Holiday Homes in Madison

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Featured Holiday Homes in Madison

Updated ranch Home 4 minutes from the beach on a quiet end street.
6.0 out of 10, (1)
"Family of 5 (2 adults, 3 teens) stayed for long weekend. Friendly and fairly quick communication with Fabian was appreciated. House is approx 1 to 1.5 miles to Long Island Sound and beach. Nice and quiet neighborhood. The place was clean with exception of downstairs which had some of the owner's personal belongings strewn about. The biggest disappoint was no hot water or heat for most of the stay. Fabian offered hot showers at another nearby location and brought in a space heater which was...
Updated ranch Home 4 minutes from the beach on a quiet end street.
Patchogue River Retreat, 8 minute walk to West Beach
10.0 out of 10, Exceptional, (6)
"House was very nice. Location is great. Easy walk to beach and convenient to Westbrook center."
Patchogue River Retreat, 8 minute walk to West Beach
Lovely Westbrook Home w/ Patio - Walk to Beach!
10.0 out of 10, Exceptional, (1)
"Beautifully decorated comfortable and clean would definitely rent again"
Lovely Westbrook Home w/ Patio - Walk to Beach!
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Spacious, beautiful home. 5-min walk to beach. 1 min to Water's Edge Resort!
10.0 out of 10, Exceptional, (42)
"Family short stay Memorial Day weekend for a graduation. House a short walk from a lovely little beach, near shopping. Nice neighborhood with comfortable beds, great kitchen, reclining couch and fabulous back yard patio. Owner attentive and responsive."
Spacious, beautiful home. 5-min walk to beach. 1 min to Water's Edge Resort!
Beautiful 4BR Beach House with Private Beach Access.
10.0 out of 10, Exceptional, (65)
"Visited family back in CT and this was the perfect place to stay. Kind of like a Tardis, it was bigger on the inside! Thank you!"
Beautiful 4BR Beach House with Private Beach Access.
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
10.0 out of 10, Exceptional, (71)
"Beautiful inn in a wonderful setting. The farm is beautiful and the lake is nearby. Delicious dinner was prepared for us."
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
9.8 out of 10, Exceptional, (106)
"Very nice stay. Only disappointment was the lack of a hot tub. Otherwise a perfect venue for our group."
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
10.0 out of 10, Exceptional, (1)
"Beautiful new home and property! Would one back for sure!"
The price is NZ$1,378
per night
12 Jun - 13 Jun
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
1820 Whaling Captain's Home
10.0 out of 10, Exceptional, (46)
"We had a wonderful stay at Marcia’s beautiful house in Greenport. Marcia was incredibly welcoming and accommodating and the house was perfect for our trip. The location is ideal - a short walk to everything the NoFo has to offer. Marcia was very responsive and gave great recommendations. We will definitely be back!"
1820 Whaling Captain's Home
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (111)
"We were looking for a nice relaxing weekend getaway from NYC and happened to find this listing. The check in process was easy, and the owners were lovely! We'd absolutely book again."
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Beach House
9.8 out of 10, Exceptional, (43)
"My daughter graduated from coast guard academy so we were staying for several days. The cottage is located in black point in Niantic. So close to the ocean. The cottage was adorably decorated, and very comfortable. Plenty of beds to accommodate a bigger group. Slept very well in comfortable bed. The owner had left some bagels and muffins for us as well. Small but nice kitchen with plenty of room for a family to sit at larger table. My favorite is proximity to water and the daily multiple walks....
Beach House
gorgeous victorian direct ocean front single family six bedroom, ten rooms
10.0 out of 10, Exceptional, (51)
"Wonderful host. Easy communication. Great house."
gorgeous victorian direct ocean front single family six bedroom, ten rooms
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
10.0 out of 10, Exceptional, (30)
"Spacious comfortable and inviting home. Well-stocked everything. Lovely outdoor spaces and gracious hosts."
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Sea Breeze Paradise: Beachfront & Panoramic Views
9.4 out of 10, Exceptional, (16)
"We've found that fall is a great time to visit the North Fork and the property was the perfect place for relaxing. Even when the weather was bad, we had the indoor fireplace to add ambiance and then the outdoor firepit when the weather cleared up. The views are fantastic and so nice to sit outside and relax at night. Had a couple of quick questions come up but got responses very quickly and it didn't interrupt the trip. We had a great time."
Sea Breeze Paradise: Beachfront & Panoramic Views
Cozy Westbrook Vacation Rental - Walk to Beach!
10.0 out of 10, Exceptional, (2)
"A lot bigger than it seems and you can beat the location, right on the water. House was clean and cute."
Cozy Westbrook Vacation Rental - Walk to Beach!
Amazing Lakefront Property
10.0 out of 10, Exceptional, (15)
"This was my second go round staying at this property. My family and I enjoyed it the first time. More so the second time with the upgrades. Being familiar with the area was a great help. This time we went in the lake and enjoyed ourselves. We are looking forward to returning back again. Thank you Raymond for letting us stay at your property. Richard and Joanne"
Amazing Lakefront Property
Direct Waterfront Private Beach Escape
9.8 out of 10, Exceptional, (8)
"We had a beautiful time . Kids didn’t wanted to leave. Amazing views from house , mostly just hung out by the water, watched the birds, and enjoyed the amazing views of the sky. We will be definitely back."
Direct Waterfront Private Beach Escape
Respite Ranch: Private Pool, Hot Tub, Beach Access
10.0 out of 10, Exceptional, (2)
"Great stay and wonderful property. The first stay that didn’t have a book and list full of restrictions and checkout instructions. After a whirlwind weekend celebrating our daughter ‘s engagement, this was a welcomed surprise! Everyone enjoyed their stay, including our two labs. Great fenced in yard that gave them plenty of room to exercise. We will be back!"
Respite Ranch: Private Pool, Hot Tub, Beach Access
The SandPiper
9.4 out of 10, Exceptional, (3)
"This listing was exactly as described and was a great little apartment in Greenport with everything we needed. About a 10 minute walk to downtown area which was very convenient. It sits on a busy street so there is some noise from the road but it did not bother us too much and the host provided noise machines in the bedrooms which was very helpful. Overall I recommend this apartment and would definitely stay in the future!"
The SandPiper
Cozy Modern Home
9.6 out of 10, Exceptional, (26)
"Very nice place, stay there for a couple of nights for a get together, plenty of room. Only problem was some of the cleaning supplies where locked away where we couldn’t access it so we had to bring a mop and other supplies."
Cozy Modern Home
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Madison

Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
10.0 out of 10, Exceptional, (16)
"My month-long stay was absolutely wonderful. Hunter was an amazing, proactive host. The weather wasn't cooperative in the beginning of my stay, but Hunter went above and beyond to make sure whatever issues arose were taken care of and I couldn't be happier to have made this choice. I will definitely be back!"
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
New Haven Village Suites
3.0 star property
7.6 out of 10, Good, (1840)
"Ok"
The price is NZ$184
per night
1 Jul - 2 Jul
New Haven Village Suites
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (183)
"Wonderful stay and super clean! Can’t wait to come back. "
The price is NZ$519
per night
27 Jun - 28 Jun
Cliffside Resort Condominiums
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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