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

Town of Southold Town holiday rentals

We found 4,440 holiday rentals — enter your dates for availability

Select from 284 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 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 pebble beach at sunset with a calm sea 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 coastal landscape with a sandy beach, clear blue water, and a distant lighthouse.

Greenport West

Holiday rentals with weekly discounts – Town of Southold Town

Showing deals for:25 Dec - 1 Jan

Wonderful

(59 reviews)

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

Old Lyme

8% off

AU$3,616

for 7 nights, 1 cottage

AU$517 per night

includes taxes & fees

Exceptional

(12 reviews)

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

Orient

8% off

AU$17,057

for 7 nights, 1 room

AU$2,437 per night

includes taxes & fees

Heated pool with gorgeous water and natural wetland view

Dining table and picnic table
water view

2nd floor deck with additional dining and leisure seating.

Chef kitchen with breakfast area on 2nd floor

Exceptional

(38 reviews)

Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!

Southampton

5% off

AU$20,743

for 7 nights, 1 home

AU$2,963 per night

includes taxes & fees

Exceptional

(39 reviews)

Cottage near the beach

Niantic

7% off

AU$2,488

for 7 nights, 1 cottage

AU$355 per night

includes taxes & fees

Exceptional

(103 reviews)

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

Sag Harbor

16% off

AU$11,959

for 7 nights, 1 home

AU$1,708 per night

includes taxes & fees

Exceptional

(64 reviews)

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

Groton

8% off

AU$8,188

for 7 nights, 1 home

AU$1,170 per night

includes taxes & fees

Exceptional

(29 reviews)

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

Niantic

12% off

AU$6,581

for 7 nights, 1 home

AU$940 per night

includes taxes & fees

Exceptional

(28 reviews)

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

Pawcatuck

8% off

AU$13,385

for 7 nights, 1 home

AU$1,912 per night

includes taxes & fees

Exceptional

(6 reviews)

Comfort room

New London

8% off

AU$773

for 7 nights, 1 room

AU$110 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

AU$6,387

for 7 nights, 1 home

AU$912 per night

includes taxes & fees

Exceptional

(28 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off

AU$12,100

for 7 nights, 1 home

AU$1,729 per night

includes taxes & fees

This area is perfect for reading and relaxing

Kitchen is stocked with a selection of pots dishes and utensils

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

Plenty of comfortable chairs for lounging

Exceptional

(109 reviews)

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

Westhampton Beach

8% off

AU$8,877

for 7 nights, 1 home

AU$1,268 per night

includes taxes & fees

Exceptional

(29 reviews)

Incredible Beachfront Home w/ Private Beach!

Mattituck

7% off

AU$5,272

for 7 nights, 1 cottage

AU$753 per night

includes taxes & fees

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

Exceptional

(56 reviews)

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

New London

8% off

AU$6,849

for 7 nights, 1 home

AU$978 per night

includes taxes & fees

Third floor mezzanine, between bedroom and bathroom. Overlooks living area

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

(80 reviews)

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

Stonington

8% off

AU$4,523

for 7 nights, 1 home

AU$646 per night

includes taxes & fees

Exceptional

(26 reviews)

Vineyard View, Bike to the Most Beautiful Beach

Mattituck

8% off

AU$9,943

for 7 nights, 1 home

AU$1,420 per night

includes taxes & fees

Exceptional

(56 reviews)

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

Old Lyme

8% off

AU$2,828

for 7 nights, 1 cottage

AU$404 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$17,656

for 7 nights, 1 home

AU$2,522 per night

includes taxes & fees

An elegant dining room (to 10 ppl, joins kitchen +8 and outdoor dining +10,)

Lower deck With Pool, 9 Loungers, plus 6 pool-chairs. Upper deck dining seats 10

Exceptional

(26 reviews)

Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

Southampton

30% off

AU$14,436

for 7 nights, 1 home

AU$2,062 per night

includes taxes & fees

Exceptional

(83 reviews)

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

Hampton Bays

6% off

AU$11,725

for 7 nights, 1 home

AU$1,675 per night

includes taxes & fees

Exceptional

(29 reviews)

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

Mystic

8% off

AU$8,331

for 7 nights, 1 home

AU$1,190 per night

includes taxes & fees

Exceptional

(41 reviews)

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

Riverhead

8% off

AU$7,400

for 7 nights, 1 home

AU$1,057 per night

includes taxes & fees

Exceptional

(20 reviews)

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

Greenport

8% off

AU$6,716

for 7 nights, 1 home

AU$959 per night

includes taxes & fees

Exceptional

(18 reviews)

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

Cutchogue

8% off

AU$7,028

for 7 nights, 1 cottage

AU$1,004 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

Premier Host

Beach, Pool, Wine, Shopping!

Sleeps 6 · 2 bedrooms · 3 bathrooms

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

Sleeps 5 · 2 bedrooms · 1 bathroom

Premier Host

11 Bedroom Tranquil Waterfront Getaway

Sleeps 24 · 11 bedrooms · 6 bathrooms

Private Getaway - corner Home with rights to private beach - Tip of North Fork

Sleeps 8 · 3 bedrooms · 1+ bathroom

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.

More holiday ideas

Holiday homes