A man carrying a woman in front of a pool with two American flags, surrounded by greenery and a monument.

Photo by Brittany Schreiber

Town of Southampton holiday homes

We found 3,659 holiday rentals — enter your dates for availability

Select from 1646 houses, 45 apartments and other holiday rentals to find the perfect place for your stay in Town of Southampton. Whether you’re staying in a holiday home with family or friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a hot tub. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Popular Town of Southampton destinations on Bookabach

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

Riverhead

Southampton

A marina with several boats docked, a community bandstand, and a restaurant named American Legion.

Sag Harbor

A sandy beach path with wooden fences on either side leading to the ocean.

Hampton Bays

A lake surrounded by residential properties, a tennis court, and a large house with a swimming pool.

Bridgehampton

A coastal landscape with green marshland and a distant shoreline.

Westhampton Beach

Holiday rentals with weekly discounts – Town of Southampton

Showing deals for:15 Jan - 22 Jan

view from living room towards pool, outdoor dining

kitchen with large island and breakfast table

Exceptional

(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off

NZ$103,111

for 7 nights, 1 home

NZ$14,730 per night

includes taxes & fees

Exceptional

(15 reviews)

Beautiful Hamptons Family Escape.

Westhampton

8% off

NZ$12,680

for 7 nights, 1 home

NZ$1,811 per night

includes taxes & fees

Exceptional

(33 reviews)

“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath

Mastic Beach

9% off

NZ$5,623

for 7 nights, 1 home

NZ$803 per night

includes taxes & fees

Living Room | Game Room | Home Theater System

Exceptional

(14 reviews)

Luxe Westhampton Beach Home w/ Pool & Hot Tub

Westhampton Beach

5% off

NZ$13,669

for 7 nights, 1 home

NZ$1,953 per night

includes taxes & fees

Stairs to the upstairs living room, kitchen and dining room

Exceptional

(27 reviews)

Modern Family Retreat with Heated Pool, Playground and Peloton

Hampton Bays

7% off

NZ$15,481

for 7 nights, 1 home

NZ$2,212 per night

includes taxes & fees

Exceptional

(47 reviews)

Westhampton Beach Town and Country

Westhampton Beach

8% off

NZ$14,407

for 7 nights, 1 home

NZ$2,058 per night

includes taxes & fees

Exceptional

(6 reviews)

Shirley Bayfront Getaway – Kayak, Swim & Relax

Shirley

8% off

NZ$10,113

for 7 nights, 1 home

NZ$1,445 per night

includes taxes & fees

Exceptional

(9 reviews)

Beautiful Colonial Mint Condition Summer House Walking Distance to Beach

Jamesport

12% off

NZ$7,706

for 7 nights, 1 home

NZ$1,101 per night

includes taxes & fees

Exceptional

(18 reviews)

Newly renovated 4-bedroom farmhouse on beautiful vineyard - Great location.

Jamesport

16% off

NZ$10,016

for 7 nights, 1 home

NZ$1,431 per night

includes taxes & fees

Exceptional

(18 reviews)

NEW DECK! Private 1 Acre Family Friendly Home - Heated Pool, Home Office & Gym

Westhampton

7% off

NZ$10,423

for 7 nights, 1 home

NZ$1,489 per night

includes taxes & fees

Exceptional

(6 reviews)

Newly Built Hamptons House, Pool, Beach Access + Easy Access off Montauk Highway

Hampton Bays

7% off

NZ$19,557

for 7 nights, 1 home

NZ$2,794 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

NZ$18,556

for 7 nights, 1 home

NZ$2,651 per night

includes taxes & fees

Exceptional

(84 reviews)

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

Hampton Bays

7% off

NZ$14,385

for 7 nights, 1 home

NZ$2,055 per night

includes taxes & fees

Excellent

(10 reviews)

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

Water Mill

7% off

NZ$77,062

for 7 nights, 1 home

NZ$11,009 per night

includes taxes & fees

Exceptional

(45 reviews)

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

Riverhead

8% off

NZ$9,074

for 7 nights, 1 home

NZ$1,296 per night

includes taxes & fees

Wonderful

(20 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off

NZ$29,624

for 7 nights, 1 home

NZ$4,232 per night

includes taxes & fees

Exceptional

(17 reviews)

Charming Riverhead home with large outdoor patio & backyard firepit

Riverhead

12% off

NZ$5,362

for 7 nights, 1 home

NZ$766 per night

includes taxes & fees

Exceptional

(104 reviews)

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

Sag Harbor

16% off

NZ$15,188

for 7 nights, 1 home

NZ$2,170 per night

includes taxes & fees

Hydrangeas blooming all summer.these are the August bloomers

Featured as one of most beautiful poolsides

Living area on 1st floor with wood burning fireplace

Couches on covered porch and outdoor dining table for 8

Exceptional

(7 reviews)

IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES

Southampton

8% off

NZ$35,437

for 7 nights, 1 home

NZ$5,062 per night

includes taxes & fees

Exceptional

(5 reviews)

Hampton Retreat near the Beach

Remsenburg

15% off

NZ$5,405

for 7 nights, 1 apartment

NZ$772 per night

includes taxes & fees

Exceptional

(29 reviews)

9BR Sag Harbor w/ Pool-Tennis Court- B-ball- HotTub-VBall-7Acres-NIGHTCLUB

Sag Harbor

8% off

NZ$24,252

for 7 nights, 1 home

NZ$3,465 per night

includes taxes & fees

Exceptional

(14 reviews)

House of Peace

Mastic

11% off

NZ$4,767

for 7 nights, 1 home

NZ$681 per night

includes taxes & fees

Exceptional

(15 reviews)

Sunsets Sweeping Farmland Views, Great Retreat Minutes from Flying Point Beach

Water Mill

8% off

NZ$29,941

for 7 nights, 1 home

NZ$4,277 per night

includes taxes & fees

Exceptional

(29 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off

NZ$15,371

for 7 nights, 1 home

NZ$2,196 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 Southampton

North Fork Resort

Sleeps 4 · 1 bedroom

Ocean,pool, boardwalk bay, bed,new kitch,new bath,new furn, steps to ocean

Sleeps 16 · 7 bedrooms · 4 bathrooms

Premier Host

Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.

Sleeps 8 · 4 bedrooms · 3 bathrooms

Premier Host

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly

Sleeps 12 · 6 bedrooms · 4+ bathrooms

Luxury Home W/ Huge Rap Around deck largest Pool on ocean private large dining

Sleeps 14 · 6 bedrooms · 4 bathrooms

New Reno Hamptons Waterfront Beach House wBackyard Pool Oasis, and Private Beach

Sleeps 16 · 3 bedrooms · 2+ bathrooms

Find the perfect holiday rental for your Town of Southampton getaway

Learn about the unique charm of Town of Southampton with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Town of Southampton

Are you looking for attractions to visit during your stay? Venture out of your cosy holiday rental and check out everything that Town of Southampton has to offer. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

Shinnecock Hills Golf Course (3.1 mi / 5 km)
Duck Walk Vineyards (6.9 mi / 11 km)
Jamesport Vineyards (7.6 mi / 12.2 km)
Macari Vineyards (8.8 mi / 14.1 km)
Palmer Vineyards (9.6 mi / 15.5 km)
Peconic Bay Winery (10.1 mi / 16.2 km)

Exploring the natural features in Town of Southampton

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Town of Southampton is a great place to get outside. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city centre:

Meschutt Beach (1.6 mi / 2.5 km)
Ponquogue Beach (2.6 mi / 4.2 km)
Cooper's Beach (4.5 mi / 7.3 km)
The Hamptons Beaches (10.5 mi / 17 km)
Crescent Beach (15.1 mi / 24.3 km)
Sunset Beach (15.4 mi / 24.7 km)

Transport to and around Town of Southampton

Fly into Westhampton, NY (FOK-Francis S. Gabreski), the closest airport, located 8.1 mi (13 km) from the city centre.

If you're travelling by train, Hampton Bays Station, Southampton Station and Westhampton Station are the main stations that serve the city.

Frequently asked questions

What is the best area to stay in Town of Southampton when booking a holiday home?

Snap up a holiday home in Village of Southampton and experience one of Town of Southampton's most renowned areas. Coopers Beach and Southampton Historical Museum are two major attractions here that'll keep you occupied during your visit.

What is the most popular type of holiday home accommodation in Town of Southampton?

The most desirable types of holiday homes in Town of Southampton are houses. Searching for something different? Bookabach has a variety of options to match the unique needs of our guests, so you'll see properties in loads of shapes and sizes. The ideal fit is ready and waiting for you — grab yours today.

How much does it cost to rent a holiday home in Town of Southampton?

The average price for a holiday home in Town of Southampton is based on a number of factors, such as time of year, length of stay and property type. Whether you're in search of a sprawling villa with a pool or a quaint cottage for you and your other half, just add your travel dates to discover stays that offer great value.

How much does it cost to rent a beach house in Town of Southampton?

The average price for a holiday home near the beach in Town of Southampton depends on when you're visiting the area and the size and type of property you're searching for. You can easily find prices on Bookabach by entering your dates of travel. Then use our filters to select the number of bedrooms and amenities important to you, like WiFi, air conditioning and a pool.

Are there pet-friendly holiday homes in Town of Southampton?

Pack a travel bag and a bone for your pup because Town of Southampton has 1,537 properties that put out the welcome mat to pets. Let your four-legged friend get in on the family fun 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 Southampton?

Add a whole other level of fun to your getaway by booking one of the 1,125 houses with a private pool in Town of Southampton. Use our search filter to find properties with pools on Bookabach, then spend carefree days frolicking in a swimming pool that's exclusively for you.

What are popular home amenities in Town of Southampton?

When it comes to home amenities that people are on the lookout for in Town of Southampton, a swimming pool, a sauna and a nearby waterfront are the most popular. With Bookabach holiday homes, you'll discover options to match your style and taste, whether you're going on a trip with friends, family or even pets.

Are there large group holiday homes in Town of Southampton?

Choose from 449 holiday homes in Town of Southampton that can accommodate a group of 10 or more guests. Whether you're organising a family holiday or some kind of special event, there's ample space to get your favourite people together under one roof.

Are there holiday homes in Town of Southampton that welcome kids?

Gather your whole crew for an adventure in Town of Southampton at one of our 1,534 family-friendly properties. Many of these stays offer amenities that are ideal for getaways with children, such as full kitchens, extra bedrooms and pools. Simply check the "Properties good for families" filter and book your favourite.

What are the top attractions for families in Town of Southampton?

There's a ton of fabulous things to see and do with the family in Town of Southampton, such as:

Coopers Beach
The Hamptons Beaches
Long Island Aquarium and Exhibition Centre

Are there one-bedroom holiday homes in Town of Southampton?

Yes, you'll find 79 one-bedroom properties in Town of Southampton to pick from. A one-bedroom holiday property is a wonderful choice if it's just the two of you or if you're holidaying alone. Throw in more convenience, space and privacy than a standard hotel, and you're sure to have a trip to remember.

Can I find two-bedroom holiday homes in Town of Southampton?

Take off with your loved ones and enjoy peace, privacy and comfort in one of the 112 two-bedroom holiday homes Town of Southampton has to offer.

Are there holiday homes with WiFi in Town of Southampton?

Whether you want to keep up with the headlines, look over emails or post a pic to social media, there are 555 holiday homes with WiFi in Town of Southampton. Check the "WiFi" box when searching on Bookabach and stay connected on your holiday.

How can I find holiday homes with air conditioning in Town of Southampton?

Choose from 1,484 holiday homes with air conditioning in Town of Southampton providing that cool, cool breeze and extra touch of comfort. Just enter your preferred dates of travel and then use our filter tool to help you book properties with air conditioning.

How old do you have to be to rent a holiday home in Town of Southampton?

The minimum age can vary across properties on Bookabach, so check the rules of the holiday home in Town of Southampton you're interested in. But usually, it's 16, 18 or 21.

How long can I rent a holiday home in Town of Southampton for?

The length of time you can rent a holiday home in Town of Southampton varies according to the property. Simply enter your preferred dates to view a list of options offering extended stays. With tons of creature comforts such as air conditioning and laundries, as well as some offering weekly or monthly discounts, you're sure to discover someplace just right to call your home away from home in Town of Southampton.

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