Town of Southold Town holiday homes

We found 4,375 holiday rentals — enter your dates for availability

Select from 434 homes, 52 cottages and other holiday rentals in Town of Southold Town to find one that's perfect for your trip. Holiday homes provide the amenities that you need and want for your family, friends or furry companion, such as a garden and pool. Whatever you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Choose a holiday rental for your Town of Southold Town getaway

Learn about the unique charm of Town of Southold Town with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Town of Southold Town

Are you searching for attractions to visit in the area? Venture out of your cosy holiday rental and experience everything that makes Town of Southold Town a one-of-a-kind holiday spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Raphael Winery (2.7 mi / 4.3 km)
  • Pindar Vineyards (3 mi / 4.8 km)
  • Peconic Bay Winery (4.2 mi / 6.7 km)
  • Kontokosta Winery (4.8 mi / 7.7 km)
  • Macari Vineyards (9.1 mi / 14.6 km)
  • Wolffer Estates Vineyard (11.5 mi / 18.5 km)

Exploring the natural landscape of Town of Southold Town

Whether you're an outdoor enthusiast or just want to take in the scenery, Town of Southold Town is a great spot to appreciate mother nature. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Sunset Beach (3.3 mi / 5.4 km)
  • 67 Steps Beach (4.9 mi / 7.9 km)
  • The Hamptons Beaches (11.7 mi / 18.8 km)
  • Orient Point County Park (11.8 mi / 19 km)
  • Meschutt Beach (12.4 mi / 19.9 km)
  • LongHouse Reserve (13.3 mi / 21.4 km)

Transport options to and around Town of Southold Town

Fly into Fishers Island, NY (FID-Elizabeth Field), the closest airport, located 24.5 mi (39.4 km) from the city centre.

If you're travelling by train, Southold Station, Greenport Station and Mattituck Station are the main stations in the city.

Frequently asked questions

What is the best area to stay in Town of Southold Town when booking a holiday home?
Greenport West is among the most in-demand locations to book a holiday property in Town of Southold Town. Stay here and delight in the privacy and convenience that comes with having the whole place to yourself.
What is the most popular type of holiday home accommodation in Town of Southold Town?
Houses are the most popular style of holiday home in Town of Southold Town, according to our data. Even if you’ve got something else in mind, Bookabach has properties in many shapes and sizes. Browse our many options to find your ideal match.
How much does it cost to rent a holiday home in Town of Southold Town?
The average price for a holiday home in Town of Southold Town is determined by several factors, including property type, season and length of stay. Whether you’re looking for a sprawling villa with space for extended family or a cosy cabin for you and your other half, just enter your travel dates to view stays with unbeatable value.
How much does it cost to rent a beach house in Town of Southold Town?
The average price for a holiday home close to the beach in Town of Southold Town will depend on when you’re going and the size and style of property you’re searching for. Find prices easily and quickly on Bookabach by entering the dates you’ll be travelling. Then use the filter tool to choose the number of bedrooms and amenities that you prefer, like WiFi, a pool and air conditioning.
Are there pet-friendly holiday homes in Town of Southold Town?
Pack a bone and a squeezy toy for your canine companion because Town of Southold Town has 483 properties that roll out the welcome mat to doggie guests. Let your furriest pal join in on the family trip at one of our pet-friendly holiday homes on Bookabach. Simply enter your destination and dates, then check our “Pets allowed” filter box.
Can I rent a house with a pool in Town of Southold Town?
Pack your swimsuit and inflatable swan, because there are 140 houses with a private pool in Town of Southold Town. Make a booking at one of these popular holiday homes and make every day a pool day. Simply enter your dates into Bookabach, then use the “pool” filter to find the perfect place to make a splash!
What are popular home amenities in Town of Southold Town?
The most popular home amenities people search for in Town of Southold Town are an electric car charging station, tennis and a fireplace. Whether you’re hitting the road with buddies, family or even pets, Bookabach holiday homes come with the best amenities for fun and relaxation with the people that matter most.
Are there large group holiday homes in Town of Southold Town?
With 83 holiday homes that can host 10 guests or more in Town of Southold Town, there’s no need to keep your invite list short. From fun family get-togethers to special events like Thanksgiving or Christmas parties, Bookabach can help you find a large group home that fits the occasion.
Are there holiday homes in Town of Southold Town that welcome kids?
With 478 family-friendly holiday homes to select from in Town of Southold Town, there’s never been a better time to introduce the kiddos to the thrills of travel. Just click on our “Properties good for families” filter box to find stays that come with conveniences ideal for holidaying families, such as dining rooms, yards, bunk beds and hot tubs.
What are the top attractions for families in Town of Southold Town?
Keeping the kids entertained during your holiday in Town of Southold Town is a cinch with these leading family-friendly attractions:

  • 67 Steps Beach
  • Railroad Museum of Long Island
  • Crescent Beach

Are there one-bedroom holiday homes in Town of Southold Town?
Yes, you’ll find 28 one-bedroom properties in Town of Southold Town to select from. A one-bedroom holiday home is a wonderful choice if it’s just you and your partner or if you’re flying solo. Throw in more convenience, space and privacy than a hotel, and you’ll be sure to have a memorable trip.
Can I find two-bedroom holiday homes in Town of Southold Town?
Town of Southold Town has 94 two-bedroom holiday homes to choose from. Enjoy a holiday home with all the comfort and privacy you’re looking for at an attractive price on Bookabach.
Are there holiday homes with WiFi in Town of Southold Town?
You’ll have a choice of 197 holiday homes with WiFi in Town of Southold Town. If you want to disconnect from the world during your trip, but still need to be connected to the internet, these properties have what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Town of Southold Town?
Select your travel dates and then use the filter tool to search for holiday homes with ac in Town of Southold Town on Bookabach. With 465 air-conditioned properties available, you can enjoy a cool and comfortable stay.
How old do you have to be to rent a holiday home in Town of Southold Town?
The minimum required age is typically 16, 18 or 21. It can change from one property to another on Bookabach, so check the rules of your preferred Town of Southold Town holiday home before you book.
How long can I rent a holiday home in Town of Southold Town for?
The amount of time you can book a Town of Southold Town holiday home for depends on the property. Just enter your dates of travel to view available options that offer long-term stays. They have everything you need to make your extended trip more enjoyable and comfortable, such as laundries and air conditioning. Some properties may also offer weekly or monthly discounted prices, so you can stay longer for less money.

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