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Compare 471 Vacation Homes in Madison with updated reviews, rates, and availability.

Exterior
Updated ranch Home 4 minutes from the beach on a quiet end street.
Updated ranch Home 4 minutes from the beach on a quiet end street.
Exterior
Enjoy the North Fork of Long Island at Our Lovely Home
Enjoy the North Fork of Long Island at Our Lovely Home
Gateway to tranquility at the private beach is only a 5 minute walk.
Spacious, beautiful home. 5-min walk to beach. 1 min to Water's Edge Resort!
10.0 out of 10, Exceptional, (41)
"Very nice place. Would definitely stay there again (actually this our second stay at the property). Clean, well equipped and the pictures are accurate."
Spacious, beautiful home. 5-min walk to beach. 1 min to Water's Edge Resort!
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Beach
Waterfront Beach House
9.6 out of 10, Exceptional, (33)
"The cottage is a perfect cozy stay on the water - we stayed in the winter and still were able to enjoy the sand and the sunrises right outside the window. House is well-appointed and well-located within area with access to restaurants and shops in Clinton, Madison, Westbrook, Old Saybrook, etc."
Waterfront Beach House
Property grounds
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
Private kitchen
Beach Cottage, > .5 walk to beach, quaint, Beach community
10.0 out of 10, Exceptional, (1)
"Pretty gingerbread cottage, well appointed. Lovely area, 2 min walk to the beach. Owners super helpful. Overall beautiful, serene, highly recommmend."
The price is SAR 608
SAR 1,222 total
includes taxes & fees
29 Jum. I - 30 Jum. I
Beach Cottage, > .5 walk to beach, quaint, Beach community
Living area
Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!
Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!
Our access point to Limewood Beach.
Beautiful 4BR Beach House with Private Beach Access.
10.0 out of 10, Exceptional, (65)
"Small house a short walk from beach that well accommodated our party of five. Clean and comfortable, well laid out and equipped with everything you’d need."
Beautiful 4BR Beach House with Private Beach Access.
Living area
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
Property grounds
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
Beach
Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️
10.0 out of 10, Exceptional, (21)
"Our group of four friends in our 50s loved our stay here. Heather was a responsive, welcoming, flexible host who left us a card, bottle of wine and a prepped wood pile in the fire pit. The decor was tasteful and beautiful, clean and modern. The mattresses were firm, which we liked. We made use of the comfortable couch on the deck as well as the gas fireplace in the living room. The location is lovely and we had a short, 5-minute walk to the beach. Birders would enjoy the tremendous diversity of...
Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️
Outdoor dining
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
10.0 out of 10, Exceptional, (162)
"Got away for a girls weekend and this was perfect. It was close to wineries, and a short Uber away to Greenport. The house was comfortable, clean, and private with enough space for all 8 of us. The outside was also beautiful- right on the water. Highly recommend!!"
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
Interior
Lovely Family sized 3 bedroom Colonial home, close to restaurant.
8.6 out of 10, Excellent, (10)
"Nice house..Good area.."
Lovely Family sized 3 bedroom Colonial home, close to restaurant.
Bridal Suite
Charming Castle Cottage
Charming Castle Cottage
Living area
Summer Cottage 1 week minimum!!
10.0 out of 10, Exceptional, (2)
"A wonderful stay with incredible, attentive hosts. The house is a couple of blocks from the water and recently remodel with a charming beach vibe! Highly recommend."
Summer Cottage 1 week minimum!!
Private kitchen
Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
10.0 out of 10, Exceptional, (10)
"Perfect spot for a weekend on the North Fork"
Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
Pool
Newly built ranch, beautifully landscaped with pool, large yard, patio,...
9.6 out of 10, Exceptional, (5)
"Beautiful, well appointed new construction in desirable Greenport area. Minutes to local vineyards and the shoreline. Comfortable for 3 couples. Kitchen was perfect for simple meals. Off season, so we didn’t get to use the pool but it looked amazing!"
Newly built ranch, beautifully landscaped with pool, large yard, patio,...
Living area
Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
10.0 out of 10, Exceptional, (37)
"We had the best time visiting Sam & Matt’s place in Southold. The house is the perfect size for us- 3 adults and 3 kids plus 2 dogs. And it was an ideal location to explore all the north fork has to offer. We can’t wait to return!"
Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
Front of House
adorable ranch in beach community
10.0 out of 10, Exceptional, (42)
"Old Saybrook is a nice little CT beach town and the property is perfect for a small family. Check in and everything was very easy and the hosts are super responsive if you need anything or have any questions. We'll definitely be going back when we need a couple of days away!"
The price is SAR 1,313
SAR 2,423 total
includes taxes & fees
28 Jum. I - 29 Jum. I
adorable ranch in beach community
Sit back and relax
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
9.0 out of 10, Wonderful, (6)
"Lovely location!"
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
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See all available properties in Madison
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

Interior
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!
Front of property
New Haven Village Suites
3.0 star property
7.6 out of 10, Good, (1830)
"We got upgraded To a 2 bed room room and we were so happy. The room was spacious and beautiful and clean. Def will be going back and getting that room again. "
The price is SAR 392
SAR 436 total
includes taxes & fees
10 Jum. II - 11 Jum. II
New Haven Village Suites
Room
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (181)
"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling. "
The price is SAR 699
SAR 960 total
includes taxes & fees
28 Jum. I - 29 Jum. I
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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