Cutchogue Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Cutchogue holiday rentals

Free WiFi, bed sheets

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is HK$1,457
HK$1,664 total
includes taxes & fees
20 Apr - 21 Apr
North Fork Cottages & RV Resort
Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (249 reviews)
"Great stay - beautiful place"
United States
Rebecca
The price is HK$1,128
HK$1,629 total
includes taxes & fees
29 Apr - 30 Apr
Cliffside Resort Condominiums
Exterior detail

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Calverton
8.6 out of 10, Excellent, (8 reviews)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
The price is HK$3,517
HK$6,640 total
includes taxes & fees
16 Apr - 17 Apr
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Terrace/patio

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (16 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is HK$3,281
HK$9,576 total
includes taxes & fees
26 Apr - 27 Apr
Black Swan Beachfront Home with Jacuzzi year round
Property grounds

Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (11 reviews)
"Super location - just near The beautiful village of Greenport with a sweeping view of the bay, A very happy house - super Clean, and we had everything that we needed. Meghan was a wonderful host, and answered us quickly with any question that we had. I loved the NorthFork and this home was the perfect place to stay!"
United States
Carine J.
The price is HK$4,898
HK$8,540 total
includes taxes & fees
16 Apr - 17 Apr
Beachfront Greenport Villa
Beach

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is HK$1,723
HK$4,755 total
includes taxes & fees
21 Apr - 22 Apr
Beachside Bliss w/ Game Room, Gym & Golf Green
Beach nearby

Charming 1-bedroom apartment with AC, 3 minute walk to beach, and new hot tub

Charming 1-bedroom apartment with AC, 3 minute walk to beach, and new hot tub
Westbrook Center
9.0 out of 10, Wonderful, (2 reviews)
"Very clean and well informed about the beach accessibility, and places to eat around the area. "
United States
Nickolas S.
Charming 1-bedroom apartment with AC, 3 minute walk to beach, and new hot tub
Interior

Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (5 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is HK$5,482
HK$7,086 total
includes taxes & fees
16 Apr - 17 Apr
Cozy Hamptons Escape 3BR Minutes From Beach!
Fridge, microwave, oven, stovetop

Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (53 reviews)
"This place is a perfect oasis in an already special environment. The host was wonderful and thoughtful. The cottage was magical and had everything to offer that one could want. "
United States
Adam M.
The price is HK$5,638
HK$10,423 total
includes taxes & fees
16 Apr - 17 Apr
Work and Play Special! Extended Stay Discount
Interior

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (136 reviews)
"This house was in a great location for our extended family Christmas gathering in Deep River. There was more than enough room for 3 adult couples and 2 older children tonstay comfortably & enjoy a cosy fire in fireplace one evening. "
United States
Karen B.
The price is HK$1,763
HK$4,244 total
includes taxes & fees
19 Apr - 20 Apr
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Living area

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is HK$11,700
HK$15,273 total
includes taxes & fees
16 Apr - 17 Apr
Cozy 5 Bedroom With Wi-fi And Air Condition
Property grounds

Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Southampton
10.0 out of 10, Exceptional, (15 reviews)
"We loved our stay here it was a lovely, warm and beautifully appointed home with a great pool and walkable to town. We hope to be able to return here again soon!"
United States
Deborah V.
The price is HK$9,906
HK$13,619 total
includes taxes & fees
26 Apr - 27 Apr
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Property grounds

Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean
Clinton
10.0 out of 10, Exceptional, (1 review)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is HK$940
HK$2,201 total
includes taxes & fees
25 Apr - 26 Apr
Stylish Modern Stay Steps from the Ocean
Interior

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is HK$7,823
HK$13,179 total
includes taxes & fees
1 May - 2 May
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Smart TV, fireplace, stereo

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (4 reviews)
"perfect for families"
United States
Okito H.
The price is HK$5,286
HK$10,987 total
includes taxes & fees
23 Apr - 24 Apr
Minutes from the beach, brand new 4 bedroom
Interior

Sag Harbor Water View w Dock 1.5ml from town

Sag Harbor Water View w Dock 1.5ml from town
Bay Point
The price is HK$14,096
HK$22,484 total
includes taxes & fees
26 Apr - 27 Apr
Sag Harbor Water View w Dock 1.5ml from town
1 bedroom, desk, iron/ironing board, travel cot

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (40 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is HK$648
HK$1,434 total
includes taxes & fees
27 Apr - 28 Apr
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV, fireplace, ping pong, books

NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock

NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock
Water Mill
10.0 out of 10, Exceptional, (6 reviews)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is HK$21,144
HK$42,901 total
includes taxes & fees
16 Apr - 17 Apr
NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock
Interior

Cozy beach hose minutes from Hamptons

Cozy beach hose minutes from Hamptons
Calverton
10.0 out of 10, Exceptional, (1 review)
"Beautiful home and location. Owner was very helpful. Would love to rent again!"
United States
Evelyn D.
The price is HK$3,263
HK$6,251 total
includes taxes & fees
20 Apr - 21 Apr
Cozy beach hose minutes from Hamptons
Beach nearby

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Westbrook Center
The price is HK$1,080
HK$3,028 total
includes taxes & fees
19 Apr - 20 Apr
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
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

The Preston House & Hotel

The Preston House & Hotel

10/10 Excellent
"Absolutely adorably chic hotel in the heart of Riverhead. Clean modern comfy clean. Wonderful lavassa expresso machine in room and fabulous buffet style breakfast including pastries croissants fruit yogurt cold cereal juice and coffee. Staff super friendly. I would Definitely recommend & will be back again someday I’m sure!"
DINA 2-night trip
Posted 2 hours ago
The Preston House & Hotel

Find out more about Cutchogue

Search for holiday rentals in Cutchogue on Expedia! You can easily find your home rentals, villas, holiday apartments in Cutchogue using one of the methods below:

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Look no further and take a look at our great range of rental properties in Cutchogue!

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?

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!: This holiday home rental outside of Cutchogue is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Cutchogue?

With 40 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 Pellegrini Vineyards 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.