Holiday rentals with a kayak in Greenport West

The North Star: Greenport Waterview Beach Getaway

Welcome to our charming home in Greenport, NY. Right across the street from the private community beach! We are neighbors to the most famous wineries on the North Fork. 3 bedrooms, 2 baths, & a den that has a pull-out queen sleeper sofa. Private beach. Outdoor shower. Comes fully equipped with towels & linens. 2 miles from the town of Greenport. Perfect house for families/groups. DOG(s) FRIENDLY (w/ a pet fee) with fenced front yard & deck- sorry no cats! Looking for adults aged 30 or over.

The Sandy Shack - Coastal Escape

Escape to your own private oasis at this charming beach house in Greenport. This beachfront home offers views of the ocean in every room. Inside, the living space gives plenty of natural light and sitting areas. The kitchen has everything you need to cook for family & friends. There are 4 beds to choose from, which can sleep 6 total. Outside, enjoy your own private beach as well as kayaks to use at your leisure. Located next to Greenport's best restaurants and wineries, book your stay today!

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

Waterfront Joshua Cove Cottage with private beach.

Beautiful architecturally designed 1 Bedroom + loft Cottage on Joshua Cove in Guilford. The sunsets are spectacular from your own private beach. Enjoy Fall Foliage, swimming, fishing, and some of the best Kayaking from this perfect setting. Minutes from the Guilford train station, restaurants, shopping, and historic town green. The property is just 15 minutes from New Haven, and the Yale campus. The Thimble Island cruise, and the Ct. river steam train/cruise are nearby as well.

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

𓇼Walk to the Beach! ༄Location: quiet oasis by nature preserve, vineyards, breweries, farm stands, restaurants + attractions, 5 min to Greenport Village + Southold 𓇼Firepit, outdoor dining with string lights, grill, beverage cooler ༄Equipped kitchen w/blender, coffee, waffle maker + more! 𓇼Bathrooms w/heated floors + a clawfoot soaking tub (Please note there is only 1 shower) ☼Family Friendly: Board games, packNplay, high chair, beach chairs + toys ༄Kayak + bikes 𓇼Smart TVs

North Fork Sound Front Home with Pool

This Long Island Sound front property on nearly three acres of land with an inground, custom designed, gunite pool is the perfect vacation home. Walk down the ramp to your private beach for a kayak, paddle board or swim in the summer and enjoy a luxurious outdoor shower afterwards. In the fall and winter months, enjoy the extensive book collection and stay cozy by the fireplaces. Spacious and bright, this home has a unique aesthetic and can accommodate 8 guests comfortably.

Waterfront Greenport Boathouse

Watch the boats go by from this waterfront 1840's Greenport boathouse. Step back in time with this home that was originally part of Greenport's working waterfront. It has been recently restored while retaining its wide-plank floors and exposed beams. Private dock and beach area for launching kayaks (provided in season). It has three bedrooms with queen sized beds as well as two full bathrooms. New central air-conditioning throughout house. Wifi, Smart TV, Bose stereo

The Katalpa House -by the beach

-Our beach is private, key and beach tag provided- (in brown shed) This 1000+ sf home, features a newly renovated kitchen, outdoor shower, and many quirks that come with a 90 year old home. The furnishings are eclectic and vintage. Most of the flooring is also new. The beach and bluffs are only about a 2 minute walk. The 1/4 acre lot is shared with a secondary unit as you can see in the photos which is occupied by my sister.

The Cottage at Indian Cove

A charming original turn of the century cottage that was recently renovated. One main room plus a full bathroom and Ikea kitchen. It includes a back porch that gets a perfect amount of late afternoon sun. The cottage has electric baseboard heat for cool nights. We are located in Indian Cove beach Association with a two block walk to the beach. You are welcome to enjoy our kayaks, bikes to tour the area and a fire pit.

Coastal New England Waterfront Home-The Reed House

The Reed House – Waterfront Getaway in Waterford, CT Enjoy the best of both relaxation and adventure at The Reed House, located in the peaceful Pleasure Beach neighborhood of Waterford. This charming home offers breathtaking views of Jordan Cove and is just steps away from the beach, making it the ideal retreat for families, friends, or anyone looking to unwind by the water..

Walk to Breakwater Beach in Heart of Wine Country

Private and peaceful cottage walking distance to Breakwater Beach and Old Mill Inn Restaurant on the water opening Spring 2025. There are two large decks to relax by the firepit and drink your wine from the local wineries. Bikes, kayak, and paddle board are stored in the barn for guests use. Easy access to the marina, fishing, fine dining, vineyards, and farm stands.

Laid Back Relaxation

Kick back and relax in this calm, stylish space. Nice newly updated home on a quiet street within walking distance to beaches, restaurants and a golf course. Great location near Shelter Island heights town, Crescent beach and Sunset beach. The location provides both privacy and relaxation at home with just a short walk or ride to popular Shelter Island spots.