Waterfront holiday rentals in Madison

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Popular amenities for Madison waterfront rentals

Waterfront apartment accommodation

Top Guest favourite
Apartment in Northport
4.99 out of 5 average rating, 147 reviews

Amazing one bdrm flat at the beach!

BethRating, 5 stars1 week ago
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.
Guest favourite
Apartment in Stonington
4.95 out of 5 average rating, 289 reviews

Mystical Ocean View in Historic Stonington Borough

YuwenRating, 5 stars1 month ago
Sam's place exceeded our expectations! The view was marvelous, and the house was beautifully decorated with a wonderful collection of books we truly enjoyed. The kitchen was fully equipped with everything we needed, and the room was super clean. We had a great time during our two-day stay. The small town offered so much to explore, and the nearby seafood market was a delightful surprise. we had fresh lobster at a very reasonable price. We highly recommend Sam's place for a relaxing and enjoyable getaway!
Top Guest favourite
Apartment in Stonington
4.97 out of 5 average rating, 217 reviews

Mystic River Getaway - Walk To Downtown & Seaport!

SarahRating, 5 stars1 week ago
We just came home from our long weekend in Mystic and Anthony’s place was a great find. We comfortably fit myself, my husband, and my 2 year old with ample space. The house was walking to distance to many amenities including downtown Mystic which we enjoyed. I would highly recommend Anthony’s place to anyone else traveling to Mystic!
Top Guest favourite
Apartment in Chester
4.99 out of 5 average rating, 95 reviews

The Millhouse Downtown Chester

PhilipRating, 5 stars1 month ago
This is our second time staying at this property. Four of us were visiting people in the area and The Millhouse is a great location to explore the area, with nice places to eat only steps away on Chester Center Main Street. The stream-side location makes it a very unique experience and the interior of the property is very nicely decorated and maintained.
Superhost
Apartment in Stonington
4.59 out of 5 average rating, 51 reviews

Bowline Landing-#1 · walk Mystic-Train/EV Lvl-2

EricRating, 5 stars1 week ago
Great location and nice quiet neighborhood.
Guest favourite
Apartment in Middlebury
4.92 out of 5 average rating, 121 reviews

Cozy Apartment with Water View of Brook

EvelindaRating, 5 stars1 week ago
We were recently in town to visit family, staying at Traci’s made our visit enjoyable and relaxing. Check-in was easy, the apartment was clean with a comfortable bed and a peaceful view of the brook. Overall, we had a pleasant stay, thank you Traci!
Guest favourite
Apartment in Milford
4.95 out of 5 average rating, 64 reviews

Steps to the Beach. Lovely 2-Bedroom apt

Matthew JoelRating, 5 stars9 months ago
Solid stay. Very clean and as pictured/described. Seemed newly renovated. Steps from the beach. Hope to stay here again next year.
Guest favourite
Apartment in Middletown
4.82 out of 5 average rating, 163 reviews

Lakeside apartment 2.5 miles from Wesleyan campus!

ElisaRating, 5 stars2 weeks ago
The apartment was beautiful and as soon as we walked in I could feel myself relax. The view is stunning and the apartment is warm and inviting. We reserved the apartment on very short notice and Mark was so helpful and responsive. Highly recommend!

Waterfront house rentals

Guest favourite
Home in Milford
4.96 out of 5 average rating, 222 reviews

Designer Beach Retreat on Exclusive Cedar Beach

SaraRating, 5 stars1 day ago
We had a great stay! Incredible one-of-a-kind view over the marsh. We saw so many different beautiful sea birds and an incredible sunset. Very short walk from the beach. Great place to stay with young kids. Well stocked kitchen with supplies and basic seasonings. Would return! Very cozy great family getaway! There are extensive requirements for clean up upon check out.
Guest favourite
Home in Coventry
4.98 out of 5 average rating, 113 reviews

Cozy cottage 5 minutes from UConn

JdRating, 5 stars2 days ago
Immaculate space. Location and views are incredible. Check in was easy, hosts were very communicative and you can tell they put a great deal of energy into their home. They also included fresh eggs from their farm. We were obsessed with it and will definitely rebook.
Top Guest favourite
Home in Woodmont
5 out of 5 average rating, 96 reviews

Oceanfront Retreat: Modern Beach House

ShannonRating, 5 stars1 week ago
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!!
Guest favourite
Home in North Fork
5 out of 5 average rating, 12 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

TimothyRating, 5 stars1 month ago
We had a wonderful weekend stay at Eileen's beautiful waterfront home. The view from the living room and primary bedroom of the water was so peaceful. The kitchen was well appointed and the cozy living room made for a wonderful family gathering spot when we weren't dining out at the fabulous nearby restaurants, visiting wineries, or viewing local scenery. Eileen was incredibly responsive to small questions we had. We would definitely book again!!
Top Guest favourite
Home in New Haven
4.95 out of 5 average rating, 113 reviews

Beach Haven - waterfront, near Yale, sunsets

Lauren RRating, 5 stars1 week ago
My family and I had such a wonderful stay at this house. The house was immaculate and well stocked for our stay. Matthew and Celia are great hosts. We really appreciated the basket of snacks and dog cookies that were left for us and our fur babies (Thank you!). They truly thought of everything and it felt like “home” the entire time we were there. The views from the back deck are truly spectacular. We spent many hours sitting in the sunroom and out on the deck enjoying the sights. My pups enjoyed daily walks at the sea wall park that was steps from the house. I can’t say enough great things about our stay. Thanks to our hosts for sharing their beautiful home with me and my family.
Guest favourite
Home in Southington
4.95 out of 5 average rating, 117 reviews

Connecticut Chalet - Private Pond, Firepit, Views!

RamonaRating, 5 stars2 weeks ago
My family had a great stay at Amanda's place. It was the perfect vacation spot - we really enjoyed the panorama view! Everything was just as described and we felt right at home.
Top Guest favourite
Home in New Haven
4.98 out of 5 average rating, 174 reviews

WaterviewsTakeWedding pics,CollegeTours Yale&Beach

LaurrenRating, 5 stars1 week ago
Cannot say enough good things about this charming home! The house had beautiful bay windows with a spectacular view, large bedrooms with plenty of room, and was very clean. Directly across the street was a waterfront park with trails along the coastline that were a blast to explore. And it was close to everything. Highly recommend!
Top Guest favourite
Home in Clinton
5 out of 5 average rating, 13 reviews

Waterside retreat! 4BR/3BA with private dock/views

LindaRating, 5 stars1 week ago
I wanted to have a very special 50th birthday celebration for my daughter whose 49th year had not been that great! I came across Alan's property online , booked it and hoped it would work for my gathering. Believe me it was everything I could have wanted... plus. A perfect backdrop to my weekend event. The online pictures certainly represent the property accurately, but it's the feeling you get when you walk into this home that is unique, and it really can't be explained in print. (Sorry AI). The location, views and provisions make it multigenerational user friendly. It was nice to know that Alan was there in case we needed something. You will NOT regret this one!!

Waterfront condo accommodation

Guest favourite
Condo in North Fork
4.84 out of 5 average rating, 106 reviews

Beautiful condo on Long Islands Northfolk

LauraRating, 5 stars1 month ago
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!
Top Guest favourite
Condo in Montauk
5 out of 5 average rating, 229 reviews

Montauk Waterfront Condo w/ Sunset Views

RachelRating, 5 stars1 week ago
We loved Montauk - low key, wild and upmarket at the same time. This apartment was perfect, super quiet yet near everything and loved seeing wild deer from the terrace
Guest favourite
Condo in Norwich
4.94 out of 5 average rating, 32 reviews

Cozy Vacation Villa 5 minutes from Mohegan

WilliamRating, 5 stars3 weeks ago
The stay was very peaceful, friendly neighbors. The scenery was great, Desiree was there for any concerns we had, and with timely response. I would anyone that want a pleasurable stay while in Norwich, this is the place to be. Thanks again, for a wonderful stay. William & Potreen
Guest favourite
Condo in North Fork
4.89 out of 5 average rating, 153 reviews

Beautiful Waterview Condo on the North Fork of LI

JeffreyRating, 5 stars3 weeks ago
Great retreat for a long weekend. Enough space for family of four. Easy access to everything in the Greenport area. Mia was very responsive, and the place was great. We would stay here again!
Superhost
Condo in Montauk
4.89 out of 5 average rating, 9 reviews

Endless Summer Studio Condo w Balcony Bayview

StephenRating, 5 stars22 months ago
We really enjoyed staying at Lynn’s place! Very clean and had a great view of the ocean from the deck. Lynn was very responsive and made the experience seamless. We would definitely stay with Lynn again.
Superhost
Condo in North Fork
4.9 out of 5 average rating, 125 reviews

Seaside Summer Escape –2BR Waterfront Condo w/Pool

DebbieRating, 5 stars1 month ago
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!
Guest favourite
Condo in North Fork
4.92 out of 5 average rating, 139 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

MorganRating, 5 stars2 weeks ago
We had a great stay! Instructions were clear and the home had everything we needed.
Top Guest favourite
Condo in Norwich
4.98 out of 5 average rating, 82 reviews

King Bed - hot tub - saunas - 1 mile Mohegan Sun

SeannaRating, 5 starstoday
We considered staying at Mohegan Sun for our weekend event there, but we are so glad we chose to stay here instead. It was a peaceful little escape! Taylor thought of everything and we never ran into any issues. Thanks for a great stay!

Quick stats about waterfront rentals in Madison

  • Total rentals

    20 properties

  • Nightly prices starting at

    $249 NZD before taxes and fees

  • Total number of reviews

    680 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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