
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.
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Popular amenities for cottage rentals in Madison
Cottage rentals with a hot tub

Waterfront cottage overhanging the water!
We thoroughly enjoyed our time at the cottage. It was so very peaceful and we loved being literally right around n the water! Slept amazingly well and the cottage was just lovely! Robert was also a great host. 5 stars all around and we hope to return again!

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes
My boyfriend and I had a nice and relaxing one night stay at Martin’s place. It’s a cute house and we enjoyed relaxing in the hot tub! Martin was responsive and communicative. Overall a nice little getaway.

Lakefront Escape | Cool Tub | Game Room | Fire Pit
Such a lovely home! actually better than I expected! Will definitely book again. It’s honestly a no brainer after staying there. I can recommend this place 100%!

Cozy Getaway | Pet Friendly | Litchfield Cty
I wanted a weekend getaway for my son’s 13th birthday that landed on Friday the 13th, I came across this cabin airbnb and decided to book and give it a try. this location is an hour away from our home and gave us that peace of paradise we were looking for. the cabin felt like home and had everything you can possibly need. I honestly wish I can give higher than a 5 star because this cabin was perfect. I’ll be booking again for a winter weekend getaway. thank you for hosting my family and I.

NEW - Hot Tub - Mohawk Mtn - Appalachian Trl
Martin was a very responsive host! The property was great overall.

Lakeside cottage with beautiful views up the lake!
We always love going to this cottage. It’s our favorite. It’s actually one of our favorite places. To go a few times a year winter summer. We just spent memorial weekend there. A little doggies loved it. Home away from home so cozy. Bobby the host is wonderful. My daughter boyfriend came up and they absolutely loved it and my son came from Texas to spend one night. It was his first time there he loved it. We already planning on going back. Fantastic getaway. If you need to distress and want calmness. This is the place to come to. And the town of Mystic has great restaurants Like I said it’s our favorite place to come to and I’ve been to quite a few…. Just got home today and I’m seeing if I can book some sometime in October to go back we love it.

Lovely 2 BR Beach House No. Shore
beautiful house, great location and very nice and peaceful neighborhood close to the beach and the vineyards the house is very well equipped ! Richard was very nice and even find a little bed for our baby boy ! thanks !

Private Beach Cottage
Great communication with host, beach within walking distance was so nice, overall good spot within 30 mins of mystic aquarium and Foxwoods casino
Pet-friendly cottage rentals

Lake Beseck cottage
We loved our stay here. It was the perfect place for two of us and our dog. The home was just as described, welcoming, cosy and well equipped, and we appreciated all the local recommendations. We enjoyed local walks, the lake, and the great dog park, as well as easy access to Middletown to visit our son. Elisabeth and Daniel were fantastic hosts!

Private and Serene home close to I-84 and shopping
Very communicative and perfect description of what was expected.

Mystic, CT Pet-Friendly Cottage with Hiking Trails
My sister, dog and I stayed at the cottage for the weekend and had a great experience! Erika is a wonderful host and the property is beautiful. The cottage itself was exactly as pictured. Breakfast in the inn, cooked with natural and organic ingredients, is an absolute must. The location of the inn is great as well, with direct access to the Lantern Hill trail (which our dog loved) and only a short drive from downtown. Would definitely recommend staying here!

Serene Waterfront Cottage
We love it here! Our home away from home! Since we’ve moved out of Connecticut, this is the perfect place to stay when we come for a visit. Farah is the best host, and we love everything here! Especially her amazing gift basket! Bella always loves her surprises!

Cozy Cottage by the pond
Jamie & Rose are the consummate hosts: clear communicators, friendly, helpful and supportive of their guests' (and their animals') experience. The cottage is New England cute on steroids, and super private. All was tip top, first rate for a country cottage experience. Thanks for making our experience so smooth and relaxing.

Charming Fairfield Beach 3BR Cottage By The Sea
We enjoyed our stay! Such easy access to the beach was so convenient. You’re definitely better off venturing out after high tide to enjoy the most amount of beach and there are a lot of shells that make being barefoot challenging. We did arrive after major storms which could have contributed to that. The house was spotless with everything you need to be comfortable! We did not utilize the outdoor space but definitely would have if the weather was drier! Definitely would stay here again.

Montauk Oceanview
My girlfriend and I had an amazing time at Ron’s Cottage, it was beautiful and incredibly peaceful, very easy to get around steps from the beach. Listening to the waves crash on the beach from the kitchen was my favorite part. 10/10 wound stay again!

Remodeled Cottage Private Old Kelsey Point Beach
Had a great stay. Very comfortable and well equipped. Close to shopping, restaurants, and a quick and easy walk to a private beach! Definitely want to stay again next year.
Private cottage rentals

Waterfront Beach Cottage in Connecticut
Eglantine’s place was an absolute DREAM! The pictures do not do it justice, it is much bigger than expected! It really feels like you are on your own private beach. It is so private and calm and peaceful. Both indoor and outdoors are absolute perfection and no matter where you sit, it’s the best seat in the house. Eglantine is also extremely friendly and always responsive. We most certainly would recommend her place to anyone looking for a peaceful and beautiful getaway and would love to book again sometime soon!!

Beautiful Updated Cottage walk to the Beach
Joe’s place was really nice and in a great location. One block from the public beach in Westbrook, it’s in an area where there are lots of great restaurants and cute breakfast places. Joe was proactive in reaching out to ask if I needed anything. Great stay!

Cozy Lakefront Cottage Perfect for Families
What a beautiful view! We had a great time despite the weather. The house was very comfortable and the location right on the lake is hard to beat.

Enchanted Cottage on the Marsh, walk to beach
I had a wonderful relaxing time in this charming, well-apportioned cottage. There is a beautiful view over the marsh to short beach and it’s a great spot to see local birds - herons, red-winged blackbirds, etc. A trolley line that’s been converted to a hiking trail runs through the marsh and makes for a great walk. Lots of other fun walks nearby. it’s very quiet and cozy but still just a quick 10 minute jaunt to New Haven The piano and turntable were neat features and the house was nicely maintained and decorated. You can tell the host is very attentive to detail and committed to keeping things pristine. He was also super friendly and responsive I would gladly return to this spot next time Im in the area and heartily recommend to anyone looking to relax and recharge

Cheerful 3 Bedroom Cottage with Fire Place
We had a great stay at Jonathan's cottage. The location could not be beat - right on the beach. Jonathan was very easy to communicate with and quick to respond. There were a couple of minor hiccups that occurred but Jonathan was quick and responsive. Overall, a beautiful home in a great location.

Oceanside home steps to private beach!
Spent the weekend here for my husband’s birthday with our kids. They loved the big private beach. Almost no one else was on it. We needed an air mattress for our daughter and they quickly brought one over. The place was STOCKED with everything you could need!

Ocean view cottage in Indian Neck
This home was a restful, peaceful retreat from a busy graduation weekend. We walked on the beach, enjoyed the careful, relaxing decor, and were happy to find coffee and an iron available. Our family truly enjoyed this house!

Chic Coastal Retreat with Short Walk to Beach
This beach house is super cute. I did have trouble with the lock box, but, that could have been operator error. Super cute, super clean, super responsive to questions.
Quick stats about cottage rentals in Madison
Total rentals
10 properties
Nightly prices starting at
$167 SGD 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
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Napeague Beach
- Shinnecock Hills Golf Club
- Walnut Public Beach
- TPC River Highlands
- Ocean Beach Park
- Woodmont Beach
- Amagansett Beach
- Blue Shutters Beach
- Jennings Beach
- Seaside Beach
- Silver Sands Beach
- Bushnell Park
- Quotonset Beach
- Heckscher State Park
- Ninigret Beach
- Sunken Meadow State Park
- Calf Pasture Beach