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Search results; Over 1,000 homes in Old Saybrook

Top guest favourite
Cottage in Old Saybrook
The Cottage
1 bedroom, 2 beds, 1 private bathroom
6–11 Sept
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4.75 out of 5 average rating, 253 reviews
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
4.95 out of 5 average rating, 22 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
Superhost
Home in Old Saybrook
Cozy beach side home Chalker Beach Old Saybrook
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Flat in Old Saybrook
Charming Center of it All Location
4.99 out of 5 average rating, 68 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Guest favourite
Cottage in Old Saybrook
Osprey Cozy Cottage | Near Downtown & Beaches
5.0 out of 5 average rating, 13 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 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
23–28 Sept
Guest favourite
Home in Old Saybrook
Steps to Beach! *Cozy Cottage* Pet Friendly
4.92 out of 5 average rating, 104 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
Top guest favourite
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
Top guest favourite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
5.0 out of 5 average rating, 99 reviews, 3 bedrooms, 6 beds, 1.5 bathrooms
24–29 Aug
Guest favourite
Home in Old Saybrook
Beach House Getaway
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 5 beds, 1.5 bathrooms
31 Aug – 7 Sept
Top guest favourite
Home in Old Saybrook
The Channelside
4.98 out of 5 average rating, 61 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Home in Old Saybrook
Cornfield Point Charmer–Walk to Beach
5.0 out of 5 average rating, 36 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
19–24 Aug
Top guest favourite
Tiny home in Deep River
Safari inspired little house
5.0 out of 5 average rating, 17 reviews, 1 bedroom, 2 beds, 1 bathroom
11–16 Aug
Guest favourite
Tiny home in Old Saybrook
The Ingham Guest House-quaint & quiet, near beach
4.9 out of 5 average rating, 21 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Aug
Guest favourite
Tiny home in East Lyme
Lakefront Dream Tiny House
4.98 out of 5 average rating, 53 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Home in Old Saybrook
3BR Updated Cottage w/ Pool in Old Saybrook
4.97 out of 5 average rating, 74 reviews, 3 bedrooms, 4 beds, 1 bathroom
7–12 Sept
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
4.95 out of 5 average rating, 20 reviews, 2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Room in Deep River
Her tiny Parisian boat house
4.92 out of 5 average rating, 53 reviews, 1 single bed, 2 bathrooms
1–6 Aug
Top guest favourite
Cottage in Old Saybrook
Rachel’s Retreat
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 4 beds, 1 bathroom
7–12 Sept