
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.

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!

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.

Beautiful 1930s 4 bed 3 bath! Walk to Beach
Beautiful 1930s fully renovated cottage with 4 gorgeous bedrooms & 3 full baths. Spacious outdoor living space including an outdoor shower & fire pit. 1 block from a beautiful life guarded, sandy bay beach. Relax with the family at this peaceful place to stay in exclusive Fleets Neck and close to multiple spectacular wineries, breweries, farms, shopping outlets and worldclass restaurants. Stunning waterscapes abound! Enjoy a country retreat in a slice of heaven! Southold town permit 1137

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.

Enjoy a relaxing getaway to the North Fork
One bedroom suite, with separate entrance in quiet Nassau Point; a peninsula, surrounded by beaches. Nassau Point is a great place to bike, walk and enjoy nature. Fully functioning WiFI for guests looking to extend their stay, while working from home. Fishermen's beach is a 5 minute walk Causeway beach is a 10 minute walk with parking. Point beach, 1.5 mile walk, a Southold Parking Permit required. You will find 20 wineries within 5 miles, just a short Uber ride away.

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. Less than 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, and Love Lane.

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.

North Fork Farm House
This home is located on the North Fork of Long Island in the heart of wine country. We have a beautiful winery within close walking distance. We are surrounded by beautiful beaches and a short ferry ride to Shelter Island. There’s great restaurants and shopping just 15 minutes east in the town of Greenport or 5 minutes west to Love Lane in Mattituck. There is also lots to do in the town of Riverhead, including shopping at Tanger Outlets.

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.

Secluded Farmhouse - Studio Apartment Style Unit
Private studio suite with separate entrance and full bath in a modern North Fork farmhouse on a peaceful farm property. Enjoy a screened porch, fire pit, and outdoor seating. Includes mini fridge, Keurig, tea, homemade granola, and seasonal eggs/produce. Attached to our home, so some light household noise is possible. Private chef + yoga services available.

Walk to Vineyards, Beaches, Farms & Town
Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!
Popular amenities for Cutchogue vacation rentals
Other great vacation rentals in Cutchogue

North Fork Paradise

Southold- Adorable 1 Bedroom Cottage

Nassau Point, North Fork Home w/ Pool

Beach Cottage 3 | New Suffolk | Northfork

Coastal Cottage on the Water

Le Petit Cottage, Southold, NY

Secluded Soundfront 1910 Rustic Getaway

Southold Sea'renity
When is the best time to visit Cutchogue?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $588 CAD | $700 CAD | $700 CAD | $700 CAD | $700 CAD | $770 CAD | $842 CAD | $840 CAD | $700 CAD | $700 CAD | $700 CAD | $665 CAD |
| 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 |
Frequently Asked Questions
Are there family-friendly vacation rentals in Cutchogue?
Cutchogue has more than 100 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Cutchogue?
Experience the best of Cutchogue with our house rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Cutchogue?
Four-legged friends are welcome in Cutchogue. Choose from more than 40 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Cutchogue?
Yes! Work meets play with ease at over 50 vacation rentals in Cutchogue featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Cutchogue vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Cutchogue, available on Airbnb. Make a splash and soak up the sun in style!
Where should I stay in Cutchogue?
Make yourself at home in Cutchogue by choosing from our most frequently booked neighborhoods. We have over 290 vacation rentals in Cutchogue, over 100 vacation rentals in New Suffolk, and over 190 vacation rentals in Peconic.
Do house rentals in Cutchogue have air conditioning?
Absolutely! We offer over 90 house rentals with air conditioning in Cutchogue. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Cutchogue have a kitchen?
Absolutely! We offer over 90 house rentals with a kitchen in Cutchogue. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Cutchogue have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Cutchogue. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Cutchogue have free parking?
Absolutely! We offer over 90 house rentals with free parking in Cutchogue. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Cutchogue

Total vacation rentals
Explore 120 vacation rentals in Cutchogue

Nightly prices starting at
Cutchogue vacation rentals start at $126 CAD per night before taxes and fees

Verified guest reviews
Over 3,880 verified reviews to help you choose

Family-friendly vacation rentals
100 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
120 of Cutchogue vacation rentals include wifi 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!
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- Rentals with beach access Cutchogue
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- Pet-friendly rentals Cutchogue
- Rentals with a fireplace Cutchogue
- Rentals with outdoor seating Cutchogue
- Rentals with pools Cutchogue
- Fitness-friendly rentals Cutchogue
- Beach
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