Waterfront vacation rentals in Northwest Harbor

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Top-rated waterfront rentals in Northwest Harbor

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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.

Apr 14 – 21

G$155,649 GYD 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.

Feb 19 – 26

G$170,976 GYD per night

Superhost

Tent in East Hampton

4.97 out of 5 average rating, 33 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 2022, we have 12 tents with queen beds and linens. Tents are covered with large rain flies that make a covered porch for the Adirondack Chairs.

Aug 31 – Sep 7

G$45,567 GYD per night

Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 512 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 22 – 29

G$41,988 GYD per night

Guest favorite

Cottage in Westbrook

4.86 out of 5 average rating, 97 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Oct 17 – 24

G$28,482 GYD per night

Guest favorite

Condo in Montauk

4.99 out of 5 average rating, 181 reviews

Montauk Waterfront Condo w/ Sunset Views

Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool area only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy fishing and swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)

Sep 12 – 19

G$89,619 GYD 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 20 – 27

G$63,232 GYD per night

Guest favorite

Condo in Greenport

4.92 out of 5 average rating, 125 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.

May 23 – 30

G$132,312 GYD per night

Guest favorite

Apartment in Sag Harbor

4.98 out of 5 average rating, 117 reviews

Sag Harbor Retreat

Experience the many wonderful things the Hamptons has to offer in the Summer in centrally-located Sag Harbor. Our place is a professionally-decorated luxury apartment with its own entrance, yard and two parking spaces. This home-away-from-home is an immaculate and well-appointed retreat located in Sag Harbor. Great for couples and solo adventurers. Close to Sag Harbor's Main Street with abundant recreational activities, shopping and restaurants.

Sep 20 – 27

G$156,071 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!

Aug 3 – 10

G$84,103 GYD per night

Guest favorite

Cottage in Montauk

4.87 out of 5 average rating, 217 reviews

Waterfront Cottage, Fort Pond MTK

Perfect cottage perched above Fort Pond with epic views and relaxed bohemian vibes. The cottage is private with a private deck on shared grounds with a fire pit, hammocks, paddle boards, kayak, and lake access. The grounds are expertly landscaped and take full advantage of fort pond views. We do live on the property full time and enjoy making our space a safe and clean environment.

Feb 1 – 8

G$191,129 GYD per night

Guest favorite

Cottage in Groton

4.95 out of 5 average rating, 273 reviews

Restored Historic Schoolhouse, Mystic River Views

This newly renovated, historic 1 BR/1 Bath former school house, is located directly on the Mystic River with amazing River views. . It started life as a one room school house. In 1857, it was moved to it's current location. Our design team meticulously furnished to create a unique historic atmoshpere.

Feb 19 – 26

G$32,145 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Northwest Harbor waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

Superhost

Apartment in New London

4.8 out of 5 average rating, 293 reviews

Large Waterfront Luxury Apartment

Jan 26 – Feb 2

G$48,658 GYD per night

Guest favorite

Apartment in Stonington

4.95 out of 5 average rating, 222 reviews

Mystical Ocean View in Historic Stonington Borough

Sep 2 – 9

G$81,145 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

Sep 13 – 20

G$23,905 GYD per night

Guest favorite

Apartment in Stonington

4.97 out of 5 average rating, 181 reviews

Mystic River Getaway - Walk To Downtown & Seaport!

Nov 9 – 16

G$43,090 GYD per night

Guest favorite

Apartment in Branford

4.89 out of 5 average rating, 9 reviews

Stony Crk Studio ideal for trvl nurses…

Nov 28 – Dec 5

G$20,609 GYD per night

Guest favorite

Apartment in Groton

4.96 out of 5 average rating, 74 reviews

Rare find beautiful studio on the Mystic River

Jan 18 – 25

G$35,441 GYD per night

Guest favorite

Apartment in Milford

5.0 out of 5 average rating, 50 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

Sep 3 – 10

G$33,388 GYD per night

Superhost

Apartment in Greenport

4.75 out of 5 average rating, 4 reviews

Junior Suite One King + Sofa Bed

Jun 27 – Jul 4

G$147,045 GYD per night

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Waterfront house rentals

Guest favorite

Home in East Lyme

4.96 out of 5 average rating, 164 reviews

Beachfront Paradise

Apr 28 – May 5

G$90,065 GYD per night

Guest favorite

Home in Groton

4.95 out of 5 average rating, 160 reviews

True Ocean Front Vacationing - Groton/Mystic

Dec 11 – 18

G$95,789 GYD per night

Guest favorite

Home in Stonington

4.95 out of 5 average rating, 166 reviews

Romantic Seaside Cottage in Mystic

Jan 3 – 10

G$45,349 GYD per night

Guest favorite

Home in Milford

4.98 out of 5 average rating, 154 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Dec 16 – 23

G$65,959 GYD per night

Guest favorite

Home in New Haven

4.99 out of 5 average rating, 190 reviews

Q River House - 2 bdrm, minutes from Yale/Downtown

Dec 31 – Jan 7

G$38,020 GYD per night

Guest favorite

Home in East Lyme

4.94 out of 5 average rating, 102 reviews

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC

Sep 13 – 20

G$239,514 GYD per night

Guest favorite

Home in Milford

4.89 out of 5 average rating, 124 reviews

The Beach House!

May 7 – 14

G$49,981 GYD per night

Guest favorite

Home in Mattituck

4.92 out of 5 average rating, 92 reviews

Modern Farmhouse Steps to Beach & Love Lane

Apr 3 – 10

G$98,390 GYD per night

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Waterfront condo rentals

Guest favorite

Condo in Montauk

4.82 out of 5 average rating, 158 reviews

Coastline View Studio

Nov 2 – 9

G$238,667 GYD per night

Superhost

Condo in Greenport

4.83 out of 5 average rating, 100 reviews

Seaside Escape w Pool, Private Beach + Patio

Jan 12 – 19

G$77,473 GYD per night

Guest favorite

Condo in Greenport

5.0 out of 5 average rating, 90 reviews

"Breathtaking Waterfront Water's Edge view"

Sep 28 – Oct 5

G$117,641 GYD per night

Guest favorite

Condo in Montauk

4.82 out of 5 average rating, 87 reviews

Beautiful Condo on the Ocean Bluffs

Apr 14 – 21

G$95,711 GYD per night

Superhost

Condo in Montauk

Sun N Sound Resort, Montauk, NY

Sep 6 – 13

G$52,755 GYD per night

Guest favorite

Condo in Greenport

4.87 out of 5 average rating, 90 reviews

Waterfront Condo C-204 at The Cliffside Resort

Oct 17 – 24

G$113,938 GYD per night

Condo in Montauk

4.85 out of 5 average rating, 20 reviews

Condo on the ocean in Montauk

Apr 13 – 20

G$133,868 GYD per night

Condo in Shelter Island Heights

5.0 out of 5 average rating, 5 reviews

Peaceful and Relaxing Waterfront.

Apr 11 – 18

G$119,876 GYD per night

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Quick stats about waterfront rentals in Northwest Harbor

Total rentals
20 properties
Local attractions
Cedar Point County Park, LongHouse Reserve, and Cedar Island Light
Popular amenities
Kitchen, Wifi, and Pool
Pet-friendly rentals
20 properties allow pets
Total number of reviews
560 reviews
Nightly prices starting at
G$45,977 GYD before taxes and fees

Waterfront vacation rentals in Northwest Harbor

Top-rated waterfront rentals in Northwest Harbor

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Northwest Harbor waterfront rentals

Waterfront apartment rentals

Apartment in New London

Apartment in Stonington

Apartment in New Haven

Apartment in Stonington

Apartment in Branford

Apartment in Groton

Apartment in Milford

Apartment in Greenport

Waterfront house rentals

Home in East Lyme

Home in Groton

Home in Stonington

Home in Milford

Home in New Haven

Home in East Lyme

Home in Milford

Home in Mattituck

Waterfront condo rentals

Condo in Montauk

Condo in Greenport

Condo in Greenport

Condo in Montauk

Condo in Montauk

Condo in Greenport

Condo in Montauk

Condo in Shelter Island Heights

Quick stats about waterfront rentals in Northwest Harbor

Total rentals

Local attractions

Popular amenities

Pet-friendly rentals

Total number of reviews

Nightly prices starting at

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