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Vacation rentals in Cutchogue

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Top-rated vacation rentals in Cutchogue

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Home in North Fork

4.98 out of 5 average rating, 128 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals available (inquire!)

Guest suite in North Fork

4.9 out of 5 average rating, 256 reviews

Beachy En Suite /Gateway to The North Fork

Adorable,quiet,clean, w private entrance, private bedroom and bathroom,breakfast nook and patio.We are located in a beach front town dubbed“Gateway to the North Fork”. Walking/driving directions to local beaches,15minute walk to our community beach(.6mi away).Niks deli nearby.Minutes by car to wineries breweries,farm stands,EastWind 2 mi,TangerOutlets15min away,35min to Hamptons,Greenport!Hosts live in adjoining house. Rarely need access to your hallway to get to our basement.Would arrange.

Cottage in North Fork

5 out of 5 average rating, 30 reviews

Renovated 2-Bedroom Cottage on the North Fork

Serenity awaits as you step into this totally renovated Cottage. The property is perfectly located in the heart of Long Island's Wine Country. Centered on the North Fork this home allows you to explore all that there is to offer…. antique shops, restaurants, vineyards, breweries, farm stands and the beautiful Causeway Beach is just steps from this home. The home is newly renovated with a new kitchen, appliances, new bathroom, outdoor gas grill, fire pit and a beautiful screened in porch.

Rental unit in North Fork

4.96 out of 5 average rating, 139 reviews

Upscale Newly Constructed Apartment

Upscale 2- story building offers 3 bedrooms, 2 baths spacious apartment in the heart of Greenport. A vaulted ceiling in the great room (kitchen, dining & living room) with large windows and hardwood floors with plenty of natural light. Utilities included. CAC, Laundry. Less than a mile to a public beach, public transportation, restaurants, shops and Mitchell park. Off street parking for 2-3 cars. It is a week minimum during the peak season ( memorial day weekend until labor day weekend)

Rental unit in North Fork

4.96 out of 5 average rating, 118 reviews

Bright, Southold Studio Apt near beach & town

Pied a terre on the North Fork, in the heart of Southold village. Gorgeous bay beach 5 minute walk, as are farmstands, supermarket, Historic Southold Village with quaint shops, Hampton Jitney & LIRR. Lots of light, new contemporary space featuring full bathroom with bathtub. Perfect for one, suitable for a couple for weekend getaway. Small kitchenette perfect for simple food prep, morning coffee/tea. Chickens on property, fresh pastured eggs in your kitchenette upon arrival!

Rental unit in Sag Harbor

4.95 out of 5 average rating, 173 reviews

Sag Harbor / Noyack Pad - private STUDIO apartment

500sq ft studio apartment, with private entrance, private bathroom, outdoor deck area with table/chairs, private kitchenette (but no stove). Close to Noyack Bay/Long Beach. 5 min drive to Sag Harbor village. 15 min to East Hampton village. 15 min to Ocean beaches. Responsive host: you will be greeted and handed keys when you arrive. No waiting around. Host will respond to all calls or messages rapidly if any issues arise. Lockbox entry with spare key also for 24 hour access

Home in North Fork

4.98 out of 5 average rating, 51 reviews

Cozy Cottage with Views

Take it easy at this unique and tranquil getaway centrally located in Cutchogue on the North Fork of Long Island. This newly renovated cottage has plenty of natural light, a full kitchen with all new appliances, one bedroom with a queen size bed, a bathroom with a walk in shower, a spacious living room with vaulted ceilings and a private outdoor space with a gas grill. A short drive in either direction allows you the opportunity to experience all that the North Fork has to offer.

Guest suite in North Fork

4.91 out of 5 average rating, 301 reviews

The Greenport Suite—private entry + near the beach

Welcome to The Greenport Suite! With its separate entrance, secluded outdoor patio space and ideal location, this newly-redesigned private suite in our contemporary Village home is perfect for enjoying a North Fork getaway. We are located just a few short blocks from bay beaches, the harbor, and public transport, while the area's celebrated wineries are a short drive or bike ride away. Come see why Forbes named Greenport one of the 11 prettiest villages in the United States!

Home in North Fork

4.93 out of 5 average rating, 166 reviews

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Guest suite in North Fork

4.95 out of 5 average rating, 117 reviews

Comfortable Suite, a walk to the beach

Keep it simple at this spacious and peaceful home. Built in 2019, this home was specially designed for sustainable, green living; ground-source heating, and super insulation allow for minimal environmental impact. Less than five minute walk to McCabe’s Beach. Very near to wineries, farms, and the quaint shops and bakeries of Southold and Greenport. Little Fish restaurant and oyster sales all down the street. Short drive from Sparkling Pointe vineyard, and Love Lane.

Home in North Fork

4.93 out of 5 average rating, 115 reviews

Modern Farmhouse Steps to Beach & Love Lane

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

Home in North Fork

4.97 out of 5 average rating, 200 reviews

Private Oasis W/Stunning Vinyard and Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Vacation rentals for every style

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Popular amenities for Cutchogue vacation rentals

Free parking on premises

Air conditioning

Stay near Cutchogue's top sights

King Kullen77 locals recommend

Love Lane Kitchen76 locals recommend

Croteaux Vineyards70 locals recommend

Bedell Cellars62 locals recommend

Greenport Harbor Brewery and Restaurant54 locals recommend

Pindar Vineyards41 locals recommend

Other great vacation rentals in Cutchogue

Home in North Fork

5 out of 5 average rating, 10 reviews

Sunset Ranch

Loft in North Fork

5 out of 5 average rating, 20 reviews

Walk to Town/Beach/Train/Wine/Farms-Private Loft

Home in North Fork

4.96 out of 5 average rating, 24 reviews

NorthFork FarmHouse, Amazing Pool, Beach,Vineyards

Home in North Fork

5 out of 5 average rating, 16 reviews

Waterfront with private dock & bocce court

Home in North Fork

4.88 out of 5 average rating, 16 reviews

Eat, Love, Stay, and Swim

Home in North Fork

4.75 out of 5 average rating, 8 reviews

Updated Private Home

Home in North Fork

5 out of 5 average rating, 24 reviews

Horton House

Cottage in North Fork

4.97 out of 5 average rating, 91 reviews

Cozy Seaside Cottage

Quick stats about vacation rentals in Cutchogue

Total rentals
110 properties
Nightly prices starting at
$80 before taxes and fees
Total number of reviews
3.6K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
30 properties have a pool

Frequently Asked Questions

How much does it cost to stay in house rentals in Cutchogue?
Experience the best of Cutchogue with our house rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Cutchogue?
Enhance your stay in our House Rentals with the most popular amenities: over 70 homes with free parking, over 80 homes with wifi, over 80 homes with air conditioning, over 70 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there vacation rentals with a dedicated workspace in Cutchogue?
Yes! Work meets play with ease at over 60 vacation rentals in Cutchogue featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Cutchogue?
Four-legged friends are welcome in Cutchogue. Choose from more than 40 vacation rentals for guests traveling with pets.
Do cottage rentals in Cutchogue have a kitchen?
Absolutely! We offer over 10 cottage rentals with a kitchen in Cutchogue. Enjoy a tailored experience with all the comforts you desire.
Are there Cutchogue vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Cutchogue, available on Airbnb. Make a splash and soak up the sun in style!
Do cottage rentals in Cutchogue have free parking?
Absolutely! We offer over 10 cottage rentals with free parking in Cutchogue. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Cutchogue have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Cutchogue. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Cutchogue?
Cutchogue has more than 90 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do cottage rentals in Cutchogue have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Cutchogue. Enjoy a tailored experience with all the comforts you desire.

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