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Cutchogue Holiday Rentals

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Our top choices for Cutchogue holiday rentals

Seabreeze #4: Charming Cottage Footsteps to the Beach

Seabreeze #4: Charming Cottage Footsteps to the Beach
Hampton Bays
8.8 out of 10, Excellent, (3)
"Great stay. Would stay again. "
United States
Weston B.
The price is NZ$776
includes taxes & fees
20 Jan - 21 Jan 2026
Seabreeze #4: Charming Cottage Footsteps to the Beach

Blackberry: Private home with jacuzzi year-round

Blackberry: Private home with jacuzzi year-round
East Hampton
9.0 out of 10, Wonderful, (4)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is NZ$1,586
includes taxes & fees
4 Jan - 5 Jan 2026
Blackberry: Private home with jacuzzi year-round

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Hampon Bays
9.6 out of 10, Exceptional, (22)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is NZ$2,209
includes taxes & fees
4 Jan - 5 Jan 2026
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.2 out of 10, Wonderful, (36)
"Very clean rustic cabin. The host was very accommodating. Fresh flowers and fruit were a nice touch from the host"
United States
Deb P.
The price is NZ$362
includes taxes & fees
6 Jan - 7 Jan 2026
1-bedroom cottage with Grove Beach 🏖️ access.

Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach
Hampton Bays
10.0 out of 10, Exceptional, (1)
The price is NZ$768
includes taxes & fees
4 Jan - 5 Jan 2026
Seabreeze #3: Cozy Cottage by the beach

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Hampton Bays
9.6 out of 10, Exceptional, (14)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is NZ$2,211
includes taxes & fees
4 Jan - 5 Jan 2026
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Saybrook Manor
9.6 out of 10, Exceptional, (133)
"We loved our stay!"
United States
Deana L.
The price is NZ$1,005
includes taxes & fees
22 Dec - 23 Dec
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (14)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
Adorable Cottage, 5 min walk to water & town

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is NZ$431
includes taxes & fees
22 Dec - 23 Dec
American Beech in Greenport - Petite King Room 7

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is NZ$1,010
includes taxes & fees
7 Jan - 8 Jan 2026
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

LONG-TERM Relaxing Glass House - Fall Leaves/Beach 5mins/Ski 25mins

LONG-TERM Relaxing Glass House - Fall Leaves/Beach 5mins/Ski 25mins
2.0 star property
Clinton
10.0 out of 10, Exceptional, (3)
"Vincent was amazing to work with! We decided to change the dates and he was very patient and helpful while we got it updated with VRBO. The home is in a peaceful neighborhood with beautiful trees and active squirrels (my daughter’s favorite part). The location was convenient for our needs. We all enjoyed the game tables and the convenience of the washer and dryer. We even tried out the projector one night to watch a couple of episodes of Gilmore Girls – so fun! Vincent checked in once we arrived...
United States
Erin S.
LONG-TERM Relaxing Glass House - Fall Leaves/Beach 5mins/Ski 25mins

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
Westbrook
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is NZ$891
includes taxes & fees
7 Jan - 8 Jan 2026
Beachside Bliss w/ Game Room, Gym & Golf Green

Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5)
"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$1,115
includes taxes & fees
22 Dec - 23 Dec
Immaculate Waterfront 2 bedroom!

Shoreline Oasis

Shoreline Oasis
Clinton
9.2 out of 10, Wonderful, (7)
"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "
United States
Tom S.
The price is NZ$453
includes taxes & fees
22 Dec - 23 Dec
Shoreline Oasis

Northfork Townhouse- walk to all/ newly renovated

Northfork Townhouse- walk to all/ newly renovated
Greenport
9.6 out of 10, Exceptional, (9)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
The price is NZ$970
includes taxes & fees
22 Dec - 23 Dec
Northfork Townhouse- walk to all/ newly renovated

Charming Northfork Townhouse- walk to all

Charming Northfork Townhouse- walk to all
Greenport
10.0 out of 10, Exceptional, (5)
"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$1,157
includes taxes & fees
22 Dec - 23 Dec
Charming Northfork Townhouse- walk to all

Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass
Guilford
9.2 out of 10, Wonderful, (90)
"The location of this place is best!"
United States
Dr. Maureen C.
The price is NZ$712
includes taxes & fees
1 Jan - 2 Jan 2026
Historic New England home ,Reunions Beach pass

Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean
Clinton
10.0 out of 10, Exceptional, (1)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is NZ$627
includes taxes & fees
22 Dec - 23 Dec
Stylish Modern Stay Steps from the Ocean

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (3)
"perfect for families"
United States
Okito H.
The price is NZ$1,927
includes taxes & fees
22 Dec - 23 Dec
Minutes from the beach, brand new 4 bedroom
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

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, 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 NZ$453 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 OPEN,Beach,Fam Fr: 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 45 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.