Vacation rentals with lake access in Southold

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Top-rated lake access rentals in Southold

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Guest favorite

Home in East Marion

4.87 out of 5 average rating, 15 reviews

Waterfront NoFo Cottage w/ public beach access

Modern and chic waterfront cottage overlooking Marion Lake. 2 bedroom, 1 bath home with an open plan living room/kitchen plus a breakfast nook and outdoor deck overlooking the lake. Observe Osprey, Snowy Egrets, Swans, waterfowl, turtles and other wildlife on the lake, walk 400 feet to the bay beach, drive 7 minutes to downtown Greenport or 10 minutes to Orient Point. Enjoy all the North fork has to offer including fishing, sailing, farm stands, vineyards, and fine dining. Rental Permit #1060

May 4 – 11

G$88,062 GYD per night

Superhost

Apartment in Greenport

4.78 out of 5 average rating, 46 reviews

2 Bedroom Greenport Waterfront Coastal Cottage

An amazing & unique experience on the North Fork of Long Island, New York. Sitting on a bluff 15’ above a huge private beach, this year-round multi-family property boasts panoramic views of the Long Island Sound. Amazing sunset/sunrise views, fishing, beach combing, swimming, wineries, restaurants, shopping. Huge 2nd story deck perfect for evening cocktails. Full kitchen, BBQ, loads of amenities. Completely updated inside & out. Private beach shared only with other guests of the property

Mar 29 – Apr 5

G$143,659 GYD per night

Guest favorite

Home in Peconic

5.0 out of 5 average rating, 11 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 September 30th.

Oct 4 – 11

G$118,866 GYD per night

Guest favorite

Guesthouse in Southampton

4.98 out of 5 average rating, 45 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.

Sep 23 – 30

G$137,195 GYD per night

Guest favorite

Apartment in New Haven

4.89 out of 5 average rating, 467 reviews

Fair Haven Heights Entire 1 Bedroom Apartment

Renovated and private one bedroom apartment with modern amenities within a traditional setting with amazing water views, feel like home in our cozy and nice apt with full new Kitchen ,bedroom, living room, bathroom. You can get downtown and Yale in 10 minutes by car, or 15 minutes by bus using line D that goes direct to Downtown. Convenience store, Pizza place and Wine store in the corner (five minutes walk from home), also walk to the Marina and Anastasios Boat Cafe.

Oct 4 – 11

G$23,917 GYD per night

Guest favorite

Home in Southold

4.92 out of 5 average rating, 12 reviews

Beach/Lake house Fireplace & Hot Tub, By Wineries

Welcome to The Dune Retreat, a Beach & Lake House in the charming North Fork, close to all wineries. Perfect for 8 to 10 guests, enjoy the indoor fireplace, outdoor fire table and fire pit, ensuring a memorable getaway for Friends & Family. Enjoy a Private access to Great Pond Lake directly from our backyard and a 5min walk to Kenney's Beach. Soak in the hot tub on the deck after a day exploring the North Fork, kayak on the lake, swim in the Sound, relax and stay a while.

Jun 11 – 18

G$137,720 GYD per night

Guest favorite

Home in Southold

4.79 out of 5 average rating, 14 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.

Jun 12 – 19

G$60,177 GYD per night

Guest favorite

Guest suite in Greenport

4.94 out of 5 average rating, 141 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.

Feb 15 – 22

G$77,042 GYD per night

Guest favorite

Home in Southold

4.97 out of 5 average rating, 35 reviews

Water & Vineyard views, 4 bedrooms

Take a break and unwind at this peaceful oasis in the heart of wine country. Completely-Renovated Home Has Been Transformed with Picturesque Views From Every Window! Enjoy Vineyard Views of Croteaux Vineyards in the Front and Water Views of Goose Creek in the back. This house has an open floor plan and is a wonderful place to entertain. Escape, Relax and Enjoy your North Fork Retreat with all the Vineyards, Beaches and Farms that the East End is Known For.

Jan 3 – 10

G$215,688 GYD per night

Guest favorite

Cottage in Laurel

4.88 out of 5 average rating, 51 reviews

Beach and Wine Time Country Cottage

This charming country cottage is easy walking distance to the beach, within a 3 mile radius of choice golf courses and dozens of vineyards and has a right of way with water access just across the road. Set on 3/4 of an acre with a large backyard, this home has 3 bedrooms, 2 full baths, a kitchen, dining room, fireplace, and a front and back enclosed porch. If you like, watch the sunrise over the bay and the sunset over the golf course in the backyard.

Nov 13 – 20

G$91,034 GYD per night

Guest favorite

Guesthouse in Shelter Island

5.0 out of 5 average rating, 50 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!

Jul 13 – 20

G$84,142 GYD per night

Guest favorite

Cottage in Water Mill

4.98 out of 5 average rating, 55 reviews

Head of Pond House - Waterfront Cottage

Charming Cottage with lake access. Close to beaches, wineries, restaurants and all the Hamptons have to offer. One bedroom, and two king beds (one in the loft area), one bath cottage with WIFI and projector. Kitchen including fridge, stove, oven and dishwasher for your perfect weekend or weeklong getaway. Ideal for anyone looking for a peaceful oasis while close to all the action of the East End.

May 8 – 15

G$83,013 GYD per night