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

Vacation Rentals in Town of Southold Town

Top Cities in Town of Southold Town

An aerial view of a harbor with boats, a ship, and a dock extending into the water.
Vacation RentalsVacation Rentals

Greenport

Greenport

Our top choices for Town of Southold Town vacation rentals

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (285 reviews)
"Great place!"
United States
Christine
$385 nightly
The price is $439
Sep 7 - Sep 8
Total with taxes and fees
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (48 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
$275 nightly
The price is $314
Sep 7 - Sep 8
Total with taxes and fees
North Fork Resort
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

3. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (47 reviews)
"Lovely place, very clean, host was very responsive. Thanks so much!"
United States
Marie H.
$329 nightly
The price is $376
Sep 10 - Sep 11
Total with taxes and fees
The SandPiper
A beach with people relaxing on chairs and sunbathing.

4. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (23 reviews)
"Close to the train, beach and restaurant, very convenient on foot"
United States
Nigel
$337 nightly
The price is $385
Sep 13 - Sep 14
Total with taxes and fees
Harbor Heights
A beach with people relaxing, a pier extending into the water, and a clear sky.

5. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"We had a great stay!! "
United States
Callie E.
$449 nightly
The price is $513
Sep 7 - Sep 8
Total with taxes and fees
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
An outdoor dining area with hanging lights, palm trees, and a bar.

6. 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.
$391 nightly
The price is $447
Sep 7 - Sep 8
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

7. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (41 reviews)
"Nice clean space, well appointed and easy walking access to downtown area."
United States
Molly G.
$337 nightly
The price is $385
Sep 8 - Sep 9
Total with taxes and fees
Aqua Vista
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

8. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (13 reviews)
"yes the house had everything we needed"
United States
patricia m.
$1,309 nightly
The price is $1,495
Sep 10 - Sep 11
Total with taxes and fees
Beachfront Greenport Villa
A modern dining area with a wooden table, white chairs, and a chandelier.

9. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (7 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.
$849 nightly
The price is $969
Sep 17 - Sep 18
Total with taxes and fees
Northfork Townhouse walk to all
A wooden pathway leading to a beach with scattered rocks and greenery.

10. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (8 reviews)
"Everything about Beach Block Hideaway was perfect! The house was absolutely immaculate, the kitchen well stocked with plenty of kitchenware, beds very comfortable. Easy walk to town. We have stayed at a number of homes when visiting Greenport over the years but this place is truly the best - highly recommend! "
United States
maureen f.
$480 nightly
The price is $548
Sep 8 - Sep 9
Total with taxes and fees
Beach Block Hideaway
A modern living room with a sofa, coffee table, and dining area.

11. 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.
$991 nightly
The price is $1,132
Sep 14 - Sep 15
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a staircase with wooden railings.

12. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (12 reviews)
"We had a wonderful girls weekend in Greenport. The house was perfect for the three of us. Loved the location. We didn’t get to use the back area due to the weather, but it looked so inviting. Next time!"
United States
Melissa A.
$617 nightly
The price is $705
Sep 17 - Sep 18
Total with taxes and fees
Renovated Townhouse walk to all
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

13. American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6
Greenport
2.0 out of 10, (1 review)
"Not as advertised. Very disappointed "
United States
Jeffrey
$448 nightly
The price is $512
Sep 7 - Sep 8
Total with taxes and fees
American Beech in Greenport - Deluxe King 6
A spacious hallway with high ceilings, arched columns, and chandeliers.

14. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,388 reviews)
"Property and room very clean Friendly staff and plenty of parking"
United States
Amelia
$314 nightly
The price is $359
Sep 7 - Sep 8
Total with taxes and fees
Montauk Manor

15. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (247 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
$263 nightly
The price is $300
Sep 13 - Sep 14
Total with taxes and fees
Driftwood Resort

16. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (322 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
$265 nightly
The price is $303
Sep 14 - Sep 15
Total with taxes and fees
Windward Shores Ocean Resort

17. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (293 reviews)
"Found mold under the pull-out couch"
United States
Anna
$359 nightly
The price is $410
Sep 9 - Sep 10
Total with taxes and fees
The Surf Club
A row of tents with a grassy field and trees in the background.

18. Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely Beautiful view The vibe and food was great. Just beware of the tics."
United States
Christina V.
$259 nightly
The price is $296
Aug 20 - Aug 21
Total with taxes and fees
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
A sandy beach path leading to the ocean with grass on either side.

19. Town walking distance-Bridgehampton Cottage

Town walking distance-Bridgehampton Cottage
Bridgehampton
9.6 out of 10, Exceptional, (12 reviews)
"Walking distance to Bridgehampton and a short drive to sag harbor. Great for 2 couples."
United States
Jim M.
$1,058 nightly
The price is $1,209
Aug 20 - Aug 21
Total with taxes and fees
Town walking distance-Bridgehampton Cottage
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

20. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (52 reviews)
"We enjoyed our stay"
United States
JM B.
$197 nightly
The price is $222
Sep 15 - Sep 16
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
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 Town of Southold Town Hotel Reviews

Sound View Greenport

Sound View Greenport

10/10 Excellent
"Hotel very well situated with a nice beach and a great pool. The rooms were clean and spacious. There were a lot of families so we couldn’t just sit and enjoy the view with toddlers running around - but that was me 20 years ago. I would recommend but next time I would want to book the private patio rooms. Continental breakfast was great - all around fantastic stay."
Karen 2-night trip
Posted 18 hours ago
Sound View Greenport

Find out more about Town of Southold Town

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How many vacation rentals are available in Town of Southold Town?


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The selection of Town of Southold Town vacation rentals we have selected for you start as low as $314 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Town of Southold Town?


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What amenities are available in a vacation rental in Town of Southold Town?


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