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Cutchogue Holiday Rentals

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Holiday Rentals in Cutchogue

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (226)
"Very nice, clean and cosy place! Highly recommend!"
The price is HK$2,640
HK$3,358 total
includes taxes & fees
14 Jul - 15 Jul
Cliffside Resort Condominiums

Canoe Place Waterfront Residences

4.0 star property
Canoe Place Waterfront Residences

Hamptons Retreat

Hamptons Retreat

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (68)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool

Escape to Sag Harbor

10.0 out of 10, Exceptional, (47)
"Amazing house and location!! Would stay again "
Escape to Sag Harbor

Shoreline Oasis

6.0 out of 10, (1)
"So the listing said house number 26 but it's really 25. So we circled the block a few times. Then the key was not in the key safe. Called the owner who apologized profusely. Had to wait a half hour for the key. Not ideal. Otherwise ok. "
The price is HK$1,405
HK$2,061 total
includes taxes & fees
10 Jul - 11 Jul
Shoreline Oasis

Perfect Mid-Century Private Waterfront East Hampton Retreat!

10.0 out of 10, Exceptional, (79)
"Very nice and relaxing stay in Springs! "
Perfect Mid-Century Private Waterfront East Hampton Retreat!

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (33)
"We had a amazing stay and plan to come back next July again"
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

adorable ranch in beach community

10.0 out of 10, Exceptional, (45)
"Close to the shore and the heart of Old Saybrook. The house is very comfortable."
The price is HK$2,747
HK$5,071 total
includes taxes & fees
10 Jul - 11 Jul
adorable ranch in beach community

Private Beach Community in East Hampton! Pool, HotTub, Trampoline & Pirate Ship!

10.0 out of 10, Exceptional, (85)
"It was a great stay"
Private Beach Community in East Hampton! Pool, HotTub, Trampoline & Pirate Ship!

July Flash Sale: Luxury Beach House, Heated Pool, Dune Rd beaches, pets ok

10.0 out of 10, Exceptional, (10)
"An absolute perfect home for a family looking to enjoy"
July Flash Sale: Luxury Beach House, Heated Pool, Dune Rd beaches, pets ok

East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard

10.0 out of 10, Exceptional, (75)
"Stayed here over Thanksgiving. Beautiful house, well appointed, great location. The Hamptons at Thanksgiving are very vibrant. Highly recommend a stay here. "
East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard

Charming East Hampton Home, private yard with fenced in pool, perfect for...

Charming East Hampton Home, private yard with fenced in pool, perfect for...

Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum

10.0 out of 10, Exceptional, (45)
"Great house, kitchen is well equipped which made dining in very easy. Loved the pool and backyard."
Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum

Lovely North Fork Beach Cottage (2 BR/2 bath)!

10.0 out of 10, Exceptional, (114)
"We were pleased with our stay. The house was very clean. My contact with the property manager were great. Would stay again."
Lovely North Fork Beach Cottage (2 BR/2 bath)!

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (87)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

2.0 star property
8.0 out of 10, Very good, (6)
"We had a fantastic stay! The home was exactly as described — clean and very comfortable. The location was perfect. We loved being close to town. Communication was smooth and easy — Frank was quick to respond. We’d absolutely stay here again and recommend it to anyone visiting the area! "
The price is HK$3,140
HK$5,641 total
includes taxes & fees
5 Aug - 6 Aug
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

Southampton cozy cottage by the beach

The price is HK$3,760
HK$7,471 total
includes taxes & fees
27 Jul - 28 Jul
Southampton cozy cottage by the beach

Walk to town, Bike to beach, Private pool oasis !

10.0 out of 10, Exceptional, (18)
"Nice house with very great outdoor. Well located, with the bikes, we can access the beaches, the city center and some restaurants very easily."
Walk to town, Bike to beach, Private pool oasis !

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (92)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
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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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?

Escape to 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. It has 3 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 patio, a garden and a pool table 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.