Cutchogue holiday rentals

We found 1,035 holiday rentals — enter your dates for availability
Discover a selection of 36 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:20 Nov - 27 Nov

Dining
Living area
Exterior
Pool
Exceptional
(10 reviews)

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

Orient

8% off
AU$16,911
for 7 nights, 1 room
AU$2,416 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Living area
Outdoor dining
Living area
Private kitchen
Exceptional
(13 reviews)

Explore the Hampton in this Shelter Island Getaway. Weekly Bookings

Shelter Island Heights

31% off
AU$8,168
for 7 nights, 1 home
AU$1,167 per night
includes taxes & fees
Explore the Hampton in this Shelter Island Getaway. Weekly Bookings
Outdoor dining
Exterior
Private kitchen
Interior
Exceptional
(8 reviews)

Beautiful Colonial Mint Condition Summer House Walking Distance to Beach

Jamesport

12% off
AU$6,963
for 7 nights, 1 home
AU$995 per night
includes taxes & fees
Beautiful Colonial Mint Condition Summer House Walking Distance to Beach
Living area
Dining
Outdoor dining
Private kitchen
Exceptional
(18 reviews)

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

Cutchogue

8% off
AU$6,968
for 7 nights, 1 cottage
AU$995 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Living area
Crushpad of Charming Boutique vineyard nearby-  Rosehill
Kitchen Fireplace Eat In Kitchen & in the next photo includes new kitchen table
8 Hands Farm
Exceptional
(30 reviews)

North Fork Ranch Home in Wine Country with Pool- 2 Beaches 5 Min Walk

Laurel

9% off
AU$5,331
for 7 nights, 1 home
AU$762 per night
includes taxes & fees
North Fork Ranch Home in Wine Country with Pool- 2 Beaches 5 Min Walk
Private kitchen
Exterior
Property grounds
Interior
Exceptional
(35 reviews)

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

Riverhead

8% off
AU$7,336
for 7 nights, 1 home
AU$1,048 per night
includes taxes & fees
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
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
AU$13,940
for 7 nights, 1 home
AU$1,991 per night
includes taxes & fees
Bohemian Old Life Saving Station with Beach & Pool
Exterior
Private kitchen
Living area
Living area
Exceptional
(34 reviews)

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Cutchogue

8% off
AU$3,774
for 7 nights, 1 cottage
AU$539 per night
includes taxes & fees
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Private kitchen
Living area
Exterior
Living area
Exceptional
(29 reviews)

Incredible Beachfront Home w/ Private Beach!

Mattituck

7% off
AU$5,226
for 7 nights, 1 cottage
AU$747 per night
includes taxes & fees
Incredible Beachfront Home w/ Private Beach!
Dining
Private kitchen
Private kitchen
Property grounds
Exceptional
(14 reviews)

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

Southold

8% off
AU$6,438
for 7 nights, 1 home
AU$920 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Living area
Outdoor dining
Exterior
More vineyard views
Exceptional
(25 reviews)

Vineyard View, Bike to the Most Beautiful Beach

Mattituck

8% off
AU$9,858
for 7 nights, 1 home
AU$1,408 per night
includes taxes & fees
Vineyard View, Bike to the Most Beautiful Beach
Interior
Property grounds
Room
Exterior
Exceptional
(15 reviews)

Charming Riverhead home with large outdoor patio & backyard firepit

Riverhead

12% off
AU$4,170
for 7 nights, 1 home
AU$596 per night
includes taxes & fees
Charming Riverhead home with large outdoor patio & backyard firepit
Exterior
Kitchen
Room
Living Room
Exceptional
(5 reviews)

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

New Suffolk

8% off
AU$4,851
for 7 nights, 1 home
AU$693 per night
includes taxes & fees
Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach
Comfortable living room with gas fireplace for ambiance in colder months.
View from main living area
kitchen /dining/living area with beautiful view of the pond
Lovely pond front  cottage on the North Fork.
Exceptional
(32 reviews)

Lovely Cottage in the Heart of Long Island Wine country

Southold

8% off
AU$3,192
for 7 nights, 1 cottage
AU$456 per night
includes taxes & fees
Lovely Cottage in the Heart of Long Island Wine country
Private kitchen
Terrace/patio
Interior
Dining
Exceptional
(19 reviews)

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

Greenport

8% off
AU$6,658
for 7 nights, 1 home
AU$951 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
The front porch
A view of the house and pool from the creek, looking south
The front walkway
The kitchen is all glass with a spectacular view of the pool and creek
Exceptional
(20 reviews)

Unique Southold waterfront luxury home with heated pool on Long Creek

Southold

7% off
AU$6,192
for 7 nights, 1 home
AU$885 per night
includes taxes & fees
Unique Southold waterfront luxury home with heated pool on Long Creek
Terrace/patio
Exterior detail
Private kitchen
Living area
Exceptional
(8 reviews)

5 minute walk to beaches and beautiful downtown Greenport

Greenport

8% off
AU$3,511
for 7 nights, 1 home
AU$502 per night
includes taxes & fees
5 minute walk to beaches and beautiful downtown Greenport
Attention to details and fine workmanship was a sign of wealth both then and now
Every season brings special flower blooms
Second living room once called the "parlour"
Our porch is furnished with plants for a Gilded Age feel
Exceptional
(37 reviews)

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

Greenport

12% off
AU$10,864
for 7 nights, 1 home
AU$1,552 per night
includes taxes & fees
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Living area
Pool
Room
Private kitchen
Exceptional
(11 reviews)

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

East Marion

8% off
AU$8,719
for 7 nights, 1 home
AU$1,246 per night
includes taxes & fees
Newly renovated ranch w/ large Pool in quiet neighborhood 1 mile from Greenport
Living Room
Kitchen
Backyard
Exterior
Exceptional
(105 reviews)

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

Greenport

8% off
AU$5,680
for 7 nights, 1 home
AU$811 per night
includes taxes & fees
Relax in this light-filled home, steps from the beach and a short walk to town!
Property grounds
Property grounds
Interior
Exterior
Exceptional
(86 reviews)

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

Greenport

8% off
AU$4,790
for 7 nights, 1 apartment
AU$684 per night
includes taxes & fees
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
  • 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, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

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)
  • Martha Clara Vineyards (5.8 mi / 9.3 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:

  • Elizabeth A. Morton National Wildlife Refuge (6.2 mi / 10 km)
  • Crescent Beach (7.3 mi / 11.7 km)
  • Sunset Beach (7.6 mi / 12.2 km)
  • Meschutt Beach (8.1 mi / 13 km)
  • 67 Steps Beach (9.7 mi / 15.6 km)
  • Cooper's Beach (11 mi / 17.7 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 most popular type of holiday home accommodation in Cutchogue?
The most in-demand types of holiday homes in Cutchogue are houses. Searching for something different? Stayz offers a variety of options to match the unique needs of our guests, so you'll see properties in loads of shapes and sizes. The ideal fit is ready and waiting for you — get yours today.
How much does it cost to rent a holiday home in Cutchogue?
The average price for a holiday home in Cutchogue can vary based on factors like time of year, length of stay and property type. Whether you'd like a villa with space for extended family or a cosy cottage perfect for just you and the kids, just enter your travel dates to discover stays with fantastic value.
How much does it cost to rent a beach house in Cutchogue?
Prices for beach houses in Cutchogue can vary depending on the size and style of the property and when you plan to travel. Simply enter your dates of travel into Stayz and how many guests to view your home options and prices. From there you can use the filters to narrow down your search by nearby activities, amenities, ratings and more.
What are popular home amenities in Cutchogue?
Nearby museums, a barbecue grill and a beach view rank as the most popular home amenities in Cutchogue. Whether you're heading away as a party of one, with your better half or a group of family members, Stayz can help you find a holiday home that matches your style with all the features you'll enjoy.
What are the top attractions for families in Cutchogue?
There's a ton of fabulous things to see and do with the family in Cutchogue, including:
  • Railroad Museum of Long Island
  • East End Seaport Maritime Museum
  • Hallockville Museum Farm
Can I find two-bedroom holiday homes in Cutchogue?
Take off with your loved ones and enjoy a relaxing escape in one of the eight two-bedroom holiday properties Cutchogue has to offer.
Are there holiday homes with WiFi in Cutchogue?
Cutchogue has 20 holiday homes with WiFi, so you'll be able to stay connected when you're away. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming TV shows with the family to scrolling social media, these Stayz homes make it easy to get online.
How old do you have to be to rent a holiday home in Cutchogue?
It's advisable to check with the Cutchogue holiday home you're looking at on Stayz as the minimum age differs. However, it's typically 16, 18 or 21.
How long can I rent a holiday home in Cutchogue for?
It's up to the Cutchogue property. To look over a list of options offering extended stays, just type your travel dates and number of guests into Stayz. Look forward to having the entire place to yourself, as well as comforts such as a fully-equipped kitchen, air conditioning and outdoor spaces where the kids can run and play. Keep your eyes peeled for any long-term stays that offer discounted weekly or monthly prices.

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