Photo by Andrew Barney Kavesh

Village of Southampton holiday rentals

We found 1,941 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

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

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

Southampton

5% off
AU$20,456
for 7 nights, 1 home
AU$2,922 per night
includes taxes & fees
Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!
Pool
Private kitchen
Exterior
Pool
Exceptional
(6 reviews)

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

Hampton Bays

8% off
AU$14,240
for 7 nights, 1 home
AU$2,034 per night
includes taxes & fees
Newly Built Hamptons House, Pool, Beach Access + Easy Access off Montauk Highway
Exterior
Private kitchen
The Harbor
Patio
Exceptional
(103 reviews)

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

Sag Harbor

16% off
AU$11,925
for 7 nights, 1 home
AU$1,704 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
kitchen with large island and breakfast table
master bedroom with balcony
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off
AU$81,110
for 7 nights, 1 home
AU$11,587 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Outdoor dining
Exterior
Interior
Private kitchen
Exceptional
(8 reviews)

Beautiful Colonial Mint Condition Summer House Walking Distance to Beach

Jamesport

12% off
AU$6,049
for 7 nights, 1 home
AU$864 per night
includes taxes & fees
Beautiful Colonial Mint Condition Summer House Walking Distance to Beach
Living area
Terrace/patio
Living area
Exterior
Excellent
(10 reviews)

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

Water Mill

8% off
AU$54,593
for 7 nights, 1 home
AU$7,799 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Lower deck With Pool, 9 Loungers, plus 6 pool-chairs. Upper deck dining seats 10
Living area
An elegant dining room (to 10 ppl, joins kitchen +8 and outdoor dining  +10,)
Front entrance, park-like grounds
Exceptional
(26 reviews)

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

Southampton

30% off
AU$14,236
for 7 nights, 1 home
AU$2,034 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Enjoy nearby North Fork and South Fork wineries and many other local attractions
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

8% off
AU$8,754
for 7 nights, 1 home
AU$1,251 per night
includes taxes & fees
Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach
Living area
Living area
Pool
Outdoor dining
Exceptional
(15 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

8% off
AU$10,664
for 7 nights, 1 home
AU$1,523 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
3 acres of beautiful land
.
Private kitchen
Interior
Exceptional
(82 reviews)

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

Hampton Bays

6% off
AU$11,563
for 7 nights, 1 home
AU$1,652 per night
includes taxes & fees
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Pool
Living area
Exterior detail
Exceptional
(11 reviews)

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

Sag Harbor

8% off
AU$14,546
for 7 nights, 1 cottage
AU$2,078 per night
includes taxes & fees
Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house
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
Kitchen walks out to covered porch across length of entire back
Exceptional
(7 reviews)

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

Southampton

8% off
AU$25,862
for 7 nights, 1 home
AU$3,695 per night
includes taxes & fees
IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES
kitchen
Dining
outdoor shower
Pool
Exceptional
(60 reviews)

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

Southampton

8% off
AU$19,701
for 7 nights, 1 home
AU$2,814 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
Living area
Exterior
Hot tub open all year
Dining area
Exceptional
(45 reviews)

Westhampton Beach Town and Country

Westhampton Beach

8% off
AU$11,203
for 7 nights, 1 home
AU$1,600 per night
includes taxes & fees
Westhampton Beach Town and Country
Exterior
Dining
Room
Living area
Exceptional
(10 reviews)

Southampton Village Charmer - South of Highway

Southampton

8% off
AU$30,443
for 7 nights, 1 home
AU$4,349 per night
includes taxes & fees
Southampton Village Charmer - South of Highway
Large wrap-around lawn
Pool
Living room
Stairs to the upstairs living room, kitchen and dining room
Exceptional
(27 reviews)

Modern Family Retreat with Heated Pool, Playground and Peloton

Hampton Bays

8% off
AU$11,379
for 7 nights, 1 home
AU$1,626 per night
includes taxes & fees
Modern Family Retreat with Heated Pool, Playground and Peloton
Living area
Dining
Private kitchen
Room
Exceptional
(18 reviews)

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

Cutchogue

8% off
AU$6,931
for 7 nights, 1 cottage
AU$990 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
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
Frankel Residence
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
AU$23,152
for 7 nights, 1 home
AU$3,307 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Exterior
Pool
Interior
Private kitchen
Wonderful
(20 reviews)

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

Riverhead

8% off
AU$6,009
for 7 nights, 1 home
AU$858 per night
includes taxes & fees
2-Acre Modern Estate in Southampton. Beach, winery, farm, pool, and hot tub
Living Room
Kitchen
Room
Backyard Water View
Exceptional
(6 reviews)

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

New Suffolk

8% off
AU$4,825
for 7 nights, 1 home
AU$689 per night
includes taxes & fees
Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach
Crushpad of Charming Boutique vineyard nearby-  Rosehill
Kitchen Fireplace Eat In Kitchen & in the next photo includes new kitchen table
Living area
Exceptional
(30 reviews)

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

Laurel

26% off
AU$3,514
for 7 nights, 1 home
AU$502 per night
includes taxes & fees
North Fork Ranch Home in Wine Country with Pool- 2 Beaches 5 Min Walk
primary bedroom #1main floor
seating area rear deck
dining area, expandable table
view of pool
Exceptional
(15 reviews)

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

Water Mill

8% off
AU$23,364
for 7 nights, 1 home
AU$3,338 per night
includes taxes & fees
Sunsets Sweeping Farmland Views, Great Retreat Minutes from Flying Point Beach
Second living room
Wrap around deck
Exterior
Living room
Exceptional
(34 reviews)

Our Peaceful, Beach Escape From the City

Sag Harbor

8% off
AU$11,574
for 7 nights, 1 home
AU$1,653 per night
includes taxes & fees
Our Peaceful, Beach Escape From the City
Shaded Table & Chairs
Living Room View#1
Living Room View#8
Sidewalk View #1
Exceptional
(85 reviews)

Whaling Captain Pierson's Cottage

Sag Harbor

8% off
AU$3,932
for 7 nights, 1 cottage
AU$562 per night
includes taxes & fees
Whaling Captain Pierson's Cottage
  • 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 best area to stay in Village Of Southampton when booking a holiday rental?
When considering a holiday rental in the Village of Southampton, a delightful area to stay is the historic district. This charming neighbourhood boasts an enchanting blend of beautiful architecture and lush landscapes, making it an appealing choice for visitors. You'll find numerous properties available here, ranging from quaint cottages to luxurious homes, each contributing to the area's picturesque atmosphere.A highlight of staying in this area is the proximity to Southampton's stunning beaches, particularly the renowned Coopers Beach, which is superb for sunbathing and enjoying the seaside. Additionally, you can explore the fascinating Southampton Historical Museum, which offers insight into the town's rich heritage. The historic district also provides easy access to various boutique shops and exquisite dining options, ensuring you have everything you need for a memorable holiday.
What are the top attractions in Village Of Southampton?
In the Village of Southampton, visitors can enjoy a variety of attractions that showcase the area's rich history and natural beauty. The Southampton Village Historic District features charming streets lined with 19th-century buildings, boutique shops, and art galleries, providing a pleasant atmosphere for leisurely strolls. The iconic Southampton Cultural Centre hosts a range of events and exhibitions, making it a hub for local arts and culture.The nearby Cooper's Beach is known for its stunning ocean views and soft sands, great for sunbathing and swimming during the warmer months. For those interested in history, the Southampton History Museum offers insights into the village's past, including the fascinating Shinnecock Nation exhibit.In addition, the area boasts various parks, such as Agawam Park, which is ideal for picnics and outdoor activities.
Are all fees included in the Village of Southampton holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Village of Southampton holiday homes with parking?
Stayz offers a wide selection of holiday homes in Village of Southampton with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Village of Southampton holiday homes?
You can find great discounts on holiday homes in Village of Southampton on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Village of Southampton holiday home booking on Stayz?
To find Village of Southampton holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Village of Southampton?
A long-stay holiday home in Village of Southampton is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Village of Southampton holiday home?
Book your Village of Southampton holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Village of Southampton?
Prices for holiday homes in Village of Southampton vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Village of Southampton to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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