Pet-friendly holiday rentals in Cutchogue

Cozy Farmhouse Retreat in North Fork, NY

A 1905 farmhouse with modern touches, Arthur's Vineyard is a cozy 3-bed, 2-bath home in walking distance of Greenport village's beaches, marina, restaurants and boutiques. An open plan living area, breezy decor and a large landscaped backyard for spending relaxed summer days and nights with your family and friends, including the 4-legged ones. Walk to the train station/jitney or take a short drive to the wineries & farm stands of the North Fork. Recent updates: central heat/AC & new bathrooms.

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown / restaurants / Havens beach, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds and 2.5 baths + pool house - Pool house with twin sofa bed + full bath - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond - Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Calf Creek Cottage (Water Mill/Bridgehampton)

Enjoy the peaceful seclusion of this charming, updated 3 bedroom, 2 bath cottage located on a private, acre-sized flag-lot south of the highway right on the border of Water Mill and Bridgehampton. Each bedroom (1 king, 2 queen) features ample closet space and new smart TVs . The new, fully-stocked kitchen, propane BBQ, outdoor dining table for 8, outdoor shower and spa with lounge furniture, and wood burning fireplace make it the perfect getaway for either summer or the winter season. Pets OK.

The Silver Pine Cone

Welcome to the hamlet of Ridge. The gateway to Long Islands many treasures. Whether you are venturing out to the North Fork wineries or a scenic drive on the south shore beaches on your way to the Hamptons. A beautiful cozy private (not a shared space) full one bedroom downstairs lower level apartment, living room w/full size sofa sleeper, kitchen/dining room, full bathroom and a completely separate yard with patio furniture exclusively for your use. Everything you need to enjoy your stay.

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

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!)

Private 1st flr apt w/ patio 3 blocks from beach

We are centrally located in a quiet neighborhood within blocks from the heart of Greenport Village, Peconic Bay Beach, LIRR/Jitney, restaurants, shopping, Mitchell Park, and more! Explore local farms, wineries, breweries and all the North Fork has to offer. Beautifully furnished, ground floor apt with private entrance & patio area comfortably sleeps four, features a queen Tempur-Pedic mattress & convertible couch. Friendly, housetrained pets are welcome for an additional charge.

The Sandpiper

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).

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.

Winter Getaway 2 miles from Ocean Beaches

Entire House! Large fenced in yard, great for pets. Two bedrooms, one song ride away from Ponquogue Beach. Have the beach to yourself for walks and exercise! Perfect place to get away and Unwind. The house is located on a quiet residential street close to the hamlet of Hampton Bays. Enjoy the patio and fire pit (use non-windy days) on 1/4 acre property. Still plenty to do here, we are 20 minutes from Wine Country and Tanger Outlets.

The Cooper-Burke House

Many Main Street restaurants such as the American Hotel, Lulu's, Page 63, Wolffer Kitchen, Sen, Sag Pizza and Goldberg's, etc are a few minutes away. On Main Street one finds the Sag Harbor Cinema, The Bay Street Theater, Schiavoni's Market and Yoga Shanti. The house is a 12-minute walk to Haven's Beach. 1-minute around the corner from the house is Cavaniola's Wine, Cheese and Kitchen shops as well as the Sag Harbor Beverage store.