Holiday rentals in Cutchogue

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Top-rated holiday rentals in Cutchogue

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Guest favourite

Home in Cutchogue

4.94 out of 5 average rating, 49 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

19–26 Mar

£349 per night

Guest favourite

Home in Cutchogue

4.96 out of 5 average rating, 74 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. Home was designed by well known home and garden designer, Conni Cross. 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.

18–25 Mar

£260 per night

Guest favourite

Cottage in Cutchogue

5.0 out of 5 average rating, 18 reviews

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.

13–20 Dec

£321 per night

Guest favourite

Guest suite in Cutchogue

4.9 out of 5 average rating, 83 reviews

Enjoy a relaxing getaway to the North Fork

Newly renovated, 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.

1–8 Sept

£167 per night

Guest favourite

Home in Cutchogue

4.97 out of 5 average rating, 30 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.

13–20 Jan

£277 per night

Guest favourite

Home in Southold

5.0 out of 5 average rating, 9 reviews

Gorgeous home with heated gunnite pool!

Built in 1928, this gorgeous home is fully equipped to host your getaway. You're within easy walking distance of Horton's Lighthouse, where lovely beach walks and stunning sunsets await you. The local wineries are all within short drives of this lovely retreat. Enjoy the new heated gunnite pool with plenty of poolside seating. The family friendly layout features plenty of seating inside and out. You're just 100 yards north of a public beach, come enjoy the sunsets!

23–30 Nov

£403 per night

Guest favourite

Home in Mattituck

4.92 out of 5 average rating, 92 reviews

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.

26 Dec – 2 Jan

£280 per night

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.

23–30 Mar

£725 per night

Guest favourite

Guest suite in Cutchogue

4.88 out of 5 average rating, 584 reviews

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!

5–12 Oct

£145 per night

Guest favourite

Home in Cutchogue

4.98 out of 5 average rating, 52 reviews

Good Vibrations on the North Fork

In the heart of wine country within walking distance of a dozen wineries and farm stands with a spacious backyard. Perfect for a bachelorette party or family getaway. Crib and high chair available! Big driveway for lots of cars. About 2 miles or a 5 minute drive from the serene Cutchogue beach. 12 minute drive to the village of Greenport.

21–28 Feb

£515 per night

Guest favourite

Home in Cutchogue

4.87 out of 5 average rating, 115 reviews

The Perfect North Fork Escape

This 3 bedroom home with pool is 1 mile from the bay and surrounded by vineyards. Close to shopping, restaurants and the North Fork's beautiful wineries . Perfect for all seasons. This home has a 14 day minimum stay...Please feel free to reach out with any questions.

8–15 May

£488 per night

Guest favourite

Cottage in Southold

4.9 out of 5 average rating, 151 reviews

Comfortable Cottage on the Great Pond near beach.

In the heart of wine country is the adorable , nautical inspired cottage surrounded by nature, on a beautiful freshwater pond, a quick walk or bike ride away from a beautiful beach on Long Island Sound. Hiking, fishing, wine tours, farmstands abound!

7–14 Mar

£239 per night