Photo by Adriana T

Holiday Rentals in Cutchogue

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Holiday Rentals in Cutchogue

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (207)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
Cliffside Resort Condominiums

Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

10.0 out of 10, Exceptional, (81)
"Very relaxing place to stay 2 minutes from the beach and fabulous sunsets. Property was spotless with tons of room. "
Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

10.0 out of 10, Exceptional, (167)
"Group of 6 women getting together. Beautiful spacious home. We all had our own bedrooms. Having 4.5 baths was great. Plenty of space for all of us. Host was excellent and had great recommendations. Quick ride to the beautiful beach. "
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

Gorgeous private Hamptons house with pool and volleyball court

8.4 out of 10, Very good, (17)
"Enjoyed this house in a great location. It was perfect for attending a family wedding!"
Gorgeous private Hamptons house with pool and volleyball court

Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!

10.0 out of 10, Exceptional, (34)
"This home is quintessentially charming! I arrived late at night, alone. It has a charming curved drive in and there sat the wood home with a large front porch and Forrest behind it. It seemed like little house on a prairie with the porch and dormer windows. The motion lights went on immediately, which I was grateful for. There is a narrow stairwell up to 3 bedrooms, as is customary in older style homes. High ceilings and windows everywhere enhance this property. When I woke there was a family of...
Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (106)
"Wonderful place to spend time with the family in this cozy cottage. Would love to come back in the summer to enjoy the beach. "
The price is €473
includes taxes & fees
21 Jan - 22 Jan
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

Summer getaway

9.2 out of 10, Wonderful, (10)
"Overall, we had a terrific time at the house. Thank-you so much Andres for sharing your home with us. Getting there, checking in, all simple and easy. House was very well stocked. There was plenty of room for the eight of us. The beds were all comfortable. The deck was delightful. A couple of minor things that we had happen, or noticed that might want to be addressed. Given the house is controlled by Alexa, some detailed instructions as to how to work with "her" might be a good idea for...
Summer getaway

Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!

10.0 out of 10, Exceptional, (33)
"The house was perfect, a home away from home located in a nice quiet area, with stores and restaurants close by. House was clean, spacious and stocked with the essentials. The kids loved the pool and the ping pong table. Thank you Val for the perfect weekend, hope to see you next Summer!!"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

9.8 out of 10, Exceptional, (26)
"When my hometown sib couldn't host, we rented here and had our family Thanksgiving! It was great!"
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Soundview Beach House: 4BR, Panoramic Views

9.8 out of 10, Exceptional, (64)
"The house was exactly as advertised, the water views were beautiful! Easy access to the North Fork of Long Island."
Soundview Beach House: 4BR, Panoramic Views

Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms

10.0 out of 10, Exceptional, (18)
"The property was amazing and I highly recommend it! From the initial reservation to check-out - just fabulous! I have already suggested to 2 friends. "
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms

Beautiful Family Home Nestled In The Heart Of Sagaponack

10.0 out of 10, Exceptional, (30)
"Great space and location. We loved the house and enjoyed our stay. "
Beautiful Family Home Nestled In The Heart Of Sagaponack

Beachfront Romance: Rustic Home w/ Private Beach

9.2 out of 10, Wonderful, (46)
"We were looking for a small and private beach house getaway for the weekend and found this hidden gem. Our property manager, Debbie, made herself available throughout our stay to answer all of our questions. Everything needed for our comfort weekend was provided. We strongly recommend this place for those who are looking to get away from the hustle and bustle of city life. We will be returning! "
Beachfront Romance: Rustic Home w/ Private Beach

Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets

10.0 out of 10, Exceptional, (79)
"Second time staying here, great house right on the water. Owners are extremely responsive and helpful"
Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets

Private 2.1 acre gated home with heated pool and tennis & pickleball court

10.0 out of 10, Exceptional, (18)
"My family and I went to the Southamptons for our Christmas vacation. Since it was during the winter we didn’t try out the on-site tennis court or pool. The house is gorgeous and looks exactly as advertised. The host was in communication from 2-days before we arrived until checkout to assist as needed. We brought most of our gifts and a pop-up tree. All rooms have their own bathroom which is convenient. Plenty of linens and anything else you may need. If you’re used to using more than one oven...
Private 2.1 acre gated home with heated pool and tennis & pickleball court

Location and views! Located directly on Shinnecock Bay!

9.2 out of 10, Wonderful, (23)
"Stay was relaxing, space was very cozy. we enjoyed our stay. "
Location and views! Located directly on Shinnecock Bay!

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

10.0 out of 10, Exceptional, (11)
"The house is very nice. Very updated and clean. Best bathrooms in any house we have stayed in. The kitchen was large and very nice. Backyard is nice and private with plenty of room. My only issue is that there are so many trees that it blocks a lot of the sun. The pool is in the shade most of the time. In the hot summer it might be great to get some shade but our week was in the low 70's and we could have used a little more sun on the pool. House is in a good location, close to town and the...
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

Southampton Serenity Walk to beach. Kayaks on lake Park-like grounds Pool Tennis

9.8 out of 10, Exceptional, (25)
"Ken was great and easy to work with. The house was nice and perfect for our stay!"
Southampton Serenity Walk to beach. Kayaks on lake Park-like grounds Pool Tennis

Sag Harbor Suite by the Beach

8.8 out of 10, Excellent, (10)
"Trvis and Alice are great host and the property was a great place to stay close to the beach and downtown Sag Harbor."
Sag Harbor Suite by the Beach

1.5 Acre Luxury Escape - Saltwater Pool with Water Views

10.0 out of 10, Exceptional, (1)
"Very nice house In great shape and outstanding pool area."
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
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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Other types of properties in Cutchogue you may be interested in

Hyatt Place Long Island East End

3.0 star property
9.0 out of 10, Wonderful, (1004)
"Just Great!"
The price is €132
includes taxes & fees
28 Jan - 29 Jan
Hyatt Place Long Island East End

Hilton Garden Inn Riverhead

3.0 star property
8.6 out of 10, Excellent, (1000)
"I had 'dinner' at the bar. Just a chicken sandwich which was not especially good. Chicken had FAR to much breading and the chicken was overcooked. I was starved. Hadn't eaten all day. I ate it and left. "
The price is €131
includes taxes & fees
28 Jan - 29 Jan
Hilton Garden Inn Riverhead

Residence Inn by Marriott New York Long Island East End

3.0 star property
9.0 out of 10, Wonderful, (894)
"My family of five stayed here and really enjoyed our experience. The hotel was located within a quick drive of shops and restaurants. The staff were friendly. Our suite was clean, quiet, and nicely decorated. The beds were comfortable. The shower was spacious and had ample hot water and water pressure. The pool area was fun- my kids enjoyed the lights! If it had been warmer we would have gone outside to enjoy the firepit and lounge area. We had an early start the next morning and were...
The price is €141
includes taxes & fees
22 Jan - 23 Jan
Residence Inn by Marriott New York Long Island East End
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.

Frequently asked questions

Are there holiday rentals in Cutchogue?

Yes, there are holiday rentals close to the most popular sights in Cutchogue, 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?

Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!: This holiday home rental outside of Cutchogue is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Cutchogue?

With 42 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?

Explore the area and family-friendly sights such as Railroad Museum of Long Island, or get out into nature at a spot like Fisherman Beach. 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.