Book Holiday Homes in Cutchogue

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Featured Holiday Homes in Cutchogue

The SandPiper

The SandPiper

Greenport,
Stay at this vacation home in Greenport. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Railroad Museum of Long Island and East End Seaport ...
Opens in a new windowThe SandPiper
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12  Linens Included

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

Old Saybrook
The price is NZ$2,072 per night from 27 Nov to 28 Nov
NZ$2,072
27 Nov - 28 Nov
includes taxes & fees
Stay at this vacation home in Old Saybrook. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chalker Beach and Harvey's Beach are located ...
Opens in a new windowOceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

Amagansett
Stay at this vacation home in Amagansett. Enjoy laundry facilities, in-room fireplaces, and air conditioning. Popular attractions Amagansett Beach and Atlantic ...
Opens in a new windowWalk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access
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The Cooper-Burke House

The Cooper-Burke House

Sag Harbor
Stay at this vacation home in Sag Harbor. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions BookHampton and Sag Harbor Marine Park are located ...
Opens in a new windowThe Cooper-Burke House
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Sag Harbor
Book a stay at this family-friendly vacation home in Sagaponack. Enjoy free WiFi, private pools, and a fitness center. Our guests praise the helpful staff in ...
Opens in a new windowGrab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

Eastport
Book a stay at this family-friendly vacation home in Eastport. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Long Island Skydiving ...
Opens in a new window11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
Large Charming Historic House close to Beaches

Large Charming Historic House close to Beaches

Clinton
Stay at this vacation home in Clinton. Enjoy a garden, laundry facilities, and patios. Popular attractions Adam Stanton House and General Store Museum and Indian ...
Opens in a new windowLarge Charming Historic House close to Beaches
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Hampton Bays
Book a stay at this beach vacation home in Hampton Bays. Enjoy a beach locale, a garden, and laundry facilities. Popular attractions Cooper's Beach and Meschutt ...
Opens in a new windowBeautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...

Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...

Southampton
Stay at this vacation home in Southampton. Enjoy private pools, laundry facilities, and patios. Popular attractions Cooper's Beach and North Main Street Historic ...
Opens in a new windowQuintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
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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.

Cutchogue Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Cutchogue vacation homes are the perfect way for you to wing it.

Holiday houses in Cutchogue let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Cutchogue in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Cutchogue adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Cutchogue with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Cutchogue vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Cutchogue Holiday Homes essential information

Accommodation
1848 Holiday Homes
Lowest Price
NZ$161
Highest Price
NZ$2,072
Popular accommodation
The SandPiper , Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included, Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access, The Cooper-Burke House, Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available , 11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms, Large Charming Historic House close to Beaches, Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!, Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...

Top trending hotels in Cutchogue

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is NZ$161 per night from 6 Nov to 7 Nov
NZ$161
6 Nov - 7 Nov
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Opens in a new windowPier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is NZ$399 per night from 18 Nov to 19 Nov
NZ$399
18 Nov - 19 Nov
includes taxes & fees
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Opens in a new windowSound View Greenport
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is NZ$523 per night from 12 Nov to 13 Nov
NZ$523
12 Nov - 13 Nov
includes taxes & fees
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
Opens in a new windowSaybrook Point Resort & Marina
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The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
Stay at this hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
Opens in a new windowThe Atlantic Hotel
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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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^Subject to availability and chosen travel dates.