Cutchogue holiday rentals

We found 1,012 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:15 Jan - 22 Jan

Interior
Exterior
Interior
Private kitchen
Exceptional
(9 reviews)

Beautiful Colonial Mint Condition Summer House Walking Distance to Beach

Jamesport

12% off
S$5,664
for 7 nights, 1 home
S$809 per night
includes taxes & fees
Beautiful Colonial Mint Condition Summer House Walking Distance to Beach
Property grounds
Outdoor dining
Interior
Dining
Exceptional
(22 reviews)

The Lane House | Private Beach Escape

Orient

16% off
S$6,181
for 7 nights, 1 home
S$883 per night
includes taxes & fees
The Lane House | Private Beach Escape
Fenced, backyard Hampton-style pool area with lounge chairs and patio
Dining
Private kitchen
Den/ play room has a sofa with queen sized pullout sofa
Exceptional
(14 reviews)

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

Riverhead

8% off
S$8,035
for 7 nights, 1 home
S$1,148 per night
includes taxes & fees
Renovated Farmhouse on Vineyard-Heated Pool + mins from Beach + Walk to Harbes!
Exterior
Exterior
Spacious Main Floor Living room
Large Dining/Kitchen Space
Exceptional
(12 reviews)

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

Southold

7% off
S$11,792
for 7 nights, 1 home
S$1,685 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Interior
Exterior
Property grounds
Property grounds
Exceptional
(44 reviews)

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

Riverhead

7% off
S$6,697
for 7 nights, 1 home
S$957 per night
includes taxes & fees
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
Room
Private kitchen
Living area
Interior
Exceptional
(18 reviews)

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

Jamesport

16% off
S$7,232
for 7 nights, 1 home
S$1,033 per night
includes taxes & fees
Newly renovated 4-bedroom farmhouse on beautiful vineyard - Great location.
Master bedroom with ensuite bathroom
Pool
Exterior
Dining Room with seating for Ten
Exceptional
(29 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off
S$11,155
for 7 nights, 1 home
S$1,594 per night
includes taxes & fees
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
Living area
Property grounds
Exterior
Room
Exceptional
(17 reviews)

Charming Riverhead home with large outdoor patio & backyard firepit

Riverhead

11% off
S$3,889
for 7 nights, 1 home
S$556 per night
includes taxes & fees
Charming Riverhead home with large outdoor patio & backyard firepit
The front of the house
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 porch
Exceptional
(21 reviews)

Unique Southold waterfront luxury home with heated pool on Long Creek

Southold

7% off
S$5,822
for 7 nights, 1 home
S$832 per night
includes taxes & fees
Unique Southold waterfront luxury home with heated pool on Long Creek
Living area
Dining
Room
Outdoor dining
Exceptional
(18 reviews)

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

Cutchogue

8% off
S$6,457
for 7 nights, 1 cottage
S$922 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Pool overlooking horse farm
American Beech (Greenport)
Sunroom can easily convert into a queen sleeping area with armoire for storage
Bright and open living room
Exceptional
(20 reviews)

Modern farmhouse w/ heated pool, beach, horses and winery in heart of North Fork

Mattituck

7% off
S$3,140
for 7 nights, 1 home
S$449 per night
includes taxes & fees
Modern farmhouse w/ heated pool, beach, horses and winery in heart of North Fork
Interior
Terrace/patio
Private kitchen
Interior
Exceptional
(21 reviews)

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

Greenport

7% off
S$6,321
for 7 nights, 1 home
S$903 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
Terrace/patio
Exterior detail
Living area
Room
Exceptional
(8 reviews)

5 minute walk to beaches and beautiful downtown Greenport

Greenport

7% off
S$3,348
for 7 nights, 1 home
S$478 per night
includes taxes & fees
5 minute walk to beaches and beautiful downtown Greenport
Exterior
Property grounds
Room
Private kitchen
Exceptional
(8 reviews)

Waterfront Property on Shelter Island

Shelter Island

7% off
S$6,898
for 7 nights, 1 home
S$985 per night
includes taxes & fees
Waterfront Property on Shelter Island
Morning breakfast room
Every season brings special flower blooms
Our porch is furnished with plants for a Gilded Age feel
Attention to details and fine workmanship was a sign of wealth both then and now
Exceptional
(37 reviews)

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

Greenport

12% off
S$10,064
for 7 nights, 1 home
S$1,438 per night
includes taxes & fees
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Room
Kitchen
Living Room
Exterior
Exceptional
(7 reviews)

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

New Suffolk

7% off
S$4,520
for 7 nights, 1 home
S$646 per night
includes taxes & fees
Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach
Exterior
Terrace/patio
Living area
Living area
Exceptional
(8 reviews)

North Fork Waterfront Gem

East Marion

5% off
S$6,464
for 7 nights, 1 home
S$923 per night
includes taxes & fees
North Fork Waterfront Gem
Shed
Kitchen
Living Room
Backyard
Exceptional
(109 reviews)

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

Greenport

7% off
S$4,553
for 7 nights, 1 home
S$650 per night
includes taxes & fees
Relax in this light-filled home, steps from the beach and a short walk to town!
Terrace/patio
Pool
Living area
Room
Exceptional
(11 reviews)

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

East Marion

7% off
S$6,694
for 7 nights, 1 home
S$956 per night
includes taxes & fees
Newly renovated ranch w/ large Pool in quiet neighborhood 1 mile from Greenport
Terrace/patio
Private kitchen
Exterior
Dining
Exceptional
(15 reviews)

Relaxation in Greenport

Greenport

7% off
S$7,741
for 7 nights, 1 home
S$1,106 per night
includes taxes & fees
Relaxation in Greenport
Room
Outdoor dining
Exterior
Dining
Exceptional
(7 reviews)

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

Shelter Island

7% off
S$1,830
for 7 nights, 1 home
S$261 per night
includes taxes & fees
Cozy Ranch five minutes from Mashomack Preserve, beaches and miniature golf.
Wonderful screened in porch for enjoying the sights and sounds of nature .
View from main living area
kitchen /dining/living area with beautiful view of the pond
Lovely pond front  cottage on the North Fork.
Exceptional
(33 reviews)

Lovely Cottage in the Heart of Long Island Wine country

Southold

7% off
S$3,045
for 7 nights, 1 cottage
S$435 per night
includes taxes & fees
Lovely Cottage in the Heart of Long Island Wine country
  • 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)
  • 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 most popular type of holiday rental accommodation in Cutchogue?
The most in-demand types of holiday rentals in Cutchogue are houses. Searching for something different? Vrbo 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 rental 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 Vrbo and how many guests to view your rental 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 rental amenities in Cutchogue?
Nearby museums, a barbecue grill and a beach view rank as the most popular rental amenities in Cutchogue. Whether you're heading away as a party of one, with your better half or a group of family members, Vrbo can help you find a holiday rental 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 rentals 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 rentals with WiFi in Cutchogue?
Cutchogue has 20 holiday rentals 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 Vrbo homes make it easy to get online.
How old do you have to be to rent a holiday rental in Cutchogue?
It's advisable to check with the Cutchogue holiday rental you're looking at on Vrbo as the minimum age differs. However, it's typically 16, 18 or 21.
How long can I rent a holiday rental 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 Vrbo. 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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