
Waterfront holiday rentals in Madison
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Top-rated waterfront rentals in Madison
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Popular amenities for waterfront rentals in Madison
Waterfront apartment rentals

Amazing one bdrm flat at the beach!
Jeanette is a wonderful host. She met us on our arrival and gave us a tour of our rental ensuring that she answered any questions. She is very responsive and quick to answer any follow up. questions or concerns. The space is beautifully decorated and comfortable. The location is great, across the street from Long Island Sound and bordering a large nature preserve. All this and easy access to shops, groceries, and restaurants. We highly recommend this rental.

Mystical Ocean View in Historic Stonington Borough
It was great to browse through Sam's library! Amazing to wake up to beautiful sunlight. Adorable and fun layout for a home. Sam was extremely attentive, considerate, and responsive. Thanks for a great experience!

Mystic River Getaway - Walk To Downtown & Seaport!
We thoroughly enjoyed our week at this charming home. The location truly is perfect - we walked over to the Seaport one day and took many walks into the downtown area for shopping, meals at amazingly good restaurants, ice cream, and bake shops. Anthony and Kelly were wonderful hosts - the home was just as described and their communication was clear and friendly- just what you want from hosts. We couldn't have asked for more and would be happy to stay here again.

Water View SONO 2 Bedroom Walk to Metro & Dining
We were in town for a figure skating competition. The layout was perfect for enough privacy traveling with a teammate and the house was super clean and cozy. House was super quaint and beautifully restored!!! We loved the picturesque area, proximity to shopping malls and great restaurants AND local skating rinks. One of our best stays ever, thanks to the attentive host — we will absolutely book again.

Bright, private 1,000 sq. ft. 1-Bedroom Apartment
The whole experience was perfect. There were even fresh flowers to greet me. The location is easy, a beautiful neighborhood that is very quiet and safe. I'm ready to return!

Cozy Apartment with Water View of Brook
Our stay was extremely quiet until the upstairs neighbors returned. We don't have kids or pets so we're very used to quiet. Getting used to hearing upstairs neighbors took getting used to for me. The place was chock full of supplies, coffee, Scrabble and welcoming decor. The bed was outstandingly comfortable. The bathroom was modern and creative! The outdoor patio, activities and view of the creek were impressive. This is definitely on our "to return to" list.

Steps to the Beach. Lovely 2-Bedroom apt
Perfect house for a family/couple visit to the beach. It was great for my kids and I. We loved the space that the house offered and how close it was to the beach. Everyone was very pleasant that we spoke to. The house was clean, safe and felt like a home away from home.

Lakeside apartment 2.5 miles from Wesleyan campus!
Always nice to stay with Mark and Tina. Wonderful people. Very convenient location for us. Beautiful setting. We keep coming back!!
Waterfront house rentals

Amagansett, Waterfront retreat
My family had a wonderful time at Robert’s home. The house was clean and cozy and the view of the water was peaceful. He was super communicative and friendly and check in/out was a breeze. The house is in a great area and super close to East Hampton, Amagansett, and Montauk. Highly recommend!

Waterfront Home, Mystic, CT
This house is in an idyllic, lovely location with a fabulous water view. It is spacious and well-supplied to have a comfortable stay. Enjoyed every minute of our visit.

Waterfront with private dock & bocce court
We thoroughly enjoyed our stay and would definitely book again ! Close to the many wineries and cute towns, and peaceful and comfortable to come back and relax at. We enjoyed the fire pit , the view from the dock of the changing tree colors and the flow of the kitchen. ❤️

Water front home with lake amenities
We wanted a place to gather with our adult children and 2 very young grandchildren. The layout provided sleep and bathroom space for each family that gave privacy. The open concept living-kitchen space helped us feel like we were together and sharing in the cooking and child care. Even in winter the lake view is peaceful and lovely. Cozy, well equipped, and the lake vibe made this a wonderful family get away. So glad we chose the lake house for our Holiday get together.

True Ocean Front Vacationing - Groton/Mystic
The pictures don't do this place justice! The home itself is gorgeous and the view is stunning. The neighborhood is peaceful and it was perfect for me and four friends to stay the weekend.

Large Island Lake House, near casinos
The location and Shana’s house were amazing! It’s even better than the pictures. Shana has created a clean ,beautiful, welcoming and cozy place that makes you feel at home! The house has everything you may need and even more. But most of all is that view of the lake through the huge windows all around the house! Thank you, Shana! Looking forward to visiting this special place again in the spring!!

Waterfront Lake House
Absolutely loved this location! The kitchen was perfect to cook our own dinner, and the dining room table is absolutely awesome. Love the chairs & bench, along with the view of the tv. Everything that was needed, was there. It was an awesome staycation. Thankyou so much!

3BR Waterfront Oasis on Joshua Cove, Private Beach
The option wasn’t there but the photos don’t truly show how amazing the views are. Better than photos! Though our stay here was short and sweet we would highly recommend to family and friends. Each room has a beautiful view of the water giving way to a peaceful and serene stay. We loved that the kitchen and eating space was open to the living space. The tv’s were great and easy to log in and stream the Masters. The decor and styling was cohesive, stylish, and comfortable. Katherine was a great communicator and was very responsive when we had to sadly cut our trip short. Book this place!
Waterfront apartment rentals

Montauk Sunset at your fingertip!
Picture perfect! Newly updated accommodations with all the comforts of home. Extremely clean and very well managed. The view from this place is incredible. The perfect oasis in Montauk. Khrisna was extremely responsive and accommodating in our needs. Will definitely be back again!

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!

Montauk Waterfront Condo w/ Sunset Views
Absolutely wonderful stay and host. I've stayed at dozens of Airbnbs and this is one of my favorites! Doug's place is even better in person than the photos. We were a little nervous taking our first trip away with our baby, but it was extremely clean and comfortable, and Doug was so kind and responsive. The condo complex has a lovely boardwalk for taking walks, and the deck furniture was so comfortable to lounge in and take in the beautiful view. We hope to be back!

Cozy Vacation Villa 5 minutes from Mohegan
My husband and I stayed at Desiree’s place for New Years weekend. The space was beautiful, clean, comfortable and perfect for our getaway. Close to the casino and spa and anything you need. Would definitely recommend!

Beautiful Waterview Condo on the North Fork of LI
Such a beautiful condo by the water! Too bad we stayed in November, we would have enjoyed the terrace way more! Mia was so responsive and helpful with my questions prior to the weekend at her place.

Endless Summer Studio Condo w Balcony Bayview
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.

Beachside Waterview 2Br Condo w/ Pool in Greenport
The place was perfect nice and clean what I like the best is the it was close to the beach to go for a walk.

King Bed - hot tub - saunas - 1 mile Mohegan Sun
This villa is a perfect spot for a weekend getaway. Though in a condo complex, the villa itself felt private. The villa is just a few minutes walk from the clubhouse, which has a jacuzzi and pool (open in summers), and the Norwich Inn. We did not get to go to the clubhouse, but the Inn had a great spa and restaurants. The villa is also a 5 minute drive from Mohegan Sun and is accessible via Uber. The fireplace made the villa very cozy. Would definitely stay again!
Quick stats about waterfront rentals in Madison
Total rentals
20 properties
Nightly prices starting at
£113 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
Destinations to explore
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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Napeague Beach
- Ocean Beach Park
- Cooper's Beach, Southampton
- Quotonset Beach
- Walnut Public Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Giants Neck Beach
- Seaside Beach
- Blue Shutters Beach
- TPC River Highlands
- Clinton Town Beach
- Jennings Beach
- Amagansett Beach
- Shennecossett Beach
- Sunken Meadow State Park
- Marvin Beach
- Anchor Beach