
Cottage holiday rentals in Madison
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Top-rated cottage rentals in Madison
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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!

Cozy Lakefront Cottage w/Swim Spa & Firepit
We had a GREAT time at Feyza’s cabin. It was clean, quiet and exactly as described. We especially loved the secluded setting, the lake views and the jacuzzi. Feyza was helpful, communicative and very responsive. Her digital guidebook was very insightful as to the local attractions and restaurants. We would definitely stay here 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 !
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!

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.

Private cottage in horse country &1 hour from NYC!
Great stay! Fergus was a great host - we drove from Boston with our dog and were attending a wedding the same day, so when I reached out to ask for earlier check in, Fergus didn’t hesitate and had the spot ready for us! They even were kind enough to drop off some bananas for us before the wedding. Check in was easy, an adorable, cozy cottage, and delicious muffins for us the next morning! Thank you!

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more
My family and myself loved every square inch of this property! From the serene views and well landscaped garden, to the sound of a stream to fall asleep to, the spotless interior and attention to detail…the pet bowls and bed, the labeled cabinets, the toiletries and games, we never wanted to leave! We last minute had to accommodate family members to be picked up later than the check out time and Michael was kind enough to extend our stay until 2pm so we could relax and enjoy more time together! We might make an annual trip out of this house and can’t thank the host enough for his immediate responses and making us feel right at home. Beautiful home, we loved sharing it! The first night we ate at the near by restaurant on the water, Housatonic House, also a recommendation on the fridge! Great food and service and BEAUTIFUL views! It ended up raining Saturday, but we still got a Hike in on our last morning at Osbornedale State Park, beautiful trails and picnic areas! Wonderful time.

Adorable cottage
Angela was a great host and very accommodating after an unfortunate personal event we encountered just after arriving. The cottage was very comfortable and immaculately clean. Love the keyless entry. Neighborhood is quiet and we felt extremely safe. Deer pass through the yard throughout the day and what's more beautiful than that!!! We absolutely recommend Angela as a host and would not hesitate to book again in the future.

1920’s charming dollhouse near South Cove
The cottage was fantastic, and Jodi was an amazing host. Communication was effortless and timely, and Jodi was helpful, proactive and generous. I loved how close the sound was to the cottage - hopefully I'll be able to stay there again, and if I do I'll bring a kayak with me. For the purposes of this stay, though, maybe the best thing was how close it was to where I was working for the week - less than a 5-minute drive to downtown Old Saybrook.
Private cottage rentals

Beachfront Cottage Serene Private Beach, Kayaks
We loved it. Redefines “fully stocked” - David’s place had everything we could ask for. The water at high tide was magical. Kayaking, fishing and we found over 100 (literally) hermit crabs.

A Beach House Gem
We continue to visit Rose’s house for our yearly weekend girls getaway. It’s the perfect cozy beautiful place to catch up with friends and relax. Rose is an amazing host!

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!

The Beach Nest-Lux Cottage Steps to the Beach
Great, beachy location within easy driving distance of a bunch of great waterfront restaurants. Easy, clean, and very comfortable.

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

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!

Cottage at the Marina
My stay at Chris and Ann’s listing was the perfect last stop on my stay in CT……beautiful, welcoming accommodations enhanced by the natural, peaceful, setting of the salt marsh and wildlife. It’s absolutely a favorite place the next time I’m visiting CT.
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