
Waterfront holiday rentals in Wading River
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Top-rated waterfront rentals in Wading River
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Waterfront apartment rentals

Kicking off Summer, on the beach in Milford, CT!
Great place; wonderful 2 bed place, clean, cosy and top end, one of the nicer places I've stayed. Alison was super easy to communicate with and the location was great for a Christmas break. Was very happy with everything!

Amazing one bdrm flat at the beach!
Jeannette was there to greet us and made sure we knew where everything was and that we had everything we needed. She even provided breakfast. Her place was immaculate. The location was amazing. She made our departure very easy. We are looking forward to staying there again. If you looking for a great place to stay, this is it.

Phoenix Engine #1
Nathan’s a great host and he provided a great welcome pack. Great home for my wife and I and adult son. Plenty of space and walkable to coffee shops and river. Awesome communication and offered a very helpful relaxed late check out at no cost. Totally recommend this host and this property

Cozy Getaway Retreat /South Shore/ NYC 40min
We had a wonderful stay at Anthea’s place! It was private, cozy, and a perfect haven between busy activities with our 4 month old! It was clean, well stoked, and very homey. Anthea was friendly and very responsive with any questions we had. I would definitely recommend!

Bayside Boho Retreat
Location was convenient, place matched description and host was friendly and reachable. Would stay here again!

Bright, private 1,000 sq. ft. 1-Bedroom Apartment
I had an excellent stay! Andy is responsive and accommodating. The space is lovely and as described , clean, and comfortable, tastefully decorated and stocked with starters needed for an easy stay, …. Example, dish soap, salt, pepper, bathroom supplies.

Turtle Dove Cozy Gem on the Bay
We had a wonderful stay at this lovely home! The house was bright, clean, and full of positive energy. One of the highlights was the beautiful deck right on the canal – perfect for relaxing and enjoying the view. Inside, everything was thoughtfully arranged, with clear notes and instructions that made our stay smooth and easy. The kitchen was spacious and well-equipped with everything we needed. Overall, it was a perfect home base, and we’d happily return. Highly recommended!

Steps to the Beach. Lovely 2-Bedroom apt
Solid stay. Very clean and as pictured/described. Seemed newly renovated. Steps from the beach. Hope to stay here again next year.
Waterfront house rentals

Once a Pond - time and stress slow down.
Spacious home with a nice outside area. Enjoyed coffee with birds and bunnies. Will stay here again.

Best View + Private Beach + Putting Green
Overall a very nice and pleasant stay. The house is very nice, super nicely decorated and amazing views. Really worth staying here.

Oceanfront Retreat: Modern Beach House
We had a relaxing overnight with our two pups! The bay/sound area is so peaceful. Our dogs enjoyed swimming before the tide came in and we kayaked along the shoreline. The inside was stunning and had everything you needed and more! We door dashed lobster rolls from the Bonfire Grille nearby (10/10) and ended the night in the hot tub! Coffee on the sunny patio was a great perk, too! Thanks again!!

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!
We loved Laura and Dana’s Big Easy home by the beach. It was big and comfortable and every detail had been thought about to maximize our enjoyment. Drawers and closets and cabinets were all labeled so we didn’t have to search for anything or guess where anything was. Literally every need had been anticipated! Amazing. The beds and bedding and linens and towels were abundant and soft and comfortable. The kitchen amenities were awesome, from an air fryer, to a full set of bar tools and blender, to great appliances. The decor was happy and cheerful and creative and fun. There were so many places to sit and enjoy, both inside and out. Do not hesitate to choose this wonderful place for a visit of any length. You will love it!

Captain’s Cottage Water Views -3 Bdrm
The Captain’s Cottage was beautiful and exactly like the pictures. We walked (with umbrellas) to the quaint shops and restaurants and along the harbor. It was a perfect location to breathe some sea air, and just a short drive to the Long Island Railroad for time in the city. We just had the best time and Kim was a wonderful and accessible host!

Beachfront Retreat - 5BR Home with Stunning Views
Beautiful property on the beach. Lots of seating outside. Easy to find with GPS. Friendly neighborhood. Would definately stay there again if our travels take us to the East end of the Island. Water was calm and peaceful. Would love to stay a week here next time. Plenty of parking for the guests 5 cars. We saved money eating Breakfast at the house each day and enjoyed quality family time. The king bedroom has a wonderful view of the Peconic Bay. Dual thermostats make climate control easy.

Luxury Beach House | 3 Bd-King | Chef Kitchen |4 TV
We had the best time at the beach house! We have two toddlers and the location of the house was perfect! Easy walk to the beach. They played in low, medium and high tide and loved them all equally. Sunsets from the deck are breathtaking. Morning walks on the quiet block and along the beach were so peaceful. The surrounding town is adorable with some great restaurants. Kids had a blast at dockside brewery. House was super clean, host always responsive and neighbors were kind. We can’t wait to come back!

Stunning sunset charming waterfront home 4 seasons
Absolutely stunning! This house has an amazing view from gigantic glass doors in the main room. Details in the house are well thought out and of great quality, including a high end coffee maker and other appliances. The place has lots of premium touches that make this experience a cut above the rest. Steven is an amazing, friendly, and communicative host. Incredible experience all around, I would definitely book here again.
Waterfront apartment rentals

Beautiful 2 Bedroom 2 Bathroom Pool-Side Condo
Stay was great and the place was very clean

Waterfront Condo C-204 at The Cliffside Resort
Had an amazing stay in Greenport. The condo was exactly as listed, extremely clean and has a ton of amenities. Tom communicated from when the reservation was booked until the end, he was readily available, answered quickly and gave tons of informations. The location is ideal with the private beach and pool and a quick 5 minute drive into town. The condo offers a great little kitchen, a wonderful balcony with a water view and an unbeatable sunset and all the amenities you need for your stay. Pool towels are provided, plenty of bathroom towels, there’s a coffee machine, 3 tvs, a variety of dishware and there’s coin operated laundry in the basement. The staff that works the grounds and property are also super friendly. The town of Greenport and other surrounding towns are all close, you have endless options for vineyards in close vicinity and there’s tons of amazing restaurants within a 5-15 minute car ride. I highly recommend booking this property, I will definitely be rebooking! (If yo

Water front, sunsets, sail boats, Wi-fi, birds
John and Cathy are amazing hosts. This was our second consecutive summer stay in their condo and it does not disappoint. The place and the amenities they provide are amazing and they are a wonderful couple who respects your privacy but are there for anything you need. I recommend anyone to stay here and know they would want to return. Thank you John and Cathy for making our second summer with you a fantastic vacation!

Beautiful condo on Long Islands Northfolk
We very much enjoyed our stay at the Cliffside for our wedding weekend! Alice was very flexible with us, which we appreciated because getting married is chaotic enough LOL. Would highly recommend staying here. The unit was spotless and had a wonderful view. We could not have asked for a better stay!

Seaside Summer Escape: 2BR Waterfront Condo w/Pool
We had a great stay at Julie’s place. There was a slight hiccup with check-in times but Julie was very communicative and sorted it out promptly. The place itself was great, beautiful waterfront views and a private beach. The weather wasn’t the best but we still made the most of it. The apartment was compact but big enough for 4 adults.

Beautiful Waterview Condo on the North Fork of LI
Mia’s place is excellent. Exactly what the listing describes and more — Mia is a great host and super attentive despite us being a last minute booking, she even helped us through a tough time late in the day when I thought my daughter’s stuffie had been picked up by the maid service. Above and beyond!

Seaside Summer Escape –2BR Waterfront Condo w/Pool
We had a great time at Julie’s place. Would love to visit again…perhaps in the Fall. Loved the balcony overlooking the Sound. Julie was very responsive to my questions. She got back to me immediately. I would highly recommend Julie’s home!

Beachside Waterview 2Br Condo w/ Pool in Greenport
We had a great stay! Instructions were clear and the home had everything we needed.
Quick stats about waterfront rentals in Wading River
Total rentals
10 properties
Nightly prices starting at
₹11,989 before taxes and fees
Total number of reviews
160 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Beach
- Jones Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Rye Beach
- Gilgo Beach
- Rye Playland Beach
- Napeague Beach
- Cooper's Beach, Southampton
- Point Lookout Beach District Park
- Robert Moses State Park
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Dunewood
- Bethpage State Park
- Ocean Beach Park
- Woodmont Beach
- Amagansett Beach
- Rye Town Beach
- Seaside Beach
- Quotonset Beach
- Amityville Beach