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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
20–25 Jul
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4.92 out of 5 average rating, 109 reviews
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
4.93 out of 5 average rating, 15 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 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
The Cottage
4.74 out of 5 average rating, 250 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Aug
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Cottage in Old Saybrook
Serene Coastal Cottage steps from South Cove
4.97 out of 5 average rating, 38 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 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
16–21 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
11–16 Oct
Guest favourite
Home in Old Saybrook
Romantic Couples Retreat with Private Sandy Beach
4.93 out of 5 average rating, 56 reviews, 2 bedrooms, 4 beds, 1 bathroom
8–13 Jul
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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Guest suite in Old Saybrook
Cozy Loft Getaway
4.98 out of 5 average rating, 109 reviews, 1 bedroom, 2 beds, 1 bathroom
9–14 Aug
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Cottage in Old Saybrook
Beautiful View Cottage
4.99 out of 5 average rating, 161 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
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Flat in Old Saybrook
Charming Center of it All Location
4.98 out of 5 average rating, 65 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
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Home in Old Saybrook
Summertime in Old Saybrook on the Oyster River
5.0 out of 5 average rating, 6 reviews, 5 bedrooms, 6 beds, 2.5 bathrooms
13–18 Sept
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Home in Old Saybrook
3BR Ranch W/ Pool House and Stunning Sunsets
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 3 beds, 1 bathroom
8–13 Sept
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Home in Westbrook
Sea Salt Air Changes Everything
4.97 out of 5 average rating, 78 reviews, 3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
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Loft in Essex
Unique apartment in former art gallery.
4.94 out of 5 average rating, 469 reviews, 2 bedrooms, 4 beds, 1 bathroom
1–6 Aug
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Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
5.0 out of 5 average rating, 98 reviews, 3 bedrooms, 6 beds, 1.5 bathrooms
24–29 Aug
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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
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Home in Old Lyme
Modern Farmhouse with Hot Tub in Old Lyme, CT
4.97 out of 5 average rating, 226 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept