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

Town of Southold Town holiday rentals

We found 4,495 holiday rentals — enter your dates for availability

Select from 275 homes, 39 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.

Popular Town of Southold Town destinations on Stayz

A pebbled beach at sunset with the sun setting over the horizon.

Greenport

A pebbled beach at sunset with the sun reflecting on the water.

Southold

A sunflower field at sunset with a wind turbine in the background.

Mattituck

A vineyard with rows of grapevines under a partly cloudy sky.

Cutchogue

A coastal landscape with a sandy beach, clear blue water, and a distant lighthouse.

Greenport West

A pebble beach at sunset with a calm sea in the background.

Orient Point

Holiday rentals with weekly discounts – Town of Southold Town

Showing deals for:13 Nov - 20 Nov

Exceptional

(10 reviews)

Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Orient

8% off

AU$16,959

for 7 nights, 1 room

AU$2,423 per night

includes taxes & fees

Wonderful

(58 reviews)

2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT

Old Lyme

8% off

AU$3,595

for 7 nights, 1 cottage

AU$514 per night

includes taxes & fees

Exceptional

(97 reviews)

Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town

Sag Harbor

16% off

AU$11,890

for 7 nights, 1 home

AU$1,699 per night

includes taxes & fees

Exceptional

(11 reviews)

New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!

Southold

8% off

AU$13,757

for 7 nights, 1 home

AU$1,965 per night

includes taxes & fees

Exceptional

(89 reviews)

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Clinton

7% off

AU$2,073

for 7 nights, 1 cottage

AU$296 per night

includes taxes & fees

Whitefield Rock and rear view of Ludington House (Whitefield Suite is at left)

Exceptional

(20 reviews)

Ludington House, Historic CT Shoreline Mansion filled with luxury and antiques

Old Lyme

10% off

AU$21,093

for 7 nights, 1 home

AU$3,013 per night

includes taxes & fees

Exceptional

(34 reviews)

Cottage near the beach

Niantic

7% off

AU$2,474

for 7 nights, 1 cottage

AU$353 per night

includes taxes & fees

Exceptional

(20 reviews)

Mystic Pearl, Charming 4 Bedroom Home, Downtown Mystic

Mystic

8% off

AU$4,116

for 7 nights, 1 home

AU$588 per night

includes taxes & fees

Exceptional

(18 reviews)

Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe

Cutchogue

8% off

AU$6,987

for 7 nights, 1 cottage

AU$998 per night

includes taxes & fees

Exceptional

(8 reviews)

Stunning fall sunsets, coveted location on Mecox Bay - recently furnished

Water Mill

8% off

AU$55,040

for 7 nights, 1 home

AU$7,863 per night

includes taxes & fees

Exceptional

(25 reviews)

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS

Niantic

11% off

AU$4,756

for 7 nights, 1 home

AU$679 per night

includes taxes & fees

Exceptional

(32 reviews)

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Riverhead

8% off

AU$7,466

for 7 nights, 1 home

AU$1,067 per night

includes taxes & fees

Exceptional

(5 reviews)

Comfort room

New London

8% off

AU$715

for 7 nights, 1 room

AU$102 per night

includes taxes & fees

Exceptional

(41 reviews)

A Peaceful Mystical Stay!!!

Mystic

8% off

AU$4,735

for 7 nights, 1 home

AU$676 per night

includes taxes & fees

Crushpad of Charming Boutique vineyard nearby- Rosehill

Exceptional

(30 reviews)

North Fork Ranch Home in Wine Country with Pool- 2 Beaches 5 Min Walk

Laurel

9% off

AU$3,979

for 7 nights, 1 home

AU$568 per night

includes taxes & fees

Exceptional

(34 reviews)

Bohemian Old Life Saving Station with Beach & Pool

East Marion

8% off

AU$13,979

for 7 nights, 1 home

AU$1,997 per night

includes taxes & fees

Exceptional

(89 reviews)

Casa De Las Olas - Cute cozy cottage in Westerly, RI

Westerly

7% off

AU$2,434

for 7 nights, 1 cottage

AU$348 per night

includes taxes & fees

Plenty of comfortable chairs for lounging

Kitchen is stocked with a selection of pots dishes and utensils

Spacious living room with sliders to the patio pool and backyard

Enjoy nearby North Fork and South Fork wineries and many other local attractions

Exceptional

(107 reviews)

Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach

Westhampton Beach

8% off

AU$6,877

for 7 nights, 1 home

AU$982 per night

includes taxes & fees

Exceptional

(29 reviews)

Incredible Beachfront Home w/ Private Beach!

Mattituck

7% off

AU$5,241

for 7 nights, 1 cottage

AU$749 per night

includes taxes & fees

Exceptional

(34 reviews)

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Cutchogue

8% off

AU$3,785

for 7 nights, 1 cottage

AU$541 per night

includes taxes & fees

Exceptional

(53 reviews)

2Bdr Beachfront; 11B second floor, Old Colony Beach , CT

Old Lyme

8% off

AU$2,812

for 7 nights, 1 cottage

AU$402 per night

includes taxes & fees

living room is very sunny with two sets of sliding glass doors opening to deck

This side of the house faces Stonington Harbor, over a large yard w/ sea view

Exceptional

(79 reviews)

Sunny Scandinavian House on Wamphassuc Pt. Harbor view. Short walk to the beach

Stonington

8% off

AU$4,410

for 7 nights, 1 home

AU$630 per night

includes taxes & fees

Exceptional

(25 reviews)

Vineyard View, Bike to the Most Beautiful Beach

Mattituck

8% off

AU$9,885

for 7 nights, 1 home

AU$1,412 per night

includes taxes & fees

Exceptional

(14 reviews)

Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country

Southold

8% off

AU$6,456

for 7 nights, 1 home

AU$922 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Find the best place to stay - Town of Southold Town

North Fork Resort

Sleeps 4 · 1 bedroom

Premier Host

6BR, Pool, walk to beach, minutes to vineyards, town - WEEKLY DISCOUNT 8/24-8/31

Sleeps 12 · 7 bedrooms · 4 bathrooms

Perfect Waterfront Family Vacation Home next to the best vineyards in NY!

Sleeps 8 · 3 bedrooms · 3 bathrooms

Rose Cottage by the Bay.

Sleeps 4 · 2 bedrooms · 2+ bathrooms

Premier Host

Greenport Walk to beach & vineyard from this brand new home

Sleeps 6 · 3 bedrooms · 2+ bathrooms

Premier Host

Walk to Sandy Bay Beach~North Fork Wine Country Cottage SRP#0270

Sleeps 6 · 2 bedrooms · 2 bathrooms

Top rated rentals - Town of Southold Town

Image of Private Coastal Two Bedroom Cottage on the Water

Lovely place right on a lake

Loved this place. It was so nice to lie in bed and hear the ducks and swans talk to each other. Plus so close to the beach! The kitchen was well equipped and easy to use. Lots of modern conveniences to make you feel comfortable.

Jess L.

Stayed Feb 2022

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)
Bedell Cellars (3.3 mi / 5.2 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)

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)
Elizabeth A. Morton National Wildlife Refuge (6.2 mi / 9.9 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)

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, Stayz 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 Stayz 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 Stayz. 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 Stayz, 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, Stayz 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, Stayz 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 Stayz.

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 Stayz.

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 Stayz. 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 Stayz, 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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