Photo by Andrew Barney Kavesh

Village of Southampton holiday lettings

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
2nd floor deck with additional dining and leisure seating.
Heated pool with gorgeous water and natural wetland view
Exceptional
(38 reviews)

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

Southampton

5% off
£11,418
for 7 nights, 1 home
£1,631 per night
includes taxes & fees
Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!
Pool
Private kitchen
Exterior
Dining
Exceptional
(6 reviews)

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

Hampton Bays

8% off
£7,646
for 7 nights, 1 home
£1,092 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
£6,454
for 7 nights, 1 home
£922 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
master bedroom with balcony
aerial view
kitchen with large island and breakfast table
living room
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off
£44,761
for 7 nights, 1 home
£6,394 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Pool
Terrace/patio
Exterior
Living area
Excellent
(10 reviews)

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

Water Mill

8% off
£29,580
for 7 nights, 1 home
£4,226 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Interior
Exterior
Private kitchen
Interior
Exceptional
(8 reviews)

Beautiful Colonial Mint Condition Summer House Walking Distance to Beach

Jamesport

11% off
£3,389
for 7 nights, 1 home
£484 per night
includes taxes & fees
Beautiful Colonial Mint Condition Summer House Walking Distance to Beach
Pool
Dining
outdoor shower
living room
Exceptional
(60 reviews)

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

Southampton

8% off
£10,778
for 7 nights, 1 home
£1,540 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
An elegant dining room (to 10 ppl, joins kitchen +8 and outdoor dining  +10,)
Living area
park-like grounds
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
£7,834
for 7 nights, 1 home
£1,119 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Pool
Living area
Interior
Outdoor dining
Exceptional
(14 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

7% off
£5,850
for 7 nights, 1 home
£836 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
Outdoor dining
.
Private kitchen
Interior
Exceptional
(82 reviews)

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

Hampton Bays

6% off
£6,153
for 7 nights, 1 home
£879 per night
includes taxes & fees
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Interior
Living area
Exterior detail
Exceptional
(11 reviews)

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

Sag Harbor

8% off
£7,854
for 7 nights, 1 cottage
£1,122 per night
includes taxes & fees
Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house
Living area
Exterior
Hot tub open all year
Dining area
Exceptional
(45 reviews)

Westhampton Beach Town and Country

Westhampton Beach

8% off
£6,248
for 7 nights, 1 home
£893 per night
includes taxes & fees
Westhampton Beach Town and Country
Spacious living room with sliders to the patio pool and backyard
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
(108 reviews)

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

Westhampton Beach

7% off
£4,900
for 7 nights, 1 home
£700 per night
includes taxes & fees
Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach
Dining
Dining
Room
Living area
Exceptional
(10 reviews)

Southampton Village Charmer - South of Highway

Southampton

8% off
£16,733
for 7 nights, 1 home
£2,390 per night
includes taxes & fees
Southampton Village Charmer - South of Highway
Open entry foyer with wall of windowed doors to Zen Garden
Thermador chefs kitchen with expansive island open to dining room & family room
Frankel Residence
View from entry foyer into double height living room, skylights, leading to pool
Exceptional
(6 reviews)

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

Wainscott

8% off
£12,861
for 7 nights, 1 home
£1,837 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Living area
Dining
Private kitchen
Room
Exceptional
(18 reviews)

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

Cutchogue

8% off
£3,937
for 7 nights, 1 cottage
£562 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
Couches on covered porch and outdoor dining table for 8
Hydrangeas blooming all summer.these are the August bloomers
Exceptional
(7 reviews)

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

Southampton

8% off
£14,301
for 7 nights, 1 home
£2,043 per night
includes taxes & fees
IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES
Living room
Pool
Terrace/patio
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
£6,052
for 7 nights, 1 home
£865 per night
includes taxes & fees
Modern Family Retreat with Heated Pool, Playground and Peloton
Private kitchen
Pool
Dining
Interior
Wonderful
(20 reviews)

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

Riverhead

8% off
£3,187
for 7 nights, 1 home
£455 per night
includes taxes & fees
2-Acre Modern Estate in Southampton. Beach, winery, farm, pool, and hot tub
8 Hands Farm
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

26% off
£1,939
for 7 nights, 1 home
£277 per night
includes taxes & fees
North Fork Ranch Home in Wine Country with Pool- 2 Beaches 5 Min Walk
Interior
Private kitchen
Living area
Dining
Exceptional
(13 reviews)

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

Sag Harbor

8% off
£10,906
for 7 nights, 1 home
£1,558 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
view of pool
Private kitchen
Exceptional
(15 reviews)

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

Water Mill

8% off
£12,796
for 7 nights, 1 home
£1,828 per night
includes taxes & fees
Sunsets Sweeping Farmland Views, Great Retreat Minutes from Flying Point Beach
Living room
Wrap around deck
Second eating area
Second living room
Exceptional
(34 reviews)

Our Peaceful, Beach Escape From the City

Sag Harbor

8% off
£6,276
for 7 nights, 1 home
£897 per night
includes taxes & fees
Our Peaceful, Beach Escape From the City
Backyard Water View
Kitchen
Exterior
Living Room
Exceptional
(6 reviews)

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

New Suffolk

7% off
£2,705
for 7 nights, 1 home
£386 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, 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.
How much does it cost to rent a holiday home in Village Of Southampton?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Village Of Southampton to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Village Of Southampton holiday house rentals?
You can find great discounts on house rentals in Village Of Southampton on Vrbo, 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 find long-stay holiday rentals in Village Of Southampton?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Village Of Southampton holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
How early should I book a Village Of Southampton holiday rental?
Book your Village Of Southampton holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Village Of Southampton home rental booking on Vrbo?
To find Village Of Southampton holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Village Of Southampton holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

More holiday ideas