Southold Cottages ￥44,780

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

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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

Greenport

Altynai

￥55,985 total

includes taxes & fees

Nov 1 - Nov 2

A residential area with houses, a driveway, and a body of water in the background.

2. Steps to the beach | Seabreeze Cottage #3

Hampton Bays

"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...

Lydia

￥76,673 total

includes taxes & fees

Nov 1 - Nov 2

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

Greenport

Jeannette M.

￥141,139 total

includes taxes & fees

Nov 9 - Nov 10

A small single-story house with a front porch, a potted plant, and two Adirondack chairs.

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

Clinton

JM B.

￥44,780 total

includes taxes & fees

Nov 1 - Nov 2

A single-story house with a gabled roof, a front porch, and a well-maintained garden.

5. Walk to Beach | Seabreeze Cottage #4

Hampton Bays

Weston B.

￥76,315 total

includes taxes & fees

Nov 8 - Nov 9

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!

Madison

Samantha D.

￥57,252 total

includes taxes & fees

Nov 6 - Nov 7

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

Clinton

Wink V.

￥56,028 total

includes taxes & fees

Nov 2 - Nov 3

A two-story house with a porch, multiple windows, and a front door.

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

Westbrook Center

Francine F.

￥86,103 total

includes taxes & fees

Oct 30 - Oct 31

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Top Southold Hotel Reviews

The Bentley Hotel Southampton

10/10 Excellent

"Excellent stay on the south fork and affordable."

Zey Hotel

10/10 Excellent

"The stay was perfect. I can't think of a single thing to criticize. As an example, when we were checking out, we called the manager on his cell to alert him that a fire truck was flushing the street hydrants, and that we noticed that the water in the room was brown. We knew that the maintenance of the hydrants was causing the dirty water. The manager promptly told us we could stay until 6:00 pm for free, so that we would be able to take clean showers. We told him that we had showered early, and that we had no problem. But his response showed how he cared for the guests."

Faraway Sag Harbor

8/10 Good

"Beautiful and charming hotel! Unfortunately the restaurant was only serving breakfast and not dinner, since we arrived off- season. However the restaurant was freezing due to the heating system not working so we had to go elsewhere in town for breakfast. Too bad because it was a lovely room with a harbor view. Our biggest disappointment by far was the coffee in the room and in the lobby. Nasty stuff! I have never tasted coffee this bad in any hotel (and we have been to many). First of all at this high- end price point per night, Faraway should be providing at least a Nespresso machine in each room for a decent morning cup of coffee instead of instant coffee packets which went out with Sanka like forty years ago. :( Then we thought that maybe the coffee urns on the bar in the common area would at least provide a half decent cup of coffee. Boy were we wrong! The fact that other filled cups of coffee which were left on the bar still full told us that other guests felt the same about the quality of coffee. Thank goodness for Goldbergs Bagel shop in town! Come on guys. If you want to be recognized as a high end getaway in an extremely wealthy part of Long Island, please find yourselves a better quality coffee source. Its not that hard these days. We speak for all true coffee lovers."

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Southold Cottages information

Number of reviews	142
Accommodation	205 Cottages
Lowest Price	￥44,780
Highest Price	￥146,930

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Check prices for these dates

Our top choices for Southold cottages

1. North Fork Resort

2. Steps to the beach | Seabreeze Cottage #3

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

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

5. Walk to Beach | Seabreeze Cottage #4

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

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

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

9. Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage

10. Westbrook Getaway-Near Beaches, Train & Shoreline

11. 5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

12. 4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

Find vacation rentals that suit your style

Top Southold Hotel Reviews

The Bentley Hotel Southampton

Seven Beach Lane

Hyatt Place Long Island East End

Saybrook Point Resort & Marina

Zey Hotel

The Shoals Suites and Slips

Faraway Sag Harbor

Sag Harbor Inn

The Atlantic Hotel

Find out more about Southold

Southold Cottages information

Frequently asked questions

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Search Southold Cottage Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Southold cottages

1. North Fork Resort

2. Steps to the beach | Seabreeze Cottage #3

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

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

5. Walk to Beach | Seabreeze Cottage #4

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

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

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

9. Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage

10. Westbrook Getaway-Near Beaches, Train & Shoreline

11. 5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

12. 4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

Find vacation rentals that suit your style

Top Southold Hotel Reviews

The Bentley Hotel Southampton

Find out more about Southold

Southold Cottages information

Frequently asked questions

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