Town of Southold Town Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Top Holiday Rentals Destinations in Town of Southold Town

Cliffside Resort Condominiums

3.0 star property
Greenport
9.0 out of 10, Wonderful, (247)
"Location good. Room could use some renos."
United States
Laura
Cliffside Resort Condominiums

The SandPiper

Pipes Cove
9.8 out of 10, Exceptional, (28)
"Excellent stay. Great location helpful host"
United States
Kevin K.
The SandPiper

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

Pipes Cove
9.8 out of 10, Exceptional, (102)
"This was my second stay at the Gatehouse. It was as good as the first time. I have already made reservations to stay again."
United States
Anonymous traveller
'The Gate House'on Beach front Estate with Dockage. Walk to Village .

Cottage on Beach front Estate with Dockage .Walk to Village

Pipes Cove
10.0 out of 10, Exceptional, (73)
"Wonderful stay at such a special spot. "
United States
Meg B.
Cottage on Beach front Estate with Dockage .Walk to Village

American Beech in Greenport - Petite King Room 7

Greenport
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is AU$468
includes taxes & fees
12 Nov - 13 Nov
American Beech in Greenport - Petite King Room 7

Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,...

Peconic
10.0 out of 10, Exceptional, (2)
"This was a perfect home base for our 40th birthday weekend. Great space and location. The home was exactly as pictured. "
United States
jen k.
Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,...

Newly Constructed 3-bedroom Modern Farmhouse - walk to Greenport Village!

Greenport
10.0 out of 10, Exceptional, (1)
"Beautiful newly renovated home, walking distance to Greenport harbor. Very accommodating to families with small children. Great backyard and playground around the corner. Will stay again! "
United States
Kim B.
Newly Constructed 3-bedroom Modern Farmhouse - walk to Greenport Village!

Modern Farmhouse Steps to Beach and Love Lane

Mattituck
10.0 out of 10, Exceptional, (38)
"The property was the perfect stay for a weekend getaway!"
United States
Kiera K.
Modern Farmhouse Steps to Beach and Love Lane

Aqua Vista

Pipes Cove
10.0 out of 10, Exceptional, (22)
"Great location and very clean."
United States
Dwight R.
Aqua Vista

Surrounded by nature, come stay in this 1 bedroom private, serene location

Southold
10.0 out of 10, Exceptional, (3)
"This home away from home provided a clean and comfortable space to rest and recharge, as we explored the area. Tranquil outdoor space, easy parking, yummy snacks, cozy bedding, and fine toiletries all contributed to a wonderful fall short-stay. We hope to return!M & MWestbrook, CT. USA"
United States
maryjo n.
Surrounded by nature, come stay in this 1 bedroom private, serene location

Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

Greenport
10.0 out of 10, Exceptional, (82)
"Very clean, very cozy, very convenient location. Great view."
United States
Bill D.
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

Harbor Heights

Pipes Cove
9.8 out of 10, Exceptional, (13)
"We had a great time in Greenport. The location of Vrbo was perfect for walking to everything we needed. "
United States
Andrea H.
Harbor Heights

Lovely Cottage in the Heart of Long Island Wine country

Southold
9.8 out of 10, Exceptional, (30)
"We booked this beautiful cottage last minute for a quick weekend getaway and it was everything we hoped it would be. Eileen was also a pleasure to work with!"
United States
Chris S.
Lovely Cottage in the Heart of Long Island Wine country

Beautifully farmhouse

Southold
10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveller
The price is AU$1,817
includes taxes & fees
12 Nov - 13 Nov
Beautifully farmhouse

“Paradise Found” - Walk to Private Beach & In-Ground Pool!

2.0 star property
Southold
10.0 out of 10, Exceptional, (7)
"Pool was beautiful nice neighborhood Screen in porch was great."
United States
William W.
“Paradise Found” - Walk to Private Beach & In-Ground Pool!

Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families

Greenport
10.0 out of 10, Exceptional, (4)
"Did a quick weekend getaway with friends. Our stay was amazing. Zero complaints and will definitely be back! "
United States
Jonathan C.
Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families

Country BEACH home!

Southold
10.0 out of 10, Exceptional, (1)
"Very comfortable and clean home! The hosts were very nice and helpful! Would definitely return!"
United States
Megan & Chris D.
Country BEACH home!

North Fork Family and Friends Getaway. Great Location

Mattituck
10.0 out of 10, Exceptional, (16)
"Our stay was great from beginning to end - the property was clean, updated, and the backyard was something to marvel at. Highly recommend staying here"
United States
Anthony P.
North Fork Family and Friends Getaway. Great Location

Waterfront, private beach, ready for adventure, light & bright!

Southold
10.0 out of 10, Exceptional, (19)
"We stayed at Long Creek for a month and it was absolute heaven. We would give this home more than 5 stars if we could. Wendy and John are amazing hosts. They are the most responsive and helpful people we have ever rented from. They were always accessible and willing to help. The home looks just like the photos and is beautiful. It’s airy and bright and you immediately exhale upon entering when you see the view of Long Creek. The outdoor setting is completely idyllic. We loved sitting outside...
United States
Lisa S.
Waterfront, private beach, ready for adventure, light & bright!

Bahia Mar Beach House, North Fork

Laurel
10.0 out of 10, Exceptional, (6)
"My family had a beautiful stay in this home right on Peconic bay! The home was huge and stunning with gorgeous landscaping in the front and the beach only steps away across the lawn in the back. We especially loved enjoying the views across the bay from in the hot tub. This home is ideal for a small family reunion, with ample space and bedrooms, especially with the separate carriage house which really is its own mini apartment-- the listing actually sort of undersells it! Communication from the...
United States
Dara I.
Bahia Mar Beach House, North Fork
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.
Save an average of 15% on thousands of hotels when you're signed in

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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Town of Southold Town holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Town of Southold Town holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Town of Southold Town holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Town of Southold Town holiday rentals we have chosen for you start as low as AU$468 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 holiday 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 holiday.

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.