Discover a selection of 3,500 vacation rentals in Town of Southampton, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $120 per night, and houses and cottages are popular options for a stay in Town of Southampton. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Town of Southampton
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Destination guide

Find the perfect vacation rental for your Town of Southampton getaway

Learn about the unique charm of Town of Southampton with a stay in a private vacation home. 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.

Things to do

Activities and attractions in and around Town of Southampton

Are you looking for top things to see and do during your stay? Venture out of your cozy vacation rental and check out everything that makes Town of Southampton a fun spot to vacation. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Shinnecock Hills Golf Course (2.9 mi / 4.6 km)
  • National Golf Club (5.1 mi / 8.2 km)
  • Jamesport Vineyards (7.2 mi / 11.6 km)
  • Duck Walk Vineyards (7.5 mi / 12.1 km)
  • Paumanok Vineyards (8.8 mi / 14.2 km)
  • Macari Vineyards (8.9 mi / 14.4 km)
Natural features

Exploring the natural features in Town of Southampton

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Town of Southampton is a great place to get outside. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Cooper's Beach (4.3 mi / 6.9 km)
  • The Hamptons Beaches (10.9 mi / 17.5 km)
  • Crescent Beach (15 mi / 24.2 km)
  • Sunset Beach (15.3 mi / 24.6 km)
  • East Hampton Main Beach (16 mi / 25.8 km)
  • LongHouse Reserve (16.8 mi / 27.1 km)
How to get there

Transportation to and around Town of Southampton

Fly into Westhampton, NY (FOK-Francis S. Gabreski), the closest airport, located 8.3 mi (13.4 km) from the city center.

If you're traveling by train, Hampton Bays Station, Southampton Station and Westhampton Station are the main stations in the area.

What are the top vacation rentals in or near Town of Southampton?

Whether you want an intimate escape for you and your honey or a sprawling house to fit all your friends, you'll find some top vacation rentals in and around Town of Southampton. Here are a couple to get you started:

  • Around 30 miles from the center of Town of Southampton, you'll want to keep coming back to "Beach House With Short Walk To Ditch Plains Beach". It has 2 bedrooms and a range of conveniences like optional golf privileges and nearby hunting activities.
  • Alternatively, make a booking at "Private And Spacious Five Room Suite Steps To Bay Beach And Walk To Village". Around 17 miles from the heart of Town of Southampton, it has 2 bedrooms and features free toiletries and children's books.

For even more great options, use the search bar at the top of the page to find the perfect Town of Southampton vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Town of Southampton?

Clock out on Friday and then forget the real world. If you're up for some fun and relaxation, these retreats in and near Town of Southampton are the ideal weekend getaway:

  • Located 12 miles to the northeast of the center of Town of Southampton, "Southold Waterfront Complete With Boat Dock" is a hit with adventurous types and nature buffs. Stay busy by exploring nearby outdoor attractions, including Walking Dunes Trailhead and Truman's Beach. If you still have time, try some hiking and biking or kayaking.
  • Alternatively, make your home away from home at "Porch On Front~ Greenport Village 1st Floor Apartment". Use it as a base to unwind, or get active and try fishing and golf. When you're ready to explore some nearby attractions, organize a visit to Meschutt Beach and LongHouse Reserve. This charming vacation rental is around 17 miles north of Town of Southampton.

Can I find studio apartments for rent in and around Town of Southampton?

Typically compact, less expensive and conveniently located, it's not difficult to be impressed by a studio apartment. Get cozy in one of these options and experience Town of Southampton up close:

  • Make "Hamptons Waterfront - On A Sandy Beach" your home for a couple of days or more. This fantastic vacation rental features amenities including a water view and towels.
  • Alternatively, spend your escape at "New Duplex Apartment", which offers conveniences including internet services and a fridge.

There are lots of attractions around Town of Southampton to add to your itinerary. Nourish the culture lover in you by visiting St Patrick's Old Cathedral and Dixon Place.

Can I find short term rentals in or near Town of Southampton?

Now and then, you just need to take some time out, even if it's only for two or three days. Enjoy the perfect combination of relaxation and adventure at one of these short-term rentals in or around Town of Southampton:

  • If you'd love to be near the action, "Porch On Front~ Greenport Village 1st Floor Apartment" has your name on it. It's within easy reach of the center of Town of Southampton and a handy base to check out sights like Times Square and Broadway.
  • "Waterfront Cottage Perfection" is another fabulous option. Consider adding Statue of Liberty and Rockefeller Center to your itinerary when you're ready to sightsee.

What are the best romantic weekend getaways in or near Town of Southampton?

Whether spent in a cabin, an apartment or a lodge, a romantic weekend getaway is an excellent way to spice up your love life. Whisk your sweetie away for a couple of relaxing days at one of these top escapes in or near Town of Southampton:

  • Slip away on Friday for a few passion-filled evenings at "Private And Spacious Five Room Suite Steps To Bay Beach And Walk To Village". Located approximately 17 miles from Town of Southampton, this property comes with plenty of nice touches, including beauty services and winery tours.
  • Alternatively, spend a few blissful days enjoying each other's company at "New House, 6bd, 5bth, 4200sqft", around 9 miles from Town of Southampton. Winery tours and a swimming pool will help set the scene for romance.

Are there mansions for rent in or near Town of Southampton?

If you're after somewhere to reconnect with your nearest and dearest this vacation, why not go all out? These mansions for rent in or around Town of Southampton will easily fit your entire crew while doing it in serious style:

  • Charm, character and style — "Ultimate Hamptons Vacation Mansion" has it all. Approximately 14 miles east of Town of Southampton and offering beauty services and golf, this place is hard to top.
  • Another popular option is "Mansion Near The Bay. 7 Bedrooms Chef’s Kitchen". Approximately 9 miles to the northeast of Town of Southampton, this swish vacation rental is the crème-de-la-crème of style and character and comes with a swimming pool, a firepit and more.

What are the best large group vacation rentals in or near Town of Southampton?

Big groups mean a whole lot of fun. They also mean finding someplace that'll effortlessly fit your crew. Check out our large group vacation rentals in or around Town of Southampton and get your favorite people together under the same roof:

  • Providing space, comfort and privacy, you'll get your guests' stamp of approval at "New House, 6bd, 5bth, 4200sqft". Up to 12 people can stay at this retreat which has 6 bedrooms, a water park and a swimming pool. This top pick is around 9 miles to the west of Town of Southampton.
  • Nothing takes priority over being together with loved ones, and "House With Pool In Hampton Bays" is the ideal place to do that. Located around 1 mile to the west of Town of Southampton, as many as 12 guests can stay in this vacation rental which has 4 bedrooms. A fireplace and a kitchen are among the numerous amenities at hand here.

Are there large vacation rentals that sleep 30 or more in or near Town of Southampton?

Whether you're organizing a shindig like a birthday party or a getaway with your favorite people, we'll help you find the ideal space to fit your group. Assemble your nearest and dearest and check out these large vacation rentals in or around Town of Southampton:

  • "Spacious Living Room, Gunite Pool Surrounded By Patio": The more guests you bring along the merrier to this popular vacation home. It has 5 bedrooms, fits up to 99 people and includes ample amenities, such as a kitchen and a fireplace.
  • "Chic Sag Harbor Beach Bungalow W": Get your entire crew's tick of approval at this escape which comes with a nearby bay and a nearby marina. Offering 2 bedrooms, up to 99 people can play and stay here.

What are the best houses for rent with a pool in or near Town of Southampton?

From lively games of freeze tag to quiet morning dips, a pool promises hours of fun for all ages. Score some serious brownie points with family or friends by choosing a house with a swimming space in or near Town of Southampton:

  • Topping our list of cool pool retreats is "New House, 6bd, 5bth, 4200sqft". Traveling groups will feel right at home here, with useful amenities like a video library and a pool table also at hand.
  • "Southampton Water View, Modern Architecture House" is another great option. After you've enjoyed a dip with the kids, make use of other conveniences like towels and coffee and tea making facilities.

What are the best large family vacation rentals in or near Town of Southampton?

Whether your ideal escape is out in the countryside or on the beach, you'll have a lot more fun if you share it with family and friends. Book one of these large family vacation rentals in or near Town of Southampton and bring the whole gang along:

  • Located around 9 miles to the west of Town of Southampton, "New House, 6bd, 5bth, 4200sqft" has 6 bedrooms and fits up to 12 guests. It's equipped with a range of amenities, including towels and coffee and tea making facilities.
  • Another top option is "Southold Waterfront Complete With Boat Dock". This property is 12 miles northeast of Town of Southampton and features childrens activities, a garden and more. With 3 bedrooms accommodating up to 10 people, you won't need to leave anyone off your invitation list.

If you're eager to visit some family-friendly attractions around the area, you won't have to go far. Broadway, Rockefeller Center and Brooklyn Bridge offer fun for both adults and kids.