Discover a selection of 1,000 holiday rentals in Town of Southampton, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 322 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.
Top rated rentals — Town of Southampton
Destination guide

Find the perfect holiday rental for your Town of Southampton getaway

Learn about the unique charm of Town of Southampton with a stay in a holiday home rental. 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 attractions to visit during your stay? Venture out of your cosy holiday rental and check out everything that Town of Southampton has to offer. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Splish Splash Water Park (12.9 mi / 20.8 km)
  • Shinnecock Hills Golf Course (3.1 mi / 5 km)
  • Jamesport Vineyards (7 mi / 11.3 km)
  • Duck Walk Vineyards (7.8 mi / 12.5 km)
  • Macari Vineyards (8.8 mi / 14.2 km)
  • Martha Clara Vineyards (9.1 mi / 14.7 km)
Natural features

Exploring the natural features in Town of Southampton

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Town of Southampton is a great place to get outside. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Meschutt Beach (1.6 mi / 2.5 km)
  • Ponquogue Beach (2.6 mi / 4.2 km)
  • Cooper's Beach (4.5 mi / 7.3 km)
  • The Hamptons Beaches (11.1 mi / 17.9 km)
  • Sag Harbor Marine Park (13.7 mi / 22 km)
  • Georgica Beach (15.1 mi / 24.2 km)
How to get there

Transport to and around Town of Southampton

Fly into Westhampton, NY (FOK-Francis S. Gabreski), the closest airport, located 8.1 mi (13 km) from the city centre.

If you're travelling by train, Hampton Bays Station, Southampton Station and Westhampton Station are the main stations that serve the city.

What are the top holiday 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 holiday rentals in and around Town of Southampton. Here are a couple to get you started:

  • Around 30 miles from the centre 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 holiday rental for you.

What are the top-rated holiday 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 centre 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, organise a visit to Meschutt Beach and LongHouse Reserve. This charming holiday 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 cosy 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 holiday 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 centre 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 Centre 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 holiday, 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 Holiday 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 holiday rental is the crème-de-la-crème of style and character and comes with a swimming pool, a firepit and more.

What's the best place to stay if you're looking to rent a house for a weekend in or near Town of Southampton?

Roughly 4 miles east of Town of Southampton, Village of Southampton is an awesome spot to rent a property for a weekend. Spend Saturday checking out the local area and then Sunday being as lazy as you please. Bay Point is another good choice for a weekend trip. It's located 12 miles northeast of Town of Southampton.

What are the best large group holiday 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 holiday rentals in or around Town of Southampton and get your favourite 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 holiday rental which has 4 bedrooms. A fireplace and a kitchen are among the numerous amenities at hand here.

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

Whether you're organising a shindig like a birthday party or a getaway with your favourite people, we'll help you find the ideal space to fit your group. Assemble your nearest and dearest and check out these large holiday 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 holiday home. It has 5 bedrooms, fits up to 99 people and includes ample amenities, such as a kitchen and a fireplace.
  • "Chic Sag Harbour 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". Travelling 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.