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Cutchogue Vacation Rentals

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Vacation Rentals in Cutchogue

Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (70)
"Ricks home is STUNNING and very thoughtfully decorated. He was responsive and flexible. Thank you for an amazing stay!"
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (27)
"Communicative property manger!! Clean, cute, and quaint. Had the perfect weekend here!!"
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Contemporary home, newly built, heated pool and hot tub, large deck and...
10.0 out of 10, Exceptional, (4)
"The property manager was incredibly helpful in providing check-in and check-out information, and was readily available to answer any questions during our stay. The house perfectly matched what we saw in the photos and was ideal for our getaway. We're already looking forward to returning in the summertime to fully enjoy the pool."
Contemporary home, newly built, heated pool and hot tub, large deck and...
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Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, (82)
"Great property in a great location"
The price is $650
$971 total
includes taxes & fees
May 3 - May 4
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Patchogue River Retreat, 8 minute walk to West Beach
10.0 out of 10, Exceptional, (6)
"House was very nice. Location is great. Easy walk to beach and convenient to Westbrook center."
Patchogue River Retreat, 8 minute walk to West Beach
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
10.0 out of 10, Exceptional, (144)
"We had an amazing time at Mark's house. The home is clean and well maintained with many amenities that made the weekend extra special (cool nights by the fire pit were especially awesome)! Mark gave detailed directions about the house and provided us with lots of information about the neighborhood. Plenty of space for all 12 of us to be together. Highly recommend this rental!"
The price is $495
$782 total
includes taxes & fees
May 29 - May 30
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (88)
"Positive experience, great location, and cozy accommodations for a centrally located family weekend."
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
10.0 out of 10, Exceptional, (22)
"Celebrated the holidays with my grown children to be near my dad and brother. The house is lovely. We had a wonderful time. My daughter suggested we come back in the summertime to take advantage of the amenities - beautiful pool and nearby beaches. Highly recommend!!!"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets
10.0 out of 10, Exceptional, (73)
"Wonderful home and location on Westhampton Beach. Very clean home, spacious bedrooms and modern kitchen. Better than advertised."
Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets
Recently renovated private 2.1 acre gated home with heated pool and tennis court
10.0 out of 10, Exceptional, (11)
"This beautiful home was a great vacation home for our entire family! The house was impeccably clean with a ton of amenities, everything we wanted or needed was provided. The basketball/tennis court provided hours of entertainment for our family and the swimming pool made for a great leisurely morning or afternoon of swimming and relaxing poolside. Julie was a very attentive host and responded to our text messages for suggestions on Gurney's Seawater Spa, Vegan restaurants and more. We had a...
Recently renovated private 2.1 acre gated home with heated pool and tennis court
AMAZING LUXURY HOME ~ HUGE PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
10.0 out of 10, Exceptional, (9)
"This is a beautiful, comfortable and recently renovated home in a lovely neighborhood. The yard is also very nice, it was too cold for the pool but we enjoyed the hot tub and outdoor seating areas. We had a wonderful stay!"
AMAZING LUXURY HOME ~ HUGE PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Summer getaway
9.6 out of 10, Exceptional, (5)
"We had a great stay at the house! It was much larger than we even expected and came outfitted with everything you could need for a weekend away in July. Our host was super communicative and flexible. The pool is perfect and the location is ideal for a comprehensive weekend away in the Hamptons. We will be back- thank you again!"
Summer getaway
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, (18)
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (11)
"Since I stay for 2 days only it was fine. Check the shades , toilet paper and more towels. "
Location and views! Located directly on Shinnecock Bay!
Beachfront Romance: Rustic Home w/ Private Beach
9.2 out of 10, Wonderful, (39)
"The house is small but it has everything you need. The ocean was lovely to watch and good scavenging for rocks and sea glass. Very private place. My pup and I had a good time!"
Beachfront Romance: Rustic Home w/ Private Beach
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (179)
"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling. "
The price is $209
$282 total
includes taxes & fees
May 19 - May 20
Cliffside Resort Condominiums
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.0 out of 10, Wonderful, (69)
"We very much enjoyed our stay and the host had everything prepared for us. The check in/out process was very easy as well!"
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Airstream Art Studio Sculpture/Nature Preserve
The price is $150
$235 total
includes taxes & fees
May 2 - May 3
Airstream Art Studio Sculpture/Nature Preserve
Beautiful 3 bedroom Residence in the Hamptons
Beautiful 3 bedroom Residence in the Hamptons
Don't see what you're looking for?
See all available properties in Cutchogue
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.

Other types of properties in Cutchogue you may be interested in

Saybrook Point Resort & Marina
3.5 star property
9.4 out of 10, Exceptional, (1001)
"A beautiful resort in a quiet location. There wasn’t much to do this time of year. Most places in town closed pretty early. It was a relaxing time nonetheless. Would definitely return. Staff were top notch!"
The price is $295
$360 total
includes taxes & fees
May 7 - May 8
Saybrook Point Resort & Marina
Residence Inn by Marriott New York Long Island East End
3.0 star property
9.2 out of 10, Wonderful, (761)
"Staff is Great!! lovely area and one of the best hotels. "
The price is $143
$163 total
includes taxes & fees
May 5 - May 6
Residence Inn by Marriott New York Long Island East End
Hyatt Place Long Island East End
3.0 star property
9.0 out of 10, Wonderful, (1002)
"Front desk very good attitude and attention "
The price is $152
$174 total
includes taxes & fees
May 19 - May 20
Hyatt Place Long Island East End
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.

Everything you need to know about Cutchogue vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cutchogue vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cutchogue vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cutchogue in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cutchogue rentals

At Expedia, we put the best Cutchogue vacation 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 vacation.

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 vacation rentals in Cutchogue?

Yes, you can find vacation rentals in Cutchogue close to Peconic Bay Winery, or you can choose a more secluded option if you want a relaxing stay.

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

Contemporary home, newly built, heated pool and hot tub, large deck and...: This vacation home rental outside of Cutchogue offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a stovetop, a microwave, and a coffee maker, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a spa tub.

How many vacation rentals are there in Cutchogue?

With 44 Expedia vacation rentals, you're sure to find just the right place for your Cutchogue stay.

What’s there to see and do in Cutchogue?

Family-friendly attractions include Peconic Bay Winery, whereas Fisherman Beach is a spot to enjoy the outdoors. While here, Bedell Cellars and Pugliese Vineyards are other places worth a visit.

What’s a vacation rental in Cutchogue like?

Vacation rentals are private properties you can stay in for short or long periods in Cutchogue. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.

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