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Search results; Over 1,000 homes in Old Saybrook

Top guest favourite
Home in Old Saybrook
Year Round Beach House in Old Saybrook, CT.- Pets
4 bedrooms, 7 beds, 2 private bathrooms
8–13 Sept
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4.97 out of 5 average rating, 145 reviews
Top guest favourite
Cottage in Old Saybrook
The Cottage
1 bedroom, 2 beds
8–13 Sept
4.75 out of 5 average rating, 256 reviews
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms, 3 beds
7–12 Sept
4.96 out of 5 average rating, 24 reviews
Superhost
Home in Old Saybrook
Cozy beach side home Chalker Beach Old Saybrook
3 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds
27 Aug – 1 Sept
Guest favourite
Cottage in Old Saybrook
Osprey Cozy Cottage | Near Downtown & Beaches
1 bedroom, 1 queen bed
7–12 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds
26–31 Aug
5.0 out of 5 average rating, 102 reviews
Top guest favourite
Room in Deep River
Safari inspired little house
2 single beds
6–11 Sept
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Cottage in Old Saybrook
Beautiful View Cottage
2 bedrooms, 3 beds
28 Sept – 3 Oct
4.98 out of 5 average rating, 165 reviews
Top guest favourite
Room in Deep River
Riverwind Willow Room in Deep River
1 queen bed
4–9 Oct
4.98 out of 5 average rating, 52 reviews
Guest favourite
Home in Old Lyme
Waterfront! The Perfect Cozy Cottage in Old Lyme
2 bedrooms, 3 beds
13–18 Sept
4.83 out of 5 average rating, 6 reviews
Guest favourite
Home in Essex
Historic Essex Home w/ Large Yard Near Downtown!
2 bedrooms, 3 beds
11–16 Oct
4.91 out of 5 average rating, 140 reviews
Top guest favourite
Room in East Lyme
Private house, your own room and bath. Near shore.
1 bed
13–18 Sept
4.98 out of 5 average rating, 121 reviews
Top guest favourite
Tiny home in East Lyme
Waterfront Bliss Tiny Home
1 bedroom, 1 bed
31 Aug – 5 Sept
4.99 out of 5 average rating, 172 reviews
Top guest favourite
Guest house in Portland
Guesthouse Farm Stay
1 bedroom, 2 beds
31 Oct – 5 Nov
4.98 out of 5 average rating, 342 reviews
Top guest favourite
Cottage in East Haddam
Historic Hearthstone Cottage
1 bedroom, 3 beds
23–28 Aug
5.0 out of 5 average rating, 109 reviews
Guest favourite
Home in Old Saybrook
Steps to Beach! *Cozy Cottage* Pet Friendly
1 bedroom, 1 queen bed
18–23 Sept
4.92 out of 5 average rating, 104 reviews
Top guest favourite
Cabin in Colchester
The Colchester Cottage
1 bedroom, 3 beds
25–30 Oct
5.0 out of 5 average rating, 16 reviews
Guest favourite
Bungalow in Westbrook
Adorable single story cottage-by-the-sea
2 bedrooms, 2 queen beds
15–20 Sept
4.87 out of 5 average rating, 55 reviews