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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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Serviced apartment in North Fork

4.79 out of 5 average rating, 56 reviews

2 Bedroom Greenport Waterfront Coastal 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

Home in North Fork

5 out of 5 average rating, 22 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.

Rental unit in Patchogue

4.95 out of 5 average rating, 133 reviews

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.

Home in Bayport

4.83 out of 5 average rating, 161 reviews

Exquisite spacious waterfront all modern-sleeps 8

READ THE CONSISTENT FINE REVIEWS! Its heart-warming providing such a nice sanctuary! This MEMORABLE Sayville / Bayport Vacation rental home has a picturesque backyard & amazing water views. 3Br 2 full bath. Enjoy the 2-person steam shower & huge 10-person whirlpool bath for spa-like living. Perfect for quiet getaways. All new furniture w/ coastal chic decor. Feed 6 ducks, 2 swans, 2 cranes. The serenity & one-of-a kind view sets this Sayville vacation home apart from all others.

Home in North Fork

4.95 out of 5 average rating, 21 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.

Cottage in Water Mill

4.97 out of 5 average rating, 64 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.

Guesthouse in Southampton

4.98 out of 5 average rating, 57 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.

Rental unit in New Haven

4.88 out of 5 average rating, 479 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.

Guest suite in North Fork

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.

Home in Clinton

5 out of 5 average rating, 6 reviews

Boulder Lake House Retreat

Experience the magic of fall at our beautiful 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 blend of comforts and adventure. Enjoy the crisp autumn air while kayaking on the lake, savor a warm cup of coffee on the deck as you take in the vibrant fall foliage, or gather around the fire pit for a cozy evening under the stars!

Cottage in North Fork

4.9 out of 5 average rating, 60 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.

Guesthouse in Shelter Island

5 out of 5 average rating, 64 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!

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Popular amenities for Southold lake access rentals

Free parking on premises

Air conditioning

Lake access house rentals

Home in Yaphank

5 out of 5 average rating, 34 reviews

Long Island Getaway w/ Heated Pool & Lake

Home in North Fork

4.85 out of 5 average rating, 20 reviews

The Lindsay Luxurious Estate: Heated Pool, Hot tub

Home in Westhampton Beach

4.96 out of 5 average rating, 25 reviews

Dune Rd Village Waterfront Private Beach Access

Home in Shinnecock Hills

4.96 out of 5 average rating, 77 reviews

Hampton Waterview Gorgeous Yard w/Pool /Pizza Oven

Home in Westhampton

5 out of 5 average rating, 13 reviews

1940’s Westhampton renovated bungalow

Home in Hampton Bays

5 out of 5 average rating, 3 reviews

Hamptons Waterview Cottage

Home in New Haven

4.86 out of 5 average rating, 76 reviews

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Home in Westbrook

5 out of 5 average rating, 19 reviews

Secret Seaside Stone Cottage

Lake access apartment rentals

Rental unit in New Haven

5 out of 5 average rating, 7 reviews

New Haven East Haven Border Inn

Rental unit in West Haven

5 out of 5 average rating, 3 reviews

Beach Suite - 1Bdrm

Rental unit in Coram

4.92 out of 5 average rating, 12 reviews

Modern 1 bed studio

Rental unit in Shirley

5 out of 5 average rating, 3 reviews

Cozy Ground Floor 1BD Apartment

Rental unit in Patchogue

4.85 out of 5 average rating, 41 reviews

Pet Friendly ! Private Apartment. Close to main st

Lake access cottage rentals

Cottage in Southampton

4.76 out of 5 average rating, 25 reviews

Spectacular Water Views! Swim, kayak, nature.

Cottage in Yaphank

4.86 out of 5 average rating, 56 reviews

Beautiful Waterfront Cottage

Cottage in Southampton

4.91 out of 5 average rating, 80 reviews

Waterfront Beach Home with Fab Gardens, AC, Kayaks

Cottage in Northampton

4.92 out of 5 average rating, 26 reviews

Private Waterfront Hamptons Cottage

Cottage in North Fork

4.6 out of 5 average rating, 10 reviews

Unique Lakefront cottage walk 2 Kenney's beach

Cottage in New Haven

4.94 out of 5 average rating, 79 reviews

Ocean View Cottage: Yale, Beach, Golf & WeddingPic

Quick stats about vacation rentals with lake access in Southold

Total rentals
20 properties
Nightly prices starting at
$190 before taxes and fees
Total number of reviews
520 reviews
Family-friendly rentals
10 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

Destinations to explore