Book Holiday Homes in Cutchogue

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Featured Holiday Homes in Cutchogue

Large Charming Historic House close to Beaches

Large Charming Historic House close to Beaches

Clinton CT
Stay at this holiday 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
Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

Jamesport NY
Stay at this holiday home in Riverhead. Enjoy laundry facilities, patios and in-room jetted baths. Popular attractions Terra Vite North Fork Winery & Vineyard ...
Opens in a new windowComfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!
Aqua Vista

Aqua Vista

Greenport, NY
Stay at this holiday home in Greenport. Enjoy free Wi-Fi, laundry facilities and balconies. Popular attractions Railroad Museum of Long Island and East End Seaport ...
Opens in a new windowAqua Vista
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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 NY
Stay at this holiday 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
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 NY
Stay at this family-friendly holiday home in Sagaponack. Enjoy free Wi-Fi, private pools and a fitness centre. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowGrab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

Guilford CT
Stay at this holiday home in Guilford. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Chaffinch Island State Park and Guilford Town Green ...
Opens in a new windowA TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Hampton Bays NY
The price is NZ$2,196 per night from 4 Jan to 5 Jan
NZ$2,196
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this beach holiday home in Hampton Bays. Enjoy a beach locale, a garden and laundry facilities. Popular attractions Ponquogue Beach and Tiana Beach are ...
Opens in a new windowBlack Swan: Beachfront Home w/ Year-Round Jacuzzi
Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living

Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living

East Hampton NY
Stay at this holiday home in East Hampton. Enjoy an in-room coffee maker, in-room fireplaces and air conditioning. Popular attractions Georgica Beach and The ...
Opens in a new windowCharming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

East Hampton NY
Stay at this holiday home in East Hampton. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Pollock-Krasner House and Study Center and Kaplan ...
Opens in a new windowMid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
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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
1778 Holiday Homes
Lowest Price
NZ$248
Highest Price
NZ$2,196
Popular accommodation
Large Charming Historic House close to Beaches, Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!, Aqua Vista , Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access, Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available , A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!, Black Swan: Beachfront Home w/ Year-Round Jacuzzi, Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living, Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Top trending hotels in Cutchogue

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is NZ$484 per night from 1 Jan to 2 Jan
NZ$484
1 Jan - 2 Jan 2026
includes taxes & fees
Stay at this beach resort in Westbrook. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowWater's Edge Resort & Spa
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
Stay at this hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowPier Blue Inn Old Saybrook - Essex
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
The price is NZ$248 per night from 20 Jan to 21 Jan
NZ$248
20 Jan - 21 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Southampton. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowThe Bentley Hotel Southampton
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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$651 per night from 22 Jan to 23 Jan
NZ$651
22 Jan - 23 Jan 2026
includes taxes & fees
Stay at this spa hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in their reviews. ...
Opens in a new windowSaybrook Point Resort & Marina
Don't see what you're looking for?
See all available properties in Cutchogue
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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.