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Search results; Over 1,000 homes in Old Saybrook

Top guest favourite
Cottage in Old Saybrook
The Cottage
1 bedroom, 2 beds, 1 private bathroom
6–11 Sept
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4.75 out of 5 average rating, 254 reviews
Superhost
Home in Old Saybrook
Cozy beach side home Chalker Beach Old Saybrook
3 bedrooms, 4 beds
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
7–12 Sept
4.95 out of 5 average rating, 22 reviews
Guest favourite
Home in Old Saybrook
Red Bird Waterfront Home. Dock available extra!
3 bedrooms, 3 beds
8–13 Aug
4.94 out of 5 average rating, 35 reviews
Top guest favourite
Home in Old Saybrook
Water Views and Walk to Beach
4 bedrooms, 4 beds
30 Aug – 4 Sept
4.95 out of 5 average rating, 65 reviews
Top guest favourite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds
26–31 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
27 Aug – 1 Sept
New place to stay
Top guest favourite
Home in Old Saybrook
Waterfront Oasis 4Bdr/2b
4 bedrooms, 4 beds
11–16 Oct
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Old Saybrook
Steps to Beach! *Cozy Cottage* Pet Friendly
1 bedroom, 1 queen bed
27 Sept – 2 Oct
4.92 out of 5 average rating, 104 reviews
Top guest favourite
Flat in Old Saybrook
Charming Center of it All Location
2 bedrooms, 2 beds
23–28 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
4–9 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
3 bedrooms, 3 beds
22–27 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Cottage in Old Saybrook
Rachel’s Retreat
3 bedrooms, 4 beds
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
14–19 Sept
4.92 out of 5 average rating, 113 reviews
Top guest favourite
Guest suite in Old Saybrook
Cozy Loft Getaway
1 bedroom, 2 beds
16–21 Aug
4.98 out of 5 average rating, 109 reviews
Guest favourite
Home in Old Saybrook
Beach House Getaway
3 bedrooms, 5 beds
31 Aug – 7 Sept
5.0 out of 5 average rating, 7 reviews
Cottage in Old Saybrook
Cornfield Point Beach Cottage
3 bedrooms, 4 beds
22–28 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Old Saybrook
Summertime in Old Saybrook on the Oyster River
5 bedrooms, 6 beds
13–18 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Cottage in Old Saybrook
Charming Old Saybrook Cottage < 1 Mi to Beach
4 bedrooms, 4 beds
13–18 Sept
4.87 out of 5 average rating, 39 reviews