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

Vacation 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 vacation rentals

Flat-screen TV

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
The price is ￥46,065
￥52,631 total
includes taxes & fees
Sep 13 - Sep 14
North Fork Resort
Condo | Terrace/patio

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
The price is ￥44,381
￥64,399 total
includes taxes & fees
Oct 5 - Oct 6
Cliffside Resort Condominiums
Beach

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.
The price is ￥22,273
￥48,966 total
includes taxes & fees
Oct 5 - Oct 6
Harbor Heights
Sun loungers, beach towels

4. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (45 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is ￥22,273
￥49,141 total
includes taxes & fees
Oct 7 - Oct 8
Aqua Vista
Sun loungers, beach towels

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.
The price is ￥26,959
￥62,389 total
includes taxes & fees
Sep 15 - Sep 16
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Sun loungers, beach towels

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.
The price is ￥29,954
￥57,742 total
includes taxes & fees
Sep 28 - Sep 29
The SandPiper
Terrace/patio

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 ￥36,713
￥54,934 total
includes taxes & fees
Sep 16 - Sep 17
American Beech in Greenport - Petite King Room 7
Beach

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.
The price is ￥29,954
￥64,232 total
includes taxes & fees
Sep 14 - Sep 15
Beach Block Hideaway
Smart TV, fireplace

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.
The price is ￥55,991
￥104,335 total
includes taxes & fees
Sep 17 - Sep 18
Renovated Townhouse walk to all
Dining

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 ￥71,889
￥130,046 total
includes taxes & fees
Sep 13 - Sep 14
Northfork Townhouse walk to all
Smart TV, books

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 ￥82,642
￥147,946 total
includes taxes & fees
Sep 30 - Oct 1
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Property grounds

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.
The price is ￥150,000
￥227,186 total
includes taxes & fees
Sep 17 - Sep 18
Beachfront Greenport Villa
Property grounds

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
The price is ￥45,929
￥64,060 total
includes taxes & fees
Sep 17 - Sep 18
American Beech in Greenport - Deluxe King 6
1 bedroom, desk, iron/ironing board, travel crib

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.
The price is ￥18,525
￥35,566 total
includes taxes & fees
Oct 6 - Oct 7
1-bedroom cottage with Grove Beach 🏖️ access.
Iron/ironing board, WiFi (free), individually decorated

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
The price is ￥18,272
￥25,053 total
includes taxes & fees
Oct 12 - Oct 13
Windward Shores Ocean Resort
Apartment | WiFi (free), individually decorated, individually furnished, bed sheets

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
The price is ￥25,129
￥33,715 total
includes taxes & fees
Oct 5 - Oct 6
Driftwood Resort
Smart TV, offices

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
The price is ￥13,057
￥70,891 total
includes taxes & fees
Sep 20 - Sep 21
Seabreeze #3 Cozy Cottage steps to the beach
Lobby

18. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,400 reviews)
"Beautiful property"
United States
John
The price is ￥19,816
￥25,647 total
includes taxes & fees
Oct 12 - Oct 13
Montauk Manor
Exterior

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.
The price is ￥17,281
￥41,994 total
includes taxes & fees
Sep 14 - Sep 15
Cozy, comfy,quiet &close to casinos
Smart TV

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.
The price is ￥13,687
￥18,813 total
includes taxes & fees
Sep 14 - Sep 15
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.
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

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

Vacation Apartments in Town of Southold Town

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

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