Town of Southold Town Holiday Rentals

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Top Holiday Rentals Destinations in Town of Southold Town

"Stove it’s not efficient and refrigerator blocked with the corner of wall"

"Very nice house In great shape and outstanding pool area."

"Beautiful and cozy lakeside retreat. Super serene and peaceful place to stay."

"My sister and I stayed at Aqua Vista the last weekend in October. The weather was amazing. The house is located just a block form the ferry to Shelter Island and a couple of blocks to all the shops in Greenport.The apartment was clean well equipped and well maintained. Located in a lovely area close to all the shops. We would definitely stay there again . The"

"Very nice spot for a couple to stay. Fully equipped and thoughtfully laid out. Comfortable bed. Updated in all ways. Exceptionally clean and well stocked. Very convenient to downtown and extremely walkable."

"Loved our stay at Whitecap. Great location, spotlessly clean. Very comfortable with everything you need for a wonderful stay."

"We loved o weekend getaway with the family. The house was beautiful. Everything was perfect. "

"Awesome property with everything you need for a great getaway. European chic touches throughout and a location that is just fantastic!! Spectacular Sunrises on the deck with breakfast overlooking Orient Harbor, Bug Light, and Shelter Island are mesmerizing. The view and the setting just never gets old-a real gem!! Nicole was terrific to deal with - we’ll be back!!"

"Such a cute little place to stay. We enjoyed our time there. "

"House was great! Walking distance to town and beach. Had a wonderful time in November! "

"Our married children and our granddaughter had an absolutely wonderful time at this home. The house was clean and beautiful. The view from the master bedroom and from the whole first floor were spectacular. Unfortunately, the weather was not great so we didn’t get much time outdoors, but the house was so beautiful. We had a blast. We hope to be back again. "

"Maritza and John were very friendly hosts and we even met their lovely dog Sara! Central location to Greenport. You have access to the top floor of the house where it is both homely and inviting. Would stay here again"

"Great private location. Awesome if you have a dog. Easy to get to everything."

"12 of us were in town for a friends wedding nearby and really enjoyed our stay at this place! The property is huge with plenty of parking and plenty space both inside and outside. Vicky was very communicative and gave us a tour, instructions for our stay, and recommendations in the area upon arrival. We were able to check-in early and our check-out time was flexible too which was super helpful given our large group and a late night at the wedding. If we ever need somewhere to stay on the North...

"This house is in the perfect location. Close to the town of Green port and so close to the wineries. The house was clean and comfortable. "

"We had the best time! We spent a lot of time sitting outside and were also able to easily take in the beautiful view while inside on the couch. The house was clean and a perfect size for the 5 of us. The property manager was very responsive to our questions. It was a good location for a weekend in Greenport and/or the wineries. Thanks for a great weekend!"

Beach nearby, sun-loungers, beach towels

"A five star review is not enough for this beautiful property! It is so well appointed, with everything you can possibly imagine to make your stay nothing less than perfect! It is an immaculate place that is decorated beautifully and the moment you open the door here you know you’ve chosen a charming and beautiful place to stay. The owner, Bill, was readily available prior to arriving to answer any questions we had. Even after we were here, he was in communication with us, which is always a...

"Such a cute cottage and perfect location. We loved the cottage decor and cleanliness. (I’m picky) Wineries and towns were close by and easily accessible. All communication was timely and helpful. Would stay again. "

"We love coming here-Eileen makes it so easy and we can’t get enough of the overall coziness and warmth of the place. Perfect for a quiet getaway!"

"If you’re looking for a quick visit to the winery’s this is the perfect place. Beautifully decorated, very responsive host and location is ideal!"

Save an average of 15% on thousands of hotels when you're signed in

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 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.