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

Cutchogue Holiday Rentals

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Our top choices for Cutchogue holiday rentals

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 NZ$540
includes taxes & fees
15 Nov - 16 Nov
Cliffside Resort Condominiums

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (72 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is NZ$637
includes taxes & fees
4 Nov - 5 Nov
North Fork Resort

3. Walk to Beach | Seabreeze Cottage #4

Walk to Beach | Seabreeze Cottage #4
Hampton Bays
8.8 out of 10, Excellent, (9 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is NZ$796
includes taxes & fees
30 Nov - 1 Dec
Walk to Beach | Seabreeze Cottage #4

4. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is NZ$403
includes taxes & fees
15 Nov - 16 Nov
Harbor Heights

5. 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 NZ$403
includes taxes & fees
10 Nov - 11 Nov
The SandPiper

6. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (52 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is NZ$426
includes taxes & fees
9 Nov - 10 Nov
Aqua Vista

7. 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 NZ$606
includes taxes & fees
10 Nov - 11 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

8. 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 NZ$833
includes taxes & fees
30 Nov - 1 Dec
Steps to the beach | Seabreeze Cottage #3

9. 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 NZ$2,129
includes taxes & fees
10 Nov - 11 Nov
Breakwater Estate: Heated Saltwater Pool, Sleeps 12

10. 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, (6 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 NZ$548
includes taxes & fees
11 Nov - 12 Nov
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

11. 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 NZ$505
includes taxes & fees
15 Nov - 16 Nov
American Beech in Greenport - Petite King Room 7

12. 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 NZ$3,007
includes taxes & fees
4 Nov - 5 Nov
Jacuzzi year-round - Villa Luz Private Home

13. 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 NZ$759
includes taxes & fees
15 Nov - 16 Nov
Beach Block Hideaway

14. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is NZ$840
includes taxes & fees
9 Nov - 10 Nov
Charming Accommodations in the Hamptons

15. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (21 reviews)
"What an amazing view!!!!! Great place to stay!!! Highly recommend the Black Swan home."
United States
John M.
The price is NZ$2,210
includes taxes & fees
10 Nov - 11 Nov
Beachfront Jacuzzi All Year - Black Swan Home

16. 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 NZ$1,890
includes taxes & fees
4 Nov - 5 Nov
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

17. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (8 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 NZ$1,099
includes taxes & fees
16 Nov - 17 Nov
Northfork Townhouse walk to all

18. Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage

Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is NZ$714
includes taxes & fees
15 Nov - 16 Nov
Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage

19. Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is NZ$956
includes taxes & fees
10 Nov - 11 Nov
Immaculate Waterfront 2 bedroom!

20. COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
Southampton
9.2 out of 10, Wonderful, (29 reviews)
"I loved the area and the home was beautiful and very spacious."
United States
Melissa
The price is NZ$4,821
includes taxes & fees
9 Nov - 10 Nov
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
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

Find out more about Cutchogue

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cutchogue holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cutchogue. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cutchogue. Seeing all the best attractions is bound to make you fall in love with Cutchogue. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cutchogue short-term rentals, that won’t be hard to do.

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.