Photo by Andrew Barney Kavesh

Village of Southampton holiday rentals

We found 1,943 holiday rentals — enter your dates for availability
Discover a selection of 123 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:25 Dec - 1 Jan

Main Entrance
Dining table and picnic table
water view
Heated pool with gorgeous water and natural wetland view
Chef kitchen with breakfast area on 2nd floor
Exceptional
(38 reviews)

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

Southampton

5% off
S$19,049
for 7 nights, 1 home
S$2,721 per night
includes taxes & fees
Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!
Pool
Exterior
Private kitchen
Pool
Exceptional
(6 reviews)

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

Hampton Bays

8% off
S$13,159
for 7 nights, 1 home
S$1,880 per night
includes taxes & fees
Newly Built Hamptons House, Pool, Beach Access + Easy Access off Montauk Highway
Exterior
Walk to  Private Beach
Patio
Dining Room
Exceptional
(103 reviews)

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

Sag Harbor

16% off
S$10,986
for 7 nights, 1 home
S$1,569 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
view from living room towards pool, outdoor dining
aerial view
master bedroom with balcony
kitchen with large island and breakfast table
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

16% off
S$77,045
for 7 nights, 1 home
S$11,006 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Living area
Terrace/patio
Exterior
Pool
Excellent
(10 reviews)

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

Water Mill

8% off
S$50,455
for 7 nights, 1 home
S$7,208 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Private kitchen
Exterior
Outdoor dining
Interior
Exceptional
(8 reviews)

Beautiful Colonial Mint Condition Summer House Walking Distance to Beach

Jamesport

12% off
S$5,645
for 7 nights, 1 home
S$806 per night
includes taxes & fees
Beautiful Colonial Mint Condition Summer House Walking Distance to Beach
kitchen
Dining
Pool
living room
Exceptional
(60 reviews)

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

Southampton

8% off
S$18,345
for 7 nights, 1 home
S$2,621 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
park-like grounds
Living area
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

28% off
S$13,242
for 7 nights, 1 home
S$1,892 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Pool
Living area
Interior
Living area
Exceptional
(14 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

7% off
S$9,946
for 7 nights, 1 home
S$1,421 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
Private kitchen
.
3 acres of beautiful land
Interior
Exceptional
(82 reviews)

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

Hampton Bays

6% off
S$10,593
for 7 nights, 1 home
S$1,513 per night
includes taxes & fees
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Exterior detail
Living area
Pool
Interior
Exceptional
(11 reviews)

Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house

Sag Harbor

8% off
S$13,276
for 7 nights, 1 cottage
S$1,897 per night
includes taxes & fees
Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house
Hot tub open all year
Exterior
Pool, gazebo, fire table
Living area
Exceptional
(45 reviews)

Westhampton Beach Town and Country

Westhampton Beach

8% off
S$10,408
for 7 nights, 1 home
S$1,487 per night
includes taxes & fees
Westhampton Beach Town and Country
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
Spacious living room with sliders to the patio pool and backyard
Exceptional
(108 reviews)

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

Westhampton Beach

7% off
S$8,277
for 7 nights, 1 home
S$1,182 per night
includes taxes & fees
Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach
Room
Dining
Exterior
Living area
Exceptional
(10 reviews)

Southampton Village Charmer - South of Highway

Southampton

8% off
S$28,254
for 7 nights, 1 home
S$4,036 per night
includes taxes & fees
Southampton Village Charmer - South of Highway
Dining room seating 12 leading to chef's kitchen and doors leading to pool
Thermador chefs kitchen with expansive island open to dining room & family room
View from entry foyer into double height living room, skylights, leading to pool
Open entry foyer with wall of windowed doors to Zen Garden
Exceptional
(6 reviews)

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

Wainscott

8% off
S$21,560
for 7 nights, 1 home
S$3,080 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Living area
Dining
Room
Private kitchen
Exceptional
(18 reviews)

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

Cutchogue

8% off
S$6,555
for 7 nights, 1 cottage
S$936 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Kitchen walks out to covered porch across length of entire back
Featured as one of most beautiful poolsides
Hydrangeas blooming all summer.these are the August bloomers
Living area on 1st floor with wood burning fireplace
Exceptional
(7 reviews)

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

Southampton

8% off
S$24,066
for 7 nights, 1 home
S$3,438 per night
includes taxes & fees
IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES
Terrace/patio
Pool
Stairs to the upstairs living room, kitchen and dining room
Living room
Exceptional
(27 reviews)

Modern Family Retreat with Heated Pool, Playground and Peloton

Hampton Bays

8% off
S$10,417
for 7 nights, 1 home
S$1,488 per night
includes taxes & fees
Modern Family Retreat with Heated Pool, Playground and Peloton
Private kitchen
Pool
Exterior
Dining
Wonderful
(20 reviews)

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

Riverhead

8% off
S$5,486
for 7 nights, 1 home
S$784 per night
includes taxes & fees
2-Acre Modern Estate in Southampton. Beach, winery, farm, pool, and hot tub
Kitchen Fireplace Eat In Kitchen & in the next photo includes new kitchen table
Crushpad of Charming Boutique vineyard nearby-  Rosehill
Living area
Exceptional
(30 reviews)

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

Laurel

25% off
S$3,358
for 7 nights, 1 home
S$480 per night
includes taxes & fees
North Fork Ranch Home in Wine Country with Pool- 2 Beaches 5 Min Walk
Dining
Private kitchen
Living area
Outdoor dining
Exceptional
(13 reviews)

Enjoy a lovely summer retreat in Sag Harbor Village, 1 mile to Main Street

Sag Harbor

8% off
S$18,565
for 7 nights, 1 home
S$2,652 per night
includes taxes & fees
Enjoy a lovely summer retreat in Sag Harbor Village, 1 mile to Main Street
dining area, expandable table
seating area rear deck
Private kitchen
view of pool
Exceptional
(15 reviews)

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

Water Mill

8% off
S$22,025
for 7 nights, 1 home
S$3,146 per night
includes taxes & fees
Sunsets Sweeping Farmland Views, Great Retreat Minutes from Flying Point Beach
Exterior
Wrap around deck
Second eating area
Second living room
Exceptional
(34 reviews)

Our Peaceful, Beach Escape From the City

Sag Harbor

8% off
S$10,679
for 7 nights, 1 home
S$1,526 per night
includes taxes & fees
Our Peaceful, Beach Escape From the City
Room
Kitchen
Backyard Water View
Exterior
Exceptional
(6 reviews)

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

New Suffolk

7% off
S$4,501
for 7 nights, 1 home
S$643 per night
includes taxes & fees
Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach
  • 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:

  • Cooper's Beach (1.7 mi / 2.7 km)
  • The Hamptons Beaches (5.4 mi / 8.7 km)
  • Meschutt Beach (5.8 mi / 9.4 km)
  • Ponquogue Beach (6.5 mi / 10.4 km)
  • Tiana Beach (7 mi / 11.2 km)
  • Havens Beach (9.7 mi / 15.7 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 rental accommodation in Village of Southampton?
The most sought-after types of holiday rentals in Village of Southampton are houses. Looking for something different? Vrbo 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 rental in Village of Southampton?
Several factors affect how much you'll pay for a holiday rental in Village of Southampton, such as the type of property, season and length of stay. But, all Vrbo 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 Vrbo 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 rentals 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 rentals and find your pawfect pad on Vrbo.
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 Vrbo. Lazy soak or races and ball games? Free time is up to you when your Vrbo holiday property comes with a swimming pool.
What are popular rental amenities in Village of Southampton?
When it comes to rental amenities that guests search for in Village of Southampton, a beach view, a barbecue grill and a fireplace rank the highest. With Vrbo holiday rentals, 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 rentals in Village of Southampton?
With nine holiday rentals 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, Vrbo can help you find a large group rental that fits the occasion.
Are there holiday rentals 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 Vrbo'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 rentals in Village of Southampton?
Gather your nearest and dearest and enjoy a relaxing escape in one of the two two-bedroom holiday rentals Village of Southampton has to offer.
Are there holiday rentals with WiFi in Village of Southampton?
Village of Southampton has 10 holiday rentals 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 Vrbo homes make it a breeze to get online.
How can I find holiday rentals with air conditioning in Village of Southampton?
Pick from 30 holiday rentals 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 rental in Village of Southampton?
The minimum required age is usually 16, 18 or 21. It can differ between properties on Vrbo, so check the rules of your preferred Village of Southampton stay before making a booking.
How long can I rent a holiday rental 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 Vrbo'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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