Vacation rentals with lake access in Southold

A waterfront home is set among lush greenery, offering a spacious yard that gently slopes towards the water. Lounge chairs are positioned in the sun, while garden beds are visible in the landscaped area. The tranquil pond reflects the surrounding trees and open sky.

5 out of 5 average rating, 24 reviews

Beautiful waterfront 3 bedroom home in Southold

Beautiful waterfront home with stunning views of Hashamomuck Pond, making it the perfect escape for a memorable family vacation. Enjoy beaches, wine country, farm stands, and excellent restaurants. Featuring 3 bedrooms and 2 full baths. 1st floor, master bedroom, a guest room, and a bonus room with a pull-out couch. The second floor offers an additional guest room with two queen beds. BBQ, paddle boards, kayaks, fire pit, and plenty of seating to enjoy the beauty that surrounds this home.

4.95 out of 5 average rating, 147 reviews

A cozy sleeping area features a spacious bed adorned with soft linens and decorative pillows. A ceiling fan offers airflow, while a framed artwork hangs above the headboard. A bedside table holds a lamp, and a tray with decor sits on the bed.

Apartment in Patchogue

Spend A Few Days In This Cozy Getaway

Enjoy a stylish experience at this centrally-located place. This is a brand new cozy & quaint studio apartment that includes everything you need to enjoy a nice getaway. Less than a mile from Patchogue Village with many choices of fine dining, casual dining, or nightlife. A quick 7 minute drive to Davis Park ferry Terminal which will take you to beautiful Davis Park on Fire Island. A 60 minute drive to historic Montauk Point. A great weekend escape with everything Long Island has to offer.

Guest suite in East Patchogue

A wooden dock extends into a serene lake, surrounded by lush greenery and trees. The water reflects the blue sky and a few scattered clouds, while lily pads float peacefully on the surface, creating a tranquil atmosphere.

5 out of 5 average rating, 11 reviews

Lake Shore Oasis

Escape to our serene, historical lakefront oasis! Nestled on a sprawling 2-acre property, this charming 2-bedroom, 2-bathroom suite offers the perfect blend of relaxation and luxury. The elegantly furnished suite, with its own separate entrance, ensures privacy and comfort. Rest easy on beds with 800-thread-count linens. A separate office with a desk allows for remote work. Unwind in the whirlpool tub. Enjoy the balcony overlooking the lake, or take a dip in the salt water heated pool.

4.99 out of 5 average rating, 98 reviews

The entrance of the cottage is shown, featuring a set of stairs leading to a welcoming door. Lush greenery and well-maintained flower beds with colorful blooms line the path, contributing to a serene outdoor setting. Paved parking is available nearby.

Guesthouse in Guilford

Guilford Lakes Cottage, with hot tub and fire pit.

Kick back and relax in this calm, stylish home, yards from private lakes for kayaking, swimming, fishing or skating in season. For the adventurer, enjoy year round access to extensive forest trail systems for hiking, mountain biking, cross country skiing, and snowshoeing, only a 2 minute walk from our door. Nicknamed " Guilford's Little Augusta," the 9 hole, par 27 executive Guilford Lakes Golf Course is only 1/4 mile away. Five miles south lies one of the 5 most beautiful town greens.

A patio area features a circular wooden table surrounded by several chairs, shaded by a large umbrella. Lush green grass leads to a tranquil water view, framed by trees under a clear blue sky, creating a welcoming outdoor space.

4.91 out of 5 average rating, 23 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.

An aerial view provides insight into the waterfront cottage's layout, showcasing the grassy yard surrounding the home. A patio area with seating is visible, alongside a garden shed and trees offering shade. The peaceful lake borders the property, enhancing the serene environment.

4.94 out of 5 average rating, 31 reviews

Waterfront NoFo Cottage w/ public beach access

Enjoy this waterfront cottage overlooking Marion Lake surrounded by lush landscape and wildlife. Experience the local Vineyards, take a leisurely stroll in downtown Greenport, ferry to Shelter Island, drive to Orient, or discover local hiking trails. Savor the culinary delights at the area's great restaurants, with fresh seafood and farm-to-table dining. Nestled between Greenport and Orient Point, East Marion provides access to all the North Fork has to offer. Rental Permit #1060

4.94 out of 5 average rating, 17 reviews

An aerial view captures the unique structure of the waterfront home, surrounded by rocky landscapes and water on three sides. A pool is seen in the backyard, bordered by landscaped greenery, alongside a small beach area and a pier extending into the water.

Home in Branford

Breathtaking Panoramic Waterfront

Relax to sweeping views from every room in this unique, 4600 sq foot direct-waterfront home with two small private beaches, boulders by the water, large pool, hot-tub, outdoor bar, kayaks, and fire pit. 2 floors of wraparound patio/deck, plus 3rd floor loft and roof patio. Open floor plan, sweeping staircase, 5 bedrooms plus loft, 3.5 bath plus half bath and outdoor shower by pool. A real oasis! (Note: pool not heated and open mid-may to mid-Oct only; hot tub closed Jan-March)

4.85 out of 5 average rating, 13 reviews

The lake house features a spacious deck overlooking the water, with a private dock extending into the lake. Surrounded by lush greenery, the home has multiple outdoor seating areas and provides easy access to kayaks and boats, enhancing the scenic lakeside environment.

Home in Clinton

Boulder Lake House Retreat

Experience the beauty of spring at our charming lake house—an ideal retreat for families, friends, or a romantic getaway! Nestled along Boulder Lake and just under 3 miles from Hammonasset State Park, our home offers the perfect mix of comfort and outdoor adventure. Wake up to the sight of the sparkling lake, sip your morning coffee on the deck, and soak in the fresh spring air! Spend your days fishing, exploring nearby trails, or dining outdoors as the season comes to life!

A serene outdoor space is depicted, featuring a well-maintained lawn with two lounge chairs positioned under the shade of large trees. The cottage’s stone chimney is visible alongside the water, which reflects the greenery surrounding it.

4.88 out of 5 average rating, 25 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.

4.92 out of 5 average rating, 155 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.

Superhost

An outdoor balcony deck is presented with a wooden dining table surrounded by several chairs. A view of the beach and ocean is visible in the background, illuminated by sunlight filtering through the trees.

Home in New London

4.91 out of 5 average rating, 178 reviews

Sunset Oasis 1 @ Ocean Beach: $1Mil View 6 Queen

INSTANT BOOK NOW = May '25 - Sept '25 All Open Availability + SUMMER '25 **FULL RENOVATION COMPLETED** ALL NEW: TILED FLOORS, 2 BATHROOMS, MINI-SPLIT AC/HEAT UNITS, WASHER/DRYER, AND FURNITURE *certain holidays/summer excluded in booking minimums *discounts applied to nightly rate only *we can not combine multiple discounts, yet highest % will apply *if available, also apply 10% non-refundable booking option