Photo by Andrew Barney Kavesh

Village of Southampton holiday rentals

We found 1,961 holiday rentals — enter your dates for availability
Discover a selection of 129 homes and other holiday rentals in Village of Southampton that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll find the amenities that you need and want, including parking and a TV. What you'll find is a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Village of Southampton

Showing deals for:6 Nov - 13 Nov

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.
Main Entrance
Exceptional
(35 reviews)

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

Southampton

8% off
AU$12,368
for 7 nights, 1 home
AU$1,767 per night
includes taxes & fees
Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!
Exterior
Pool
Dining
Exterior
Exceptional
(5 reviews)

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

Hampton Bays

8% off
AU$14,426
for 7 nights, 1 home
AU$2,061 per night
includes taxes & fees
Newly Built Hamptons House, Pool, Beach Access + Easy Access of Montauk Highway
master bedroom with balcony
aerial view
living room
view from living room towards pool, outdoor dining
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off
AU$82,167
for 7 nights, 1 home
AU$11,738 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Patio
Private kitchen
Dining Room
Exterior
Exceptional
(97 reviews)

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

Sag Harbor

16% off
AU$11,947
for 7 nights, 1 home
AU$1,707 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Lower deck With Pool, 9 Loungers, plus 6 pool-chairs. Upper deck dining seats 10
Living area
park-like grounds
An elegant dining room (to 10 ppl, joins kitchen +8 and outdoor dining  +10,)
Exceptional
(26 reviews)

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

Southampton

30% off
AU$14,422
for 7 nights, 1 home
AU$2,060 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Pool
Terrace/patio
Living area
Exterior
Exceptional
(8 reviews)

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

Water Mill

8% off
AU$55,305
for 7 nights, 1 home
AU$7,901 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Exterior
Dining
Living area
Room
Exceptional
(10 reviews)

Southampton Village Charmer - South of Highway

Southampton

8% off
AU$30,840
for 7 nights, 1 home
AU$4,406 per night
includes taxes & fees
Southampton Village Charmer - South of Highway
View from entry foyer into double height living room, skylights, leading to pool
Thermador chefs kitchen with expansive island open to dining room & family room
Dining room seating 12 leading to chef's kitchen and doors leading to pool
Frankel Residence
Exceptional
(6 reviews)

Completely Renovated Home on ~2 Private Acres, Near Beach/Town

Wainscott

8% off
AU$23,454
for 7 nights, 1 home
AU$3,351 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
outdoor shower
Dining
living room
kitchen
Exceptional
(60 reviews)

Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool

Southampton

8% off
AU$19,957
for 7 nights, 1 home
AU$2,851 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
Room
Dining
Private kitchen
Outdoor dining
Exceptional
(18 reviews)

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

Cutchogue

8% off
AU$7,021
for 7 nights, 1 cottage
AU$1,003 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Interior
Exterior
Private kitchen
Interior
Exceptional
(8 reviews)

Beautiful Colonial Mint Condition Summer House Walking Distance to Beach

Jamesport

12% off
AU$6,878
for 7 nights, 1 home
AU$983 per night
includes taxes & fees
Beautiful Colonial Mint Condition Summer House Walking Distance to Beach
Terrace/patio
Pool
Stairs to the upstairs living room, kitchen and dining room
Large wrap-around lawn
Exceptional
(27 reviews)

Modern Family Retreat with Heated Pool, Playground and Peloton

Hampton Bays

8% off
AU$11,527
for 7 nights, 1 home
AU$1,647 per night
includes taxes & fees
Modern Family Retreat with Heated Pool, Playground and Peloton
Dining area
Exterior
Pool, gazebo, fire table
Hot tub open all year
Exceptional
(44 reviews)

Westhampton Beach Town and Country

Westhampton Beach

8% off
AU$11,349
for 7 nights, 1 home
AU$1,621 per night
includes taxes & fees
Westhampton Beach Town and Country
Exterior
Pool
Interior
Dining
Wonderful
(20 reviews)

2-Acre Modern Estate in Southampton. Beach, winery, farm, pool, and hot tub

Riverhead

8% off
AU$6,088
for 7 nights, 1 home
AU$870 per night
includes taxes & fees
2-Acre Modern Estate in Southampton. Beach, winery, farm, pool, and hot tub
Interior
Living area
Pool
Exterior detail
Exceptional
(10 reviews)

Just Posted for Summer 2026! SECLUDED SAG HARBOR COTTAGE w/ HUGE POOL

Sag Harbor

8% off
AU$20,727
for 7 nights, 1 cottage
AU$2,961 per night
includes taxes & fees
Just Posted for Summer 2026! SECLUDED SAG HARBOR COTTAGE w/ HUGE POOL
Crushpad of Charming Boutique vineyard nearby-  Rosehill
Kitchen Fireplace Eat In Kitchen & in the next photo includes new kitchen table
8 Hands Farm
Exceptional
(30 reviews)

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

Laurel

9% off
AU$4,036
for 7 nights, 1 home
AU$577 per night
includes taxes & fees
North Fork Ranch Home in Wine Country with Pool- 2 Beaches 5 Min Walk
Plenty of comfortable chairs for lounging
Kitchen is stocked with a selection of pots dishes and utensils
This area is perfect for reading and relaxing
Spacious living room with sliders to the patio pool and backyard
Exceptional
(107 reviews)

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

Westhampton Beach

8% off
AU$6,910
for 7 nights, 1 home
AU$987 per night
includes taxes & fees
Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach
Living area
Private kitchen
Exterior
Living area
Exceptional
(34 reviews)

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

Cutchogue

8% off
AU$3,803
for 7 nights, 1 cottage
AU$543 per night
includes taxes & fees
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Night time at the pool
Dining
Interior
Main living room and dining room
Exceptional
(27 reviews)

9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub

Sag Harbor

8% off
AU$20,624
for 7 nights, 1 home
AU$2,946 per night
includes taxes & fees
9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub
Dining
Interior
Interior
Living area
Exceptional
(27 reviews)

Heated Pool + Hot Tub - Luxe 7BR Villa

Hampton Bays

9% off
AU$13,270
for 7 nights, 1 home
AU$1,896 per night
includes taxes & fees
Heated Pool + Hot Tub - Luxe 7BR Villa
view of pool
seating area rear deck
dining area, expandable table
primary bedroom #1main floor
Exceptional
(15 reviews)

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

Water Mill

8% off
AU$23,669
for 7 nights, 1 home
AU$3,381 per night
includes taxes & fees
Sunsets Sweeping Farmland Views, Great Retreat Minutes from Flying Point Beach
Room
Kitchen
Backyard Water View
Exterior
Exceptional
(5 reviews)

Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach

New Suffolk

8% off
AU$5,038
for 7 nights, 1 home
AU$720 per night
includes taxes & fees
Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach
Exterior
Private kitchen
Living area
Living area
Exceptional
(5 reviews)

Hamptons Contemporary 4 beds cozy home minutes to beaches, village, US Open disc

Hampton Bays

7% off
AU$10,090
for 7 nights, 1 home
AU$1,441 per night
includes taxes & fees
Hamptons Contemporary 4 beds cozy home minutes to beaches, village, US Open disc
Outdoor dining
Private kitchen
Living area
Property grounds
Exceptional
(8 reviews)

Best View + Private Beach + Putting Green

Hampton Bays

8% off
AU$7,466
for 7 nights, 1 home
AU$1,067 per night
includes taxes & fees
Best View + Private Beach + Putting Green
  • 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

Lively Village of Southampton will entice you

Enjoy the area's opera, churches and monuments with a rental holiday home in Village of Southampton. Renowned for its theatres, entertainment and beaches, this city welcomes all visitors. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Village of Southampton

Do you want to discover things to do while you're in town? Venture out of your cosy holiday rental and experience everything that Village of Southampton has to offer. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Duck Walk Vineyards (1.8 mi / 2.8 km)
  • Shinnecock Hills Golf Course (2.7 mi / 4.4 km)
  • Wolffer Estates Vineyard (7.2 mi / 11.6 km)
  • Peconic Bay Winery (10.4 mi / 16.7 km)
  • Bedell Cellars (10.8 mi / 17.4 km)
  • Pindar Vineyards (10.9 mi / 17.6 km)

Exploring the natural landscape of Village of Southampton

Whether you're an adventurous traveller or just want to appreciate the scenery, Village of Southampton is a great spot to appreciate mother nature. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • The Hamptons Beaches (5.4 mi / 8.7 km)
  • Cooper's Beach (1.7 mi / 2.7 km)
  • Meschutt Beach (5.8 mi / 9.4 km)
  • Ponquogue Beach (6.5 mi / 10.4 km)
  • Tiana Beach (7 mi / 11.2 km)
  • Elizabeth A. Morton National Wildlife Refuge (7.3 mi / 11.7 km)

Transport options to and around Village of Southampton

Fly into East Hampton, NY (HTO), the closest airport, located 9.1 mi (14.7 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Westhampton, NY (FOK-Francis S. Gabreski), which is 13.5 mi (21.7 km) away.

If you prefer train travel, you can make your way to Southampton Station.

Frequently asked questions

What is the most popular type of holiday home accommodation in Village of Southampton?
The most sought-after types of holiday homes in Village of Southampton are houses. Looking for something different? Stayz offers a variety of options to match the diverse needs of our guests, so you'll see properties in all shapes and sizes. The perfect fit is waiting for you — find yours today.
How much does it cost to rent a holiday home in Village of Southampton?
Several factors affect how much you'll pay for a holiday home in Village of Southampton, such as the type of property, season and length of stay. But, all Stayz homes have one thing in common — unbeatable value. Simply enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Village of Southampton?
Prices for beach houses in Village of Southampton vary depending on the style and size of the property and when you're travelling. All you need to do is enter your travel dates into Stayz and how many guests to see available options and prices. From there you can use the filters to narrow your search results by nearby activities, amenities, ratings and more.
Are there pet-friendly holiday homes in Village of Southampton?
With 30 properties that host four-legged guests, your furry companion can also come along on your Village of Southampton getaway. Use the filter tool to browse our pet-friendly holiday homes and find your pawfect pad on Stayz.
Can I rent a house with a pool in Village of Southampton?
Tick the "pool" box in our handy filter tool and you'll find 24 houses with private pools in Village of Southampton on Stayz. Lazy soak or races and ball games? Free time is up to you when your Stayz holiday property comes with a swimming pool.
What are popular home amenities in Village of Southampton?
When it comes to home amenities that guests search for in Village of Southampton, a beach view, a barbecue grill and a fireplace rank the highest. With Stayz holiday homes, you'll find options to match your taste and style, whether you're planning to get away with your partner, your family or even pets.
Are there large group holiday homes in Village of Southampton?
With nine holiday homes that can sleep 10 people or more in Village of Southampton, you don't have to keep anyone off the invite list. 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 Village of Southampton that welcome kids?
Village of Southampton has 30 family-friendly holiday homes to choose from. And discovering a stay that welcomes kids is a breeze with Stayz's "Properties good for families" filter. Besides having the entire place to yourselves, you can also look forward to amenities and perks like bunk beds, kitchens and private pools.
What are the top attractions for families in Village of Southampton?
Keep the kids amused at these fabulous family-friendly attractions in Village of Southampton:
  • Coopers Beach
  • Shinnecock Nation Cultural Centre and Museum
  • Southampton Historical Museum
Can I find two-bedroom holiday homes in Village of Southampton?
Gather your nearest and dearest and enjoy a relaxing escape in one of the two two-bedroom holiday homes Village of Southampton has to offer.
Are there holiday homes with WiFi in Village of Southampton?
Village of Southampton has 10 holiday homes with WiFi, so you can stay connected while you're travelling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming TV shows with the family to checking emails, these Stayz homes make it a breeze to get online.
How can I find holiday homes with air conditioning in Village of Southampton?
Pick from 30 holiday homes with air conditioning in Village of Southampton giving you that cooling breeze and extra touch of comfort. Simply enter your travel dates and then take advantage of our filters to help you book properties with air conditioning.
How old do you have to be to rent a holiday home in Village of Southampton?
The minimum required age is usually 16, 18 or 21. It can differ between properties on Stayz, so check the rules of your preferred Village of Southampton stay before making a booking.
How long can I rent a holiday home in Village of Southampton for?
It's down to the Village of Southampton property. To look over a list of options offering extended stays, just type your travel dates and guest number into Stayz's search page. Look forward to having the property to yourself, along with home comforts such as a kitchen, air conditioning and outdoor spaces where your little ones can play. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.

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