Discover a selection of 2,500 vacation rentals in Sag Harbor, NY 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 $110 per night, and houses and cottages are popular options for a stay in Sag Harbor. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Sag Harbor
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Destination guide

Sag Harbor oozes charm and offers sweeping views

Tucked away in Suffolk County, Sag Harbor is one of New York’s best kept secrets. Locals love to refer to it as the insider’s alternative to the more stuffy Hamptons villages, and it’s easy to see why. The laid-back former whaling town is dotted with beautifully restored historic homes, offering sweeping views over Peconic Bay. To experience the town like a local, swap a run of the mill hotel for a characterful Sag Harbor vacation rental. The seaside community may be small, but it serves up an inspired dining scene, covering everything from freshly caught seafood to artisan ice cream.

Activities

Slow down the pace in Sag Harbor

Sag Harbor is steeped in history, and one of the best ways to soak it all up is on a walking tour of the town. Pick up a map from the Chamber of Commerce, and spend a few hours admiring historic homes, exploring the harbor, and sifting through antique stores. For something a little more upbeat, why not sign up for a sailing class, private charter, or catamaran cruise? Thanks to its calm bay, water sports are big in Sag Harbor. You could rent a paddle board, zoom around on a jet ski, or try your luck at flyboarding.

Weather

Summer sunshine in the Hamptons

Traditionally, sunseekers flock to Sag Harbor from Memorial Day through to Labor Day. The weather is beautiful, the ocean is calm, and the days are luxuriously long. If you’re not keen on crowded beaches, Sag Harbor vacation rentals are the perfect way to secure a private pool and soak up the Long Island sunshine. Sag Harbor starts to empty out come September, and while it may be a little colder, early fall is still a fantastic time to enjoy the unique charms of the Hamptons.

Natural features

Beaches, bike trails, and world class wineries

Sandwiched between the villages of East Hampton and Southampton, Sag Harbor is one of several seaside communities that make up the prestigious Hamptons strip. Overlooking Peconic Bay, the harbor is well protected from the wind, waves, and wild weather of the Atlantic Ocean. Spend the day beach hopping, or rent a car and work your way through Long Island’s famous North Fork winery trail. If you’re craving fresh air, why not explore Sag Harbor on 2 wheels? Winding through pine forests, horse ranches, and beachfronts, Sag Harbor cycling routes are seriously picturesque. Wash it all down with a post-pedal brunch at a farm-to-table restaurant.

How to get there

Transportation to and around Sag Harbor

The nearest airport is in MacArthur Airport (ISP), located 44.4 mi (71.5 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into East Hampton, NY (HTO), which is 3.5 mi (5.6 km) away.

What are the top vacation rentals in or near Sag Harbor?

From extravagant condos to affordable cottages, Vrbo has properties to fit all budgets and tastes. Here are some of the top vacation rentals in Sag Harbor:

  • "Close To Nyc In Historic Brownstone": This Van Vorst Park retreat offers 2 bedrooms and is rated highly among visitors. Amenities such as a hair dryer and a kitchen help make your stay a memorable one.
  • "Disney / Universal / Seaworld 4 Condos - Vista Cay": Put your luggage down and your weary feet up at this favorite in Town of Southampton. It features 3 bedrooms, a nearby marina, spa and beauty services and more.

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

What are the top-rated vacation rentals for weekend getaways in or near Sag Harbor?

There's nothing better than a quick trip to clear away the cobwebs. Pack your overnight bag and settle into one of these enticing weekend getaways in and around Sag Harbor:

  • "4 Bedroom, 4 Bathroom; Minutes To Sag Village" is a popular option around 0.1 miles south of the center of Sag Harbor. You don't have to go far to find something fun to do around here. Get outdoors and discover Montauk County Park and Menhadden Lane Beach. Activities like surfing and boogie boarding and fishing will nicely round off your short break.
  • Alternatively, enjoy a slower pace of life at "Charming Cape Cod In The Hamptons". About 0.1 miles southwest of Sag Harbor, fun activities around here include hiking and biking and basketball. Rather go sightseeing? Don't miss Montauk County Park and Montauk Downs State Park Golf Course.

Can I find studio apartments for rent in and around Sag Harbor?

Usually small, easy on the hip pocket and well located, it's difficult not to be charmed by a studio apartment. Settle into one of these options and discover the culture of Sag Harbor up close:

  • Make "Charm On Pond Near Sag Harbor Village" your temporary home. This fantastic vacation rental comes with amenities including nearby museums and an ice maker.
  • Alternatively, spend your escape at "Sag Harbor Quiet Retreat Steps From The Bay", which offers conveniences such as an iron and ironing board and a garden.

There are lots of attractions around Sag Harbor to add to your agenda. Feed the culture vulture within by visiting Southampton Cultural Center and Bay Street Theatre.

Can I find short term rentals in or near Sag Harbor?

Locating a short-term rental in and around Sag Harbor won't be a problem if you only have a couple of nights free. Whether you're searching for a one-bedroom apartment just for one or a house that'll fit your family, you'll find a place to suit on Vrbo. Here are some of our best picks:

  • Book a few days at "Cove View Manor Of Sag Harbor" in central Sag Harbor. Here, you'll enjoy easy access to top attractions like Cooper's Beach.
  • Or maybe "Behind Serene Green Farm And Two Minute Drive To Gorgeous Long Beach" is better suited. Explore nearby sights such as Meschutt Beach during the daytime and then rest and relax in your comfy digs at night.

What are the best romantic weekend getaways in or near Sag Harbor?

Nothing says "I love you" like a romantic weekend together. If you'd like to spend a couple of evenings away with your sweetheart, we've got some romantic getaways in and around Sag Harbor that will get your heart racing:

  • Slip away on Friday for a couple of passionate nights at "New House, 6bd, 5bth, 4200sqft". Located approximately 20 miles from Sag Harbor, this place comes with lots of nice touches, like winery tours and shopping facilities.
  • Otherwise, spend a few magical days drinking wine and canoodling at "Sag Harbor Cottage On Nature Preserve Waterfront", around 0.1 miles from Sag Harbor. A fireplace and a swimming pool will help set the mood for romance.

Are there mansions for rent in or near Sag Harbor?

You'll find some awesome mansions for rent in and around Sag Harbor. If you're in search of somewhere with ample room as well as a large serve of wow factor, these stunners will tick your boxes:

  • Situated 4 miles to the southwest of Sag Harbor, "Mansion Near The Bay. 7 Bedrooms Chef’s Kitchen" is the perfect place for a luxurious escape. Amenities on offer here include a swimming pool and a firepit.
  • Alternatively, catapult your vacation to a new level and spend a few days at "Newly Redesigned 11 - Bedroom Mansion With An Outdoor Pool - 10. 5 Bathrooms". It's approximately 25 miles to the southwest of Sag Harbor and offers amenities like a fireplace, a swimming pool and more.

Are there large vacation rentals that sleep 30 or more in or near Sag Harbor?

If you're planning a get-together and your guest list is lonnnng, don't worry about finding someplace big enough for all those people. We've got large vacation rentals in and around Sag Harbor perfect for family breaks, wedding parties and more. Here are a few ideas:

  • "Spacious Living Room, Gunite Pool Surrounded By Patio": With 5 bedrooms accommodating up to 99 people, there's room enough for all of you. You and your group will have access to a host of amenities including a swimming pool and a fireplace.
  • "Chic Sag Harbor Beach Bungalow W": Get your entire party's nod of approval at this property which comes with a nearby beach and a nearby bay. With 2 bedrooms, up to 99 people can play and stay here.

What are the best houses for rent with a pool in or near Sag Harbor?

Of all the conveniences a vacation rental can have, a pool is one of the most desired. Have a look at these houses for rent with a pool in or near Sag Harbor and spend your days splashing about. Just remember to take your inflatable unicorn:

  • Get comfortable at "New House, 6bd, 5bth, 4200sqft", where your main priority will be lounging by the pool. Amenities including a fridge and pet-friendly facilities help make this getaway a favorite with guests.
  • Spend leisurely days splashing around or catching a few peaceful moments by the water at "Sag Harbor Zenpagoda House With Pool+poolhouse+artist Cottage". This vacation home is another favorite and comes with a balcony, a kitchen island and more.

Not sure how to pack your bags for your Sag Harbor escape? This impressive destination has a humid subtropical climate. During summer, expect average temperatures ranging from 70 ºF to 75 ºF. Browse our range of Sag Harbor vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more great ideas about where to stay.

What are the best large family vacation rentals in or near Sag Harbor?

Cousin Reggie, Great-Aunt Jean ... You can put them on your guest list when you choose a large family vacation rental in or near Sag Harbor. Get all the people you love together at one of these spacious properties:

  • Make your trip an unforgettable one at "New House, 6bd, 5bth, 4200sqft". This escape has 6 bedrooms, has space for 12 guests and comes with a range of amenities, including a separate dining area and a dishwasher. It's around 20 miles southwest of Sag Harbor.
  • "4 Bedroom, 4 Bathroom; Minutes To Sag Village" is another property your guests will love. Invite as many as 8 friends and family to this escape which offers 4 bedrooms, a fenced pool, a fridge and more. It's located 0.1 miles to the south of central Sag Harbor.

If you're eager to visit some family-friendly attractions around the area, Elizabeth A. Morton National Wildlife Refuge is a fun outing for all ages.

What are the best large houses to rent with indoor pools in or near Sag Harbor?

Take a dip anytime you like when you stay at one of our large rental houses with an indoor pool. Pack your favorite swimsuit and consider these getaways in or near Sag Harbor that feature this fancy perk:

  • Book a few nights at "New Luxury Retreat In The Hamptons" and spend your days kicking back poolside. This popular option has 5 bedrooms that sleep up to 12 guests and a host of other great amenities. A swimming pool and a garden are among them.
  • In addition to its swish indoor pool, "2 - Acre Modern Estate In Southampton. 10 Mins To Wineries" comes with a swimming pool and a garden. It has 4 bedrooms that can cater for up to 10 people, so you can bring the whole gang along.

Want to see our full range of options? Find your dream stay by using the search bar at the top of the page. Simply adjust the filters to find the Sag Harbor vacation rental that's perfect for you.