Discover a selection of 100 vacation rentals in Cutchogue, 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 $600 per night, and houses and cottages are popular options for a stay in Cutchogue. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Cutchogue
Destination guide

Book a vacation rental for your Cutchogue getaway

Learn about the unique charm of Cutchogue with a stay in a private vacation home. There's no shortage of things to see and do in the area.Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Things to do

Activities and attractions in and around Cutchogue

Are you looking for attractions to visit while you're in town? Venture out of your vacation home and experience everything that Cutchogue has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Splish Splash Water Park (14.2 mi / 22.9 km)
  • Peconic Bay Winery (0.6 mi / 1 km)
  • Bedell Cellars (1.5 mi / 2.5 km)
  • Pindar Vineyards (1.8 mi / 2.9 km)
  • Raphael Winery (2.1 mi / 3.4 km)
  • Macari Vineyards (4.7 mi / 7.6 km)
Natural features

Exploring the natural landscape of Cutchogue

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in Cutchogue. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Crescent Beach (7.3 mi / 11.7 km)
  • Sunset Beach (7.6 mi / 12.2 km)
  • Meschutt Beach (8.1 mi / 13 km)
  • 67 Steps Beach (9.7 mi / 15.6 km)
  • Sag Harbor Marine Park (10 mi / 16.1 km)
  • Cooper's Beach (11 mi / 17.7 km)
How to get there

Transportation to and around Cutchogue

The nearest airport is in MacArthur Airport (ISP), located 35.5 mi (57.1 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to East Hampton, NY (HTO), which is 12.8 mi (20.7 km) away.

What are the top vacation rentals in or near Cutchogue?

Elegant mansions, unique houseboats and spacious homes — everyone's dream getaway is different. Whatever you're into, you're sure to find something that catches your eye among these top vacation rentals in Cutchogue:

  • "Barn Life In Cutchogue": If you're chasing a comfy living space in North Fork, unpack your bags here. It offers 2 bedrooms and great amenities including winery tours and a stereo.
  • "Barn Luxury Living In Town Center Near Public Golf Course": Stay a week or so at this escape in North Fork and take advantage of a living room, nearby ecotour services and more. It has 2 bedrooms to accommodate your friends and family.

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

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

We all deserve a break every once in a while. If you're eager to spend a couple of uninterrupted mornings lingering in your PJs hugging a coffee, you'll find some fantastic weekend getaways in and near Cutchogue. Check out a few of our favorites:

  • Put your feet up at "Porch On Front~ Greenport Village 1st Floor Apartment". Located around 9 miles to the northeast of Cutchogue, this delightful escape has all you need for a chilled out stay, including an iron and ironing board and WiFi.
  • "Fabulous Waterfront Property In The Heart Of Wine Country" is another top-rated option. It's around 2 miles to the north of Cutchogue and features a TV, a free nearby fitness center and more.

Can I find short term rentals in or near Cutchogue?

Whether you're chasing a cozy cottage or a house to fit the whole family, you'll find the ideal place on Vrbo. Squeeze in a quick break at one of these retreats in or near Cutchogue:

  • For a memorable few nights away, settle in at "Spectacular Beachfront Contemporary In Wine Country • Private Beach • 5br". It's close to the center of Cutchogue, along with plenty of things to see and do.
  • Another terrific option is "Barn Life In Cutchogue". Round up your squad and enjoy a comfy stay close to the heart of Cutchogue.

What are the best romantic weekend getaways in or near Cutchogue?

Forget about roses and chocolates. Sometimes all you need is to get away for the weekend, just you and your honey. At Vrbo, we've got romantic getaways in and around Cutchogue that would make even old Cupid green with envy. Here are some we think you'll fall hard for:

  • Sneak off on Friday afternoon for a few passion-filled nights at "Private And Spacious Five Room Suite Steps To Bay Beach And Walk To Village". Located around 8 miles from Cutchogue, this place comes with lots of nice touches, like winery tours and beauty services.
  • Another place where you can enjoy a few relaxing days together is "Southold Waterfront Complete With Boat Dock". Located 5 miles from Cutchogue, a fireplace and winery tours add to the atmosphere here.

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

Of all the conveniences a vacation rental can offer, a pool is one of the most desired. Have a look at these houses for rent with a pool in or near Cutchogue and spend your time splashing around. Just don't forget your unicorn floatie:

  • Get into vacay mode at "North Fork Beach House - Walk To Beach", where your biggest priority will be enjoying the pool. Amenities such as outdoor furniture and a living room help make this escape a favorite with guests.
  • Spend laid-back days splashing around or enjoying peaceful moments by the water at "Waterfront Beach House On The Bay". This vacation home is another favorite and features pet-friendly facilities, nearby ecotour services and more.

Not sure what the weather's like in Cutchogue? It has an oceanic climate, with average temperatures in summer ranging from 70 ºF to 75 ºF. If you're searching for more inspiration on where to stay in this popular destination, use the search bar at the top of the page and adjust the filters to browse through our entire selection of Cutchogue vacation rentals.

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

Whether you're getting away with a small group or you're bringing your long-lost relatives along, family vacations equal fun. These large rentals in and around Cutchogue have room for everybody — along with everything you need to keep them happy:

  • With 3 bedrooms that sleep as many as 10 guests, "Southold Waterfront Complete With Boat Dock" gives you space to connect with loved ones. It's around 5 miles east of Cutchogue and comes with amenities that'll keep your group happy, such as a DVD player and free toiletries.
  • Another excellent option is "Spectacular Beachfront Contemporary In Wine Country • Private Beach • 5br". It's about 5 miles southwest of Cutchogue, has 5 bedrooms and can accommodate up to 10 guests. Useful amenities here include a kitchen island and on-site watersports.

If you're looking for family-friendly attractions while you're in the area, Greenport Carousel is a fun day out for all ages.

Can I find two-bedroom vacation rentals in or near Cutchogue?

Yes, you can. From funky apartments to comfortable cabins, Vrbo offers a selection of great rentals. Small families will adore these two-bedroom properties in or near Cutchogue:

  • "Barn Life In Cutchogue" is a winning choice for smaller groups or families. Along with two bedrooms, this relaxing stay offers handy amenities like a firepit and a garden.
  • Another highly recommended option is "Barn Luxury Living In Town Center Near Public Golf Course". With useful amenities such as a garden and a kitchen, it'll be plain sailing making yourselves at home here. Choose your favorite room, unpack your bags and let the fun begin!

What are the best three-bedroom vacation rentals in or near Cutchogue?

Three-bedroom rentals in or near Cutchogue give you space and freedom to make the most out of your vacation with loved ones. Check out a couple of the fantastic options available here:

  • Offering the trifecta of space, comfort and privacy, you'll get everyone's stamp of approval at "Fabulous Waterfront Property In The Heart Of Wine Country". This retreat comes with many handy amenities, including a fireplace and a kitchen.
  • "Newly - Remodeled Waterfront Cottage" is another superb option that has three bedrooms. A water view and a nearby waterfront are just a couple of things that will help make your stay here even more comfortable and enjoyable.

Are there vacation rentals with fire pits in or near Cutchogue?

Crackers, chocolate, marshmallows and a campfire are the four ingredients you need to make a sweet snack and unforgettable vacation memories. If you like the sound of huddling around a fire pit munching on s'mores, look into these retreats in or around Cutchogue:

  • Catch-up with old and new friends around the fire at "Southold Waterfront Complete With Boat Dock". This getaway comes with lots of other great amenities, such as a fireplace and a firepit.
  • "Porch On Front~ Greenport Village 1st Floor Apartment" is another top property where you can spend your days or nights socializing around a nice, warm fire. It also offers a garden and a fireplace.