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Top Cities in Town of Southold Town

Beautiful spot on the #longisland sound surfing
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Greenport

Greenport

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Dec 8 - Dec 9
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Dec 9 - Dec 10
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

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Compare 545 hotels in Town of Southold Town with room rates, reviews, and availability. Most hotels are fully refundable.

Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

4.0 star property
Greenport
8.6 out of 10, Excellent, (598)
"Staff was amazing , room clean view phenomenal "
United States
Denise
$213 nightly
The price is $243
Dec 24 - Dec 25
Total with taxes and fees
Sound View Greenport
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn

The Harbor Front Inn

3.5 star property
Greenport
8.8 out of 10, Excellent, (543)
"Awesome stay!!! Great Location "
United States
Bryan
$174 nightly
The price is $199
Dec 29 - Dec 30
Total with taxes and fees
The Harbor Front Inn
Garden Suite King | Premium bedding, down comforters, individually decorated
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 star property
Southold
9.6 out of 10, Exceptional, (226)
"Food!"
United States
Ryan
$174 nightly
The price is $199
Dec 29 - Dec 30
Total with taxes and fees
The Shoals Suites and Slips
Exterior
Zey Hotel

Zey Hotel

3.5 star property
Greenport
9.2 out of 10, Wonderful, (290)
"Loved this place. Lots of places to relax and play games. Super-friendly staff. Can't wait to go back b"
United States
Susie
$182 nightly
The price is $208
Dec 22 - Dec 23
Total with taxes and fees
Zey Hotel
Beach bar
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

4.0 star property
Greenport
9.8 out of 10, Exceptional, (140)
"Great get away "
United States
Charles
$225 nightly
The price is $257
Dec 14 - Dec 15
Total with taxes and fees
Silver Sands Motel & Beach Bungalows
Property entrance
The Menhaden

The Menhaden

3.5 star property
Greenport
9.6 out of 10, Exceptional, (171)
"Wonderful stay in a quaint hotel..The small town was amazing and had such cozy welcoming atmosphere! "
United States
Cory
$309 nightly
The price is $347
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Menhaden
Property grounds
Greenporter Hotel

Greenporter Hotel

2.0 star property
Greenport
9.2 out of 10, Wonderful, (282)
"Great location, great service, very clean."
United States
Christian
Greenporter Hotel
Luxury Tent | Free WiFi, bed sheets
North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3.0 star property
Greenport
9.4 out of 10, Exceptional, (6)
"great place to stay, clean and quiet....loved it"
United States
Darlin
North Fork Cottages & RV Resort
Exterior
American Beech Hotel

American Beech Hotel

3.5 star property
Greenport
8.8 out of 10, Excellent, (195)
"The property was clean beautiful and pleasant. Loved the trendy decor."
United States
Jennifer
$234 nightly
The price is $267
Dec 9 - Dec 10
Total with taxes and fees
American Beech Hotel
Interior entrance
Vine & Sand

Vine & Sand

3.0 star property
Southold
9.6 out of 10, Exceptional, (13)
"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."
United States
Sandra
$320 nightly
The price is $366
Dec 16 - Dec 17
Total with taxes and fees
Vine & Sand
Exterior
Arbor View House B&B

Arbor View House B&B

3.5 star property
East Marion
9.2 out of 10, Wonderful, (15)
"Two mid age couples just had a good and relaxing time with great hospitality. "
United States
Michail
Arbor View House B&B
Beach
Harbor Heights

Harbor Heights

Pipes Cove
9.8 out of 10, Exceptional, (14)
"This was a perfect location and such a cute place! The apartment was spotless and well appointed. "
United States
Pamela
Harbor Heights
Terrace/patio
American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7

Greenport
9.0 out of 10, Wonderful, (4)
"Great job "
United States
emilio
$242 nightly
The price is $277
Dec 9 - Dec 10
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
Living area
Harbor Knoll Bed & Breakfast

Harbor Knoll Bed & Breakfast

3.0 star property
Pipes Cove
9.2 out of 10, Wonderful, (12)
"It was very pleasant. We would stay again someday. Very convenient to restaurants in town and ferry. "
United States
Andrea
Harbor Knoll Bed & Breakfast
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool umbrellas
Hotel Moraine

Hotel Moraine

2.0 star property
Greenport
9.8 out of 10, Exceptional, (22)
"Our 3rd stay - we love the beauty of the property and the luxurious serenity of this boutique hotel. Great views of the water; fantastic large pool and lounging areas."
United States
Amy
Hotel Moraine
Beach/ocean view
Stirling House Bed & Breakfast

Stirling House Bed & Breakfast

3.0 star property
Greenport
9.8 out of 10, Exceptional, (24)
"Our stay was only 2 nights but felt like 5. Well rested 3 days. Would return in a Heart Beat. Clay was awesome and the breakfasts were over the top !"
United States
Adam
Stirling House Bed & Breakfast
Sun loungers, beach towels
Aqua Vista

Aqua Vista

Pipes Cove
10.0 out of 10, Exceptional, (23)
"Great location and perfect for two couples. We loved staying here."
United States
laura d.
Aqua Vista
Microwave
Surrounded by nature, come stay in this 1 bedroom private, serene location

Surrounded by nature, come stay in this 1 bedroom private, serene location

Southold
10.0 out of 10, Exceptional, (3)
"We enjoyed our stay here. Great host, easy check in. Clean, comfortable and centrally located. Would definitely stay again. "
United States
Cheryl H.
Surrounded by nature, come stay in this 1 bedroom private, serene location
Terrace/patio
The SandPiper

The SandPiper

Pipes Cove
9.8 out of 10, Exceptional, (30)
"Our stay in Greenport at the Sandpiper was wonderful! Location was perfect: easy walk into town and to the ferry to shelter island. Ten out of ten!"
United States
paris t.
The SandPiper
1 bedroom, iron/ironing board, internet
American Beech in Greenport NY - King Suite 1

American Beech in Greenport NY - King Suite 1

Greenport
10.0 out of 10, Exceptional, (5)
"Perfect Great place"
United States
Dean J.
$267 nightly
The price is $305
Dec 9 - Dec 10
Total with taxes and fees
American Beech in Greenport NY - King Suite 1
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.
View all properties

Great weekend hotel deals in Town of Southold Town, NY

Showing deals for:Dec 19 - Dec 21

Image gallery for Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Beach nearby, sun loungers, beach towels

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Cutchogue
10/10Exceptional (28 reviews)
6% off
$293 nightly
Price is $986
Total with taxes and fees
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
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Top Town of Southold Town Hotel Reviews

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

10/10 Excellent
"Great get away "
Charles 2-night trip
Posted 2 days ago
Silver Sands Motel & Beach Bungalows

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