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

Search Southold Cottage Rentals from CA $321

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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, (55 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is CA $391
CA $447 total
includes taxes & fees
Oct 18 - Oct 19
North Fork Resort
A residential area with houses, a driveway, and a body of water in the background.

2. Seabreeze #3 Cozy Cottage steps to the beach

Seabreeze #3 Cozy Cottage steps to the beach
Hampton Bays
8.0 out of 10, Very good, (2 reviews)
"Camila was very communicative and helpful. The cottage clearly has a history of high traffic, and while it holds a certain rustic charm, it's undeniably showing its age. The property feels quite worn and tired, with fixtures and furnishings having seen better days. On the surface, the cottage was tidy upon arrival, but closer inspection revealed that it lacked a deep, thorough cleaning. While the main living areas were presentable, the corners, baseboards, and other area's not immediately...
United States
Anonymous traveller
The price is CA $118
CA $638 total
includes taxes & fees
Sep 20 - Sep 21
Seabreeze #3 Cozy Cottage steps to the beach
A small single-story house with a front porch, a potted plant, and two Adirondack chairs.

3. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (56 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $169
CA $321 total
includes taxes & fees
Oct 6 - Oct 7
1-bedroom cottage with Grove Beach 🏖️ access.
A white cottage with a front door, a garage, and a small porch with a potted plant.

4. 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, (28 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is CA $244
CA $425 total
includes taxes & fees
Oct 13 - Oct 14
The gardners Cottage 1 mile from long Island Sound - pet friendly
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
10.0 out of 10, Exceptional, (2 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is CA $207
CA $466 total
includes taxes & fees
Sep 28 - Sep 29
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A deck with a gray sofa, a wooden chair, and a metal fire pit.

6. 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 $761
CA $1,338 total
includes taxes & fees
Oct 6 - Oct 7
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
A single-story house with a gabled roof, a front porch, and a well-maintained garden.

7. Seabreeze 4 Charming Cottage footsteps to beach

Seabreeze 4 Charming Cottage footsteps to beach
Hampton Bays
8.6 out of 10, Excellent, (8 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is CA $194
CA $743 total
includes taxes & fees
Sep 27 - Sep 28
Seabreeze 4 Charming Cottage footsteps to beach
A coastal residential area with houses, a beach, and a pier.

8. Direct waterfront renovated cottage.

Direct waterfront renovated cottage.
Madison Center
10.0 out of 10, Exceptional, (95 reviews)
"Great cottage on the Sound!"
United States
David S.
The price is CA $877
CA $1,368 total
includes taxes & fees
Sep 28 - Sep 29
Direct waterfront renovated cottage.
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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Staff was helpful and professional. Room was clean, basic, nice. The TV was a little sketchy-some stations were static. The bathroom shower was great: good flow, hot and soothing. Overall, very good for the price."
John 1-night trip
Posted 3 hours ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Southold

Southold Cottages information

Number of reviews
191
Accommodation
211 Cottages
Lowest Price
CA $321
Highest Price
CA $1,368

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