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Jan 2 - Jan 4
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Jan 9 - Jan 11
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Jan 23 - Jan 25
In two months
Feb 20 - Feb 22

Our top choices for Southold cottages

Exterior
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.2 out of 10, Wonderful, (36)
"Very clean rustic cabin. The host was very accommodating. Fresh flowers and fruit were a nice touch from the host"
United States
Deb P.
$173 nightly
The price is $196
Jan 6 - Jan 7, 2026
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV
Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach
Hampton Bays
10.0 out of 10, Exceptional, (1)
$387 nightly
The price is $442
Jan 4 - Jan 5, 2026
Total with taxes and fees
Seabreeze #3: Cozy Cottage by the beach
Exterior
Beach Cottage, private beach and pass

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (9)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
$434 nightly
The price is $491
Jan 14 - Jan 15, 2026
Total with taxes and fees
Beach Cottage, private beach and pass
Exterior
Seabreeze #4: Charming Cottage Footsteps to the Beach

Seabreeze #4: Charming Cottage Footsteps to the Beach

Seabreeze #4: Charming Cottage Footsteps to the Beach
Hampton Bays
8.8 out of 10, Excellent, (3)
"Great stay. Would stay again. "
United States
Weston B.
$391 nightly
The price is $447
Jan 20 - Jan 21, 2026
Total with taxes and fees
Seabreeze #4: Charming Cottage Footsteps to the Beach
Terrace/patio
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

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
$509 nightly
The price is $582
Jan 7 - Jan 8, 2026
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Exterior
My Humble Abode 2BR Beachside Home | TennisPoolPKG

My Humble Abode 2BR Beachside Home | TennisPoolPKG

My Humble Abode 2BR Beachside Home | TennisPoolPKG
Napeague
10.0 out of 10, Exceptional, (1)
$1,345 nightly
The price is $1,507
Jan 14 - Jan 15, 2026
Total with taxes and fees
My Humble Abode 2BR Beachside Home | TennisPoolPKG
Exterior
Luxurious 3 BR Cottage w/ Ocean View Balcony

Luxurious 3 BR Cottage w/ Ocean View Balcony

Luxurious 3 BR Cottage w/ Ocean View Balcony
Napeague
10.0 out of 10, Exceptional, (3)
"Had a great weekend. Right on beach. Beautiful."
United States
Steven B.
$1,871 nightly
The price is $2,097
Jan 15 - Jan 16, 2026
Total with taxes and fees
Luxurious 3 BR Cottage w/ Ocean View Balcony
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 Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Room was beautiful and spacious. Staff was courteous and on point. "
Ron 2-night trip
Posted 21 hours ago
The Bentley Hotel Southampton

Find out more about Southold

Southold Cottages information

Number of reviews
17
Accommodation
193 Cottages
Lowest Price
$442
Highest Price
$2,097

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