A calm lake with a forest in the background during sunset.

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Southold cottages

A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

1. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (50 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is €314
includes taxes & fees
7 Sept - 8 Sept
North Fork Resort
A small single-story house with a front porch, a potted plant, and two Adirondack chairs.

2. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (52 reviews)
"We enjoyed our stay"
United States
JM B.
The price is €194
includes taxes & fees
15 Sept - 16 Sept
1-bedroom cottage with Grove Beach 🏖️ access.
A deck with a gray sofa, a wooden chair, and a metal fire pit.

3. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is €942
includes taxes & fees
9 Sept - 10 Sept
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
A residential area with houses, a driveway, and a body of water in the background.

4. Seabreeze #3 Cozy Cottage steps to the beach

Seabreeze #3 Cozy Cottage steps to the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is €549
includes taxes & fees
7 Sept - 8 Sept
Seabreeze #3 Cozy Cottage steps to the beach
A two-story house with a porch, a mailbox, and a lawn.

5. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
The price is €309
includes taxes & fees
3 Sept - 4 Sept
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A single-story house with a gabled roof, a front porch, and a well-maintained garden.

6. Seabreeze 4 Charming Cottage footsteps to beach

Seabreeze 4 Charming Cottage footsteps to beach
Hampton Bays
9.4 out of 10, Exceptional, (6 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is €545
includes taxes & fees
7 Sept - 8 Sept
Seabreeze 4 Charming Cottage footsteps to beach
An aerial view of J&S Reeves Cottages with a dock and boats, surrounded by greenery and houses.

7. 6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Riverhead
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay. Very quiet and relaxing. Excellent location to many wineries. Would definitely stay again."
United States
Donna M.
The price is €623
includes taxes & fees
14 Sept - 15 Sept
6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A two-story house with a porch, multiple windows, and a front door.

8. Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water

Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
Westbrook Center
9.4 out of 10, Exceptional, (3 reviews)
"We had a lovely time during our stay. The hosts were excellent with communication and quick responses throughout our stay. The 2 family suites were perfect for our families to all stay together during this trip. We would definitely book again! "
United States
Kate G.
The price is €752
includes taxes & fees
24 Aug - 25 Aug
Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
An aerial view of a marina with boats docked, surrounded by residential buildings and greenery.

9. Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (51 reviews)
"Great spot easy walk to the water and very close to town!"
United States
Genevieve G.
The price is €734
includes taxes & fees
24 Aug - 25 Aug
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

10. 5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
10.0 out of 10, Exceptional, (3 reviews)
"Fantastic experience. Cabin was clean and quiet. Beautiful mornings on the water."
United States
Leah O.
The price is €792
includes taxes & fees
26 Aug - 27 Aug
5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
An aerial view of J&S Reeves Cottages, featuring a dock, boats, and a lake.

11. 4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
9.8 out of 10, Exceptional, (19 reviews)
"Great cottage on amazing grounds! We loved the screened in porch. Sandy and john are great hosts. We also loved using the kayaks and checking out the bay."
United States
Richard C.
The price is €792
includes taxes & fees
26 Aug - 27 Aug
4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southold Hotel Reviews

The Hampton Maid

The Hampton Maid

8/10 Good
"The hotel has a sort of New England charm. The rooms are good sized and ours had a nice balcony overlooking the gardens. Prices were pretty reasonable for the Hamptons in the middle of Summer, although someone else staying there told us that the breakfast was not particularly good and yet expensive. We decided to take breakfast elsewhere. I would certainly return to the Hampton Maid if I ever go back to the area."
Ronald 2-night trip
Posted 2 hours ago
The Hampton Maid

Find out more about Southold

Southold Cottages information

Number of reviews
136
Accommodation
223 Cottages
Lowest Price
€194
Highest Price
€942

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