Book Holiday Homes in Cutchogue

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Featured Holiday Homes in Cutchogue

Enjoy Autumn with us.

Enjoy Autumn with us.

Southold
Located in Southold, this vacation home is by the sea, within a 5-minute drive of The Old Field Vineyards and Sparkling Pointe.
Enjoy Autumn with us.
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 near the beach, a 3-minute walk from Moriches Bay and within a 5-minute drive of Long Island Skydiving Center.
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
Beautiful Private 4 BR, Heated Pool. Close to Everything.

Beautiful Private 4 BR, Heated Pool. Close to Everything.

East Hampton
With a stay at this vacation home in East Hampton, you'll be near the beach, within a 10-minute drive of The Hamptons Beaches and Three Mile Harbor.
Beautiful Private 4 BR, Heated Pool. Close to Everything.
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Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub

Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub

Westhampton
With a stay at this vacation home in Westhampton, you'll be on the waterfront, within a 10-minute drive of The Hamptons Beaches and Westhampton Beach Performing ...
Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub
Cozy Westbrook Vacation Rental - Walk to Beach!

Cozy Westbrook Vacation Rental - Walk to Beach!

Westbrook
With a stay at this vacation home in Westbrook (Westbrook Center), you'll be a 1-minute drive from Westbrook Town Beach and 6 minutes from Tanger Outlets.
Cozy Westbrook Vacation Rental - Walk to Beach!
Village Fringe Available May 24th - October 31st. Family/Pet Friendly

Village Fringe Available May 24th - October 31st. Family/Pet Friendly

East Hampton
With a stay at this vacation home in East Hampton (East Hampton North), you'll be within a 5-minute drive of The Hamptons Beaches and East Hampton Historical ...
Village Fringe Available May 24th - October 31st. Family/Pet Friendly
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach

COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach

Amagansett
With a stay at this vacation home in Amagansett (Beach Hampton), you'll be steps from The Hamptons Beaches and 14 minutes by foot from Amagansett Beach.
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

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

Westhampton Beach
With a stay at this vacation home in Westhampton Beach, you'll be by the sea, within a 5-minute drive of The Hamptons Beaches and Westhampton Beach Performing ...
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Southampton
With a stay at this vacation home in Southampton, you'll be within a 10-minute drive of The Hamptons Beaches and Southampton Golf Range.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
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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
1500 Holiday Homes
Lowest Price
AU$124
Highest Price
AU$335
Popular accommodation
Enjoy Autumn with us., 11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms, Beautiful Private 4 BR, Heated Pool. Close to Everything., Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub , Cozy Westbrook Vacation Rental - Walk to Beach!, Village Fringe Available May 24th - October 31st. Family/Pet Friendly, COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach, WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr, Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

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 AU$335 per night from 9 Mar to 10 Mar
AU$335
includes taxes & fees
9 Mar - 10 Mar
With a stay at Water's Edge Resort & Spa in Westbrook (Westbrook Center), you'll be a 4-minute drive from Tanger Outlets and 8 minutes from Clinton Crossing ...
Water'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
The price is AU$124 per night from 27 Feb to 28 Feb
AU$124
includes taxes & fees
27 Feb - 28 Feb
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.
Pier Blue Inn Old Saybrook - Essex
Hyatt Place Long Island East End

Hyatt Place Long Island East End

3 out of 5
451 East Main Street, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 16 Mar to 17 Mar
AU$185
includes taxes & fees
16 Mar - 17 Mar
With a stay at Hyatt Place Long Island East End in Riverhead, you'll be on a river, just a 5-minute walk from Suffolk Theater and 6 minutes by foot from All ...
Hyatt Place Long Island East End
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Residence Inn by Marriott New York Long Island East End

Residence Inn by Marriott New York Long Island East End

3 out of 5
2012 Old Country Road, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is AU$233 per night from 24 Feb to 25 Feb
AU$233
includes taxes & fees
24 Feb - 25 Feb
With a stay at Residence Inn by Marriott New York Long Island East End in Riverhead, you'll be within a 15-minute walk of Tanger Outlet Center and Riverhead ...
Residence Inn by Marriott New York Long Island East End
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.