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

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (66 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is ￥45,695
￥52,205 total
includes taxes & fees
Nov 17 - Nov 18
North Fork Resort
A residential area with houses, a driveway, and a body of water in the background.

2. Steps to the beach | Seabreeze Cottage #3

Steps to the beach | Seabreeze Cottage #3
Hampton Bays
6.0 out of 10, (3 reviews)
"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...
United States
Lydia
The price is ￥12,016
￥71,400 total
includes taxes & fees
Oct 25 - Oct 26
Steps to the beach | Seabreeze Cottage #3
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 ￥78,536
￥142,264 total
includes taxes & fees
Nov 3 - Nov 4
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
A small single-story house with a front porch, a potted plant, and two Adirondack chairs.

4. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (62 reviews)
"We enjoyed our stay"
United States
JM B.
The price is ￥16,363
￥32,707 total
includes taxes & fees
Oct 21 - Oct 22
1-bedroom cottage with Grove Beach 🏖️ access.
A single-story house with a gabled roof, a front porch, and a well-maintained garden.

5. Walk to Beach | Seabreeze Cottage #4

Walk to Beach | Seabreeze Cottage #4
Hampton Bays
8.6 out of 10, Excellent, (8 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is ￥5,375
￥62,836 total
includes taxes & fees
Oct 18 - Oct 19
Walk to Beach | Seabreeze Cottage #4
A white cottage with a front door, a garage, and a small porch with a potted plant.

6. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (29 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is ￥24,888
￥46,044 total
includes taxes & fees
Oct 19 - Oct 20
The gardners Cottage 1 mile from long Island Sound - pet friendly
A two-story house with a porch, a mailbox, and a lawn.

7. 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
9.4 out of 10, Exceptional, (3 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is ￥23,620
￥55,740 total
includes taxes & fees
Oct 20 - Oct 21
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A living room with a sofa, armchair, coffee table, and a television.

8. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
The price is ￥37,991
￥54,244 total
includes taxes & fees
Oct 20 - Oct 21
Westbrook Getaway-Near Beaches, Train & Shoreline
A two-story house with a porch, multiple windows, and a front door.

9. Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
9.0 out of 10, Wonderful, (8 reviews)
"Very clean and comfortable"
United States
Francine F.
The price is ￥35,689
￥86,757 total
includes taxes & fees
Oct 18 - Oct 19
Adorable Cottage with Cottage porch, walk to water & town
Terrace/patio

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 ￥103,754
￥143,548 total
includes taxes & fees
Oct 22 - Oct 23
5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A sign for J&S Reeves Cottages with a view of a house and trees.

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 ￥106,828
￥147,163 total
includes taxes & fees
Oct 22 - Oct 23
4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A sign for J&S Reeves Cottages with a view of a house and trees.

12. 3rd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

3rd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
8.6 out of 10, Excellent, (7 reviews)
"We loved everything about our stay at the cottage. Such beautiful property and surroundings. If you’re looking to spend some quality time with family in a quiet setting with beautiful surroundings , look no further. Thanks Sandy. We will be Back."
United States
Wendy B.
The price is ￥118,099
￥160,240 total
includes taxes & fees
Oct 20 - Oct 21
3rd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A lakeside cottage with a covered porch, a sign for J&S Reeves Cottages, and a grassy lawn with lounge chairs.

13. 1st of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

1st of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
9.0 out of 10, Wonderful, (7 reviews)
"Nice scenery. Spartan kitchen furnishings and bathroom toiletries. Paid booking (including all ocuppants and pets) and was invoiced by vrbo. Received addtional invoice from the owner adding 250 dolars pet fee (125x2 pets) which was not listed on the property description that only mentions "pet friendly"."
United States
Simon C.
The price is ￥118,099
￥160,240 total
includes taxes & fees
Oct 19 - Oct 20
1st of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A waterfront property with a grassy lawn, a dock with boats, and a patio area with outdoor furniture.

14. 2nd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

2nd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
9.6 out of 10, Exceptional, (5 reviews)
"Great rental experience. Owners friendly and available"
United States
Patricia and Michael F.
The price is ￥118,099
￥160,240 total
includes taxes & fees
Oct 21 - Oct 22
2nd 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

Zey Hotel

Zey Hotel

10/10 Excellent
"Hotel is in a great location, central to everything. Staff was helpful and courteous. We will definitely be back!"
Joanne 1-night trip
Posted 7 hours ago
Zey Hotel

Find out more about Southold

Southold Cottages information

Number of reviews
155
Accommodation
205 Cottages
Lowest Price
￥32,707
Highest Price
￥160,240

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