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
1–6 Jul
,
4.74 out of 5 average rating, 250 reviews
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
4.93 out of 5 average rating, 14 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
New place to stay, 5 bedrooms, 7 beds, 2 bathrooms
15–22 Aug
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Home in Old Saybrook
Sunrise Beach Cottage
5.0 out of 5 average rating, 33 reviews, 2 bedrooms, 4 beds, 1 bathroom
14–19 Sept
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Cottage in Old Saybrook
Osprey Cozy Cottage | Near Downtown & Beaches
5.0 out of 5 average rating, 9 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
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Home in Old Saybrook
Best of both worlds!
4.92 out of 5 average rating, 109 reviews, 3 bedrooms, 4 beds, 2 bathrooms
20–25 Jul
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Cottage in Old Saybrook
Beautiful View Cottage
4.99 out of 5 average rating, 159 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
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Cottage in Old Saybrook
Luxury Driftwood Cottage @ Saybrook Point
4.92 out of 5 average rating, 59 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Guest favourite
Home in Old Saybrook
Bird Bliss. Our Waterview home &deep water dock.
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 3 bathrooms
6–11 Jul
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Home in Old Saybrook
Waterfront Oasis 4Bdr/2b
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 2 bathrooms
8–13 Oct
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Home in Old Saybrook
Newly renovated CT shoreline home next to Marinas
4.9 out of 5 average rating, 42 reviews, 3 bedrooms, 3 beds, 2 bathrooms
20–25 Jul
Guest favourite
Cottage in Old Saybrook
Rachel’s Retreat
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 1 bathroom
29 Aug – 3 Sept
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Home in Old Saybrook
Cornfield Point Charmer–Walk to Beach
5.0 out of 5 average rating, 34 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
21–26 Jul
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Flat in Essex
Quintessential Essex. Steps from the Steam Train!
5.0 out of 5 average rating, 16 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
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Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
5.0 out of 5 average rating, 96 reviews, 3 bedrooms, 6 beds, 1.5 bathrooms
21–26 Aug
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Flat in Chester
The Little Chestnut.
4.97 out of 5 average rating, 60 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
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Cottage in Westbrook
Beautiful Updated Cottage walk to the Beach
4.99 out of 5 average rating, 84 reviews, 3 bedrooms, 4 beds, 1 bathroom
8–13 Sept
Guest favourite
Home in Westbrook
Zion's Light Beach Cottage
4.89 out of 5 average rating, 87 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Tiny home in Deep River
Her tiny Parisian boat house
4.9 out of 5 average rating, 42 reviews, 1 bedroom, 1 bed, 2 bathrooms
16–21 Jul