A coastal landscape with a sandy beach, calm waters, and a clear sky.

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Cutchogue holiday rentals

A balcony with a view of the ocean, a lawn, and a house in the background.

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is £247
includes taxes & fees
26 Nov - 27 Nov
Cliffside Resort Condominiums
A wooden deck with a glass-top table and a portable grill.

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is £267
includes taxes & fees
17 Nov - 18 Nov
North Fork Resort
A kitchen with a wooden countertop, a black sink, and a window with a view of trees.

3. North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.

North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.
Southold
9.6 out of 10, Exceptional, (10 reviews)
"Overall we had a great stay, we weren’t in the apartment much and really only needed it for a place to stay at night. The space is the basement of a home with little natural sunlight. Overall it was ok for a weekend stay."
United States
Kelly V.
The price is £355
includes taxes & fees
10 Nov - 11 Nov
North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.
A wooden interior with a staircase, a blue sofa, and a fireplace.

4. Breakwater Estate: Heated Saltwater Pool, Sleeps 12

Breakwater Estate: Heated Saltwater Pool, Sleeps 12
Mattituck
10.0 out of 10, Exceptional, (39 reviews)
"House has so much character, I rent 7-8 weeks per year and every home is different.This house is the most organized I have ever been in but also the most character.Every room brings you to different place, the furniture is beautiful. Home is spacious.Grounds are larger than most in the Hamptons. Pool is spectacular!"
United States
Frank T.
The price is £1,025
includes taxes & fees
30 Nov - 1 Dec
Breakwater Estate: Heated Saltwater Pool, Sleeps 12
A beach with people relaxing on chairs and sunbathing.

5. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (29 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is £175
includes taxes & fees
15 Nov - 16 Nov
Harbor Heights
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

6. Steps to the beach | Seabreeze Cottage #3

Steps to the beach | Seabreeze Cottage #3
Hampton Bays
6.0 out of 10, (3 reviews)
"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...
United States
Lydia
The price is £335
includes taxes & fees
15 Nov - 16 Nov
Steps to the beach | Seabreeze Cottage #3
A brick patio with outdoor seating, a wooden staircase, and a house with a window and door.

7. Cozy Cottage by the beach - Seabreeze #1

Cozy Cottage by the beach - Seabreeze #1
Hampton Bays
The price is £327
includes taxes & fees
16 Nov - 17 Nov
Cozy Cottage by the beach - Seabreeze #1
A wooden deck with two Adirondack chairs and a fire pit, overlooking a beach at sunset.

8. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is £704
includes taxes & fees
10 Nov - 11 Nov
Beachfront Greenport Villa
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

9. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (53 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is £180
includes taxes & fees
18 Nov - 19 Nov
Aqua Vista
A house with a sliding glass door, a white door, and a small porch with potted plants.

10. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
The price is £839
includes taxes & fees
10 Nov - 11 Nov
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

11. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (57 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is £175
includes taxes & fees
10 Nov - 11 Nov
The SandPiper
An outdoor dining area with hanging lights, palm trees, and a bar.

12. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
United States
Paul F.
The price is £218
includes taxes & fees
10 Nov - 11 Nov
American Beech in Greenport - Petite King Room 7
A beach with people relaxing, a pier extending into the water, and a clear sky.

13. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (35 reviews)
"We had a great stay!! "
United States
Callie E.
The price is £258
includes taxes & fees
10 Nov - 11 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A wooden pathway leading to a beach with scattered rocks and greenery.

14. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is £310
includes taxes & fees
11 Nov - 12 Nov
Beach Block Hideaway
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

15. Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (6 reviews)
"perfect for families"
United States
Okito H.
The price is £757
includes taxes & fees
11 Nov - 12 Nov
Minutes from the beach, brand new 4 bedroom
A small cabin with a porch, surrounded by trees and a fenced area.

16. Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
6.0 out of 10, (1 review)
"For a last minute trip, we couldn't beat the location. Less than 10 minutes from Sag Harbor and Bridgehampton main streets as well as from Sagaponack beaches. The space is quaint and offers everything you need, a small kitchenette, a work desk, outdoor space. There was several communications sent regarding privacy and not interacting with other guests on property which I can appreciate but felt excessive.My two biggest complaints and likely why I would not rebook was first the cleanliness of the...
United States
Emily t.
The price is £365
includes taxes & fees
12 Nov - 13 Nov
Lovely studio with AC in charming Sag Harbor
A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

17. Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Flanders
10.0 out of 10, Exceptional, (7 reviews)
"This was a great property. Very convenient to where we like to visit. It really had everything we needed for a great weeks stay."
United States
Sherri K.
The price is £245
includes taxes & fees
9 Dec - 10 Dec
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
A hot tub with a checkered roof structure and surrounding greenery.

18. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home
Hampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is £857
includes taxes & fees
10 Nov - 11 Nov
Jacuzzi year-round - Villa Luz Private Home
A modern living room with a wooden accent wall, a flat-screen TV, a fireplace, and a dining area with a chair and table.

19. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (2 reviews)
"The property was great for our Hamptons trip! Very clean and comfortable and communication was great"
United States
Katie B.
The price is £416
includes taxes & fees
15 Nov - 16 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A modern dining area with a wooden table, white chairs, and a chandelier.

20. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (9 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is £429
includes taxes & fees
10 Nov - 11 Nov
Northfork Townhouse walk to all
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cutchogue Hotel Reviews

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Would recommend this hotel"
Marlene 2-night trip
Posted 6 hours ago
Hyatt Place Long Island East End

Find out more about Cutchogue

Everything you need to know about Cutchogue holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cutchogue holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cutchogue holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cutchogue holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cutchogue. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cutchogue holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cutchogue holiday rentals we have selected for you start as low as £171 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cutchogue rentals

At Expedia, we put the best Cutchogue holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cutchogue rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cutchogue holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cutchogue. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Cutchogue?

Yes, there are holiday rentals in Cutchogue close to 8 Hands Farm, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Cutchogue has to offer?

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly: This holiday home rental outside of Cutchogue offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Cutchogue?

With 37 Expedia holiday rentals, you're guaranteed to find just the right place for your Cutchogue stay.

What’s there to see and do in Cutchogue?

Cutchogue Village Green and Fisherman Beach are a couple of lovely local spots to get outside and enjoy nature. While here, Peconic Bay Winery and Bedell Cellars are other places worth a visit.

What’s a holiday rental in Cutchogue like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cutchogue. Holiday rentals feature amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for family gatherings.