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

Holiday Rentals in Town of Southold Town

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Our top choices for Town of Southold Town holiday 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 €335
includes taxes & fees
7 Oct - 8 Oct
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, (61 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is €268
includes taxes & fees
4 Oct - 5 Oct
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 €282
includes taxes & fees
18 Oct - 19 Oct
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 €446
includes taxes & fees
4 Oct - 5 Oct
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 €367
includes taxes & fees
1 Oct - 2 Oct
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 €1,053
includes taxes & fees
20 Oct - 21 Oct
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 €275
includes taxes & fees
4 Oct - 5 Oct
American Beech in Greenport - Petite King Room 7
A rocky beach with clear water and a forested hillside in the background.

8. North Fork Fall Escape—Vineyards, Apple Picking & Greenport

North Fork Fall Escape—Vineyards, 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 €1,206
includes taxes & fees
24 Oct - 25 Oct
North Fork Fall Escape—Vineyards, 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 €265
includes taxes & fees
5 Oct - 6 Oct
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 €628
includes taxes & fees
29 Oct - 30 Oct
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 €759
includes taxes & fees
6 Oct - 7 Oct
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 €562
includes taxes & fees
26 Oct - 27 Oct
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 €282
includes taxes & fees
7 Oct - 8 Oct
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 €309
includes taxes & fees
1 Oct - 2 Oct
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, (1,409 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is €147
includes taxes & fees
12 Oct - 13 Oct
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 €146
includes taxes & fees
7 Oct - 8 Oct
Driftwood Resort
Room

17. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (324 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 €143
includes taxes & fees
12 Oct - 13 Oct
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.
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 €855
includes taxes & fees
4 Oct - 5 Oct
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Town of Southold Town Hotel Reviews

North Fork Resort

North Fork Resort

10/10 Excellent
"Fantastic contemporary cottage. Looks brand new and it has everything. Wonderful place to stay. Check in process needs improvement with more attention paid to details by staff."
marie 1-night trip
Posted 13 hours ago
North Fork Resort

Find out more about Town of Southold Town

Holiday Homes in Town of Southold Town

Search for holiday homes in Town of Southold Town on Expedia.ie! You can easily find your home rentals, villas, holiday apartments in Town of Southold Town using one of the methods below: 

  • View our selection of featured holiday homes in Town of Southold Town
  • Use the map to find apartments and other holiday rentals in the Town of Southold Town neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday homes in Town of Southold Town while they last

Look no further and take a look at our great range of rental properties in Town of Southold Town!