Waterfront vacation rentals in Southold

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Top-rated waterfront rentals in Southold

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Guest favorite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.

Jan 11 – 18

$650 per night

Guest favorite

Home in East Hampton

4.94 out of 5 average rating, 202 reviews

Private beach Historical House with large property

Entire three-story house. 3 large bedrooms and 3 FULL BATHROOMS on a very private, 2+acre wood lot on the bay in Historical East Hampton with private beach access. Fully renovated in 2018 with modern amenities while preserving the original charm. A/C and heating. Private upper floor with bedroom + sitting area for office and extra sleeping. Modern kitchen with island that opens to living room with fireplace. Walk through the secluded backyard to enjoy the amazing sunsets. Ideal for fishing.

Jun 10 – 17

$556 per night

Guest favorite

Cottage in Guilford

4.96 out of 5 average rating, 158 reviews

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Sep 19 – 26

$450 per night

Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 511 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Oct 15 – 22

$175 per night

Guest favorite

Condo in Greenport

4.91 out of 5 average rating, 107 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

Oct 8 – 15

$275 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

$495 per night

Superhost

Cottage in Greenport

4.84 out of 5 average rating, 38 reviews

Newly Renovated 2-Bedroom Home on the LI Sound

Recently renovated 2-bedroom home directly on the LI Sound. Enjoy fishing on your private beach and sunsets from your private deck. Imagine sipping your morning coffee or afternoon cocktail while listening to the waves crash - it is as if you are sailing at sea! Walking distance to Haylard and the Soundview Hotel, and a 3 minute drive from the town of Greenport. While here, venture to the many acclaimed vineyards or purchase local produce at one of the nearby farmstands!

Oct 11 – 18

$474 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

$573 per night

Guest favorite

Condo in Greenport

5.0 out of 5 average rating, 90 reviews

"Breathtaking Waterfront Water's Edge view"

" Breathtaking Waterfront Water's Edge condominium. Newly renovated! Relax and enjoy this beautiful, luxurious space. Suite B-204 accommodates 6 guests very comfortably. Two bedrooms, two bathrooms, living room with sofa (pull-out bed), kitchen area, eating area with chairs- all newly renovated. Located on the North Fork of Long Island, Cliffside Resort Condominiums in Greenport, New York." So many activities to choose from nearby and in the quaint village of Greenport!

Jan 5 – 12

$406 per night

Guest favorite

Condo in Greenport

4.93 out of 5 average rating, 124 reviews

Beautiful Waterview Condo on the North Fork of LI

Waterview luxury suite accommodates up to 6 guests with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. This location is minutes from town as well as wineries and centrally located to the ferry which can take you to Shelter Island and the South Fork. The resort is well maintained with a pool , BBQ grills and private beach access as well as ample parking for guests.

Nov 10 – 17

$340 per night

Guest favorite

Home in Southold

4.96 out of 5 average rating, 27 reviews

Bright Oasis in Beautiful North Fork Wine Country

Enjoy this idyllic family friendly home in the heart of North Fork, Long Island. It's a newly renovated and spacious 4 bedroom and 2 bath home. The open first floor plan leads to an equally as spacious and enjoyable back yard. From the private backyard, you can launch your paddle board, kayak (we have 2 for guests to use) or boat right off the dock to enjoy the peace and tranquil Goose Creek, or walk a few minutes down the road to Croteau Winery.

Jan 24 – 31

$463 per night

Guest favorite

Cottage in Southold

4.95 out of 5 average rating, 21 reviews

Adorable Cottage

Kick back and relax in this calm, stylish space. Lounge on the spacious front porch or the enormous, fenced in yard. Bring your pup! Come enjoy all the Northfork has to offer…vineyards, farms, beaches, charming Towns all within walking/biking distance from the cottage. Fully stocked with bedroom linens, bathroom linens, chef’s kitchen…just pack your clothes, we have everything you need.

Apr 14 – 21

$324 per night