
Cottage holiday rentals in Madison
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Top-rated cottage rentals in Madison
Guests agree: these cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for cottage rentals in Madison
Cottage rentals with a hot tub

Luxury cottage by the sea with hot tub and pool
We loved this airbnb and stayed for 3 weeks. It sits right on the edge of the marsh with an extraordinary view. We greatly enjoyed how a short walk away is Chaffinch Island, which is a gorgeous park full of tides pools and hackberry trees. The space was clean and comfortable and Mary was a fantastic host. You can see a lighthouse on an island 3 miles out sea from all the rooms, even the main bed.

Cozy Lakefront Cottage w/Swim Spa & Firepit
Absolutely loved my stay here. The space was beautiful, peaceful, and had everything I needed. I would definitely come back again!

Lakeside cottage with beautiful views up the lake!
We had a relaxing, peaceful time at Bobby's place. It's wonderful to wake up right on the water. He was very communicative. It is quiet, but still close enough to everything. We had an enjoyable experience.

Lovely 2 BR Beach House No. Shore
Great spot for a long weekend! Wonderful location close to the beach and local wineries. Richard was a great host offering lots of recommendations and clear instructions for check in and using available amenities.

Lakefront Summer Escape | Hot Tub & Lake Access
Loved this stay! The views by the lake were absolutely stunning, and the hot tub was the perfect way to relax. The place was clean, cozy, and had everything we needed. Highly recommend!

Private Beach Cottage
I really enjoyed my stay and the beach was very beautiful. Thanks Keith 😁

Lil Nauti Cottage Newly Updated Steps To The Beach
Lil Nauti was perfect for our family. The bedrooms were adequate, with very comfortable beds and plenty of pillows. The wardrobe space and drawers were great as we had a long stay with a lot of baggage! Jason has absolutely everything you could possibly want or need for a stay. The kitchen is really well equipped. Cute cottage and delightful private garden.
Pet-friendly cottage rentals

Lake Beseck cottage
Was the perfect little get away for us. And it was nice to find a place that accommodated the dogs so well. We appreciated being able to get to places easily but at the same time have a peaceful place to return to.

Welcome to The Holly at Amston Lake
This place is the perfect getaway location, especially for a quiet relaxing weekend. Great host who was super responsive and flexible with me trying to check in early.

Private and Serene home close to I-84 and shopping
We Enjoyed our stay with Rio. He was kind and informative. He went above and beyond to make sure our stay was as comfortable as possible. We would definitely stay again.

Charm + location. Walk to beach, town, & harbor.
This was my fifth stay in Jeanne's wonderful cottage! The cottage gets better and better each time I visit: a newly renovated bathroom, redecoration in lighter/brighter colors, etc. The home is extremely well stocked - every kitchen item you might need (including loads of glasses/plates/silverware, pots/pans, etc.), thick towels, extra blankets and throws, and lots of cleaning and paper products. There are plenty of cozy places to sit and relax, both indoors and out. The best thing of all is Jeanne herself, who is without a doubt the most generous host I've encountered on AirBnB. She is friendly, communicates proactively, and is quick to respond to any issues/questions. She truly opens her home to her guests, encouraging visitors to use the space fully and to make themselves at home. The cottage is an easy walk to the beach ane/or to town and is lovely, homey, and peaceful. I'll definitely return!

Serene Waterfront Cottage
As always, we love our stay at the cottage. It’s becoming our home away from home when visiting our son. Thanks for all our goodies! Always a great surprise! Have a wonderful Christmas. We’ll see you next year I hope.

Spring Sale|CozyCottage|Walk to Beach|Pet-friendly
We had nice weekend at the cozy cottage. We loved that it was pet friendly and a short walk to the beach. Cameron was very friendly and responsive. She offered great suggestions for food and activities.

Montauk Cottage Escape
Wonderful time staying at Milton and Megan's. The location was perfect and the home had everything we needed and more to work remotely for the week. Thank you!

Your Nest Near The Beach
This has hands down been the best winter Airbnb I’ve ever had. Even though it has a beach theme, this could easily double as a winter wonderland cabin. I came here with my boyfriend to celebrate his birthday and before we left we were already planning our next trip back! This is hands down the cleanest feeling airbnb we’ve ever stayed at. They really put effort into making this place feel like a loved home. Everywhere you look theres a nod to the theme in home! The heating/cooling in the house is seriously impressive. The customizable fireplace upstairs (be careful on the stairs!) was a dream. Stargazing at night was incredible. I missed the sunset sleeping in on the incredible bed but the sunrise was AMAZING. Direct view on the front porch! Seeing the moon through the skylight while still being comfy on the couch and watching tv was absolutely terrific. From the endless amenities to the delicious food in the area, I can’t stop praising this place. Thank you guys for the great stay!
Private cottage rentals

Renovated beach cottage a block from private beach
April’s cozy beach cottage was perfect for my elderly parents. Everything was spotless, and although tiny, the kitchen was fully stocked with a large refrigerator and full stove, microwave etc. both the bed and the sofa were v comfortable and most importantly, April made sure there was AC in every room, even the cute porch. There’s an outdoor shower which is super convenient. You can easily walk to the beach, go to the arcade, kokomos, a crepes place and the carousel and gift shop. Very peaceful retreat. Must also mention how cheerfully it’s decorated and how spotlessly clean! Just lovely.

Cheerful 2 bedroom cottage on beach
This house is absolutely perfect. It's clean, charming, has everything you need. The beautiful back yard has plenty of space and good stuff for kids to play with. Also, it's about a 30 second walk to the beach... neighbors are out on their patch of beach but yours is yours to yourself. It's perfect. We cannot wait to come back.

Hop Skip and a Jump to the Beach
Our first ever stay at 'Hop Skip and Jump' really met all of our expectations and needs for the week of 8/10-8/17/24! I have never in my 70+ years of spending a summer week in Old Lyme been so enveloped with 5 star luxury while at the Beach! I would recommend this rental to any small family or a group of girlfriends! Hop

Adorable cottage close to beaches and downtown
Had a staycation with my girlfriends and we felt right at home. They had all the necessary kitchen utensils to make dinner for my friends. Would highly recommend to anyone looking for a home away from home.

Shalom Cottage with beach rights.
Raj was very friendly, proactive and helpful. Place was clean, quiet and comfortable. Went to Clinton for work and it was a better place by far than a local hotel.

Adorable Cottage
This magical cottage is a little slice of paradise. It’s so incredibly cute and cozy but beyond that, Erin Leigh has put in so many thoughtful touches- we wanted for nothing. It’s clean, it’s beautiful, it’s comfortable…truly one of the best places I’ve ever stayed in. Her hospitality was top notch. I felt so spoiled and so sad to leave.

Cozy cottage near Clinton Marina on CT Shoreline
My sister and I were in town for a wedding in Old Saybrook. We loved this place. So comfortable and had all the conveniences needed for a theee night stay. The kitchen was very well equipped, the beds were comfy, the house felt safe and private, the water pressure was amazing and hot water was plentiful. Jaime, the host was immediately responsive and communicative. All was just great and the neighborhood felt safe for walking or sitting on the deck in the evening. Highly recommend

Private Two-Bedroom Cottage
Absolutely loved the little cottage. Clean, and clutter free. My family and I will definitely be back!
Quick stats about cottage rentals in Madison
Total rentals
10 properties
Nightly prices starting at
£98 before taxes and fees
Total number of reviews
440 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Cooper's Beach, Southampton
- Quotonset Beach
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Clinton Town Beach
- Walnut Public Beach
- TPC River Highlands
- Amagansett Beach
- Blue Shutters Beach
- Marvin Beach
- Jennings Beach
- Seaside Beach
- Shennecossett Beach
- Connetquot River State Park Preserve
- Long Island Aquarium
- Attawan Beach
- Groton Long Point Main Beach
- Bushnell Park
- Sunken Meadow State Park