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

Vacation Rentals in Town of Southold Town

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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, (290 reviews)
"Great place!"
United States
Christine
$370 nightly
The price is $423
Sep 27 - Sep 28
Total with taxes and fees
Cliffside Resort Condominiums

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (52 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
$283 nightly
The price is $323
Sep 7 - Sep 8
Total with taxes and fees
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
$315 nightly
The price is $359
Sep 13 - Sep 14
Total with taxes and fees
Harbor Heights

4. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (44 reviews)
"Great location and nice spot."
United States
Kerri L.
$336 nightly
The price is $384
Sep 8 - Sep 9
Total with taxes and fees
Aqua Vista

5. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (51 reviews)
"access"
United States
Timothy
$304 nightly
The price is $347
Sep 10 - Sep 11
Total with taxes and fees
The SandPiper

6. 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, (30 reviews)
"We had a great stay!! "
United States
Callie E.
$372 nightly
The price is $424
Sep 8 - Sep 9
Total with taxes and fees
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

7. 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.
$365 nightly
The price is $417
Sep 7 - Sep 8
Total with taxes and fees
Beach Block Hideaway

8. 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 7 - Sep 8
Total with taxes and fees
American Beech in Greenport - Petite King Room 7

9. 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.
$779 nightly
The price is $889
Sep 17 - Sep 18
Total with taxes and fees
Northfork Townhouse walk to all

10. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (13 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.
$667 nightly
The price is $761
Sep 17 - Sep 18
Total with taxes and fees
Renovated 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.
$936 nightly
The price is $1,069
Sep 14 - Sep 15
Total with taxes and fees
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
$382 nightly
The price is $436
Sep 17 - Sep 18
Total with taxes and fees
American Beech in Greenport - Deluxe King 6

13. 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
$198 nightly
The price is $226
Sep 27 - Sep 28
Total with taxes and fees
Windward Shores Ocean Resort

14. 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
$195 nightly
The price is $223
Sep 21 - Sep 22
Total with taxes and fees
Driftwood Resort

15. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (55 reviews)
"We enjoyed our stay"
United States
JM B.
$199 nightly
The price is $225
Sep 3 - Sep 4
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

16. 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)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
$291 nightly
The price is $329
Sep 3 - Sep 4
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly

17. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,398 reviews)
"Beautiful property"
United States
John
$265 nightly
The price is $302
Sep 16 - Sep 17
Total with taxes and fees
Montauk Manor

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)
"It was close to a very pretty beach, which was nice. The neighborhood is very quiet. The only downside was that the bedrooms were up stairs and the stairs were very steep. I didn’t notice that in the write up to the property it might have changed my rental of it. I would rate it very highly for anyone that doesn’t have trouble with stairs. The air conditioning was excellent, and the property is well appointed the owners were lovely and responsive."
United States
Sandra Hart
$430 nightly
The price is $486
Sep 9 - Sep 10
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town

19. 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
$464 nightly
The price is $496
Sep 3 - Sep 4
Total with taxes and fees
Seabreeze #3 Cozy Cottage steps to the beach

20. Beautiful Private Studio Apartment!

Beautiful Private Studio Apartment!
Ridge
9.6 out of 10, Exceptional, (21 reviews)
"The parking and room access was easy to find as the host gave excellent directions. All amenities were provided in kitchen and bath, and we loved the recessed reading nook. The rain shower was the best! We were serenaded by whip-poor-wills each night at sunset, a truly beautiful experience."
United States
Wendy
$256 nightly
The price is $292
Sep 3 - Sep 4
Total with taxes and fees
Beautiful Private Studio Apartment!
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

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 $323 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?


Vacation rentals in Town of Southold Town come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Town of Southold Town vacation rentals to suit everyone. 


Why should I choose a vacation rental in Town of Southold Town?


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?


Find vacation rentals in Town of Southold Town by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Town of Southold Town.  


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.


When is the best time to stay in a vacation rental in Town of Southold Town?   


Everytime is a great time to head to Town of Southold Town! Staying in a Town of Southold Town vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


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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.