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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
14–19 Sept
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4.92 out of 5 average rating, 113 reviews
Top guest favourite
Cottage in Old Saybrook
The Cottage
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
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, 2 bathrooms
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, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 22 reviews
Guest favourite
Cottage in Old Saybrook
Osprey Cozy Cottage | Near Downtown & Beaches
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 13 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 bathrooms
27 Aug – 1 Sept
New place to stay
Top guest favourite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds, 1.5 bathrooms
26–31 Aug
5.0 out of 5 average rating, 100 reviews
Guest favourite
Home in Old Saybrook
Steps to Beach! *Cozy Cottage* Pet Friendly
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.92 out of 5 average rating, 104 reviews
Top guest favourite
Guest suite in Old Saybrook
Cozy Loft Getaway
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 109 reviews
Top guest favourite
Flat in Old Saybrook
Charming Center of it All Location
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 68 reviews
Top guest favourite
Room in Deep River
Riverwind Willow Room in Deep River
1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 51 reviews
Home in Old Lyme
Waterfront Getaway! Picture-Perfect Setting
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.67 out of 5 average rating, 3 reviews
Top guest favourite
Tiny home in East Lyme
Waterfront Bliss Tiny Home
1 bedroom, 1 bed, 1 bathroom
25–30 Aug
4.99 out of 5 average rating, 167 reviews
Guest favourite
Bungalow in Westbrook
Adorable single story cottage-by-the-sea
2 bedrooms, 2 queen beds, WC
15–20 Sept
4.87 out of 5 average rating, 53 reviews
Guest favourite
Home in Essex
Historic Essex Home w/ Large Yard Near Downtown!
2 bedrooms, 3 beds, 1.5 bathrooms
30 Sept – 5 Oct
4.91 out of 5 average rating, 139 reviews
Top guest favourite
Room in Deep River
Her tiny Parisian boat house
1 single bed, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 54 reviews
Top guest favourite
Room in Madison
Madison Cozy Studio with Private Entrance
3 beds, 1 bathroom
29 Aug – 3 Sept
4.88 out of 5 average rating, 596 reviews
Top guest favourite
Home in Old Saybrook
Year Round Beach House in Old Saybrook, CT.- Pets
4 bedrooms, 7 beds, 2 bathrooms
2–7 Sept
4.97 out of 5 average rating, 144 reviews
Top guest favourite
Cottage in East Haddam
Historic Hearthstone Cottage
1 bedroom, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 108 reviews