Cutchogue Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Cutchogue vacation rentals

9.6 out of 10, Exceptional, (37 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is CA $110
CA $246 total
includes taxes & fees
Mar 4 - Mar 5
1-bedroom cottage with Grove Beach 🏖️ access.
3.0 star property
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is CA $394
CA $450 total
includes taxes & fees
Apr 1 - Apr 2
North Fork Cottages & RV Resort
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is CA $145
CA $670 total
includes taxes & fees
Mar 7 - Mar 8
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is CA $163
CA $273 total
includes taxes & fees
Mar 4 - Mar 5
American Beech in Greenport - Petite King Room 7

Apartment in Clinton

Shoreline Oasis
9.2 out of 10, Wonderful, (7 reviews)
"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 CA $244
CA $357 total
includes taxes & fees
Apr 3 - Apr 4
Shoreline Oasis
9.6 out of 10, Exceptional, (43 reviews)
"Excellent hosts, great communication and adorable place and location.Totally recommend!!"
United States
Joan G.
The price is CA $326
CA $684 total
includes taxes & fees
Mar 5 - Mar 6
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
The price is CA $137
CA $392 total
includes taxes & fees
Mar 4 - Mar 5
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
The price is CA $229
CA $995 total
includes taxes & fees
Mar 15 - Mar 16
Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool
8.6 out of 10, Excellent, (8 reviews)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
The price is CA $614
CA $1,159 total
includes taxes & fees
Mar 4 - Mar 5
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
10.0 out of 10, Exceptional, (1 review)
"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 CA $221
CA $460 total
includes taxes & fees
Mar 12 - Mar 13
Stylish Modern Stay Steps from the Ocean
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is CA $227
CA $737 total
includes taxes & fees
Mar 4 - Mar 5
Beachside Bliss w/ Game Room, Gym & Golf Green

Apartment in East Quogue

Hamptons apartment getaway
6.0 out of 10, (3 reviews)
"The room was a lot more spacious than I anticipated and everything was very clean. There was some music playing upstairs but it was quiet by nighttime. Check in and check out was very straightforward. Turning into the driveway was a bit difficult when the highway was crowded but was otherwise easy to find "
United States
Hilary K.
The price is CA $205
CA $400 total
includes taxes & fees
Mar 4 - Mar 5
Hamptons apartment getaway

Vacation Home in Hampton Bays

Immaculate Waterfront 2 bedroom!
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 CA $444
CA $880 total
includes taxes & fees
Mar 4 - Mar 5
Immaculate Waterfront 2 bedroom!

Vacation Home in Greenport

Renovated Townhouse walk to all
9.6 out of 10, Exceptional, (10 reviews)
"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 CA $357
CA $784 total
includes taxes & fees
Mar 4 - Mar 5
Renovated Townhouse walk to all

Vacation Home in Greenport

Northfork Townhouse walk to all
10.0 out of 10, Exceptional, (5 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 CA $374
CA $806 total
includes taxes & fees
Mar 5 - Mar 6
Northfork Townhouse walk to all

Vacation Home in Calverton

Cozy beach hose minutes from Hamptons
10.0 out of 10, Exceptional, (1 review)
"Beautiful home and location. Owner was very helpful. Would love to rent again!"
United States
Evelyn D.
The price is CA $482
CA $978 total
includes taxes & fees
Mar 9 - Mar 10
Cozy beach hose minutes from Hamptons
The price is CA $443
CA $837 total
includes taxes & fees
Apr 3 - Apr 4
Prime location, walk to all, cozy cottage Westhampton Beach
10.0 out of 10, Exceptional, (3 reviews)
"perfect for families"
United States
Okito H.
The price is CA $615
CA $1,517 total
includes taxes & fees
Mar 5 - Mar 6
Minutes from the beach, brand new 4 bedroom
9.8 out of 10, Exceptional, (19 reviews)
"Great cottage on amazing grounds! We loved the screened in porch. Sandy and john are great hosts. We also loved using the kayaks and checking out the bay."
United States
Richard C.
The price is CA $780
CA $1,105 total
includes taxes & fees
Mar 4 - Mar 5
4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is CA $438
CA $875 total
includes taxes & fees
Mar 16 - Mar 17
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Cutchogue Hotel Reviews

Find out more about Cutchogue

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Cutchogue?

Yes, you can find vacation rentals in Cutchogue close to 8 Hands Farm, or you can choose a more secluded option if you want a relaxing stay.

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

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!: This vacation home rental outside of Cutchogue is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Cutchogue?

With 43 Expedia vacation rentals, you're sure 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 vacation rental in Cutchogue like?

Vacation rentals are private properties you can stay in for short or long periods in Cutchogue. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.