
Cottage vacation 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.
Vacation rentals for every style
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Popular amenities for Madison cottage rentals
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!

Walk/Bike to East Hampton Village & Ocean Beaches
I had a wonderful weekend at Andrew’s place in East Hampton. It was gorgeous, perfect location, perfect layout, and such a central location to everything. It was incredibly clean and organized and the backyard was beautiful for relaxing. Andrew was also a terrific host- he left us beverages, was super communicative and flexible and I’m so happy I stayed here. Hopefully I’ll rent again soon!!

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.

The Silent Sun Cottage Hottub/Kayak/Firepit/BBQ
The Silent Sun Cottage is a very charming & peaceful home for a getaway. Everything is modern, clean, nicely decorated, and well stocked. James & Abigail are lovely hosts that made us feel welcome and special. The best part was spending time in the back yard (back yard does not do it justice) on the hammocks or sitting with a morning coffee looking at the lake. The location is so beautiful and tranquil we didn't want to go anywhere else. Using the provided kayaks on the lake followed by a soak in the hot tub was amazing. I highly recommend a stay here & will be back in the future.

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!

Shelter Island Waterfront Getaway
Great stay, Maureen is very communicative and super helpful. Beautiful views

Direct Shoreline Long Island Sound Waterfront
Our visit was utilitarian. We needed accommodations for us, our grown children and grandchildren and a dog. But the site of the cottage, its charm, its comfort made us wish we were staying another week. James' thoughtfulness went beyond any other Airbnb hosts' that we've experienced. Everything we might need if we were staying 10 days was there, clean, labeled. Thank you, James.

Charming Historic Schoolhouse on Mystic River
We had such a fantastic stay at this special home right on the river in lovely Mystic! It came stocked with everything we needed for a fun couple’s getaway. Gerard was so friendly and accommodating - we felt right at home. Can’t wait to return!

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!

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.

Your own Thimble Islands private cottage!
We had a fabulous weekend at this lovely cottage. Located on a remote peninsula surrounded by the glistening water we couldn’t have asked for a nicer experience. The amenities were both convenient and thoughtful. Although we chose to dine out, the kitchen was very modern with upscale appliances and an espresso machine. We did bbq on our last night and had a great end to our 4 night stay!

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.
Private cottage rentals

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.

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.

Studio Four-Entire Guesthouse near CT River
Very private nicely appointed and great hosts

Cozy cottage near Clinton Marina on CT Shoreline
Cottage was cute and cozy. It was a great place for us to hang out and spend time together with lots to do in the area and great places to eat.
Quick stats about cottage rentals in Madison
Total rentals
10 properties
Nightly prices starting at
R2,342 ZAR 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