beach House in Old Saybrook, CT.- Pets
4 bedrooms, 7 beds, 2 bathrooms
10–15 Sept
4.97 out of 5 average rating, 146 reviews
Top guest favourite
Home in Westbrook
Sea Salt Air Changes Everything
3 bedrooms, 3 queen beds, 2 bathrooms
13–18 Sept
4.98 out of 5 average rating, 82 reviews
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms, 3 beds, 1 bathroom
3–8 Oct
4.96 out of 5 average rating, 28 reviews
Guest favourite
Home in Old Saybrook
The Happy Place
2 bedrooms, 2 beds, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Cottage in Old Saybrook
Rachel’s Retreat
3 bedrooms, 4 beds, 1 bathroom
14–19 Sept
4.92 out of 5 average rating, 12 reviews
Top guest favourite
Home in Essex
Ideal Historic Home in Essex Village
2 bedrooms, 3 beds, 1.5 bathrooms
9–14 Nov
4.97 out of 5 average rating, 99 reviews
Guest favourite
Home in Essex
Historic Essex Home w/ Large Yard Near Downtown!
2 bedrooms, 3 beds, 1.5 bathrooms
11–16 Oct
4.92 out of 5 average rating, 143 reviews
Guest favourite
Townhouse in Westbrook
Wake up with views of the ocean
3 bedrooms, 5 beds, 2 bathrooms
25–30 Oct
4.92 out of 5 average rating, 237 reviews
Top guest favourite
Home in Old Saybrook
3BR Updated Cottage w/ Pool in Old Saybrook
3 bedrooms, 4 beds, 1 bathroom
10–15 Sept
4.97 out of 5 average rating, 78 reviews