
Family-friendly vacation rentals in Cutchogue
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Cutchogue

Total vacation rentals
Explore 100 vacation rentals in Cutchogue

Nightly prices starting at
Cutchogue vacation rentals start at G$25,113 GYD per night before taxes and fees

Verified guest reviews
Over 2,400 verified reviews to help you choose

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
100 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 family-friendly rentals in Cutchogue
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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.

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!

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.

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.

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!

Beautiful condo on Long Islands Northfork
This condo is beautifully decorated and has a wonderful stone fire place. Gorgeous shiplap walls with Navy accents. There is also a new deck and wonderful dinning set outside. This unit has capabilities to be handicap accessible. Both bedroom have private bathrooms. The living room sectional opens up to a full sleeper making this condo able to sleep six people. All rooms have flat screen smart tv's.

Walk to Breakwater Beach in Heart of Wine Country
Private and peaceful cottage walking distance to Breakwater Beach and Old Mill Inn Restaurant on the water opening Spring 2025. There are two large decks to relax by the firepit and drink your wine from the local wineries. Bikes, kayak, and paddle board are stored in the barn for guests use. Easy access to the marina, fishing, fine dining, vineyards, and farm stands.

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 family-friendly rentals
Family-friendly home rentals with a hot tub

Greenport Village walking distance to all

Swimming pool w/Hot tub Fire Pit Coffee Bar

Oceanfront Beach House w/ Private Hot Tub

Brand new house with an all year round hot tub.

East Hampton Oasis - Pool and Hot Tub

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

Explore the Water & Woods at a Relaxing Retreat

Stylish & Chic w hot tub/ Near Beaches & Village
Family- and pet-friendly home rentals

1BR Apartment - Beach Access - Wineries, Vineyards

Hamptons Cottage.

New Suffolk Beach Cottage 1 | North Fork

Cosy North Fork Cottage with large backyard

NoFo Getaway: Pool, Farm Views, Beach Sunsets

Chic w/ pool ~ Walk 1 block to waterfront dining

Amazing Home close to Everything -

Pool Central Private Bridgehampton Home
Family-friendly home rentals with a pool

Corwin House

Beach Barn w/ Heated Pool & Sauna - Dog Friendly

Southold Home with Saltwater Pool

Creek Front home w/heated pool & endless sunsets

Stylish Beach Getaway: pool & walking location

Serene and refined North Fork home with pool

Beautiful Waterview Condo on the North Fork of LI

Waterfront Escape | Private Beach, Pool & Views
When is the best time to visit Cutchogue?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$104,637 GYD | G$125,564 GYD | G$112,380 GYD | G$125,564 GYD | G$124,518 GYD | G$136,237 GYD | G$146,492 GYD | G$146,282 GYD | G$112,799 GYD | G$104,637 GYD | G$112,171 GYD | G$104,846 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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