
House vacation rentals in Cutchogue
Find and book unique houses on Airbnb
Quick stats about house rentals in Cutchogue

Total vacation rentals
Explore 80 vacation rentals in Cutchogue

Nightly prices starting at
Cutchogue vacation rentals start at G$31,397 GYD per night before taxes and fees

Verified guest reviews
Over 1,910 verified reviews to help you choose

Family-friendly vacation rentals
80 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
80 of Cutchogue vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Cutchogue rentals

4.9 Average rating
Cutchogue stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in Cutchogue
Guests agree: these houses are highly rated for location, cleanliness, and more.

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!
4.83 out of 5 average rating, 239 reviews
Cozy Farmhouse Retreat in North Fork, NY
A 1905 farmhouse with modern touches, Arthur's Vineyard is a cozy 3-bed, 2-bath home in walking distance of Greenport village's beaches, marina, restaurants and boutiques. An open plan living area, breezy decor and a large landscaped backyard for spending relaxed summer days and nights with your family and friends, including the 4-legged ones. Walk to the train station/jitney or take a short drive to the wineries & farm stands of the North Fork. Recent updates: central heat/AC & new bathrooms.
4.92 out of 5 average rating, 135 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.
4.95 out of 5 average rating, 77 reviews
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
4.95 out of 5 average rating, 88 reviews
Modern farmhouse w/ pool, beach, horses and winery
A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.
4.93 out of 5 average rating, 138 reviews
Serene East Hampton Escape - Warm Pool til Nov
A luxuriously curated woodland escape with massive pool (heated and open May through October), fully fenced and just minutes from EH Village & Ocean Beaches. This impeccably renovated four-bedroom, four-and-a-half-bath home offers refined comfort in a serene, private setting. Sunlight floods the expansive interiors, featuring rich luxurious finishes, a separate office with queen sofa bed, a freestanding soaking tub, and a designer chef’s kitchen with a custom dining table for ten or more.
4.99 out of 5 average rating, 156 reviews
Stunning Hamptons Waterfront Escape w/ Sunset View
Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views and sunset from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Our pool will close on September 15th, 2026 and will reopen May 29, 2027.
4.87 out of 5 average rating, 142 reviews
Walk to Beautiful Beach in Heart of Wine Country
Enjoy bright, comfortable and modern home in the heart of North Fork wine and farm country located just a quick walk from a gorgeous Peconic Bay beach with tennis/pickleball courts, volleyball and playground right on the beach. You'll have easy and quick access to the best of the east end: beautiful beaches, boating, fishing, fine and casual dining, vineyards, wineries, breweries, farms and farm stands offering fresh local produce, antique and local shops.
4.96 out of 5 average rating, 167 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.
4.97 out of 5 average rating, 218 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!
4.97 out of 5 average rating, 296 reviews
The Sandpiper
100% Walking Score 1 block away from Village 3 blocks away from Beach. 1 block away from Shelter Island Ferry. Around the corner from Hampton Jitney & LIRR Newly renovated 2-Family Home! This is for rental of 1st floor apartment (only) plus cabana, plus outdoor jacuzzi. Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy.
4.95 out of 5 average rating, 397 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.
4.95 out of 5 average rating, 324 reviewsPopular amenities for Cutchogue house rentals
House rentals with a pool

Family Retreat with Heated Pool, Hot Tub, Sauna.
4.96 out of 5 average rating, 188 reviews
Coastal Retreat|Heated Saltwater Pool|5 MinToBeach
4.94 out of 5 average rating, 119 reviews
Astounding Watermill 5 Bedroom home with Pool
4.94 out of 5 average rating, 167 reviews
Southampton Village Newly Built Gem
4.97 out of 5 average rating, 103 reviews
Stylish+Modern Cape w/Saltwater Pool-5min to Beach
4.97 out of 5 average rating, 156 reviews
Luxury Hamptons Home with Heated Saltwater Pool
4.98 out of 5 average rating, 179 reviews
5BR, Luxury Home, Close to Beach,Town, PerfectYard
4.93 out of 5 average rating, 100 reviews
Southampton Charmer, 5 bedrooms w pool - Location
4.93 out of 5 average rating, 137 reviewsWeekly house rentals

Country Beach Home!
4.96 out of 5 average rating, 23 reviews
Private Waterfront Access + Hot Tub + Scenic Yard
5.0 out of 5 average rating, 45 reviews
Water Front Ospreys Nest Beach Rights Permit #1310
4.9 out of 5 average rating, 10 reviews
Le Petit Cottage Southold NY
4.89 out of 5 average rating, 90 reviews
Brand New Charming Beach House
4.98 out of 5 average rating, 45 reviews
Beautiful 1930s 4 bed 3 bath! Walk to Beach
5.0 out of 5 average rating, 30 reviews
Wine Country Home
4.96 out of 5 average rating, 51 reviews
Coastal Cottage on the Water
4.88 out of 5 average rating, 43 reviewsPrivate house rentals

Stylish Beach Getaway: pool & walking location
4.88 out of 5 average rating, 24 reviews
North Fork Sound Front Home with Pool
4.89 out of 5 average rating, 44 reviews
Mattituck Dream House - Rental Opportunity
4.98 out of 5 average rating, 80 reviews
Sprawling Modern Home Minutes from Beach
4.98 out of 5 average rating, 50 reviews
Corwin House
4.99 out of 5 average rating, 68 reviews
Greenport walk to beach & vineyard! Brand new home
5.0 out of 5 average rating, 81 reviews
Peconic Pearl Cottage
5.0 out of 5 average rating, 7 reviews
Mattituck Hideaway/ Luxury Wine Country Retreat
5.0 out of 5 average rating, 46 reviewsWhen is the best time to visit Cutchogue?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$99,423 GYD | G$125,587 GYD | G$112,401 GYD | G$112,401 GYD | G$122,448 GYD | G$144,635 GYD | G$156,984 GYD | G$153,844 GYD | G$122,866 GYD | G$104,656 GYD | G$120,145 GYD | G$104,865 GYD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
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