Vacation rentals with lake access in Southold

4.77 out of 5 average rating, 61 reviews

Two white Adirondack chairs are positioned near a fire pit, offering a scenic view of the calm water and a partially cloudy sky at sunset. Pebbles and grassy areas surround the seating, enhancing the serene beach atmosphere.

Apartment in North Fork

Incredible 2 Bedroom Waterfront Cottage!

An amazing & unique experience on the North Fork of Long Island. Sitting on a bluff 15’ above our private beach, this 3 season multi-family property boasts panoramic views of the LI Sound. Amazing sunset/sunrise views, fishing, beach combing, swimming, wineries, restaurants, shopping. Huge 2nd story deck for evening cocktails. Full kitchen, BBQ, loads of amenities. Updated inside & out. Private beach shared only with other guests of the property Please note there is some noise from passing cars

4.88 out of 5 average rating, 64 reviews

Inside a spacious safari tent, a queen bed is neatly made, flanked by nightstands on either side. Sunlight filters through the large screened windows, offering views of the outdoors. A small chair and table set are positioned at the entry, providing a cozy spot to enjoy the scenery.

Tent in East Hampton

Safari Tent Glamping,S9-CedarPt, East Hampton, NY

LoveCedarPt - Explore the Hamptons & Montauk, Eat, Provision and Glamp in Comfort at the 607 acre Cedar Point County Park on Northwest Harbor near Sag Harbor & E. Hampton. Lodge overnight in comfort & style in our furnished platform Safari Tents in a perfect tree meadow on the bluffs overlooking the bay and Shelter Island with sunsets 2nd to none. For 2025, we have 16 tents with queen beds and linens. Tents are covered with large rain flies that make a covered porch for the Adiron

A serene backyard is depicted, featuring a soft green lawn bordered by flourishing plants and flowers. Stone pathways meander gently through the garden, leading towards a view of the water. Trees provide shade, enhancing the natural, peaceful setting.

4.89 out of 5 average rating, 27 reviews

Coastal Cottage on the Water

A coastal cottage on the water surrounded by vineyards and farm stands on the North Fork. Unwind in the backyard with a private view of the Goldsmith's Inlet where you can watch the sunrise, bird watch, and admire our local swans. A quick 5-minute walk to the Long Island Sound where you can sunbathe, swim, kayak, and watch the beautiful sunset. Conveniently located near Greenport, Orient, and Southold. *IMPORTANT* Kayaks and grill are only available from May 1st to October 31st.

A hot tub sits at the edge of a serene lake, surrounded by lush greenery and trees. The gentle ripples on the water reflect the sky, enhancing the tranquil setting. The peaceful landscape invites relaxation and offers a scenic view of nature.

4.81 out of 5 average rating, 43 reviews

Southold Sea'renity

Kick back and enjoy the peaceful surroundings of this beautiful 3-bedroom, 2-bathroom house. Outdoor oasis with hot tub, BBQ, shower, brand new deck & kayaks. Steps away from a fishing lake & 6 houses away from Kenny's beach. This house has been completely remodeled & is perfectly located to fit your getaway needs. Master Bedroom- queen bed, full bath Bedroom 2&3- queen beds Pull out couch and some other extras. Towels, bed sheets, soap, toilet paper, and pillows are included

Top guest favorite

A modern two-story building is viewed from the well-maintained lawn. The heated saltwater pool features clear water surrounded by lounge chairs under colorful umbrellas. Lush green trees provide a natural backdrop, creating a peaceful outdoor space for relaxation.

Guesthouse in Southampton

4.98 out of 5 average rating, 64 reviews

Southampton Modern Barn, Private Hot Tub and Pool

This magical getaway delivers peace and relaxation. Wake up to coffee on your private deck with bucolic views. Play in your heated, saltwater pool, and relax under the stars in your hot tub (open year round). During your stay, these amenities and more will be for your personal use. Stroll to the owner’s dock on Big Fresh Pond, for paddle boarding, kayaking and sunsets. You can also drive 8 minutes to Southampton Village for shopping, restaurants, art galleries and Ocean Beaches.

A wooden bench is positioned on a grassy area, facing a tranquil lake surrounded by lush greenery. Sunlight filters through the leaves of a nearby tree, casting gentle shadows on the ground. The calm water reflects the natural beauty of the setting.

4.89 out of 5 average rating, 27 reviews

North Fork Lakefront cottage near Kenney's beach

Outdoor living on lakefront property. Walk to Kenney's beach. Cycle to many wineries, farm stands and grocery shopping. Beautiful 400 spft cottage with covered porch, living-room, fully outfitted new kitchen, 2 bedrooms (1 queen and 1 twin bed), indoor 1/2 bath, OUTDOOR new private cedar shower, indoor dining with lake view, outdoor waterfront dining and bbq grill, AC and heat, excellent wifi connection/work from home Very quiet peaceful location surrounded by nature.

Guest suite in North Fork

A spacious two-story apartment building is surrounded by well-kept greenery and manicured lawns. A paved pathway leads to the entrance, with colorful landscaping enhancing the inviting exterior. Two bright orange lounge chairs are positioned under trees on the side, offering a peaceful outdoor seating area.

4.93 out of 5 average rating, 161 reviews

GREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH

4-6 GUEST MAXIMUM PLEASE. Cozy 2 BR and 1 BTHRM apartment in private home in Greenport NY. Total privacy and separation of unit!! Perfectly situated on 1.75 acres. 3 minute drive, or easy walk, to the center of Greenport village, 2 minute ferry ride to quaint Shelter Island, and a 6 minute drive to tip of Orient. So right in the middle of the action with the peace and serenity of living outside the village. Private beach a short walk/ride down the street.

4.87 out of 5 average rating, 86 reviews

A charming cottage exuding warm hues can be seen from a well-maintained garden, surrounded by lush green foliage. The textured wooden siding and the inviting windows convey a sense of coziness, while the vibrant plants offer a natural ambiance.

Home in Southampton

Waterfront Beach House Gardens, AC, BBQ, Kyaks

Directly on the water! Garden access to beach stairs for paddles or sunbathing. Large sandy beach at end of charming country road. Positioned perfectly between Sag Harbor and Southampton. Designer home complete with glass sliders to private balcony and waterside decks. Fully equipped waterfront country kitchen. Bonus boathouse w life jackets, oars. Two single kayaks and one double by water stairs. . BBQ, teak table, AC, ceiling fans.

4.95 out of 5 average rating, 42 reviews

A dining area is showcased with a round table surrounded by four teal chairs. Large sliding doors reveal bay views, framed by sheer white curtains. A rug with black and white stripes lies beneath the table, complementing the light hardwood flooring and wall-mounted artwork.

Home in Shirley

Waterfront Designer Stay • Sunsets • Near Beach!

Welcome to The Swan House 🦢🏡 —your peaceful, designer retreat on Bellport Bay. Enjoy stunning sunsets, swans gliding by, and direct water access from the backyard. Relax on the spacious deck, fire up the grill, or take a short drive to Smith Point Beach. Inside, you’ll find an open, sun-filled layout with curated furnishings and a calming coastal vibe. This stylish escape offers serene waterfront living in any season—just 90 minutes from NYC.

Top guest favorite

A serene saltwater pool is framed by lush greenery and blooming flowers, enhancing the outdoor space. A hot tub is positioned alongside, inviting relaxation. The guest house is visible in the background, surrounded by trees and well-maintained landscaping.

Guesthouse in Shelter Island

4.99 out of 5 average rating, 69 reviews

Bayfront 1BR/2BR detached guesthouse with pool

Perfect relaxing getaway for a couple or family. Bayfront 1BR/2BR fully detached guest house with gorgeous morning views. Property has saltwater pool + hot tub (open May -October) and bay access via private dock. Central to both north & south forks (wineries + Hamptons or Montauk just short drive away). Down the road from famous Shelter Island Sunset Beach + golf course. Come explore the beauty of the Hamptons without the stress!

Top guest favorite

The main bedroom features a spacious bed with a white comforter and dark accent pillows. Sunlight filters through sheer white curtains covering French doors, leading to the outdoors. Bright wooden floors add warmth, while a ceiling fan offers comfort.

Apartment in North Fork

4.96 out of 5 average rating, 101 reviews

Lovely 2-bedroom apartment in a historic home

Restored apartment in a Victorian home, centrally located in the Village of Greenport. Short, few minutes walk to restaurants, shops, cafes in town. Also, conveniently located (10 minute walk) to the Hampton Jitney bus stop, LI Railroad and Shelter Island Ferry as well as local beaches. Enjoy the charm of a historic home, with all the convenience of modern amenities!

The living area features a soft-colored sofa resting against a light gray wall. A coffee table sits atop a striped rug, while a decorative chandelier hangs above. Two accent chairs flank the table, and a flat-screen TV is placed in a nearby console under a bright window.