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

Vacation Rentals in Town of Southold Town

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Our top choices for Town of Southold Town vacation rentals

Terrace/patio

1. 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 ￥37,104
￥59,841 total
includes taxes & fees
Oct 25 - Oct 26
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, (60 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is ￥40,503
￥46,275 total
includes taxes & fees
Oct 7 - Oct 8
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, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is ￥22,806
￥47,622 total
includes taxes & fees
Oct 18 - Oct 19
The SandPiper
A wooden pathway leading to a beach with scattered rocks and greenery.

4. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is ￥38,534
￥76,552 total
includes taxes & fees
Oct 4 - Oct 5
Beach Block Hideaway
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, (32 reviews)
"We had a great stay!! "
United States
Callie E.
The price is ￥27,603
￥62,625 total
includes taxes & fees
Oct 12 - Oct 13
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

6. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is ￥105,456
￥170,979 total
includes taxes & fees
Sep 29 - Sep 30
Beachfront Greenport Villa
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.
The price is ￥31,299
￥45,645 total
includes taxes & fees
Oct 4 - Oct 5
American Beech in Greenport - Petite King Room 7
A restaurant with wicker furniture and large windows overlooking the ocean at sunset.

8. North Fork Fall Escape - Vineyards visits - Wineries • Apple Picking • Greenport

North Fork Fall Escape - Vineyards visits - Wineries • Apple Picking • Greenport
Mattituck
9.6 out of 10, Exceptional, (7 reviews)
"Stayed with several friends for a wedding in Jamesport"
United States
Glenn F.
The price is ￥102,232
￥212,938 total
includes taxes & fees
Oct 24 - Oct 25
North Fork Fall Escape - Vineyards visits - Wineries • Apple Picking • Greenport
A beach with people relaxing on chairs and sunbathing.

9. 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.
The price is ￥20,525
￥45,013 total
includes taxes & fees
Oct 5 - Oct 6
Harbor Heights
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.
The price is ￥64,406
￥114,015 total
includes taxes & fees
Sep 30 - Oct 1
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.
The price is ￥73,450
￥129,380 total
includes taxes & fees
Oct 6 - Oct 7
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
9.6 out of 10, Exceptional, (14 reviews)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
The price is ￥50,959
￥96,676 total
includes taxes & fees
Oct 19 - Oct 20
Renovated Townhouse walk to all
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

13. 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 ￥22,806
￥47,622 total
includes taxes & fees
Oct 7 - Oct 8
Aqua Vista
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

14. 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
The price is ￥36,017
￥51,215 total
includes taxes & fees
Oct 1 - Oct 2
American Beech in Greenport - Deluxe King 6
A spacious hallway with high ceilings, arched columns, and chandeliers.

15. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,408 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is ￥20,289
￥26,260 total
includes taxes & fees
Oct 12 - Oct 13
Montauk Manor
Room

16. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (252 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is ￥23,108
￥31,525 total
includes taxes & fees
Oct 4 - Oct 5
Driftwood Resort
Room

17. 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
The price is ￥18,708
￥25,650 total
includes taxes & fees
Oct 12 - Oct 13
Windward Shores Ocean Resort
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

18. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is ￥26,226
￥70,447 total
includes taxes & fees
Oct 15 - Oct 16
Adorable Cottage, 5 min walk to water & town
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

19. Elegant 5-Bedroom Hamptons Home with Private Pool

Elegant 5-Bedroom Hamptons Home with Private Pool
Hampton Bays
9.4 out of 10, Exceptional, (43 reviews)
"My family and I really enjoyed this home. Everything you can think of is provided for you. We would definitely stay here again!"
United States
Sarah A.
The price is ￥70,776
￥145,191 total
includes taxes & fees
Sep 29 - Sep 30
Elegant 5-Bedroom Hamptons Home with Private Pool
A living room with a dark grey sofa, two wooden chairs, a small table with a tray, and a large window with a view of the sea.

20. Direct waterfront renovated cottage.

Direct waterfront renovated cottage.
Madison Center
10.0 out of 10, Exceptional, (97 reviews)
"Unbeatable views and professional hosts."
United States
Russell A.
Direct waterfront renovated cottage.
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 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 6 hours ago
The Harbor Front Inn

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Vacation Apartments in Town of Southold Town

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