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Search results; Over 1,000 homes in Southold

Top guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 private bathrooms
21–26 Jul
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4.94 out of 5 average rating, 53 reviews
Guest favourite
Home in Mattituck
Lakehouse Getaway North Fork
3 bedrooms, 5 beds
11–16 Jul
5.0 out of 5 average rating, 44 reviews
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
2 bedrooms, 4 beds
12–17 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
3 bedrooms, 3 beds
10–17 Jul
5.0 out of 5 average rating, 25 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds
15–22 Aug
New place to stay
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds
14–19 Aug
5.0 out of 5 average rating, 16 reviews
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds
12–17 Jul
5.0 out of 5 average rating, 6 reviews
Home in Amagansett
Unit 211: Cottage | Ocean View | Striper
2 bedrooms
20–25 Sept
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5 bedrooms, 10 beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 3 reviews
Home in East Hampton
Tranquil Springs Cottage
2 bedrooms, 2 queen beds
23–28 Jul
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Southold
Family and Dog Friendly Private Beach
3 bedrooms, 3 queen beds
25–30 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in East Marion
Waterfront Bungalow w/Private Beach on Peconic Bay
3 bedrooms, 4 beds
1–8 Aug
4.88 out of 5 average rating, 42 reviews
Guest favourite
Home in Madison
Fabulous pool in beach town!
4 bedrooms, 4 beds
10–15 Jul
4.95 out of 5 average rating, 22 reviews
Home in Mattituck
3 bed 2 bath sleeps 5 on north fork of Long Island
3 bedrooms, 4 beds
14–19 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cottage in East Lyme
Beach Cottage!
2 bedrooms, 2 queen beds
13–18 Sept
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Home in Clinton
Soundscape Beachfront House!
3 bedrooms, 3 queen beds
24–30 Jul
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
3 bedrooms, 3 beds
1–7 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds
9–14 Aug
5.0 out of 5 average rating, 90 reviews
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds
23–28 Jul
4.91 out of 5 average rating, 93 reviews