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House accommodation & holiday rentals in Cutchogue

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Top-rated house accommodation & 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!

31 Mar – 7 Apr

$5,826 AUD total

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.

19 – 26 Sept

$9,517 AUD total

Guest favourite

Home in Shelter Island

4.97 out of 5 average rating, 194 reviews

Huge Island Getaway Pool HotTub Walk To Beach

Relaxation begins on the 6 minute ferry ride to this magical island. Summerfield is a spectacular, grand compound that has it all. Huge main house great for groups, 4700ft w/ privacy for all overlooking serene nature reserve. Star gaze in the bubbling hot tub, grill outside after a swim, play in the rec room with movie theater, pool table or ping pong,or watch TV by the fire! Open plan layout, gourmet kitchen, heated gunite pool, separate guest house. Prime location close to beach + restaurants.

6 – 13 Feb

$11,084 AUD total

Guest favourite

Home in Holbrook

4.91 out of 5 average rating, 237 reviews

Cozy studio

We are 10 minutes away to MacArthur Airport in Islip, 5 minutes to shopping center where you can find supermarkets, restaurants, and stores. We are 10 minutes away from LIRR train station where you can get a ride to Manhattan. Although the studio is centrally located a car or Uber is recommended,. You'll have your own bathroom, kitchen with microwave, coffee maker, toaster, fridge, air conditioner, tv with cable and internet. Our study is a FREE SMOKING PLACE! Not smoking or vaping!

20 – 27 July

$1,157 AUD total

Guest favourite

Home in Greenport

4.92 out of 5 average rating, 423 reviews

Blue Bay Dream

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).

16 – 23 Feb

$1,456 AUD total

Guest favourite

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Stunning Vinyard Views - Spring Special $475/Nt!

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.

9 – 16 Jan

$9,648 AUD total

Guest favourite

Home in Greenport

4.97 out of 5 average rating, 221 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 – 16 Aug

$6,298 AUD total

Guest favourite

Home in Cutchogue

4.96 out of 5 average rating, 75 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.

25 Feb – 4 Mar

$3,403 AUD total

Guest favourite

Home in Sag Harbor

4.85 out of 5 average rating, 250 reviews

Exclusive Sag Harbor Compound

A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

4 – 11 Dec

$5,949 AUD total

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.

8 – 15 Oct

$4,145 AUD total

Guest favourite

Home in Greenport

4.98 out of 5 average rating, 143 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

10 – 17 May

$8,592 AUD total

Guest favourite

Home in Greenport

4.98 out of 5 average rating, 165 reviews

Nofo Bungalow-In The Heart of Greenport Village

This historic Greenport home has been completely renovated . The Bungalow is in the heart of Greenport Village on a quiet dead end. The home includes 1500 square feet of open concept living, two bedrooms, and two full baths. The downstairs bedroom features a queen and upstairs bedroom four twins.

4 – 11 Sept

$6,356 AUD total

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

8 – 15 Oct

$6,168 AUD total

Guest favourite

Home in Manorville

4.98 out of 5 average rating, 199 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

3 – 10 Oct

$6,909 AUD total

Guest favourite

Home in Water Mill

4.91 out of 5 average rating, 110 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

16 – 23 Nov

$10,817 AUD total

Guest favourite

Home in East Hampton

4.93 out of 5 average rating, 140 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

30 Sept – 7 Oct

$10,119 AUD total

Home in Sag Harbor

4.81 out of 5 average rating, 109 reviews

Sag Harbor Gem, private, 4 Bedrooms, Pool w Summer

6 – 13 June

$9,770 AUD total

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

9 – 16 Nov

$10,202 AUD total

Guest favourite

Home in East Hampton

4.92 out of 5 average rating, 128 reviews

Heated pool, games room, near beach, kid-friendly

23 – 30 Oct

$7,851 AUD total

Home in Sag Harbor

4.82 out of 5 average rating, 132 reviews

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

31 Oct – 7 Nov

$8,889 AUD total

Weekly house rentals

Guest favourite

Home in Cutchogue

4.97 out of 5 average rating, 30 reviews

Cozy Cottage with Views

24 – 31 Dec

$3,678 AUD total

Guest favourite

Home in Southold

5.0 out of 5 average rating, 16 reviews

Le Petit Cottage Southold NY

7 – 14 Nov

$2,591 AUD total

Guest favourite

Home in New Suffolk

5.0 out of 5 average rating, 11 reviews

Waterfront Beach Cottage

31 Jan – 7 Feb

$6,889 AUD total

Guest favourite

Home in Southold

4.96 out of 5 average rating, 28 reviews

Bright Oasis in Beautiful North Fork Wine Country

18 – 25 Jan

$6,863 AUD total

Guest favourite

Home in Southold

5.0 out of 5 average rating, 31 reviews

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

14 – 21 Sept

$5,356 AUD total

Guest favourite

Home in Southold

4.92 out of 5 average rating, 12 reviews

Beach/Lake house Fireplace & Hot Tub, By Wineries

11 – 18 June

$7,431 AUD total

Guest favourite

Home in Cutchogue

4.98 out of 5 average rating, 52 reviews

Good Vibrations on the North Fork

1 – 8 Feb

$6,857 AUD total

Guest favourite

Home in Mattituck

5.0 out of 5 average rating, 30 reviews

Immaculate NOFO Beach House Steps from Beach

5 – 12 Nov

$8,287 AUD total

Private house rentals

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 36 reviews

Beachfront Greenport Villa

8 – 15 Apr

$10,476 AUD total

Guest favourite

Home in Cutchogue

4.93 out of 5 average rating, 43 reviews

Historic Cutchogue-North Fork Home

30 Sept – 7 Oct

$5,165 AUD total

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

29 Dec – 5 Jan

$7,267 AUD total

Guest favourite

Home in Greenport

4.98 out of 5 average rating, 85 reviews

Designer's Dream - Charming Boathouse

5 – 12 Dec

$4,835 AUD total

Guest favourite

Home in Peconic

5.0 out of 5 average rating, 11 reviews

Coastal Cottage on the Water

4 – 11 Oct

$6,651 AUD total

Guest favourite

Home in Southold

4.89 out of 5 average rating, 19 reviews

Dockside Getaway in Southold NY

16 – 23 Feb

$6,562 AUD total

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 19 reviews

The Corwin House

16 – 23 May

$11,864 AUD total

Guest favourite

Home in Southold

5.0 out of 5 average rating, 32 reviews

Southold Comfort - North Fork Getaway

3 – 10 May

$8,549 AUD total

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
$245 AUD before taxes and fees

Destinations to explore