Cutchogue holiday rentals

We found 1,045 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:13 Nov - 20 Nov

Pool
Living area
Dining
Living area
Exceptional
(10 reviews)

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

Orient

8% off
S$16,013
for 7 nights, 1 room
S$2,288 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Large Dining/Kitchen Space
Exterior
Spacious Main Floor Living room
Pool
Exceptional
(11 reviews)

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

Southold

7% off
S$12,926
for 7 nights, 1 home
S$1,847 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Crushpad of Charming Boutique vineyard nearby-  Rosehill
Kitchen Fireplace Eat In Kitchen & in the next photo includes new kitchen table
Living area
Exceptional
(30 reviews)

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

Laurel

9% off
S$3,717
for 7 nights, 1 home
S$531 per night
includes taxes & fees
North Fork Ranch Home in Wine Country with Pool- 2 Beaches 5 Min Walk
Open both doors for a cool breeze while dining
Outdoor dining
Dine al fresco while watching the boats and sea planes
Property grounds
Exceptional
(16 reviews)

Relax and Enjoy!

Shelter Island Heights

7% off
S$9,210
for 7 nights, 1 home
S$1,316 per night
includes taxes & fees
Relax and Enjoy!
Room
Dining
Living area
Outdoor dining
Exceptional
(18 reviews)

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

Cutchogue

8% off
S$6,352
for 7 nights, 1 cottage
S$907 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Living area
Private kitchen
Living area
Exterior
Exceptional
(34 reviews)

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

Cutchogue

8% off
S$3,462
for 7 nights, 1 cottage
S$495 per night
includes taxes & fees
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Private kitchen
Outdoor dining
Pool
Living area
Exceptional
(13 reviews)

Explore the Hampton in this Shelter Island Getaway. Weekly Bookings

Shelter Island Heights

31% off
S$7,432
for 7 nights, 1 home
S$1,062 per night
includes taxes & fees
Explore the Hampton in this Shelter Island Getaway. Weekly Bookings
Property grounds
Living area
Living area
Exterior
Exceptional
(29 reviews)

Incredible Beachfront Home w/ Private Beach!

Mattituck

7% off
S$4,947
for 7 nights, 1 cottage
S$707 per night
includes taxes & fees
Incredible Beachfront Home w/ Private Beach!
Property grounds
Exterior
Property grounds
Private kitchen
Exceptional
(32 reviews)

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

Riverhead

7% off
S$6,788
for 7 nights, 1 home
S$970 per night
includes taxes & fees
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
Beach
Master bed onto balcony
Dining room onto porch
Dining room from kitchen
Exceptional
(34 reviews)

Bohemian Old Life Saving Station with Beach & Pool

East Marion

8% off
S$13,105
for 7 nights, 1 home
S$1,872 per night
includes taxes & fees
Bohemian Old Life Saving Station with Beach & Pool
Interior
Exterior
Interior
Outdoor dining
Exceptional
(8 reviews)

Beautiful Colonial Mint Condition Summer House Walking Distance to Beach

Jamesport

11% off
S$6,469
for 7 nights, 1 home
S$924 per night
includes taxes & fees
Beautiful Colonial Mint Condition Summer House Walking Distance to Beach
Living area
Outdoor dining
Exterior
Welcome to Vineyard View
Exceptional
(24 reviews)

Vineyard View, Bike to the Most Beautiful Beach

Mattituck

8% off
S$9,088
for 7 nights, 1 home
S$1,298 per night
includes taxes & fees
Vineyard View, Bike to the Most Beautiful Beach
Room
Private kitchen
Dining
Private kitchen
Exceptional
(14 reviews)

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

Southold

8% off
S$5,875
for 7 nights, 1 home
S$839 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Exterior
Property grounds
Living area
Interior
Exceptional
(14 reviews)

Charming Riverhead home with large outdoor patio & backyard firepit

Riverhead

11% off
S$3,878
for 7 nights, 1 home
S$554 per night
includes taxes & fees
Charming Riverhead home with large outdoor patio & backyard firepit
Outdoor dining
Private kitchen
Interior
Living area
Exceptional
(13 reviews)

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

Jamesport

16% off
S$7,845
for 7 nights, 1 home
S$1,121 per night
includes taxes & fees
Newly renovated 4-bedroom farmhouse on beautiful vineyard - Great location.
Interior
Terrace/patio
Interior
Private kitchen
Exceptional
(19 reviews)

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

Greenport

8% off
S$6,074
for 7 nights, 1 home
S$868 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
Wonderful screened in porch for enjoying the sights and sounds of nature .
View from main living area
Lovely pond front  cottage on the North Fork.
Comfortable living room with gas fireplace for ambiance in colder months.
Exceptional
(32 reviews)

Lovely Cottage in the Heart of Long Island Wine country

Southold

8% off
S$2,930
for 7 nights, 1 cottage
S$419 per night
includes taxes & fees
Lovely Cottage in the Heart of Long Island Wine country
Terrace/patio
Pool
Private kitchen
Living area
Exceptional
(11 reviews)

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

East Marion

8% off
S$7,930
for 7 nights, 1 home
S$1,133 per night
includes taxes & fees
Newly renovated ranch w/ large Pool in quiet neighborhood 1 mile from Greenport
The front walkway
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 of the house
Exceptional
(20 reviews)

Unique Southold waterfront luxury home with heated pool on Long Creek

Southold

7% off
S$5,652
for 7 nights, 1 home
S$807 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
Morning breakfast room
Attention to details and fine workmanship was a sign of wealth both then and now
Exceptional
(36 reviews)

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

Greenport

12% off
S$10,123
for 7 nights, 1 home
S$1,446 per night
includes taxes & fees
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Exterior
Kitchen
Living Room
Room
Exceptional
(5 reviews)

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

New Suffolk

7% off
S$4,512
for 7 nights, 1 home
S$645 per night
includes taxes & fees
Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach
Exterior
Kitchen
Living Room
Backyard
Exceptional
(104 reviews)

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

Greenport

7% off
S$4,563
for 7 nights, 1 home
S$652 per night
includes taxes & fees
Relax in this light-filled home, steps from the beach and a short walk to town!
Living area
Exterior detail
Room
Terrace/patio
Exceptional
(8 reviews)

5 minute walk to beaches and beautiful downtown Greenport

Greenport

8% off
S$3,218
for 7 nights, 1 home
S$460 per night
includes taxes & fees
5 minute walk to beaches and beautiful downtown Greenport
Interior
Property grounds
Exterior
Pool
Exceptional
(85 reviews)

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

Greenport

8% off
S$4,384
for 7 nights, 1 apartment
S$626 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)
  • Croteaux Vineyards (3.4 mi / 5.4 km)
  • Macari Vineyards (4.6 mi / 7.4 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 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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