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

Cutchogue Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Cutchogue holiday rentals

Terrace/patio

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is HK$1,326
HK$2,386 total
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (65 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is HK$2,091
HK$2,388 total
includes taxes & fees
18 Oct - 19 Oct
North Fork Resort
A rocky beach with clear water and a forested hillside in the background.

3. North Fork Fall Escape—Vineyards, Apple Picking & Greenport

North Fork Fall Escape—Vineyards, Apple Picking & Greenport
Mattituck
9.6 out of 10, Exceptional, (7 reviews)
"Stayed with several friends for a wedding in Jamesport"
United States
Glenn F.
The price is HK$4,002
HK$9,835 total
includes taxes & fees
24 Oct - 25 Oct
North Fork Fall Escape—Vineyards, Apple Picking & Greenport
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

4. 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 HK$471
HK$3,388 total
includes taxes & fees
18 Oct - 19 Oct
Steps to the beach | Seabreeze Cottage #3
A beach with people relaxing on chairs and sunbathing.

5. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (27 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is HK$746
HK$1,999 total
includes taxes & fees
1 Nov - 2 Nov
Harbor Heights
A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

6. Amazing Southampton Home with Private Heated Pool

Amazing Southampton Home with Private Heated Pool
Southampton
9.0 out of 10, Wonderful, (2 reviews)
"Very cozy house in a great location!"
United States
Serina R.
The price is HK$4,725
HK$10,181 total
includes taxes & fees
20 Oct - 21 Oct
Amazing Southampton Home with Private Heated Pool
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

7. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is HK$746
HK$1,937 total
includes taxes & fees
9 Nov - 10 Nov
Aqua Vista
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

8. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (55 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is HK$746
HK$1,937 total
includes taxes & fees
10 Nov - 11 Nov
The SandPiper
An outdoor dining area with hanging lights, palm trees, and a bar.

9. 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 HK$1,562
HK$2,403 total
includes taxes & fees
15 Oct - 16 Oct
American Beech in Greenport - Petite King Room 7
A wooden pathway leading to a beach with scattered rocks and greenery.

10. 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 HK$1,530
HK$3,524 total
includes taxes & fees
3 Nov - 4 Nov
Beach Block Hideaway
A beach with people relaxing, a pier extending into the water, and a clear sky.

11. 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, (34 reviews)
"We had a wonderful stay in Greenport! The location was absolutely perfect, and one of the things we loved most was being able to walk to town and the beautiful harbor. Everything was so conveniently located, from the charming shops and wonderful restaurants to the lovely waterfront, making it easy to enjoy everything Greenport has to offer without needing to drive. We would happily stay here again and highly recommend this place to anyone looking for a wonderful Greenport getaway!"
United States
Nino
The price is HK$1,138
HK$2,941 total
includes taxes & fees
2 Nov - 3 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

12. Walk to Beach | Seabreeze Cottage #4

Walk to Beach | Seabreeze Cottage #4
Hampton Bays
8.6 out of 10, Excellent, (8 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is HK$432
HK$3,327 total
includes taxes & fees
15 Oct - 16 Oct
Walk to Beach | Seabreeze Cottage #4
A sign for J&S Reeves Cottages with a view of a house and trees.

13. 6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Riverhead
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay. Very quiet and relaxing. Excellent location to many wineries. Would definitely stay again."
United States
Donna M.
6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

14. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is HK$1,342
HK$4,600 total
includes taxes & fees
18 Oct - 19 Oct
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

15. 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)
"The host was very welcoming and the house was very clean"
United States
James W.
The price is HK$1,130
HK$2,502 total
includes taxes & fees
21 Oct - 22 Oct
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

16. Elegant 5-Bedroom Hamptons Home with Private Pool

Elegant 5-Bedroom Hamptons Home with Private Pool
Hampton Bays
9.4 out of 10, Exceptional, (43 reviews)
"The house was great. Pool was beautiful and everything was a 10 minute drive! Great place to relax"
United States
Judith M.
The price is HK$3,531
HK$7,684 total
includes taxes & fees
19 Oct - 20 Oct
Elegant 5-Bedroom Hamptons Home with Private Pool
A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

17. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is HK$1,766
HK$3,999 total
includes taxes & fees
19 Oct - 20 Oct
Charming Accommodations in the Hamptons
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

18. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is HK$4,909
HK$8,559 total
includes taxes & fees
15 Oct - 16 Oct
Beachfront Greenport Villa
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

19. 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 HK$4,227
HK$9,107 total
includes taxes & fees
15 Oct - 16 Oct
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

20. 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 HK$879
HK$13,092 total
includes taxes & fees
29 Oct - 30 Oct
Jacuzzi year-round - Villa Luz Private Home
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

Zey Hotel

Zey Hotel

10/10 Excellent
"It worked out well for me."
Elizabeth 1-night trip
Posted 13 hours ago
Zey Hotel

Find out more about Cutchogue

Search for holiday rentals in Cutchogue on Expedia! You can easily find your home rentals, villas, holiday apartments in Cutchogue using one of the methods below:

  • View our selection of featured holiday rentals in Cutchogue
  • Use the map to find apartments and other holiday homes in the Cutchogue neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cutchogue while they last

Look no further and take a look at our great range of rental properties in Cutchogue!

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.