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

A modern house with a deck, outdoor seating, and a fire pit.

1. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (54 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
$275 nightly
The price is $314
Sep 14 - Sep 15
Total with taxes and fees
North Fork Resort

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (291 reviews)
"Great place!"
United States
Christine
$367 nightly
The price is $419
Oct 5 - Oct 6
Total with taxes and fees
Cliffside Resort Condominiums
A beach with people relaxing on chairs and sunbathing.

3. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (26 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
$279 nightly
The price is $319
Oct 5 - Oct 6
Total with taxes and fees
Harbor Heights
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

4. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (45 reviews)
"Great location and nice spot."
United States
Kerri L.
$280 nightly
The price is $320
Oct 7 - Oct 8
Total with taxes and fees
Aqua Vista
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, (31 reviews)
"We had a great stay!! "
United States
Callie E.
$353 nightly
The price is $403
Sep 15 - Sep 16
Total with taxes and fees
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

6. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
$329 nightly
The price is $376
Sep 28 - Sep 29
Total with taxes and fees
The SandPiper
An outdoor dining area with hanging lights, palm trees, and a bar.

7. 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.
$313 nightly
The price is $358
Sep 16 - Sep 17
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
A wooden pathway leading to a beach with scattered rocks and greenery.

8. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
$366 nightly
The price is $418
Sep 14 - Sep 15
Total with taxes and fees
Beach Block Hideaway
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.

9. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (14 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.
$590 nightly
The price is $674
Sep 17 - Sep 18
Total with taxes and fees
Renovated Townhouse walk to all
A modern dining area with a wooden table, white chairs, and a chandelier.

10. 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.
$746 nightly
The price is $852
Sep 14 - Sep 15
Total with taxes and fees
Northfork Townhouse walk to all
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.
$857 nightly
The price is $979
Oct 6 - Oct 7
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

12. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
$1,285 nightly
The price is $1,468
Sep 17 - Sep 18
Total with taxes and fees
Beachfront Greenport Villa
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
$362 nightly
The price is $414
Sep 17 - Sep 18
Total with taxes and fees
American Beech in Greenport - Deluxe King 6
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

14. 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.
$205 nightly
The price is $232
Oct 6 - Oct 7
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

15. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (323 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
$143 nightly
The price is $163
Oct 12 - Oct 13
Total with taxes and fees
Windward Shores Ocean Resort

16. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (249 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
$192 nightly
The price is $219
Oct 5 - Oct 6
Total with taxes and fees
Driftwood Resort
A spacious living room with a large sofa, a round coffee table, and a television. A kitchen with a refrigerator and cabinets is visible in the background.

17. 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 traveler
$433 nightly
The price is $462
Sep 20 - Sep 21
Total with taxes and fees
Seabreeze #3 Cozy Cottage steps to the beach
A spacious hallway with high ceilings, arched columns, and chandeliers.

18. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,400 reviews)
"Beautiful property"
United States
John
$146 nightly
The price is $167
Oct 12 - Oct 13
Total with taxes and fees
Montauk Manor
A two-story house with a covered patio area, a front door, and a mailbox.

19. Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.4 out of 10, Exceptional, (65 reviews)
"It was great ocation for a weekend get away with friends to Mohegan Sun"
United States
Teresa M.
$238 nightly
The price is $269
Sep 29 - Sep 30
Total with taxes and fees
Cozy, comfy,quiet &close to casinos
A living room with a grey sofa, an orange armchair, a small round table, and a glass-top coffee table.

20. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (11 reviews)
"Great little quiet home away from home. Tom and Stacy and all the cute animals were very friendly and welcoming. Perfect place to relax after a busy day of activity."
United States
Angela A.
$109 nightly
The price is $122
Sep 14 - Sep 15
Total with taxes and fees
The Tiny Cottage & Mini Farm
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

The SandPiper

The SandPiper

10/10 Excellent
"Host was always available to respond to my questions.The fridge was not clean. The cleaner could have paid a bit more attention to crumbs and expired milk. Please add a clean kitchen sponge and ensure dishes in the dishwasher are washed.Otherwise the stay was smooth and pleasant. Would be helpful to add a peeler and a writing implement (pens and a paper pad)."
S D. 3-night trip
Posted 1 day ago
The SandPiper

Find out more about Town of Southold Town

Discover your perfect Town of Southold Town vacation rental with Expedia

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


Expedia has plenty of vacation rentals to choose from in and around  Town of Southold Town, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Town of Southold Town?


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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Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Town of Southold Town vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Town of Southold Town?


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


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Town of Southold Town vacation rentals designed to suit every budget and trip type.


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Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Town of Southold Town vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.