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Wading River vacation rentals

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Top-rated vacation rentals in Wading River

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Cottage in North Fork

4.97 out of 5 average rating, 149 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated, 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. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.

Home in North Fork

4.98 out of 5 average rating, 181 reviews

Quiet Canoe Lake Cottage getaway

Peaceful private home on lush green resort like compound with historical outbuildings plus an additional studio apartment available for larger groups.Ideal for couples or a small family looking to explore the North or South forks of Long Islands East End and a short drive to the Hamptons famous beaches, villages and restaurants.A true garden lovers getaway with extensive flowers, vegetable and fruits and even our own apiary providing local raw honey. Near lots of wineries, restaurants and 2 miles from Tanger outlet mall shopping & top 5 rated Splish Splash Water Park. .Adjacent to the Peconic River for canoeing, kayaking, fishing or birding. The quiet winding country roads on either side of the river are a favorite destination for walking/joggers, biking and motorcycle touring. Riverhead town is a great central location and an easy drive to bay and ocean beaches. The area is still very much a rural farming area and a foodies delight with many pick your own fields,farmers markets, farm stands, wineries, horse, buffalo, and goat farms and even a potato vodka distillery and tasting room! We have an awesome Aquarium in town and our newly reopened Suffolk Theater with nightly live music and shows. Riverhead has lots of inexpensive small cafe style eateries for those on a budget.

Rental unit in Coram

4.91 out of 5 average rating, 193 reviews

Private Apartment- close to shops, Pt. Jeff., SBU

Separate apartment with private keyless entrance. Cozy one bedroom king suite and sofa with full pull out bed. Full kitchen and dining area. Bathroom with standing shower. Free parking on premise for up to 2 cars. Quiet, family friendly neighborhood. Located in the heart of Long Island. Close to everything! Wineries, Farms, breweries, golf, shopping, great dining. NYC is a only a train ride away! Conveniently located within a mile of groceries and laundromat. High speed WiFi, 55in smart tv

Rental unit in Port Jefferson Station

4.96 out of 5 average rating, 171 reviews

All Private Bright Spacious Close to All

DISINFECTED AND CLEANED BEFORE YOU ARRIVE! Spacious ground level PRIVATE apt with lots of natural light. Full kitchen/new stove/fridge/Keurig.Bedrm- queen sz bed, living rm -queen sz sofa sleeper. Also available is queen air mattress w/ topper. Washer/Dryer. Minutes away to the Port Jeff Village shops&restaurants/Ferry/LIRR, hospitals, & Stony Brook. Small beaches 10-15min drive, large beaches,Shop Outlets & Wineries 25 -60 minute. PLEASE NOTE: Extra $2 Daily Fee for charging electric car.

Cabin in Rocky Point

4.89 out of 5 average rating, 447 reviews

Great little place just for a couple

The outdoor courtyard is especially nice and private-,with a fire pit, grill and comfortable chairs. It is a rustic location easy walking distance to North Shore Beach. If you want an ocean beach you can drive straight south for 20 minutes and reach Smiths Point State Park right on the ocean. The North Fork with its vineyards is a short drive and the Hamptons also only 30 minutes to West Hampton. You can fish, golf, walk among the wooded area and relax in peace. A pleasure. linen 100% cotton!

Guest suite in North Fork

4.9 out of 5 average rating, 256 reviews

Beachy En Suite /Gateway to The North Fork

Adorable,quiet,clean, w private entrance, private bedroom and bathroom,breakfast nook and patio.We are located in a beach front town dubbed“Gateway to the North Fork”. Walking/driving directions to local beaches,15minute walk to our community beach(.6mi away).Niks deli nearby.Minutes by car to wineries breweries,farm stands,EastWind 2 mi,TangerOutlets15min away,35min to Hamptons,Greenport!Hosts live in adjoining house. Rarely need access to your hallway to get to our basement.Would arrange.

Home in Brookhaven

4.96 out of 5 average rating, 164 reviews

Beautiful & Independent Guest House near the water

Welcome to our beautiful yet very private guest house in Brookhaven. You are walking distance from the Deer Run Farm (fresh eggs every morning), Post-Morrow Nature Trails and a short drive to Bellport Village Historic District. We are also very close to Wine Country, The Hamptons & Fire Island. We offer all the accommodations you might need for longer stays Washer & Dryer; Dishwasher; High Speed internet and TVs with all the premium channels. EV Charger available (Tesla - Fees applies).

Home in Manorville

4.98 out of 5 average rating, 243 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Ultimate house with 4 Bds, 3 Baths, finished basement with entertainment area and gym. Minutes from the Hamptons and North Fork. Everything for your rest in any weather and season. Yamaha piano, Japanese massage chair, karaoke, drum set, electric guitars, ping pong, fossball and pool tables,board games. Fully landscaped backyard with flowering plants, outdoor lights. 2 BBQ areas, Gazebo with fireplace and projector. Easy access to beaches, restaurants, farms, vineyards and shopping.

Home in North Fork

4.95 out of 5 average rating, 118 reviews

⭐️Modern Farmhouse Long Island Wine Country🍷

Long Island’s North fork Long Island Wineries. Luxurious, clean , modern peaceful farmhouse. Top of the line fully stocked kitchen, stainless steel appliances, granite countertops. Keurig Coffee maker, Tea, Hot Coco. Coffee grinder . 2 fully stocked Spa like bathrooms w/ luxurious towels .4 Lg. Bedrooms. w/ luxurious linens .Cozy fireplace in Living room. Spacious dining room. Close to Farms, Wineries, Corn Mazes, Haunted Attractions, Sunflower Mazes. Pumpkin 🎃 Apple 🍎 Picking

Home in Rocky Point

4.89 out of 5 average rating, 215 reviews

The Katalpa House -by the beach

-Our beach is private, key and beach tag provided- (in brown shed) This 1000+ sf home, features a newly renovated kitchen, outdoor shower, and many quirks that come with a 90 year old home. The furnishings are eclectic and vintage. Most of the flooring is also new. The beach and bluffs are only about a 2 minute walk. The 1/4 acre lot is shared with a secondary unit as you can see in the photos which is occupied by my sister.

Cottage in Patchogue

4.95 out of 5 average rating, 226 reviews

Quaint Cottage on Long Island's South Shore.

The Cottage is a lovely space enclosed in hedges for privacy on a one acre property. I do have 3 dogs, they are kept in a separate gated area on the property. The cottage is located 3 miles from downtown Patchogue which is enjoying a renaissance. There are many restaurants and cultural activities as well as ferry access to Fire Island (Davis Park) in the warmer weather. We are also the "Gateway" to The Hamptons.

Guest suite in North Fork

4.88 out of 5 average rating, 638 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!

Vacation rentals for every style

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Popular amenities for Wading River vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Wading River's top sights

King Kullen82 locals recommend

La Plage33 locals recommend

Lewin Farms17 locals recommend

Phil's15 locals recommend

Wildwood State Park15 locals recommend

The Shoppes at East Wind12 locals recommend

Other great vacation rentals in Wading River

Home in Mastic Beach

5 out of 5 average rating, 32 reviews

Mastic Beach Surf House

Home in Shirley

4.85 out of 5 average rating, 26 reviews

Home Sweet Home by the Beach

Home in Medford

5 out of 5 average rating, 41 reviews

Stunning Guest Suite in Medford

Rental unit in Shirley

4.93 out of 5 average rating, 71 reviews

Boho Beach Vibez Retreat! Private entrance

Home in Manorville

5 out of 5 average rating, 19 reviews

Woodsy Retreat- Fireplace, HotTub, Private & Comfy

Home in North Fork

5 out of 5 average rating, 43 reviews

Amazing river views, dock, close to great places!

Rental unit in Shirley

4.97 out of 5 average rating, 35 reviews

Welcome to Bill & Debbies AirBnb

Place to stay in Coram

4.99 out of 5 average rating, 91 reviews

T&T Unique Space

Quick stats about vacation rentals in Wading River

Total rentals
50 properties
Nightly prices starting at
G$2,086 GYD before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Frequently Asked Questions

Are there pet-friendly vacation rentals in Wading River?
Four-legged friends are welcome in Wading River. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Wading River?
Yes! Work meets play with ease at over 30 vacation rentals in Wading River featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Wading River have a gym?
Absolutely! We offer over 10 house rentals with a gym in Wading River. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wading River have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Wading River. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Wading River?
Wading River has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Wading River have wireless internet?
Absolutely! We offer over 30 house rentals with wireless internet in Wading River. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Wading River?
Experience the best of Wading River with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Wading River have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Wading River. Enjoy a tailored experience with all the comforts you desire.

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