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

Town of Southold Town holiday homes

We found 4,445 holiday rentals — enter your dates for availability

Select from 285 homes, 40 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 Bookabach

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 coastal landscape with a sandy beach, calm waters, and a clear sky.

Cutchogue

A stone lighthouse with a metal lantern room, surrounded by a rocky shoreline and dense greenery.

Orient

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:18 Dec - 25 Dec

Wonderful

(59 reviews)

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

Old Lyme

8% off

NZ$4,452

for 7 nights, 1 cottage

NZ$636 per night

includes taxes & fees

Exceptional

(12 reviews)

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

Orient

7% off

NZ$22,826

for 7 nights, 1 room

NZ$3,261 per night

includes taxes & fees

Exceptional

(39 reviews)

Cottage near the beach

Niantic

7% off

NZ$3,043

for 7 nights, 1 cottage

NZ$435 per night

includes taxes & fees

Exceptional

(102 reviews)

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

Sag Harbor

15% off

NZ$15,758

for 7 nights, 1 home

NZ$2,251 per night

includes taxes & fees

Fully stocked kitchen - coffee, tea, sugar, creamer, pantry staples

Exceptional

(33 reviews)

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Waterford

8% off

NZ$3,353

for 7 nights, 1 cottage

NZ$479 per night

includes taxes & fees

Exceptional

(63 reviews)

Elevate your New England beach retreat experience - Mystic / Foxwoods / Mohegan

Groton

8% off

NZ$10,202

for 7 nights, 1 home

NZ$1,457 per night

includes taxes & fees

Exceptional

(28 reviews)

Elegant Waterfront Estate On 2 Acres ~ Private Pool ~ 12 min from Mystic!

Pawcatuck

8% off

NZ$16,951

for 7 nights, 1 home

NZ$2,422 per night

includes taxes & fees

Exceptional

(5 reviews)

NEW! Historic Mystic, Two Minute Walk to Mystic Pizza!

Mystic

5% off

NZ$10,468

for 7 nights, 1 home

NZ$1,495 per night

includes taxes & fees

Exceptional

(28 reviews)

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

Niantic

11% off

NZ$6,893

for 7 nights, 1 home

NZ$985 per night

includes taxes & fees

Exceptional

(28 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off

NZ$15,242

for 7 nights, 1 home

NZ$2,177 per night

includes taxes & fees

Exceptional

(5 reviews)

Charming 4-bedroom house with AC, WiFi in New London. Walk to the beach!

New London

8% off

NZ$8,329

for 7 nights, 1 home

NZ$1,190 per night

includes taxes & fees

Exceptional

(6 reviews)

Comfort room

New London

8% off

NZ$928

for 7 nights, 1 room

NZ$133 per night

includes taxes & fees

Exceptional

(29 reviews)

Incredible Beachfront Home w/ Private Beach!

Mattituck

7% off

NZ$6,572

for 7 nights, 1 cottage

NZ$939 per night

includes taxes & fees

Exceptional

(26 reviews)

Vineyard View, Bike to the Most Beautiful Beach

Mattituck

8% off

NZ$12,733

for 7 nights, 1 home

NZ$1,819 per night

includes taxes & fees

Furnished outdoor deck. There is NOT an umbrella on the deck area.

Exceptional

(55 reviews)

SUNSETS IN OCEAN BEACH PARK: 6 QUEEN BEDS W/ 1MIL DOLLAR VIEW OF ATLANTIC OCEAN!

New London

8% off

NZ$7,203

for 7 nights, 1 home

NZ$1,029 per night

includes taxes & fees

Exceptional

(40 reviews)

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

Riverhead

8% off

NZ$9,163

for 7 nights, 1 home

NZ$1,309 per night

includes taxes & fees

Exceptional

(82 reviews)

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Hampton Bays

7% off

NZ$13,778

for 7 nights, 1 home

NZ$1,968 per night

includes taxes & fees

Exceptional

(29 reviews)

Charming Colonial in the Heart of Mystic: Walk to Downtown, Sleeps 8

Mystic

8% off

NZ$8,554

for 7 nights, 1 home

NZ$1,222 per night

includes taxes & fees

Exceptional

(11 reviews)

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

Southold

7% off

NZ$16,329

for 7 nights, 1 home

NZ$2,333 per night

includes taxes & fees

This area is perfect for reading and relaxing

Kitchen is stocked with a selection of pots dishes and utensils

Plenty of comfortable chairs for lounging

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

Exceptional

(108 reviews)

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

Westhampton Beach

8% off

NZ$9,438

for 7 nights, 1 home

NZ$1,348 per night

includes taxes & fees

Exceptional

(18 reviews)

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

Cutchogue

8% off

NZ$8,769

for 7 nights, 1 cottage

NZ$1,253 per night

includes taxes & fees

Exceptional

(34 reviews)

Bohemian Old Life Saving Station with Beach & Pool

East Marion

7% off

NZ$25,746

for 7 nights, 1 home

NZ$3,678 per night

includes taxes & fees

Exceptional

(19 reviews)

Entire, new, roomy, village beach house close to beach, park, and town center

Greenport

8% off

NZ$8,398

for 7 nights, 1 home

NZ$1,200 per night

includes taxes & fees

Exceptional

(26 reviews)

Beautiful Watch Hill 4BR/3BA with Backyard Deck & Pool Just Steps From Beach

Westerly

8% off

NZ$13,399

for 7 nights, 1 home

NZ$1,914 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

Rose Cottage by the Bay.

Sleeps 4 · 2 bedrooms · 2+ bathrooms

One Of A Kind, Resort- Like Waterfront Cottage In Wine Country

Sleeps 5 · 2 bedrooms · 1 bathroom

Premier Host

Beach, Pool, Wine, Shopping!

Sleeps 6 · 2 bedrooms · 3 bathrooms

Premier Host

11 Bedroom Tranquil Waterfront Getaway

Sleeps 24 · 11 bedrooms · 6 bathrooms

French Country House with Pool- Beach nearby

Sleeps 6 · 3 bedrooms · 2+ bathrooms

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)
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)
Cooper's Beach (14 mi / 22.5 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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