Cutchogue holiday rentals

We found 1,011 holiday rentals — enter your dates for availability
Discover a selection of 37 homes and other holiday rentals in Cutchogue that are perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Cutchogue

Showing deals for:1 Jan - 8 Jan

Interior
Exterior
Private kitchen
Interior
Exceptional
(9 reviews)

Beautiful Colonial Mint Condition Summer House Walking Distance to Beach

Jamesport

12% off
AU$6,339
for 7 nights, 1 home
AU$906 per night
includes taxes & fees
Beautiful Colonial Mint Condition Summer House Walking Distance to Beach
Den/ play room has a sofa with queen sized pullout sofa
Exterior
Private kitchen
Fenced, backyard Hampton-style pool area with lounge chairs and patio
Exceptional
(14 reviews)

Renovated Farmhouse on Vineyard-Heated Pool + mins from Beach + Walk to Harbes!

Riverhead

8% off
AU$9,078
for 7 nights, 1 home
AU$1,297 per night
includes taxes & fees
Renovated Farmhouse on Vineyard-Heated Pool + mins from Beach + Walk to Harbes!
Large Dining/Kitchen Space
Exterior
Pool
Spacious Main Floor Living room
Exceptional
(12 reviews)

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

Southold

8% off
AU$12,254
for 7 nights, 1 home
AU$1,751 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Living area
Property grounds
Interior
Exterior
Exceptional
(17 reviews)

Charming Riverhead home with large outdoor patio & backyard firepit

Riverhead

12% off
AU$4,264
for 7 nights, 1 home
AU$609 per night
includes taxes & fees
Charming Riverhead home with large outdoor patio & backyard firepit
Private kitchen
Exterior
Interior
Property grounds
Exceptional
(42 reviews)

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Riverhead

8% off
AU$7,500
for 7 nights, 1 home
AU$1,071 per night
includes taxes & fees
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
Outdoor dining
Pool
Dining Room with seating for Ten
Master bedroom with ensuite bathroom
Exceptional
(29 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off
AU$12,264
for 7 nights, 1 home
AU$1,752 per night
includes taxes & fees
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
Room
Private kitchen
Living area
Outdoor dining
Exceptional
(17 reviews)

Newly renovated 4-bedroom farmhouse on beautiful vineyard - Great location.

Jamesport

16% off
AU$8,530
for 7 nights, 1 home
AU$1,219 per night
includes taxes & fees
Newly renovated 4-bedroom farmhouse on beautiful vineyard - Great location.
The front of the house
A view of the house and pool from the creek, looking south
The front porch
The front walkway
Exceptional
(21 reviews)

Unique Southold waterfront luxury home with heated pool on Long Creek

Southold

7% off
AU$6,331
for 7 nights, 1 home
AU$904 per night
includes taxes & fees
Unique Southold waterfront luxury home with heated pool on Long Creek
Room
Dining
Outdoor dining
Living area
Exceptional
(18 reviews)

Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe

Cutchogue

8% off
AU$7,123
for 7 nights, 1 cottage
AU$1,018 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Property grounds
Property grounds
Pool
Exterior
Exceptional
(91 reviews)

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

Greenport

8% off
AU$4,897
for 7 nights, 1 apartment
AU$700 per night
includes taxes & fees
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
Dining
Terrace/patio
Private kitchen
Interior
Exceptional
(20 reviews)

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

Greenport

8% off
AU$6,807
for 7 nights, 1 home
AU$972 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
Room
Kitchen
Living Room
Backyard Water View
Exceptional
(6 reviews)

Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach

New Suffolk

8% off
AU$4,960
for 7 nights, 1 home
AU$709 per night
includes taxes & fees
Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach
Dining
Property grounds
Private kitchen
Room
Exceptional
(8 reviews)

Waterfront Property on Shelter Island

Shelter Island

8% off
AU$7,429
for 7 nights, 1 home
AU$1,061 per night
includes taxes & fees
Waterfront Property on Shelter Island
Living Room / Entry / Dining
MINERAL SPRING POOL! 6 Lounge Chairs w/ umbrellas, Covered Cabana
Deck
Master Suite - King bed, gas fireplace, en suite lux bath, doors to terrace.
Exceptional
(61 reviews)

POOL + Beach 1 mi. to Greenport Village! Ask about Winter DEALS for 3+ nights...

East Marion

40% off
AU$3,447
for 7 nights, 1 home
AU$492 per night
includes taxes & fees
POOL + Beach 1 mi. to Greenport Village! Ask about Winter DEALS for 3+ nights...
Attention to details and fine workmanship was a sign of wealth both then and now
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
AU$11,107
for 7 nights, 1 home
AU$1,587 per night
includes taxes & fees
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Bedroom 3, Queen Bed
Kitchen
Living Room
Shed
Exceptional
(108 reviews)

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

Greenport

8% off
AU$5,541
for 7 nights, 1 home
AU$792 per night
includes taxes & fees
Relax in this light-filled home, steps from the beach and a short walk to town!
Living area
Terrace/patio
Dining
Exterior
Exceptional
(8 reviews)

North Fork Waterfront Gem

East Marion

6% off
AU$6,679
for 7 nights, 1 home
AU$954 per night
includes taxes & fees
North Fork Waterfront Gem
Private kitchen
Pool
Terrace/patio
Room
Exceptional
(11 reviews)

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

East Marion

8% off
AU$7,845
for 7 nights, 1 home
AU$1,121 per night
includes taxes & fees
Newly renovated ranch w/ large Pool in quiet neighborhood 1 mile from Greenport
Room
Outdoor dining
Dining
Exterior
Exceptional
(7 reviews)

Cozy Ranch five minutes from Mashomack Preserve, beaches and miniature golf.

Shelter Island

7% off
AU$2,021
for 7 nights, 1 home
AU$289 per night
includes taxes & fees
Cozy Ranch five minutes from Mashomack Preserve, beaches and miniature golf.

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Book a holiday rental for your Cutchogue getaway

Learn about the unique charm of Cutchogue with a stay in a holiday home rental. This city has something for everyone. 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 and around Cutchogue

Do you want to discover attractions to see in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Cutchogue a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Peconic Bay Winery (0.6 mi / 1 km)
  • Bedell Cellars (1.5 mi / 2.5 km)
  • Pindar Vineyards (1.8 mi / 2.9 km)
  • Raphael Winery (2.1 mi / 3.4 km)
  • Macari Vineyards (4.6 mi / 7.4 km)
  • Jamesport Vineyards (7.3 mi / 11.7 km)

Exploring the natural landscape of Cutchogue

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Cutchogue is a great place to get out in nature. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Sunset Beach (7.6 mi / 12.2 km)
  • Meschutt Beach (8.1 mi / 13 km)
  • Mashomack Preserve (9.5 mi / 15.3 km)
  • 67 Steps Beach (9.7 mi / 15.6 km)
  • Cooper's Beach (11 mi / 17.7 km)
  • The Hamptons Beaches (11.2 mi / 18 km)

Transport to and around Cutchogue

The nearest airport is in East Hampton, NY (HTO), located 12.8 mi (20.7 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Westhampton, NY (FOK-Francis S. Gabreski), which is 14.2 mi (22.9 km) away.

Frequently asked questions

What is the best area to stay in Cutchogue when booking a holiday rental?
When considering a holiday rental in Cutchogue, New York, the best area to stay in is the charming North Fork region. This picturesque community is celebrated for its stunning vineyards and serene coastal views, making it an idyllic retreat for those looking to unwind. You'll find a variety of properties available, ranging from quaint cottages to luxurious waterfront homes, ensuring there's something to suit every taste and budget.One of the highlights of staying in Cutchogue is the proximity to some of the area's top attractions. For wine enthusiasts, exploring the local vineyards is a must; many offer tastings and tours that allow you to savour the rich flavours of the region. Additionally, the scenic Cutchogue Harbor provides lovely spots for a leisurely stroll or a peaceful day by the water. The area is also home to the beautiful Cutchogue Village Green, where you can appreciate the charming architecture and local events that bring the community together.
Where are the best areas for renting a beach house in Cutchogue?
For renting a beach house in Cutchogue, the areas along the North Fork of Long Island are particularly appealing. The charming waterfront properties near Cutchogue Harbor offer stunning views of the water and easy access to sandy beaches. Many of these rentals feature amenities such as private docks, outdoor grills, and spacious decks, ideal for enjoying the beautiful sunsets over the bay.Additionally, the vicinity around the local wineries, such as those along the scenic Route 25, provides a lovely backdrop for holiday homes that often come with lush gardens and outdoor seating areas, great for wine enthusiasts looking to relax after a day of exploration. Properties here can range from quaint cottages to larger family homes, many equipped with modern kitchens and cosy living areas.For those interested in outdoor activities, nearby beaches like North Cutchogue Beach and the nature trails offer opportunities for swimming, fishing, and birdwatching. Rentals in these areas typically include amenities like bicycles or kayaks, allowing guests to fully embrace the coastal lifestyle.
What is the most popular type of holiday rental accomodation in Cutchogue?
In Cutchogue, holiday houses are the most popular type of holiday rental, with about 104 available throughout the area. These properties often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces great for enjoying the serene surroundings of the North Fork. Additionally, there are around 32 charming cottages that offer a more intimate and cosy atmosphere, ideal for couples or small families seeking a quaint getaway. Many cottages include amenities like fireplaces and patios for relaxing after a day of exploring local wineries and beaches.
Are there any family house rentals in Cutchogue?
In Cutchogue, New York, there are plenty of family-friendly house rentals available, with around 27 options to choose from. This charming area, located on the North Fork of Long Island, is known for its picturesque vineyards and tranquil beaches, making it an ideal spot for family gatherings.Many of the properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play safely. Visitors can expect amenities such as air conditioning, Wi-Fi, and sometimes even private pools, ensuring a comfortable stay for everyone.The locale offers easy access to nearby attractions, including beautiful beaches like New Suffolk Beach and various wineries that welcome families for tastings and tours. Additionally, the quaint town centre provides opportunities for shopping and dining, enhancing the overall experience for families looking to unwind and explore.
Can I rent a holiday home with a pool or hot tub in Cutchogue?
In Cutchogue, there are several holiday homes available for rent that feature pools and hot tubs, with around 10 options to choose from. This charming area on the North Fork of Long Island is known for its beautiful vineyards and proximity to the coastline. Many of the properties offer inviting amenities such as private swimming pools, relaxing hot tubs, spacious outdoor patios, and fully equipped kitchens, making them ideal for families or groups looking to unwind in a tranquil setting.
Are there pet-friendly house rentals in Cutchogue?
In Cutchogue, there are pet-friendly house rentals available, offering a range of options for travellers with furry companions. Many of these holiday homes come equipped with amenities such as spacious gardens, outdoor patios, and fully stocked kitchens, making them ideal for families or groups looking to enjoy a comfortable stay.The area is known for its charming surroundings, with wineries and beautiful landscapes that are great for leisurely strolls with pets. Additionally, nearby parks provide ample space for outdoor activities, ensuring both pets and their owners have plenty of opportunities to enjoy the outdoors.
Are there any remote work holiday rentals in Cutchogue?
In Cutchogue, New York, there are numerous options for remote work holiday rentals, with around 132 properties available. This charming village, located on the North Fork of Long Island, offers a tranquil setting for those looking to combine work and leisure. Many of the rentals come equipped with essential amenities for remote work, including high-speed internet, dedicated desks, and comfortable working spaces, ensuring a productive environment.The area is also known for its beautiful vineyards and proximity to the picturesque Peconic Bay, providing ample opportunities for relaxation after a day's work. Travellers can enjoy local attractions such as the Cutchogue Village Green and nearby beaches, making it an ideal spot for both work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Cutchogue?
In Cutchogue, popular rental amenities include well-equipped kitchens, which are essential for those who prefer to prepare their own meals during their stay. Many properties also feature blenders, allowing guests to whip up smoothies or other beverages. Outdoor spaces are common, with decks or patios providing superb spots for relaxation or al fresco dining while enjoying the tranquil surroundings. Additionally, many rentals come with fireplaces, adding a warm and cosy atmosphere, especially in cooler months.
When is the best time to visit Cutchogue for a holiday rental?
The optimal time to visit Cutchogue for a holiday rental is during the peak season from June to August, with July being the most popular month. This vibrant period attracts visitors eager to experience the beautiful beaches, local wineries, and charming coastal atmosphere that Cutchogue is known for. With temperatures typically ranging from 20 to 30 degrees Celsius, the warm weather is superb for outdoor activities, including wine tastings and leisurely walks along the picturesque shoreline.During these summer months, the area buzzes with activity, offering various events and festivals that highlight the region's rich culture and culinary delights. You'll find plenty of opportunities to explore the local vineyards and indulge in fresh seafood, all while soaking up the sun.For those looking for a more budget-friendly option, consider visiting in December. While the weather may be cooler, with temperatures ranging from 0 to 10 degrees Celsius, this month allows for a quieter getaway. You can enjoy the serene beauty of Cutchogue, perhaps exploring the local shops or enjoying a warm drink by a cosy fireplace.Ultimately, your choice of when to visit Cutchogue will depend on whether you seek the lively option of summer or the peaceful charm of winter.
What are the top attractions in Cutchogue?
Cutchogue, located on Long Island's North Fork, offers a charming blend of attractions that showcase its rich history and beautiful surroundings. One of the highlights is the Cutchogue Village Historic District, where visitors can explore well-preserved buildings dating back to the 17th and 18th centuries, providing a glimpse into the area's past.The North Fork is renowned for its vineyards, and Cutchogue is home to several wineries that welcome tastings and tours, allowing guests to savour local wines amidst scenic views. The nearby Greenport village, just a short drive away, features a lively waterfront with shops, restaurants, and the famous Greenport Carousel, making it a delightful excursion for families.For those who enjoy the outdoors, the area provides access to beautiful beaches and parks, such as the scenic Cutchogue Harbor and the nearby Southold Town Park, great for picnicking and enjoying the coastal landscape.
Are all fees included in the Cutchogue holiday homes prices shown on Stayz?
Stayz 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.
Are there any Cutchogue holiday homes with parking?
Stayz offers a wide selection of holiday homes in Cutchogue 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 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.
Are there any discounts for Cutchogue holiday homes?
You can find great discounts on holiday homes in Cutchogue on Stayz, 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 change or cancel my Cutchogue holiday home booking on Stayz?
To find Cutchogue holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Cutchogue?
A long-stay holiday home in Cutchogue 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Cutchogue holiday home?
Book your Cutchogue holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Cutchogue?
Prices for holiday homes in Cutchogue 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Cutchogue to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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