A white colonial-style house with a green roof and a lighthouse tower.

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Check prices for these dates

This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

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Our top choices for Town of Southold Town hotels

A spacious room with wicker furniture, large windows, and a view of the sea.

1. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (739 reviews)
"Great one night stay."
United States
Irene
The price is SAR 836
SAR 1,063 total
includes taxes & fees
6 Oct - 7 Oct
Sound View Greenport
A two-story house with a balcony, outdoor seating area, and a variety of plants.

2. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (412 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
The price is SAR 634
SAR 724 total
includes taxes & fees
4 Oct - 5 Oct
Zey Hotel
A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

3. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (342 reviews)
"Loved everything about our stay!"
United States
Melissa
The price is SAR 758
SAR 960 total
includes taxes & fees
1 Oct - 2 Oct
The Shoals Suites and Slips
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

4. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (661 reviews)
"Great location"
United States
Jordan
The price is SAR 782
SAR 1,001 total
includes taxes & fees
26 Oct - 27 Oct
The Harbor Front Inn
A modern house with a deck, outdoor seating, and a fire pit.

5. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (60 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is SAR 967
SAR 1,105 total
includes taxes & fees
30 Sep - 1 Oct
North Fork Resort
A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.

6. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (171 reviews)
"This is a great place that brings you back to a special time. Staff were exceptionally friendly and helpful. Made us feel like we were family - highly recommend."
United States
Keith
The price is SAR 1,062
SAR 1,213 total
includes taxes & fees
13 Oct - 14 Oct
Silver Sands Motel & Beach Bungalows
Terrace/patio

7. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (295 reviews)
"Great place!"
United States
Christine
The price is SAR 886
SAR 1,428 total
includes taxes & fees
25 Oct - 26 Oct
Cliffside Resort Condominiums
A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

8. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (191 reviews)
"Staff was very accommodating and extremely nice, Great stay!"
United States
Lisa
The price is SAR 1,252
SAR 1,581 total
includes taxes & fees
30 Sep - 1 Oct
The Menhaden
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

9. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (208 reviews)
"Great location, very friendly and helpful "
United States
Mary
The price is SAR 860
SAR 1,133 total
includes taxes & fees
1 Oct - 2 Oct
American Beech Hotel
A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.

10. Oyster Estate

Oyster Estate
4.0 star property
Greenport
9.2 out of 10, Wonderful, (291 reviews)
"Clean, great amenities, and friendly staff!"
United States
Elizabeth
The price is SAR 1,126
SAR 1,419 total
includes taxes & fees
21 Oct - 22 Oct
Oyster Estate
A beach with a sunset, calm water, and scattered rocks.

11. Arbor View House B&B

Arbor View House B&B
3.5 star property
East Marion
9.4 out of 10, Exceptional, (16 reviews)
"Wonderful stay! Will definitely be back!"
United States
Lekecia
Arbor View House B&B
A room with a round wooden table, a vase with branches, and a view of a dining area with chairs and a table.

12. Vine & Sand

Vine & Sand
3.0 star property
Southold
9.8 out of 10, Exceptional, (20 reviews)
"Location was perfect for visiting the wineries… breakfast was to die for!"
United States
Jennifer
Vine & Sand
A spacious living room with a large window overlooking the sea, a bar area with a view, and comfortable seating.

13. Hotel Moraine

Hotel Moraine
2.0 star property
Greenport
9.8 out of 10, Exceptional, (22 reviews)
"The property, the staff, everything was great. We would definitely stay here again"
United States
John D Fio
Hotel Moraine
A sunroom with a dining table, wicker furniture, a bookshelf, and a view of greenery outside.

14. Harbor Knoll Bed & Breakfast

Harbor Knoll Bed & Breakfast
3.0 star property
Pipes Cove
9.4 out of 10, Exceptional, (16 reviews)
"Great location you could walk to town without having to move your car. The place was neat the breakfast was good the room temperature was comfortable and the pool was was lovely."
United States
Deborah
Harbor Knoll Bed & Breakfast
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

15. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (47 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is SAR 544
SAR 1,137 total
includes taxes & fees
7 Oct - 8 Oct
Aqua Vista
A table set with a glass of orange juice, a glass of white wine, and a dessert with whipped cream and berries.

16. Stirling House Bed & Breakfast

Stirling House Bed & Breakfast
3.0 star property
Greenport
9.8 out of 10, Exceptional, (28 reviews)
"A must stay when in the area. Clay takes really good care of you! His pastries are amazing."
United States
Ecaterini
Stirling House Bed & Breakfast
A two-story house with a covered porch and a chimney.

17. The Farmhouse Bed and Breakfast

The Farmhouse Bed and Breakfast
4.0 star property
Cutchogue
10.0 out of 10, Exceptional, (16 reviews)
"The place is lovely. We loved the garden the house the host th alpacas and the beach parking pass. It is really expensive to stay in that area but the place is great"
United States
Bent
The Farmhouse Bed and Breakfast
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

18. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (52 reviews)
The price is SAR 544
SAR 1,137 total
includes taxes & fees
18 Oct - 19 Oct
The SandPiper
A modern dining area with a wooden table, white chairs, and a chandelier.

19. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (8 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is SAR 1,537
SAR 2,722 total
includes taxes & fees
30 Sep - 1 Oct
Northfork Townhouse walk to all
An outdoor dining area with hanging lights, palm trees, and a bar.

20. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
United States
Paul F.
The price is SAR 747
SAR 1,090 total
includes taxes & fees
4 Oct - 5 Oct
American Beech in Greenport - Petite King Room 7
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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Great weekend hotel deals in Town of Southold Town, NY

Showing deals for:9 Oct - 11 Oct

Image gallery for Cliffside Resort Condominiums

Cliffside Resort Condominiums

3.0 star property
Greenport
9.0/10Wonderful (295 reviews)
25% off
Price is SAR 1,756
SAR 4,846 total
includes taxes & fees
Cliffside Resort Condominiums
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Top Town of Southold Town Hotel Reviews

The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"The hotel was just what we expected, cozy and comfortable and nestled right into central Greenport. Close to everything, dinner spots just steps away. Will definitely return."
Arnold 2-night trip
Posted 9 hours ago
The Harbor Front Inn