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Vacation rentals with lake access in Southold

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Top-rated lake access rentals in Southold

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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

4.77 out of 5 average rating, 61 reviews

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

Top guest favorite

A spacious lawn is bordered by tall trees, providing a natural frame for the cottage. The vibrant green grass leads to a serene waterfront, where the lake reflects the sunlight. The peaceful setting invites relaxation and outdoor activities.

Cottage in Water Mill

4.97 out of 5 average rating, 72 reviews

Head of Pond House - Waterfront Cottage

Welcome to the charming, waterfront Cottage at Head of Pond House! Enjoy a peaceful retreat with beautiful lake access year-round and pool access from Memorial Day to October. The cottage features two comfortable king beds, including one in a cozy loft area, a full bath, WiFi, a projector for movie nights, and a fully stocked kitchen. Whether you’re looking for a relaxing escape or a comfortable base to explore the Hamptons, our waterfront cottage is the perfect spot for your getaway.

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

4.88 out of 5 average rating, 64 reviews

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.

Home in North Fork

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.

Home in North Fork

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

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.

Home in North Fork

4.89 out of 5 average rating, 28 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.

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.

Guest suite in North Fork

4.93 out of 5 average rating, 163 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.

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

4.95 out of 5 average rating, 43 reviews

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.

A waterfront home is seen with a spacious deck overlooking the calm water. Lush trees frame the property, and a boat is docked nearby. The house features large windows and multiple outdoor seating areas, blending into the natural surroundings.

Home in Southampton

4.98 out of 5 average rating, 102 reviews

Breezy Waterfront Home With private Dock

This charming waterfront home is the ideal getaway for the active family with the Hamptons' largest natural 'saline pool' (the Peconic Bay) just footsteps away. This home easily sleeps 7 - with 3 bedrooms and 3 separate kids' sleeping cabins. You can jump on our standup paddle board right off our private dock, jog along wide stretches of pebble beach, have a swim race to our floating swim platform or simply relax in the hammock.

A spacious living area features a soft sectional sofa beside a coffee table, with an American flag prominently displayed on the wall. The kitchen, equipped with modern appliances, is positioned in the background, while a dining table invites gatherings under warm lighting.

Cottage in Yaphank

4.86 out of 5 average rating, 66 reviews

Beautiful Waterfront Cottage

Historic Waterfront with Private Island (this property has a bridge to a private island). Large south facing deck, brand new kitchen and beautiful antique claw-foot bathtub and rainfall shower. The home is 10 minutes from the beach, 10 min from Bellport, 25 minutes from Southampton and 1 mile from the train station to New York City. Enjoy a quiet escape from the city in this well-appointed home.

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.

Home in North Fork

4.93 out of 5 average rating, 15 reviews

East end home away from home

Relax with the whole family at this peaceful place to stay. Perfect for small bachelorette parties, close to dozens of vineyards, walking distance to south hold beach, water views, 3 miles from Greenport village ABSOLUTELY NO SMOKING IN THE HOME Must have ID verified and no one under 25 with out older adults present

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Popular amenities for Southold lake access rentals

Free parking on premises

Air conditioning

Lake access house rentals

Home in Southampton

4.97 out of 5 average rating, 35 reviews

Aug10-17 Perfect Southampton cottage Ocean close

A wooden dining set is positioned on a deck overlooking the water, featuring a large red umbrella providing shade. Tables are set with blue plates, and greenery frames the peaceful view of the inlet and distant seating by the shore.

Home in North Fork

4.96 out of 5 average rating, 27 reviews

Shelter Bay Cove Waterfront + Beach + spectacular

Top guest favorite

An aerial view captures the heated saltwater pool surrounded by a spacious patio. Lounge chairs and shaded seating areas are arranged near the pool, with outdoor furniture positioned for relaxation. Lush greenery and a landscaped garden frame the space, providing a serene environment.

Home in Yaphank

5 out of 5 average rating, 42 reviews

Long Island Getaway w/ Heated Pool & Lake

The exterior of the house is showcased, featuring a light grey facade with white shutters and multiple windows. A welcoming front porch is highlighted, alongside a neatly maintained green lawn and surrounding trees, providing a sense of openness and tranquility.

Home in North Fork

5 out of 5 average rating, 3 reviews

North Fork Paradise

A solar-heated swimming pool is surrounded by a spacious patio, featuring a hot tub with bubbling water. A helical slide extends into the pool, while a basketball hoop stands nearby, ready for use. The area is enclosed with a fence for added privacy.

Home in North Fork

5 out of 5 average rating, 10 reviews

Luxury Southold waterfront home, heated pool & spa

A serene waterfront scene shows a peaceful dock along the water's edge. Two Adirondack chairs are positioned for relaxation, surrounded by lush greenery. A sandy beach area is visible in the distance, bordered by trees and the water's gentle ripples.

Home in Southampton

4.87 out of 5 average rating, 86 reviews

Waterfront Beach House Gardens, AC, BBQ, Kyaks

A modern kitchen features sleek white cabinetry and a large island with bar seating for four. Two woven pendant lights hang above, illuminating the space. Large windows allow natural light to fill the room, enhancing the open and airy atmosphere.

Home in Westhampton

5 out of 5 average rating, 16 reviews

1940’s Westhampton renovated bungalow

A sunset casts golden hues over the water from a waterfront deck, showcasing the tranquil bay. Two images feature a sandy beach with gentle waves and a spacious patio adorned with green grass and seating for relaxation.

Home in North Fork

4.89 out of 5 average rating, 9 reviews

Beachfront Retreat - 5BR Home with Stunning Views

Lake access apartment rentals

A sunlit seating area features a wooden bench adorned with colorful cushions. A round area rug is centered on the terracotta floor. A large mirror reflects light, while a doorway leads to a well-lit bedroom, accented by a photo and a decorative tub nearby.

Apartment in Sag Harbor

5 out of 5 average rating, 5 reviews

Artists pet friendly apartment.

A serene waterfront view is captured from the deck, showcasing a well-appointed outdoor space that includes a hot tub, dining area, and lounge chairs. The green lawns and waterway create a tranquil setting, inviting relaxation amidst nature.

Apartment in Flanders

4.93 out of 5 average rating, 76 reviews

Hamptons Waterfront Escape/ Hot Tub/ Resort Style

A safari tent interior showcases a spacious queen bed with crisp linens. Two bedside tables flank the bed, and a small dresser is positioned nearby. Large windows open to views of nature, allowing natural light to fill the tent. Adirondack chairs are set outside on the deck.

Apartment in East Hampton

4.79 out of 5 average rating, 33 reviews

Safari Tent Glamping,S10-CedarPt, East Hampton, NY

A modern kitchen showcases sleek cabinetry and a stainless steel refrigerator. Counter space is well-utilized with a coffee maker and utensils. A dining table with four stools complements the space. Textured flooring adds warmth to the contemporary design.

Apartment in Shirley

4.91 out of 5 average rating, 11 reviews

Cozy Ground Floor 1BD Apartment

Lake access cottage rentals

A country cottage features a shaded outdoor dining area with a large umbrella. Wooden chairs surround a table on a grassy lawn, with the cottage's porch visible in the background. Verdant trees provide a natural backdrop, enhancing the calm outdoor environment.

Cottage in North Fork

4.9 out of 5 average rating, 63 reviews

Beach and Wine Time Country Cottage

A modern cottage sits amid lush greenery, with a stone pathway leading to the entrance. Large windows provide glimpses of the surrounding nature, and the setting features a mix of trees and well-maintained landscaping, enhancing the inviting outdoor space.

Cottage in Southampton

4.76 out of 5 average rating, 25 reviews

Spectacular Water Views! Swim, kayak, nature.

A charming exterior view of a home surrounded by lush greenery and vibrant flowering plants. A stone pathway leads to a wooden bench positioned in a tranquil garden area, with soft filtering sunlight through the trees and a glimpse of water visible in the background.

Cottage in Southampton

Fresh water swim, kayak, fish, by lake

A view of the waterfront from the porch showcases a serene lake surrounded by trees, reflecting the changing colors of the sky. The pathway is lined with manicured grass and leads to the lake, creating an inviting entrance.

Cottage in Northampton

4.93 out of 5 average rating, 27 reviews

Private Waterfront Hamptons Cottage

A serene lake scene is captured with water lilies gently floating on the calm surface. Tall grasses and plants frame the water's edge, while the soft light of the setting sun reflects off the lake, enhancing the tranquil atmosphere.

Cottage in North Fork

4.69 out of 5 average rating, 13 reviews

Unique Lakefront cottage walk 2 Kenney's beach

Quick stats about vacation rentals with lake access in Southold

Total rentals
20 properties
Nightly prices starting at
R3,549 ZAR before taxes and fees
Total number of reviews
650 reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

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