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Search results; Over 1,000 homes in Old Saybrook

Guest favourite
Home in Old Saybrook
Steps to Beach! *Cozy Cottage* Pet Friendly
1 bedroom, 1 bed, 1 private bathroom
18–23 Sept
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4.92 out of 5 average rating, 104 reviews
Superhost
Home in Old Saybrook
Cozy beach side home Chalker Beach Old Saybrook
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Cottage in Old Saybrook
The Cottage
1 bedroom, 2 beds, 1 bathroom
5–10 Sept
4.75 out of 5 average rating, 255 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 bathrooms
27 Aug – 1 Sept
Top guest favourite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds, 1.5 bathrooms
26–31 Aug
5.0 out of 5 average rating, 101 reviews
Top guest favourite
Home in Old Saybrook
Year Round Beach House in Old Saybrook, CT.- Pets
4 bedrooms, 7 beds, 2 bathrooms
8–13 Sept
4.97 out of 5 average rating, 145 reviews
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Home in Old Saybrook
Water Views and Walk to Beach
4 bedrooms, 4 beds, 3.5 bathrooms
30 Aug – 4 Sept
4.93 out of 5 average rating, 67 reviews
Guest favourite
Cottage in Old Saybrook
Osprey Cozy Cottage | Near Downtown & Beaches
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 14 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, 165 reviews
Guest favourite
Home in Old Saybrook
Red Bird Waterfront Home. Dock available extra!
3 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
4.94 out of 5 average rating, 36 reviews
Home in Old Saybrook
Renovated beach house for rent
3 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cabin in Colchester
The Colchester Cottage
1 bedroom, 3 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Old Saybrook
Summertime in Old Saybrook on the Oyster River
5 bedrooms, 6 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 10 reviews
Home in Westbrook
Luxe 5,600-Sq-Ft Estate Waterfront + Pool
5 bedrooms, 8 beds, 5.5 bathrooms
7–12 Sept
Top guest favourite
Home in Westbrook
Sea Salt Air Changes Everything
3 bedrooms, 3 queen beds, 2 bathrooms
30 Aug – 4 Sept
4.98 out of 5 average rating, 81 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, 235 reviews
Top guest favourite
Home in Old Saybrook
Best of both worlds!
3 bedrooms, 4 beds, 2 bathrooms
12–17 Oct
4.92 out of 5 average rating, 115 reviews
Top guest favourite
Cottage in Old Saybrook
Rachel’s Retreat
3 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.91 out of 5 average rating, 11 reviews