
Holiday rentals with outdoor seating in Cutchogue
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Quick stats about holiday rentals with outdoor seating in Cutchogue

Total holiday rentals
Explore 70 holiday rentals in Cutchogue

Nightly prices starting at
Cutchogue holiday rentals start at $158 NZD per night before taxes and fees

Verified guest reviews
Over 2,190 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Cutchogue holiday 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 Holiday Houses with Outdoor Seating in Cutchogue
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

Beautiful 2 bdrm cottage on NoFo
Our "Little Piece of Heaven" on the North Fork of L. I. Located on a large Creek with fantastic sunsets! Enjoy the peaceful nature watching Egrets, blue & green Herons, Cormorants and Osprey diving into the water & retrieving a fish almost every time? It's mesmerizing! Centrally located between Riverhead (Water Park) and Orient Point, where a ferry can take you to Conn. (if you like Casinos). Farm stands galore, beautiful clean private beach (walking distance) & incredible restaurants nearby!

Hamptons Oceanfront Oasis
Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

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.

Comfortable Suite, a walk to the beach
Keep it simple at this spacious and peaceful home. Built in 2019, this home was specially designed for sustainable, green living; ground-source heating, and super insulation allow for minimal environmental impact and provide a quiet and comfortable stay. About a five minute walk to McCabe’s Beach. Very near to wineries, farms, and the quaint shops and bakeries of Southold and Greenport. Little Fish restaurant and oyster sales all down the street. Short drive from Sparkling Pointe vineyard.

Savor Ocean Sunsets at a Soothing Beachfront Haven
Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

Bright, Southold Studio Apt near beach & town
Pied a terre on the North Fork, in the heart of Southold village. Gorgeous bay beach 5 minute walk, as are farmstands, supermarket, Historic Southold Village with quaint shops, Hampton Jitney & LIRR. Lots of light, new contemporary space featuring full bathroom with bathtub. Perfect for one, suitable for a couple for weekend getaway. Small kitchenette perfect for simple food prep, morning coffee/tea. Chickens on property, fresh pastured eggs in your kitchenette upon arrival!

Modern Farmhouse Steps to Beach & Love Lane
Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

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.

Stunning waterfront modern farmhouse with dock.
Relax with the whole family or a group of friends at this peaceful, waterfront cottage. Perfect spot to bring a group for a country retreat in the heart of stunning vineyards, spectacular restaurants and stunning waterscapes. Our home’s interior is beautifully appointed where you will be comfortable both inside and outside on our patio, or deck with a breathtaking waterfront view. Peaceful, relaxing and magical place in an idyllic spot.

Renovated Townhouse, Walk to All
Discover the North Fork from our stylishly renovated 100-year-old townhouse! Perfectly located, you can walk to town, beaches, and a local brewery. This bright, airy home features a new kitchen, central AC, and a private patio with a grill. Comfortably sleeping up to 8 guests, it's the ideal base for families or groups exploring Long Island's wine country. Park your car and enjoy a walkable getaway!

North Fork Vineyard Red Farmhouse AirBnB
Come enjoy all the North Fork has to offer at this newly renovated vintage farmhouse! Located on a working vineyard in the heart of Cutchogue! Surrounded by beautiful wineries, amazing restaurants, breathtaking beaches, quirky local shops, and so much more! Soak in the local flavor and then come home and get cozy with a bottle of wine from our vineyard. Slow down and savor your NOFO time.

Cozy Seaside Cottage
The Cottage at Whitecap is part of an Historic Compound built in 1883 and is located in the heart of New Suffolk. The Cottage offers 4 Bedrooms and 2 Bathrooms. The house is steps from the beach and conveniently located by restaurants, wineries and a public boat ramp. It's the perfect location for your next vacation, small get together or winery weekend getaway.
Popular amenities for Cutchogue outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Beach House in L.I. Wine Country

The Perfect North Fork Escape

NoFo Getaway: Pool, Farm Views, Beach Sunsets

Private beach, fully updated house, on 2 acres.

Serene Hamptons oasis~1 block to waterfront dining

Harbor Heights

Beautiful 1930s 4 bed 3 bath! Walk to Beach

Charming House close to Ocean Beaches
Apartment rentals with outdoor seating

Renovated Apartment in a Historic Farmhouse Estate

Hamptons Hills Escape

The House of the Mermaid aka La Casa della Sirena

Upscale Newly Constructed Apartment

Squire Chase House

Cozy Studio 15 Min From Hampton Beaches

Private 1st flr apt w/ patio 3 blocks from beach

Walk to Bay and Ocean-Newly Renovated
Condo rentals with outdoor seating

Water front, sunsets, sail boats, 30 day minimum

1856 Trading House w/ walk to water

Beautiful condo on Long Islands Northfork

Waterfront Escape | Private Beach, Pool & Views

Beautiful Waterview Condo on the North Fork of LI

1856 Trading House close to water

Waterfront Escape | Private Beach, Pool & Views

Beachside Waterview 2Br Condo w/ Pool in Greenport
When is the best time to visit Cutchogue?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $736 NZD | $876 NZD | $745 NZD | $1,011 NZD | $876 NZD | $964 NZD | $1,132 NZD | $1,127 NZD | $876 NZD | $876 NZD | $876 NZD | $832 NZD |
| 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 |
Destinations to explore
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- Pet-friendly rentals Cutchogue
- Rentals with a patio Cutchogue
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- Rentals with a hot tub Cutchogue
- House rentals Cutchogue
- Rentals with a fireplace Cutchogue
- Beachfront rentals Cutchogue
- Rentals with a fire pit Cutchogue
- Rentals with beach access Cutchogue
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- Family-friendly rentals Cutchogue
- Rentals with pools Cutchogue
- Rentals with outdoor seating Suffolk County
- Rentals with outdoor seating New York
- Rentals with outdoor seating United States
- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Fairfield Beach
- Charlestown Beach
- Ocean Beach Park
- Robert Moses State Park Beach
- Southampton Beach
- Mystic Seaport Museum
- Mystic Aquarium
- Sunken Meadow State Park
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Compo Beach
- Yale University Art Gallery
- Wölffer Estate Vineyard
- Long Island Aquarium
- Sherwood Island State Park
- Meschutt Beach
- Blue Shutters Beach
- Ocean Beach
- Soundview Beach





