Holiday houses in Cutchogue

4.98 out of 5 average rating, 49 reviews

Home in South End

Le Petit Cottage, Southold, NY

Experience the charm of a two-bedroom cottage in Southold, New York. Enjoy easy access to nearby South Harbor Park Beach, where you can swim and soak up the sun. Immerse yourself in the local wine scene with wineries just a short distance away. Explore nearby farms to savor fresh produce and artisanal goods. Unwind on the outdoor deck in the fresh North Fork air after a day of swimming, wine tasting and farm visits. Greenport and Shelter Island Ferry are a short ten minute drive away.

5 out of 5 average rating, 33 reviews

Cottage in North Fork

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.

5 out of 5 average rating, 13 reviews

Cottage in North Fork

Exceptional! Modern Farm House by the beach

Enjoy a stylish experience at this centrally-located modern cottage. Make yourself at home this summer in this newly renovated cottage. Its down the road from a private Fleet’s Neck Beach as well as in the heart of beautiful NorthFork wine country! Guests can enjoy easy travel through the NorthFork and all it has to offer! Close to the Long Island Railroad for easy travel into the city. Enjoy your stay visiting local farms,restaurants,beaches, vineyards, breweries and seasonal festival

4.97 out of 5 average rating, 154 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 (inquire!)

Guest suite in North Fork

4.92 out of 5 average rating, 99 reviews

Enjoy a relaxing getaway to the North Fork

One bedroom suite, with separate entrance in quiet Nassau Point; a peninsula, surrounded by beaches. Nassau Point is a great place to bike, walk and enjoy nature. Fully functioning WiFI for guests looking to extend their stay, while working from home. Fishermen's beach is a 5 minute walk Causeway beach is a 10 minute walk with parking. Point beach, 1.5 mile walk, a Southold Parking Permit required. You will find 20 wineries within 5 miles, just a short Uber ride away.

4.94 out of 5 average rating, 187 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).

4.94 out of 5 average rating, 127 reviews

Guest suite in South End

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.

5 out of 5 average rating, 17 reviews

Sunny Harbor Suite

Escape to the tranquil beauty of the North Fork for a cozy romantic getaway, surrounded by lush vineyards, farm-to-table restaurants, quaint villages and blissful beaches. This completely private space includes two rooms: a large bedroom with a queen sized bed, a TV and a couch, as well as a private bathroom. The dining area includes a refrigerator, microwave and an electric tea kettle (I have organic coffee that you can make using a pour-over melita filter).

4.93 out of 5 average rating, 135 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.

4.97 out of 5 average rating, 206 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.

5 out of 5 average rating, 14 reviews

North Fork Farm House

This home is located on the North Fork of Long Island in the heart of wine country. We have a beautiful winery within close walking distance. We are surrounded by beautiful beaches and a short ferry ride to Shelter Island. There’s great restaurants and shopping in the town of Greenport and close to Love Lane in Mattituck. There is also exciting things to do in the town of Riverhead, including shopping at Tanger and the Riverhead Raceway.

5 out of 5 average rating, 35 reviews

North Fork paradise between beaches and vineyards

Kick back and relax in this calm, stylish retreat. Nestled between vineyards and farmlands, this newly renovated mid-century ranch with a beautiful 14x50' heated salt water pool is a short hop to beautiful beaches, wineries, restaurants, and farm stands. Enjoy nature in a secluded park-like setting and explore everything the NoFo has to offer all year around. Please note that there are no parties, gatherings or unannounced guests allowed.

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Other great holiday rentals in Cutchogue

5 out of 5 average rating, 10 reviews

Apartment in South End

Petite apt right in southold

GraceRating, 5 stars1 week ago

This Airbnb was the best one we have ever stayed at! The apartment was sparking clean, spacious, and perfect for a weekend getaway. Parking is easy as street parking is free. We were able to park on the side street next to the apartment. Beth is an AMAZING host; she was responsive and helpful! You cannot beat the location! The Airbnb is close to all of the vineyards, great restaurants, and shops. We hope on our annual North Fork trip that we get the chance to stay there again!

5 out of 5 average rating, 27 reviews

Stylish North Fork cottage and backyard deck!

ElizabethRating, 5 stars10 months ago

We had a wonderful stay at Steven and Justin's home! The house was charming, the location was perfect (on a quiet gravel road with friendly neighbors on both sides), and the backyard was fantastic. Not to mention the house was spotless. They also went out of their way to put together a super helpful guide to the area with an overview of beaches and restaurants - it took away all the stress of planning. Perfect for a quiet family vacation! We would love to come back!

4.8 out of 5 average rating, 5 reviews

NoFo Getaway: Pool, Farm Views, Beach Sunsets

LylyRating, 5 stars2 months ago

This was the perfect place for our family to get away from the city. It was a family friendly home that was perfect for our little one. The house was clean and came with all of the necessary essentials we needed. The location was private and serene while still accessible to lots of wonderful local restaurants and stores. The beach was easily accessible and within walking distance. Additionally, Morgan was responsive and always available to answer any questions we had. We absolutely enjoyed our stay and recommend it to any family.

5 out of 5 average rating, 13 reviews

Modern Mattituck Escape

LindaRating, 5 stars4 weeks ago

We didn’t want to Leave!We stayed for a long weekend in May. A family of 7 adults & one 3 year old. This house was perfect for our stay. The photos of Ryan’s place doesn’t do it justice. The family with the 3 year old had the entire lower level all to themselves. A Bedroom, walk in closet, full bathroom, living room with tv, walkout to the back yard. It had everything to entertain including a big playroom full of toys. The upstairs had 3 bedrooms, 2.5 baths, dining room, living room and well appointed kitchen. It is on the end of quiet street on a cul de sac. Behind the fenced yard were woods and marsh. Within a 3 minute drive to wineries. We couldn’t ask for a better location. Our grandson cried knowing we had to leave. I almost did too. I can’t wait to return

5 out of 5 average rating, 11 reviews

Beautiful 1930s 4 bed 3 bath! Walk to Beach

WilliamRating, 5 stars1 month ago

All in our family had a great time. We hope to rent again sometime in the next year. Ideal for our group-6 adults and one 8-year old. Everything worked great and we took full advantage of the outdoor spaces-deck, patio, fire pit, etc. And we were only a minutes walk to a beautiful sandy beach on Peconic Bay. Also we were only 5 minutes drive from 10 vineyards and a great Seafood Market. The house was easy to get to and keycode on front door was easy. Clear written instructions and recommendations were provided by owner. Thanks, Ike!

5 out of 5 average rating, 10 reviews

Charming home in the North Fork / Wine Country

DRating, 5 stars8 months ago

We had a great time during our trip and the best part was the location and neighborhood. We took morning walks around the neighborhood and were able to drive to so many wineries, restaurants and apple picking just a few minutes away. The host was helpful and responsive. The outdoor patio was a nice spot to have a drink or breakfast. Very peaceful!!! Kitchen was well stocked. Felt at home.

Guesthouse in North Fork

4.5 out of 5 average rating, 4 reviews

Beautiful 2 bdrm cottage on NoFo

LoriRating, 5 stars9 months ago

We stayed at The Cottage for a family wedding and to enjoy a few days away from home. The Cottage was roomy enough for myself and my spouse. There are two bedrooms - one is on the second floor, the other is on the first floor, and the bathroom is on the first floor. There was sufficient space for us to host a small breakfast gathering for two of my siblings and their spouses before the wedding. Marion is a gracious host. If we were to ever travel to the North Fork again, we would definitely check if she had availability at The Cottage.