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

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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, (71 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is CA $434
CA $496 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $91
CA $644 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $653
CA $1,212 total
includes taxes & fees
Nov 11 - Nov 12
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
9.8 out of 10, Exceptional, (66 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $227
CA $401 total
includes taxes & fees
Nov 1 - Nov 2
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
8.8 out of 10, Excellent, (9 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is CA $91
CA $612 total
includes taxes & fees
Nov 8 - Nov 9
Walk to Beach | Seabreeze Cottage #4
A two-story house with a porch, a mailbox, and a lawn.

6. 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 CA $220
CA $512 total
includes taxes & fees
Nov 4 - Nov 5
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A white cottage with a front door, a garage, and a small porch with a potted plant.

7. 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, (30 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is CA $283
CA $502 total
includes taxes & fees
Oct 31 - Nov 1
The gardners Cottage 1 mile from long Island Sound - pet friendly
A two-story house with a porch, multiple windows, and a front door.

8. 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 CA $316
CA $738 total
includes taxes & fees
Oct 31 - Nov 1
Adorable Cottage with Cottage porch, walk to water & town
Terrace/patio

9. Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage

Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage
Hampton Bays
The price is CA $279
CA $547 total
includes taxes & fees
Nov 2 - Nov 3
Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage
A living room with stone walls, a fireplace, and a seating area with a sofa and armchairs.

10. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
The price is CA $371
CA $526 total
includes taxes & fees
Nov 17 - Nov 18
Westbrook Getaway-Near Beaches, Train & Shoreline
Terrace/patio

11. 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 CA $918
CA $1,189 total
includes taxes & fees
Oct 31 - Nov 1
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.

12. 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 CA $945
CA $1,219 total
includes taxes & fees
Oct 31 - Nov 1
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

Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"Perfect experience all around. But very noisy at 8 am - maintenance trucks, etc too loud. Would be better if they started at 9 am. A little jarring to hear the noise right outside rooms so early"
Mary Ann 1-night trip
Posted 23 hours ago
Faraway Sag Harbor

Find out more about Southold

Southold Cottages information

Number of reviews
142
Accommodation
201 Cottages
Lowest Price
CA $401
Highest Price
CA $1,219

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