Vacation rentals in Cutchogue

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Top-rated vacation rentals in Cutchogue

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Guest favorite

Home in New Suffolk

5.0 out of 5 average rating, 10 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.

Dec 21 – 28

€ 500 per night

Guest favorite

Home in Cutchogue

4.94 out of 5 average rating, 50 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

Sep 24 – Oct 1

€ 547 per night

Guest favorite

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.

Dec 17 – 24

€ 307 per night

Guest favorite

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.

May 28 – Jun 4

€ 623 per night

Guest favorite

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.

Sep 1 – 8

€ 198 per night

Guest favorite

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.

Dec 21 – 28

€ 326 per night

Guest favorite

Home in Greenport

4.92 out of 5 average rating, 422 reviews

Blue Bay Dream - Apt #1

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).

Jan 3 – 10

€ 130 per night

Guest favorite

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!

Feb 27 – Mar 6

€ 476 per night

Guest favorite

Guest suite in Southold

4.94 out of 5 average rating, 97 reviews

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.

Mar 22 – 29

€ 154 per night

Guest favorite

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.

Mar 11 – 18

€ 472 per night

Guest favorite

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.

Mar 26 – Apr 2

€ 856 per night

Guest favorite

Guest suite in Cutchogue

4.88 out of 5 average rating, 585 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!

Aug 26 – Sep 2

€ 199 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Cutchogue vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Cutchogue's top sights

Pindar Vineyards41 locals recommend

New Suffolk Beach8 locals recommend

Legends23 locals recommend

Greenport Harbor Brewery and Restaurant54 locals recommend

King Kullen77 locals recommend

Cutchogue Diner21 locals recommend

Other great vacation rentals in Cutchogue

Guest favorite

Home in Southold

4.96 out of 5 average rating, 26 reviews

Bright Oasis in Beautiful North Fork Wine Country

Dec 10 – 17

€ 486 per night

Guest favorite

Home in Cutchogue

5.0 out of 5 average rating, 24 reviews

North Fork paradise between beaches and vineyards

May 25 – Jun 1

€ 909 per night

Guest favorite

Home in Cutchogue

4.98 out of 5 average rating, 52 reviews

Good Vibrations on the North Fork

Feb 24 – Mar 3

€ 608 per night

Guest favorite

Home in Southold

4.92 out of 5 average rating, 12 reviews

Beach/Lake house Fireplace & Hot Tub, By Wineries

Jun 11 – 18

€ 659 per night

Guest favorite

Cottage in New Suffolk

4.96 out of 5 average rating, 80 reviews

Cozy Seaside Cottage

Dec 14 – 21

€ 842 per night

Guest favorite

Guesthouse in Southold

4.95 out of 5 average rating, 40 reviews

Southold- Adorable 1 Bedroom Cottage

May 5 – 12

€ 249 per night

Guest favorite

Home in Southold

5.0 out of 5 average rating, 14 reviews

Le Petit Cottage Southold NY

Feb 16 – 23

€ 234 per night

Guest favorite

Guesthouse in Cutchogue

4.78 out of 5 average rating, 74 reviews

Waterfront guest cottage

Oct 15 – 22

€ 345 per night

Show all

Quick stats about vacation rentals in Cutchogue

Total rentals
110 properties
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
90 properties are a good fit for families
Total number of reviews
3.4K reviews
Nightly prices starting at
€ 94 before taxes and fees

Frequently Asked Questions

How much does it cost to stay in house rentals in Cutchogue?
Experience the best of Cutchogue with our house rentals, starting at about $160 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Cutchogue?
Enhance your stay in our House Rentals with the most popular amenities: over 70 homes with a kitchen, over 70 homes with wifi, over 70 homes with free parking, over 70 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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 pet-friendly vacation rentals in Cutchogue?
Four-legged friends are welcome in Cutchogue. Choose from more than 30 vacation rentals for guests traveling with pets.
Do house rentals in Cutchogue have a kitchen?
Absolutely! We offer over 70 house rentals with a kitchen in Cutchogue. Enjoy a tailored experience with all the comforts you desire.
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!
Do cottage rentals in Cutchogue have free parking?
Absolutely! We offer over 10 cottage rentals with free parking in Cutchogue. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Cutchogue have wifi?
Absolutely! We offer over 70 house rentals with wifi in Cutchogue. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Cutchogue?
Cutchogue has more than 90 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do cottage rentals in Cutchogue have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Cutchogue. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Cutchogue

Top-rated vacation rentals in Cutchogue

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Cutchogue vacation rentals

Stay near Cutchogue's top sights

Other great vacation rentals in Cutchogue

Home in Southold

Home in Cutchogue

Home in Cutchogue

Home in Southold

Cottage in New Suffolk

Guesthouse in Southold

Home in Southold

Guesthouse in Cutchogue

Quick stats about vacation rentals in Cutchogue

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

How much does it cost to stay in house rentals in Cutchogue?

What are the most popular amenities for House Rentals in Cutchogue?

Are there vacation rentals with a dedicated workspace in Cutchogue?

Are there pet-friendly vacation rentals in Cutchogue?

Do house rentals in Cutchogue have a kitchen?

Are there Cutchogue vacation rentals on Airbnb with pools?

Do cottage rentals in Cutchogue have free parking?

Do house rentals in Cutchogue have wifi?

Are there family-friendly vacation rentals in Cutchogue?

Do cottage rentals in Cutchogue have air conditioning?

Destinations to explore