Book Holiday Homes in Cutchogue

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Featured Holiday Homes in Cutchogue

The SandPiper

The SandPiper

Greenport,
With a stay at this vacation home in Greenport (Pipes Cove), you'll be steps from Railroad Museum of Long Island and 3 minutes by foot from 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 AU$1,819 per night from 27 Nov to 28 Nov
AU$1,819
27 Nov - 28 Nov
includes taxes & fees
Located in Old Saybrook, this vacation home is on the waterfront, a 5-minute walk from Chalker Beach and within a 5-minute drive of Crystal Lake Town Park.
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
With a stay at this vacation home in Amagansett (Beach Hampton), you'll be within a 10-minute walk of The Hamptons Beaches and Amagansett Beach.
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
A stay at this vacation home places you in the heart of Sag Harbor, within a 15-minute walk of The Hamptons Beaches and BookHampton.
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
With a stay at this vacation home in Sagaponack, you'll be by the sea, within a 10-minute drive of The Hamptons Beaches and Wolffer Estates Vineyard.
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
Located in Eastport, this vacation home is on the waterfront, a 3-minute walk from Moriches Bay and within a 5-minute drive of Long Island Skydiving Center.
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
With a stay at this vacation home in Clinton, you'll be near the beach, just a 4-minute walk from Adam Stanton House and General Store Museum and 12 minutes ...
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
When you stay at this vacation home in Hampton Bays, you'll be on the beach, within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.
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
With a stay at this vacation home in Southampton, you'll be within a 10-minute drive of Cooper's Beach and The Hamptons Beaches.
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
AU$140
Highest Price
AU$1,819
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 AU$140 per night from 2 Nov to 3 Nov
AU$140
2 Nov - 3 Nov
includes taxes & fees
Located in Old Saybrook (Saybrook Manor), Pier Blue Inn Old Saybrook - Essex is within a 5-minute drive of Chalker Beach and Crystal Lake Town Park.
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 AU$425 per night from 13 Nov to 14 Nov
AU$425
13 Nov - 14 Nov
includes taxes & fees
When you stay at Sound View Greenport in Greenport, you'll be by the ocean, within a 5-minute drive of Kontokosta Winery and 67 Steps Beach.
Opens in a new windowSound View Greenport
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 AU$224 per night from 6 Nov to 7 Nov
AU$224
6 Nov - 7 Nov
includes taxes & fees
When you stay at The Bentley Hotel Southampton in Southampton, you'll be near the airport, within a 5-minute drive of The Hamptons Beaches and Meschutt ...
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 AU$454 per night from 12 Nov to 13 Nov
AU$454
12 Nov - 13 Nov
includes taxes & fees
With a stay at Saybrook Point Resort & Marina in Old Saybrook (Old Saybrook Center), you'll be steps from Fort Saybrook Monument Park and 4 minutes by foot from ...
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.