Northwest Harbor holiday lettings

We found 2,328 holiday rentals — enter your dates for availability
Discover a selection of 290 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:25 Dec - 1 Jan

Dining
Living area
Pool
Exterior
Exceptional
(12 reviews)

Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Orient

8% off
£9,537
for 7 nights, 1 room
£1,362 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Exterior
Private kitchen
The Harbor
Dining Room
Exceptional
(103 reviews)

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

Sag Harbor

16% off
£6,306
for 7 nights, 1 home
£901 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Living area
Terrace/patio
Exterior
Living area
Excellent
(10 reviews)

Stunning fall sunsets, coveted location on Mecox Bay - recently furnished

Water Mill

8% off
£29,691
for 7 nights, 1 home
£4,242 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
view from living room towards pool, outdoor dining
aerial view
kitchen with large island and breakfast table
living room
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off
£43,890
for 7 nights, 1 home
£6,270 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Master bedroom with ensuite bathroom
Pool
Outdoor dining
Dining Room with seating for Ten
Exceptional
(28 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off
£6,611
for 7 nights, 1 home
£944 per night
includes taxes & fees
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
Exterior
Exterior
Spacious Main Floor Living room
Large Dining/Kitchen Space
Exceptional
(11 reviews)

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

Southold

8% off
£9,627
for 7 nights, 1 home
£1,375 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Hall into sitting room
Master bed onto balcony
Dining room onto porch
Kitchen from dining room
Exceptional
(34 reviews)

Bohemian Old Life Saving Station with Beach & Pool

East Marion

8% off
£10,423
for 7 nights, 1 home
£1,489 per night
includes taxes & fees
Bohemian Old Life Saving Station with Beach & Pool
Dining
Terrace/patio
Interior
Private kitchen
Exceptional
(20 reviews)

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

Greenport

7% off
£3,752
for 7 nights, 1 home
£536 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
Den
Pool
Living room w/ screen porch beyond
New Kitchen
Exceptional
(48 reviews)

Quiet Family Friendly Hideaway With Pool And Poolhouse

East Hampton

8% off
£10,548
for 7 nights, 1 home
£1,507 per night
includes taxes & fees
Quiet Family Friendly Hideaway With Pool And Poolhouse
Pool
Living area
Interior
Living area
Exceptional
(15 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

7% off
£5,905
for 7 nights, 1 home
£844 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
Living area
Pool
Exterior detail
Exceptional
(11 reviews)

Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house

Sag Harbor

8% off
£7,693
for 7 nights, 1 cottage
£1,099 per night
includes taxes & fees
Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house
The front porch
A view of the house and pool from the creek, looking south
The kitchen is all glass with a spectacular view of the pool and creek
The front walkway
Exceptional
(21 reviews)

Unique Southold waterfront luxury home with heated pool on Long Creek

Southold

7% off
£3,496
for 7 nights, 1 home
£499 per night
includes taxes & fees
Unique Southold waterfront luxury home with heated pool on Long Creek
Second living room once called the "parlour"
Every season brings special flower blooms
Our porch is furnished with plants for a Gilded Age feel
Morning breakfast room
Exceptional
(37 reviews)

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

Greenport

12% off
£5,994
for 7 nights, 1 home
£856 per night
includes taxes & fees
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Shed
Kitchen
Backyard
Living Room
Exceptional
(108 reviews)

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

Greenport

7% off
£4,898
for 7 nights, 1 home
£700 per night
includes taxes & fees
Relax in this light-filled home, steps from the beach and a short walk to town!
Frankel Residence
Thermador chefs kitchen with expansive island open to dining room & family room
Dining room seating 12 leading to chef's kitchen and doors leading to pool
Open entry foyer with wall of windowed doors to Zen Garden
Exceptional
(6 reviews)

Completely Renovated Home on ~2 Private Acres, Near Beach/Town

Wainscott

7% off
£13,012
for 7 nights, 1 home
£1,859 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Living/dining space
Facade
Front yard closeup
From the bedroom
Exceptional
(23 reviews)

Private Hamptons cottage in ideal Amagansett location

Amagansett

8% off
£4,149
for 7 nights, 1 cottage
£593 per night
includes taxes & fees
Private Hamptons cottage in ideal Amagansett location
Hydrangeas blooming all summer.these are the August bloomers
Featured as one of most beautiful poolsides
Couches on covered porch and outdoor dining table for 8
Living area on 1st floor with wood burning fireplace
Exceptional
(7 reviews)

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

Southampton

8% off
£14,670
for 7 nights, 1 home
£2,096 per night
includes taxes & fees
IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES
Guest house small private
outdoor seating area.
Living room, looking out toward Accabonac Harbor, water views.
Kitchen with Wolf stove, Sub Zero fridge, pass-through serving area to dining.
Lovely seating in pool area for morning coffee.
Exceptional
(7 reviews)

WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!

East Hampton

8% off
£12,486
for 7 nights, 1 home
£1,784 per night
includes taxes & fees
WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!
Room
Private kitchen
Property grounds
Private kitchen
Exceptional
(14 reviews)

Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country

Southold

7% off
£3,654
for 7 nights, 1 home
£522 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Dining
Pool
Private kitchen
Living area
Wonderful
(18 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off
£12,892
for 7 nights, 1 home
£1,842 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Dining
Property grounds
Terrace/patio
Exterior
Exceptional
(5 reviews)

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

East Hampton

8% off
£5,567
for 7 nights, 1 home
£795 per night
includes taxes & fees
Beautiful 4 bedroom house with tranquil gardens close to bay beaches.
Property grounds
Property grounds
Interior
Exterior
Exceptional
(91 reviews)

Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

Greenport

8% off
£2,660
for 7 nights, 1 apartment
£380 per night
includes taxes & fees
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
Living area
Terrace/patio
Exterior
Living area
Exceptional
(8 reviews)

North Fork Waterfront Gem

East Marion

6% off
£4,704
for 7 nights, 1 home
£672 per night
includes taxes & fees
North Fork Waterfront Gem
Lounge by the pool in total privacy
Dine in style overlooking the pool and grounds
Primary bedroom with stylish, new, mid-century modern furnishings and pool view
New, professional grade, stainless steel appliances including Bertazzoni range
Exceptional
(32 reviews)

Stylish East Hampton Village Retreat- Heated Pool and Sauna, Steps to Village

East Hampton

15% off
£5,350
for 7 nights, 1 home
£764 per night
includes taxes & fees
Stylish East Hampton Village Retreat- Heated Pool and Sauna, Steps to Village
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Arty Northwest Harbor will entice you

Enjoy the art galleries and other features of Northwest Harbor. Renowned for its island views, shark watching and aquarium, this city welcomes all visitors. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Northwest Harbor

Are you looking for attractions to visit while you're in town? Venture out of your holiday home and experience everything that makes Northwest Harbor a fun spot to go on holiday. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • LongHouse Reserve (2.2 mi / 3.6 km)
  • Wolffer Estates Vineyard (5.4 mi / 8.6 km)
  • Kontokosta Winery (10.4 mi / 16.8 km)
  • Duck Walk Vineyards (10.6 mi / 17 km)
  • Raphael Winery (12.6 mi / 20.3 km)
  • Pindar Vineyards (12.8 mi / 20.6 km)

Exploring the natural landscape of Northwest Harbor

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Northwest Harbor is a great spot to appreciate mother nature. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • LongHouse Reserve (2.2 mi / 3.6 km)
  • East Hampton Main Beach (4.8 mi / 7.8 km)
  • Indian Wells Beach (5.4 mi / 8.6 km)
  • Atlantic Avenue Beach (5.8 mi / 9.4 km)
  • Amagansett Beach (6 mi / 9.7 km)
  • The Hamptons Beaches (7.2 mi / 11.6 km)

Travelling to and around Northwest Harbor

The nearest airport is in East Hampton, NY (HTO), located 3.6 mi (5.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Montauk, NY (MTP), which is 16 mi (25.8 km) away.

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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