Vacation rentals in Cutchogue

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Top-rated vacation rentals in Cutchogue

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Home in Cutchogue
Nassau Point, North Fork Home w/ Pool
Whether you are looking for lots of outdoor space for the kids to explore, bike, play at the beach or splash around in the pool OR you are looking to explore all of the 38 Vineyards along Long Islands, this house is perfect for you. Open kitchen, dining and living space which then opens up to the deck and pool. 4 bedrooms, sleeping 8 comfortably. Two of the bedrooms are connected with a thru-door. Gated swimming pool. Minutes from the local sandy beach. Rental Permit: HMT24-00101 14-Day minimum
Oct. 21 – 28
$626 CAD per night
4.94 out of 5 average rating, 49 reviews
Guest favourite
Home in Cutchogue
Secluded Farmhouse - Studio Apartment Style Unit
Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Home was designed by well known home and garden designer, Conni Cross. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea.
Feb. 22 – Mar. 1
$440 CAD per night
4.96 out of 5 average rating, 70 reviews
Guest favourite
Cottage in Cutchogue
Renovated 2-Bedroom Cottage on the North Fork
Serenity awaits as you step into this totally renovated Cottage. The property is perfectly located in the heart of Long Island's Wine Country. Centered on the North Fork this home allows you to explore all that there is to offer…. antique shops, restaurants, vineyards, breweries, farm stands and the beautiful Causeway Beach is just steps from this home. The home is newly renovated with a new kitchen, appliances, new bathroom, outdoor gas grill, fire pit and a beautiful screened in porch.
Feb. 8 – 15
$593 CAD per night
5.0 out of 5 average rating, 18 reviews

Popular amenities for Cutchogue vacation rentals

Stay near Cutchogue's top sights

Pindar Vineyards41 locals recommend
New Suffolk Beach8 locals recommend
Legends23 locals recommend
Greenport Harbor Brewery and Restaurant54 locals recommend
King Kullen77 locals recommend
Cutchogue Diner21 locals recommend

Other great vacation rentals in Cutchogue

Guest favourite
Home in Southold
Le Petit Cottage Southold NY
Nov. 29 – Dec. 6
$386 CAD per night
5.0 out of 5 average rating, 14 reviews
Guest favourite
Guesthouse in Southold
Southold- Adorable 1 Bedroom Cottage
May 29 – Jun. 5
$396 CAD per night
4.95 out of 5 average rating, 39 reviews
Guest favourite
Home in Mattituck
Modern Farmhouse Steps to Beach & Love Lane
Sep. 1 – 8
$673 CAD per night
4.92 out of 5 average rating, 87 reviews
Guest favourite
Home in Southold
Beach/Lake house ~ Fireplace ~ North Fork Wineries
Mar. 27 – Apr. 3
$799 CAD per night
4.92 out of 5 average rating, 12 reviews
Guest favourite
Cottage in Southold
Adorable Cottage
Feb. 18 – 25
$501 CAD per night
4.95 out of 5 average rating, 21 reviews
Guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
Sep. 29 – Oct. 6
$334 CAD per night
4.94 out of 5 average rating, 95 reviews
Guest favourite
Home in Southold
Bright Oasis in Beautiful North Fork Wine Country
May 19 – 26
$981 CAD per night
4.96 out of 5 average rating, 25 reviews
Guest favourite
Cottage in New Suffolk
Mermaid cottage
Apr. 30 – May 7
$264 CAD per night
4.85 out of 5 average rating, 52 reviews
Guest favourite
Cottage in Cutchogue
The Melody Too
May 16 – 23
$728 CAD per night
5.0 out of 5 average rating, 48 reviews
Guest favourite
Cottage in Southold
Bordeaux meets Côte d’Azur—1763 Historic Farmhouse
Jul. 5 – 12
$851 CAD per night
4.94 out of 5 average rating, 32 reviews
Guest favourite
Home in Mattituck
North Fork Wine Country Cottage Heart of Mattituck
Oct. 10 – 17
$354 CAD per night
4.93 out of 5 average rating, 44 reviews
Guest favourite
Home in Greenport
The Sandy Shack - Coastal Escape
Feb. 14 – 21
$919 CAD per night
5.0 out of 5 average rating, 10 reviews

Quick stats about vacation rentals in Cutchogue

Total rentals

120 properties

Rentals with a pool

30 properties have a pool

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

90 properties are a good fit for families

Total number of reviews

3.6K reviews

Nightly prices starting at

$122 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Suffolk County
  5. Cutchogue