A garden with a statue, lush greenery, and a group of people walking.

Northwest Harbor holiday lettings

We found 2,295 holiday rentals — enter your dates for availability

Discover a selection of 289 homes and other holiday rentals in Northwest Harbor that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the amenities that you expect for your stay, which might include parking and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Northwest Harbor

Showing deals for:19 Feb - 26 Feb

Luxury, private, gated heated pool, hot tub, fenced in property! Child friendly!

Living area

Amagansett Beach Estate with Award Winning Outdoor Amenities

Main floor primary bathroom with heated floors

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

Pool

Chic Modern Private Designer 1.5 Acre Private Oasis

Dining

9BR Sag Harbor w/ Pool-Tennis Court- B-ball- HotTub-VBall-7Acres-NIGHTCLUB

Dining

PERFECT GETAWAY East Hampton / Sag Harbor

Living area

IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES

Featured as one of most beautiful poolsides

Beautiful 4 bedroom house with tranquil gardens close to bay beaches.

Property grounds

New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!

Exterior

Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town

Private kitchen

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Pool

Enjoy a lovely summer retreat in Sag Harbor Village, 1 mile to Main Street

Private kitchen

Our Peaceful, Beach Escape From the City

Wrap around deck

Bohemian Old Life Saving Station with Beach & Pool

Master bed onto balcony

Unique Southold waterfront luxury home with heated pool on Long Creek

A view of the house and pool from the creek, looking south

Perfect Family home, AC, Heated Pool, 3BR 2Bath

Living area

Springs Chic, Steps from private Gardiners Bay beach!

Private kitchen

Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach

Every season brings special flower blooms

Lovely Private Estate In East Hampton

Interior

Entire, new, roomy, village beach house close to beach, park, and town center

Terrace/patio

Clearwater Beach Retreat - Perfect Family Beach House That Sleeps Six

Kitchen and Dining Area

POOL + Beach 1 mi. to Greenport Village! 2 DEALS: WINTER or extended stay

MINERAL SPRING POOL!
6 Lounge Chairs w/ umbrellas, Covered Cabana

Newly renovated ranch w/ large Pool in quiet neighborhood 1 mile from Greenport

Pool

Relax in this light-filled home, steps from the beach and a short walk to town!

Kitchen

Find spaces that suit your style

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Find the best place to stay - Northwest Harbor

Out Door Theater Fire Pit Bocce court- WATCH VIDEO!!!

Image of Out Door Theater Fire Pit Bocce court-  WATCH VIDEO!!!

Premier Host

Sleeps 10 · 4 bedrooms · 3 bathrooms

Stylish East Hampton Escape! Close to Village/Beach, Modern kitchen, Heated pool

Image of Stylish East Hampton Escape! Close to Village/Beach, Modern kitchen, Heated pool

Sleeps 6 · 3 bedrooms · 2 bathrooms

Low Winter Rates in NW Woods 4 Bd 2-1/5 Bth, Hot Tub, Grill, Firepit on 2 Acres

Image of Low Winter Rates in NW Woods 4 Bd 2-1/5 Bth, Hot Tub, Grill, Firepit on 2 Acres

Sleeps 8 · 4 bedrooms · 2+ bathrooms

Beautiful 5 Bedroom, 4.5 Bathroom House With Heated, Saltwater Pool

Image of Beautiful 5 Bedroom, 4.5 Bathroom House With Heated, Saltwater Pool

Sleeps 10 · 5 bedrooms · 3+ bathrooms

Beautiful designer modern luxury home - steps from beach

Image of Beautiful designer modern luxury home - steps from beach

Sleeps 6 · 3 bedrooms · 3+ bathrooms

East Hampton Home / September available

Image of East Hampton Home / September available

Sleeps 8 · 4 bedrooms · 3+ bathrooms

Top rated rentals - Northwest Harbor

Driftwood Resort

Image of Driftwood Resort

Frequently Asked Questions

What is the best area to stay in Northwest Harbor when booking a holiday rental?

When considering a holiday rental in Northwest Harbor, New York, a fantastic area to stay is near the scenic beaches and tranquil surroundings of the Hamptons. This region offers a delightful mix of natural beauty and local charm. You can find a variety of properties ranging from quaint cottages to luxurious homes, suiting different preferences and group sizes.

One of the main attractions in this area is the stunning beaches, where you can enjoy sunbathing, swimming, or long walks along the shore. Additionally, the nearby Montauk Point State Park is a must-visit, featuring breathtaking coastal views and the iconic lighthouse, which provides a great backdrop for memorable photographs.

Northwest Harbor is not only known for its picturesque landscapes but also for its proximity to various dining and shopping options. The local eateries offer fresh seafood and farm-to-table cuisine, adding to the overall experience of your stay.

How much does it cost to rent a holiday home in Northwest Harbor?

Prices for holiday rentals in Northwest Harbor vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Northwest Harbor to more spacious homes. To get the best value, book early and take advantage of Vrbo’s free rewards program.

Are there any discounts for Northwest Harbor holiday house rentals?

You can find great discounts on house rentals in Northwest Harbor on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.

Can I find long-stay holiday rentals in Northwest Harbor?

A long-stay holiday rental in Northwest Harbor is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

Are there any Northwest Harbor holiday rentals with parking?

Vrbo offers a wide selection of holiday rentals in Northwest Harbor with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the “Parking available” filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.

How early should I book a Northwest Harbor holiday rental?

Book your Northwest Harbor holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

What are the top attractions in Northwest Harbor?

In Northwest Harbor, visitors can enjoy a serene escape with a variety of attractions centred around natural beauty and outdoor activities. The area is known for its picturesque beaches, with Northwest Harbor Beach offering a tranquil spot for sunbathing and swimming. Nearby, the scenic landscapes of the East Hampton Wildlife Refuge provide opportunities for hiking and birdwatching, making it a great destination for nature enthusiasts.

Art lovers can also explore the charming local galleries and boutiques showcasing the work of regional artists, reflecting the area's vibrant creative community.

Can I change or cancel my Northwest Harbor home rental booking on Vrbo?

To find Northwest Harbor holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.

Why should I join Vrbo as a host?

Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

Are all fees included in the Northwest Harbor holiday rental prices shown on Vrbo?

Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

What is VrboCare™ and how does it work?

Vrbo’s mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you’re protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can’t resolve, we’ll help you address it, find a similar property, or get your reservation refunded if applicable. That’s our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.

What can I expect from Vrbo customer service and VrboCare™ support?

Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.

Can I plan a group trip on Vrbo?

Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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