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

Town of Southold Town Vacation Rentals

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Top Cities in Town of Southold Town

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, (288 reviews)
"Great place!"
United States
Christine
The price is CA $416
CA $597 total
includes taxes & fees
Sep 21 - Sep 22
Cliffside Resort Condominiums

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (50 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is CA $413
CA $471 total
includes taxes & fees
Sep 20 - Sep 21
North Fork Resort

3. 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
The price is CA $268
CA $525 total
includes taxes & fees
Sep 21 - Sep 22
Harbor Heights

4. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (49 reviews)
"House is exactly as advertised. Street traffic is a little noisier than expected being near the ferry."
United States
Kendric S.
The price is CA $270
CA $531 total
includes taxes & fees
Sep 10 - Sep 11
The SandPiper

5. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (42 reviews)
"Such a wonderful stay! Christopher was such a great host, the property matched the description, was extremely clean and situated in a perfect location just a short walk from town! Would stay again & recommend to family/friends!"
United States
Anonymous traveller
The price is CA $268
CA $525 total
includes taxes & fees
Sep 21 - Sep 22
Aqua Vista

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.
The price is CA $411
CA $597 total
includes taxes & fees
Sep 15 - Sep 16
American Beech in Greenport - Petite King Room 7

7. 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, (29 reviews)
"We had a great stay!! "
United States
Callie E.
The price is CA $305
CA $665 total
includes taxes & fees
Sep 7 - Sep 8
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

8. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (10 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.
The price is CA $406
CA $737 total
includes taxes & fees
Sep 23 - Sep 24
Beach Block Hideaway

9. 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.
The price is CA $486
CA $960 total
includes taxes & fees
Sep 17 - Sep 18
Renovated Townhouse walk to all

10. 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.
The price is CA $747
CA $1,302 total
includes taxes & fees
Sep 17 - Sep 18
Northfork Townhouse walk to all

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 CA $918
CA $1,559 total
includes taxes & fees
Sep 14 - Sep 15
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

12. 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 CA $453
CA $649 total
includes taxes & fees
Sep 2 - Sep 3
American Beech in Greenport - Deluxe King 6

13. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (248 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is CA $230
CA $307 total
includes taxes & fees
Sep 20 - Sep 21
Driftwood Resort

14. 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
The price is CA $310
CA $391 total
includes taxes & fees
Sep 22 - Sep 23
Windward Shores Ocean Resort

15. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,392 reviews)
"Property and room very clean Friendly staff and plenty of parking"
United States
Amelia
The price is CA $409
CA $494 total
includes taxes & fees
Sep 10 - Sep 11
Montauk Manor

16. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (53 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $156
CA $303 total
includes taxes & fees
Sep 15 - Sep 16
1-bedroom cottage with Grove Beach 🏖️ access.

17. Cozy Studio: Indoor Hot Tub & Inground Pool Access

Cozy Studio: Indoor Hot Tub & Inground Pool Access
3.0 star property
Montville
10.0 out of 10, Exceptional, (1 review)
"Everything from the price,location,tranquility, and the host Allen was awesome. We would go back in a heartbeat. Montville is beautiful."
United States
Eduardo
The price is CA $261
CA $591 total
includes taxes & fees
Aug 26 - Aug 27
Cozy Studio: Indoor Hot Tub & Inground Pool Access

18. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (28 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is CA $248
CA $448 total
includes taxes & fees
Sep 2 - Sep 3
The gardners Cottage 1 mile from long Island Sound - pet friendly

19. Seabreeze #3 Cozy Cottage steps to the beach

Seabreeze #3 Cozy Cottage steps to the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is CA $297
CA $865 total
includes taxes & fees
Sep 15 - Sep 16
Seabreeze #3 Cozy Cottage steps to the beach

20. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (10 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
The price is CA $167
CA $220 total
includes taxes & fees
Aug 26 - Aug 27
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

Find out more about Town of Southold Town

Everything you need to know about Town of Southold Town vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Town of Southold Town vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Town of Southold Town vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Town of Southold Town vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Town of Southold Town. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. 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.  The selection of Town of Southold Town vacation rentals we have selected for you start as low as CA $471 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Town of Southold Town rentals

At Expedia, we put the best Town of Southold Town vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Town of Southold Town rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Town of Southold Town vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Town of Southold Town. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.