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Cutchogue Vacation Rentals

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Vacation Rentals in Cutchogue

Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, 185 reviews
"Had issue with check in. Nothing sent to phone as stated because of limited cell service in area. Had to go to office to get room and code. They have wrong room and had to go back for correct room. This was frustrating because it was after the check in time, which is later than most properties. The unit was fine, bare bones with decor etc. shower in one bathroom was leaking. I have stayed on property few times. This time was definitely less impressive."
The price is CA $428
CA $548 total
includes taxes & fees
Jun 27 - Jun 28
Cliffside Resort Condominiums
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, 18 reviews
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
Gorgeous private Hamptons house with pool and volleyball court
7.8 out of 10, Good, 7 reviews
"This place was nice and roomy for our family of 8 plus 3 littles kiddos. Pretty clean as well. I gave listing accuracy a 5 because it is accurate but that may be because it doesn't tell you much. We were a little short on towels, many light bulbs were burnt out or just missing. We replaced some (they were there) and moved others to balance out the light. No kitchen linens, short on bath towels, short on paper towels and definitely not enough TP. 3 partial rolls and 1 bathroom had none so we had...
Gorgeous private Hamptons house with pool and volleyball court
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Patchogue River Retreat, 8 minute walk to West Beach
10.0 out of 10, Exceptional, 6 reviews
"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
New Reno Hamptons Waterfront Beach House wBackyard Pool Oasis, and Private Beach
10.0 out of 10, Exceptional, 1 review
"Our overall expertise was great. Home was very clean and had all the essentials you need for a nice comfortable stay. The beds were very comfy, equipped with great linens and pillows. Home was cozy and comfortable. Can’t wait to stay again."
The price is CA $1,302
CA $2,420 total
includes taxes & fees
Jun 25 - Jun 26
New Reno Hamptons Waterfront Beach House wBackyard Pool Oasis, and Private Beach
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, 74 reviews
"From the minute I stepped on the property and then went inside, I fell in Love! So tranquil and peaceful, yet you can drive 10 minutes into the heart of it all and experience the reasons East Hampton’s is well known for, and then some! I have never been to a vacation home where I didn’t have to scrub down, clean and or have to pack everything I needed because it was ALL there. The attention to every detail .. I thank Rick for that and he was exceptionally responsive! ( this is my first booking...
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Location and views! Located directly on Shinnecock Bay!
9.0 out of 10, Wonderful, 13 reviews
"You have the opportunity to attend a graduation party at the Hamptons, where everyone had to find their own accommodations. The location is essentially located to town to the water and beautiful scenic paths. The host insured that the home was exceptionally clean and amenities provided. Not to mention accommodating due to last-minute change in schedule."
Location and views! Located directly on Shinnecock Bay!
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, 12 reviews
"Incredible property, incredible people to work with! We this is our second year in a row renting this house for a holiday weekend, and we look forward to renting every year forward! The house itself is stunning, clean and full of activities from the pool, to the tennis court, to the movie room. Rebecca and Shaun are truly a pleasure, and reply immediately to any questions, requests or needs. They even left us a welcome present for returning this year! Thank you for allowing us to have an annual...
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, 25 reviews
"House was very clean and host was exceptional. Very relaxing place to stay."
Beautiful Family Home Nestled In The Heart Of Sagaponack
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
10.0 out of 10, Exceptional, 4 reviews
The price is CA $8,699
CA $9,830 total
includes taxes & fees
Jul 2 - Jul 3
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, 86 reviews
"It was a cute cottage, nicely decorated. We were very comfortable. Each bedroom had a private bathroom which was very nice. It was close to downtown Southampton so that was great. The owner checked in and was very helpful. "
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.0 out of 10, Wonderful, 69 reviews
"We very much enjoyed our stay and the host had everything prepared for us. The check in/out process was very easy as well!"
The price is CA $492
CA $958 total
includes taxes & fees
Jun 21 - Jun 22
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, 52 reviews
"My family and I thoroughly enjoyed our time in Sag Harbor. The home was conveniently located and ideal for our five-day getaway. Daniel was quick to respond and offered excellent recommendations for restaurants and beach spots. The property was beautiful, and the pool provided a tranquil setting. We're eagerly anticipating future trips."
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
10.0 out of 10, Exceptional, 149 reviews
"the home was clean and as promised. The owner, Mark, was easy to work with, the pool and back yard were beautiful! I would definitely stay here again. Mark was available for all of our questions when we arrived. the location was amazing. the home is bright and airy, all beds were very comfortable, bathrooms were clean and updated. Nothing but positives to say about this property. Thank you Mark!"
The price is CA $1,638
CA $2,177 total
includes taxes & fees
Jul 2 - Jul 3
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
9.8 out of 10, Exceptional, 38 reviews
"Great place. Cozy cottage!"
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
Beachfront Romance: Rustic Home w/ Private Beach
9.2 out of 10, Wonderful, 41 reviews
"Love this place! Nice beach and quiet road. Great restaurant 5 minutes away."
Beachfront Romance: Rustic Home w/ Private Beach
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, 28 reviews
"The house was beautiful and comfortable. We enjoyed the property and watching the wildlife. The fire pit was great for a group gathering. We didn't cook but the kitchen appeared well stocked. The house was short on paper products. We left a note for the house manager when we left."
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets
10.0 out of 10, Exceptional, 75 reviews
"Great location. Pristine beach with hardly anyone else on the beach (mid May). No shampoo or conditioner in bathrooms as reported. The house needs a bit of TLC. Could be a bit cleaner. There was sand on the floor in the master bedroom upon our arrival. It seemed like there was white dog hair on the bedspread. I dont have a dog. The dishwasher seemed like it was working but was not getting the dishes clean. I think it is time for a new dishwasher."
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, 13 reviews
"Great for a large group!"
Recently renovated private 2.1 acre gated home with heated pool and tennis court
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
10.0 out of 10, Exceptional, 9 reviews
"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!"
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
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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.

Other types of properties in Cutchogue you may be interested in

The Bentley Hotel Southampton
2.0 star property
9.4 out of 10, Exceptional, 92 reviews
"Amazing hotel. "
The price is CA $388
CA $477 total
includes taxes & fees
Jun 24 - Jun 25
The Bentley Hotel Southampton
Greenview Inn Riverhead
2.0 star property
6.0 out of 10, 375 reviews
"I've been staying there when I work events in the Hamptons for a few years. Much nicer since the renovation. Still a cheap motel but cleaner and they are trying to improve the property. I'll continue to stay there when I don't want to drive to the city after a long days night."
The price is CA $139
CA $159 total
includes taxes & fees
Jul 21 - Jul 22
Greenview Inn Riverhead
Hilton Garden Inn Riverhead
3.0 star property
8.6 out of 10, Excellent, 1,001 reviews
"Okay place. Very close to freeway. TV is really screwed up. Honestly, someone has diverted channels like CNN and MSNBC. In fact, MSNBC goes directly to the right extremist InfoWars. Someone is hijacking your system."
The price is CA $231
CA $263 total
includes taxes & fees
Jun 25 - Jun 26
Hilton Garden Inn Riverhead
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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cutchogue vacation rentals we have selected for you start as low as CA $428 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 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 close to the most popular local attractions in Cutchogue, or you can select a more secluded option if you're looking for a relaxing stay.

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

Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!: This vacation home rental outside of Cutchogue is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Cutchogue?

With 42 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?

Explore the area and family-friendly sights such as Railroad Museum of Long Island, or get out into nature at a spot like Fisherman Beach. While here, Peconic Bay Winery and Bedell Cellars 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.

Recent reviews of Cutchogue properties
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