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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
27 Sept – 2 Oct
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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
23–28 Aug
New place to stay
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Home in Old Saybrook
Waterfront Oasis 4Bdr/2b
4 bedrooms, 4 beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds, 1.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 99 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 bathrooms
21–26 Aug
New place to stay
Top guest favourite
Cottage in Old Saybrook
The Cottage
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.75 out of 5 average rating, 254 reviews
Guest favourite
Home in Old Saybrook
Red Bird Waterfront Home. Dock available extra!
3 bedrooms, 3 beds, 2 bathrooms
8–13 Aug
4.94 out of 5 average rating, 35 reviews
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Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
3 bedrooms, 3 beds, 1.5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Old Saybrook
Beach House Getaway
3 bedrooms, 5 beds, 1.5 bathrooms
31 Aug – 7 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Old Saybrook
Charming Center of it All Location
2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
4.99 out of 5 average rating, 68 reviews
Guest favourite
Cottage in Old Saybrook
Osprey Cozy Cottage | Near Downtown & Beaches
1 bedroom, 1 queen bed, 1 bathroom
4–9 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Old Saybrook
Cornfield Point Charmer–Walk to Beach
2 bedrooms, 3 beds, 1.5 bathrooms
19–24 Aug
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Cottage in Old Saybrook
Rachel’s Retreat
3 bedrooms, 4 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Old Saybrook
Best of both worlds!
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.92 out of 5 average rating, 113 reviews
Home in Westbrook
Enjoy the Beach, Wine & Antique trails this FALL!
3 bedrooms, 4 beds, 1 bathroom
28 Aug – 2 Sept
New place to stay
Top guest favourite
Cottage in Old Saybrook
Beautiful View Cottage
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 164 reviews
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, 80 reviews
Top guest favourite
Home in Essex
Ideal Historic Home in Essex Village
2 bedrooms, 3 beds, 1.5 bathrooms
22–27 Sept
4.97 out of 5 average rating, 98 reviews