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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, 14 reviews, 2 bedrooms, 3 beds, 1 bathroom
14–19 Jul
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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, 37 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
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Cottage in Old Saybrook
Beautiful View Cottage
4.99 out of 5 average rating, 160 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
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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
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
20–25 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
Top guest favourite
Home in Westbrook
Sea Salt Air Changes Everything
4.97 out of 5 average rating, 78 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
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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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Flat in Old Lyme
Gateway Getaway
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
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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
4–9 Jul
Guest favourite
Loft in Essex
Unique apartment in former art gallery.
4.94 out of 5 average rating, 467 reviews, 2 bedrooms, 4 beds, 1 bathroom
1–6 Aug
Top guest favourite
Home in Westbrook
Beachside @ 455 Seaside
4.88 out of 5 average rating, 25 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 Sept
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Bungalow in Old Lyme
Pet Friendly Bungalow!!!
4.95 out of 5 average rating, 363 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Sept
Top guest favourite
Room in Westbrook
The Captain James Suite
4.92 out of 5 average rating, 100 reviews, 1 king bed, 1 bathroom
10–15 Aug