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Holiday Rentals in Cutchogue

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Holiday Rentals in Cutchogue

Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (247)
"Location good. Room could use some renos."
United States
Laura
Cliffside Resort Condominiums
1-bedroom cottage with Grove Beach 🏖️ access.
9.2 out of 10, Wonderful, (36)
"Host was very friendly and accommodating"
United States
Monika M.
The price is €194
includes taxes & fees
11 Nov - 12 Nov
1-bedroom cottage with Grove Beach 🏖️ access.
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
10.0 out of 10, Exceptional, (194)
"House was more then I can imagine , host was great , house literally have anything you forgot at home . "
United States
Isiah L.
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
10.0 out of 10, Exceptional, (89)
"Great house with awesome backyard, host responsive and very easy to work with! Would stay again!"
United States
Kilee B.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
9.6 out of 10, Exceptional, (142)
"Had a lovely time at our stay! Only regret was that we couldn’t stay longer, there were so many amenities we couldn’t take full advantage of. Such a beautiful property!"
United States
Gina K.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Shoreline Oasis
9.2 out of 10, Wonderful, (7)
"Cute apartment in a house, separate from the hosts space downstairs. Clean and walking distance to some great harbor-front restaurants. 1 bed and 2 couches (no pull-out couch)"
United States
Molly H.
The price is €232
includes taxes & fees
11 Nov - 12 Nov
Shoreline Oasis
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
10.0 out of 10, Exceptional, (95)
"Property was great! Rick was super responsive. It was a great trip to the Hamptons! "
United States
colin f.
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
10.0 out of 10, Exceptional, (35)
"This place is exactly as described. Was absolutely perfect, cozy, and comfortable. Thanks Kevin!"
United States
johanna s.
The price is €318
includes taxes & fees
10 Nov - 11 Nov
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
United States
Nicole L.
The price is €1,054
includes taxes & fees
27 Nov - 28 Nov
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Large Charming Historic House close to Beaches
9.8 out of 10, Exceptional, (34)
"We came down for a golf tournament and thoroughly enjoyed our stay. The house had plenty of room for all of us. A great beach close by."
United States
Marcia L.
Large Charming Historic House close to Beaches
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
9.8 out of 10, Exceptional, (32)
"This place was so nice and so close to so many fun places! "
United States
Daniella L.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
9.6 out of 10, Exceptional, (34)
"We had a lot of fun and created some nice memories"
United States
Scott T.
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
Cottage on Beach front Estate with Dockage .Walk to Village
10.0 out of 10, Exceptional, (72)
"Wonderful stay at such a special spot. "
United States
Meg B.
Cottage on Beach front Estate with Dockage .Walk to Village
RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston.
9.8 out of 10, Exceptional, (111)
"Cute place, very clean"
United States
Aviv P.
RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston.
American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is €250
includes taxes & fees
10 Nov - 11 Nov
American Beech in Greenport - Petite King Room 7
Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!
9.8 out of 10, Exceptional, (19)
"The house was clean and the location was magnificent. Jake was great, offered us early check in and late check out. The neighborhood was lovely, walked my pup and admired all of the beautiful homes. Definitely will stay there again. "
United States
Angela G.
Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!
Adorable Cottage, 5 min walk to water & town
9.4 out of 10, Exceptional, (14)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
Adorable Cottage, 5 min walk to water & town
Stunning Hampton Holiday Family Fantasy for your Team
9.8 out of 10, Exceptional, (74)
"This house was made for gatherings and has a massive cook's kitchen. Comfortable and tastefully decorated. A very lovely property."
United States
Linda C.
Stunning Hampton Holiday Family Fantasy for your Team
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
9.4 out of 10, Exceptional, (75)
"As always everything was excellent, This is our third stay at this property and we are booked for 2026"
United States
Michael R.
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
9.0 out of 10, Wonderful, (10)
"Enjoyed our time. House was clean, pool was a bonus for the family after a day at the beach. House was spacious and welcoming. Beds were very comfortable.Location was perfect! Would definitely come back!"
United States
Panagiota K.
The price is €1,743
includes taxes & fees
1 Dec - 2 Dec
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
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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Top Cutchogue Hotel Reviews

Find out more about Cutchogue

Everything you need to know about Cutchogue holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cutchogue holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cutchogue holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cutchogue holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cutchogue. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cutchogue holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cutchogue holiday rentals we have selected for you start as low as €194 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cutchogue rentals

At Expedia, we put the best Cutchogue holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cutchogue rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cutchogue holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cutchogue. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Cutchogue?

Yes, there are holiday rentals in Cutchogue close to 8 Hands Farm, or you can select a more secluded option if you're looking for a relaxing stay.

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

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : This holiday home rental outside of Cutchogue offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Cutchogue?

With 45 Expedia holiday rentals, you're guaranteed 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 holiday rental in Cutchogue like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cutchogue. Holiday rentals feature amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for family gatherings.