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Search results; Over 1,000 homes in Old Saybrook

Top guest favourite
Cottage in Old Saybrook
1920’s charming dollhouse near South Cove
1 bedroom, 1 bed, 1 bathroom
12–17 Sept
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4.96 out of 5 average rating, 110 reviews
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Cottage in Old Saybrook
The Cottage
1 bedroom, 2 beds, 1 bathroom
19–24 Oct
4.75 out of 5 average rating, 257 reviews
Guest favourite
Cottage in Old Saybrook
Osprey Cozy Cottage | Near Downtown & Beaches
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 15 reviews
Home in Old Saybrook
Adorable home walk to Saybrook Point !
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Old Saybrook
Cozy beach side home Chalker Beach Old Saybrook
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds, 1.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 102 reviews
Top guest favourite
Cottage in Old Saybrook
Beautiful View Cottage
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.98 out of 5 average rating, 165 reviews
Top guest favourite
Flat in Chester
The Little Chestnut: Walk to downtown Chester.
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 70 reviews
Guest favourite
Home in Old Saybrook
Steps to Beach! *Cozy Cottage* Pet Friendly
1 bedroom, 1 queen bed, 1 bathroom
18–23 Sept
4.92 out of 5 average rating, 104 reviews
Top guest favourite
Home in Branford
Adorable Beach House on LI Sound
1 bedroom, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 108 reviews
Top guest favourite
Room in Deep River
Riverwind Hearts & Flowers Room in Deep River
1 queen bed, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Home in Old Saybrook
Year Round Beach House in Old Saybrook, CT.- Pets
4 bedrooms, 7 beds, 2 bathrooms
8–13 Sept
4.97 out of 5 average rating, 145 reviews
Top guest favourite
Cabin in Colchester
The Colchester Cottage
1 bedroom, 3 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
3 bedrooms, 3 beds, 1.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Essex
Ideal Historic Home in Essex Village
2 bedrooms, 3 beds, 1.5 bathrooms
9–14 Nov
4.97 out of 5 average rating, 98 reviews
Guest favourite
Guest house in Madison
Charming Cottage is 1 Mile from Town and Beach
1 bedroom, 1 double bed, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Essex
Quintessential Essex. Steps from the Steam Train!
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Bungalow in Old Lyme
Pet Friendly Bungalow!!!
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 368 reviews