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House holiday rentals in Cutchogue

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Top-rated house rentals in Cutchogue

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Home in Greenport

4.83 out of 5 average rating, 190 reviews

The Greenport Townhouse - Amazing Location & Large Backyard

The house is located on a .35 acre lot with plenty of outdoor dining space and a huge grass area with a firepit & hammock. There are 2 floors. The first floor has an open floor plan with a connecting kitchen, dining room, and living room. The kitchen is well equipped with a dish washer, electric stove/oven, refrigerator, and coffee bar. There is also a bedroom on the 1st floor with 2 full-sized beds. The 2nd floor has 3 bedrooms and a loft/den area. The three bedrooms on this floor have 1 queen bed+futon, 2 full-sized beds, and 2 twin beds (which can be made together to form a king upon request), respectively. All rooms have AC. There are 2 full bathrooms (1 on each floor) and a washer/dryer. Guests have access to the entire house and backyard area. We respect your privacy, but we are accessible if you have questions or need anything throughout your stay. Greenport was voted one of the prettiest towns in America by Forbes magazine. It has a vibrant and relaxing culture, offering access to beaches, wine tasting, and wonderful restaurants. The Shelter Island Ferry and Hampton Jitney stops are nearby. We are just a few short blocks from the Hampton Jitney stop, the LIRR station, and the Shelter Island Ferry. No car necessary - you can walk wherever you need!

7–14 Apr

$916 NZD per night

Guest favourite

Home in Greenport

4.92 out of 5 average rating, 121 reviews

Beautiful Cottage Home W/ Beach & Dock Access

Beautiful, spacious beach side home situated within a block of a private beach. This cozy home is walking distance to Kontokosta Winery, Island's End Golf & Country Club, Lavender By the Bay and a five minute drive to the Village of Greenport. Replete with natural light and an open backyard perfect for outdoor dining and barbecues, this home is perfect for your stay in Greenport. Netflix/Hulu/Disney+ / ESPN+ / HBO MAX. Please note, 4 Bikes/1 Paddle Board/1 Kayak & Life Jackets provided May-Sept.

22–29 Sep

$1,480 NZD per night

Guest favourite

Home in New Suffolk

5.0 out of 5 average rating, 13 reviews

Waterfront Beach Cottage

Renovated New Suffolk Waterfront Beach Cottage steps from water/beach/restaurants & more w/ water views from practically every window in the heart of the most special neighborhood in the north fork. Perfect for families with twn over full bunks, pvt mstr, grill, outdr shower and new kitchen. Bonus room has comfy couches & sunset views. Dine al fresco with water views or stroll to restaurants, apple picking or famous New Suffolk beach. Minutes from everything your vacation could need, year round.

20–27 Nov

$706 NZD per night

Guest favourite

Home in Sag Harbor

4.89 out of 5 average rating, 166 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Family friendly Sag Harbor one level beach house close to Main Street. Heated pool (for a fee), hot tub, enclosed grass yard, kids play area with sandbox and toys, crib, highchair, outdoor fireplace, outdoor shower, yard is fenced and gated with separate safety fence for pool area. Backs up to a nature preserve for privacy. Quiet Neighborhood. Short drive to the beach and Main Street. Pool open April 13th-Oct 1. Pool can be heated June-August (for a fee). Hot Tub open April- November.

20–27 Oct

$975 NZD per night

Guest favourite

Home in Cutchogue

4.97 out of 5 average rating, 31 reviews

Cozy Cottage with Views

Take it easy at this unique and tranquil getaway centrally located in Cutchogue on the North Fork of Long Island. This newly renovated cottage has plenty of natural light, a full kitchen with all new appliances, one bedroom with a queen size bed, a bathroom with a walk in shower, a spacious living room with vaulted ceilings and a private outdoor space with a gas grill. A short drive in either direction allows you the opportunity to experience all that the North Fork has to offer.

19–26 Aug

$572 NZD per night

Guest favourite

Home in Southampton

4.9 out of 5 average rating, 216 reviews

PICTURE PERFECT SOUTHAMPTON HOME-

Picture Perfect 3 bedroom 1.5 Bath Cottage located in the heart of Southampton. The home is conveniently located close to Southampton, Bridgehampton and Sag Harbor towns. Additionally, there is close access to both Bay and Ocean Beaches. The Newly renovated home gives you a peaceful and serene feeling everyday. Dogs are accepted on a case by case basis. Cats are not permitted. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

9–16 Sep

$1,018 NZD per night

Guest favourite

Home in Greenport

4.96 out of 5 average rating, 306 reviews

The Sandpiper

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

5–12 Jan

$255 NZD per night

Guest favourite

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Private Oasis W/Stunning Vinyard And Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

7–14 Mar

$1,501 NZD per night

Guest favourite

Home in Greenport

4.97 out of 5 average rating, 223 reviews

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

9–14 Jun

$802 NZD per night

Guest favourite

Home in Cutchogue

5.0 out of 5 average rating, 24 reviews

North Fork paradise between beaches and vineyards

Kick back and relax in this calm, stylish retreat. Nestled between vineyards and farmlands, this newly renovated mid-century ranch with a beautiful 14x50' heated salt water pool is a short hop to beautiful beaches, wineries, restaurants, and farm stands. Enjoy nature in a secluded park-like setting and explore everything the NoFo has to offer all year around. Please note that there are no parties, gatherings or unannounced guests allowed.

7–14 Nov

$1,109 NZD per night

Guest favourite

Home in Cutchogue

4.96 out of 5 average rating, 76 reviews

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. 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.

13–20 Apr

$537 NZD per night

Guest favourite

Home in Sag Harbor

4.97 out of 5 average rating, 260 reviews

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

26 Sep – 3 Oct

$1,021 NZD per night

Holiday rentals for every style

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Popular amenities for Cutchogue house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Hampton Bays

4.98 out of 5 average rating, 112 reviews

Beach House Feel - newly renovated backyard Oasis

25 Oct – 1 Nov

$947 NZD per night

Guest favourite

Home in Water Mill

4.91 out of 5 average rating, 110 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

12–19 Nov

$1,683 NZD per night

Guest favourite

Home in Sag Harbor

4.94 out of 5 average rating, 102 reviews

Sag Harbor Village Cottage with Pool

11–18 Jun

$1,791 NZD per night

Guest favourite

Home in Sag Harbor

4.85 out of 5 average rating, 250 reviews

Exclusive Sag Harbor Compound

8–15 Dec

$925 NZD per night

Guest favourite

Home in East Hampton

4.93 out of 5 average rating, 141 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

28 Oct – 4 Nov

$1,493 NZD per night

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

15–22 Oct

$1,587 NZD per night

Guest favourite

Home in Watermill

4.88 out of 5 average rating, 128 reviews

Modern House close to the beach

16–23 Oct

$1,885 NZD per night

Home in Sag Harbor

4.82 out of 5 average rating, 132 reviews

New! Sag Harbor Village Pool, Hot Tub &Beach House

21–28 Nov

$1,328 NZD per night

Weekly house rentals

Guest favourite

Home in Southold

5.0 out of 5 average rating, 18 reviews

Le Petit Cottage Southold NY

4–11 Jan

$411 NZD per night

Guest favourite

Home in Mattituck

4.92 out of 5 average rating, 92 reviews

Modern Farmhouse Steps to Beach & Love Lane

25 Apr – 2 May

$828 NZD per night

Guest favourite

Home in Southold

4.96 out of 5 average rating, 28 reviews

Bright Oasis in Beautiful North Fork Wine Country

22 Feb – 1 Mar

$1,041 NZD per night

Guest favourite

Home in Southold

5.0 out of 5 average rating, 31 reviews

Salt & Sea House - Near wineries, farms, & beaches

9–16 Sep

$833 NZD per night

Guest favourite

Home in Cutchogue

4.98 out of 5 average rating, 53 reviews

Good Vibrations on the North Fork

26 Nov – 3 Dec

$1,067 NZD per night

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 36 reviews

Beachfront Greenport Villa

19–26 Jan

$1,039 NZD per night

Guest favourite

Home in Southold

4.92 out of 5 average rating, 12 reviews

Beach/Lake house Fireplace & Hot Tub, By Wineries

11–18 Jun

$1,134 NZD per night

Guest favourite

Home in Mattituck

5.0 out of 5 average rating, 30 reviews

Immaculate NOFO Beach House Steps from Beach

18–25 Sep

$1,479 NZD per night

Private house rentals

Guest favourite

Home in Mattituck

4.94 out of 5 average rating, 35 reviews

Walk to Love Lane! Immaculate Renovated Cottage.

9–16 Nov

$691 NZD per night

Guest favourite

Home in Southold

4.89 out of 5 average rating, 19 reviews

Dockside Getaway in Southold NY

25 Feb – 4 Mar

$1,021 NZD per night

Guest favourite

Home in Southold

4.97 out of 5 average rating, 35 reviews

Water & Vineyard views, 4 bedrooms

11–18 Jan

$1,771 NZD per night

Guest favourite

Home in Greenport

4.98 out of 5 average rating, 85 reviews

Designer's Dream - Charming Boathouse

16–23 Mar

$752 NZD per night

Guest favourite

Home in Peconic

5.0 out of 5 average rating, 11 reviews

Coastal Cottage on the Water

4–11 Oct

$1,035 NZD per night

Guest favourite

Home in Mattituck

4.93 out of 5 average rating, 45 reviews

North Fork Wine Country Cottage Heart of Mattituck

27 Oct – 3 Nov

$518 NZD per night

Guest favourite

Home in Mattituck

4.94 out of 5 average rating, 16 reviews

Elena’s Beach house

24–31 May

$978 NZD per night

Guest favourite

Home in Mattituck

5.0 out of 5 average rating, 21 reviews

Beautiful Historic Estate -New Heated Pool & Spa

9–16 May

$1,377 NZD per night

Quick stats about house rentals in Cutchogue

Total rentals
70 properties
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
1K reviews
Nightly prices starting at
$266 NZD before taxes and fees

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