Search Madison Cottages

Compare 135 Cottages in Madison with updated reviews, rates, and availability.

Shalom Cottage with private beach rights.
9.4 out of 10, Exceptional, (8)
"Has everything you need for 2, for a Summer stay. (The portable heater didn't keep up with the December evenings)."
Shalom Cottage with private beach rights.
Luxury Cottage near Saybrook Point Marina- Dog Friendly!
9.4 out of 10, Exceptional, (30)
"I was in the area for my niece's college graduation at Wesleyan University and loved the chance to explore this beautiful part of the country. Being so close to the water in Old Saybrook was amazing, and the house itself was both fresh and cozy. The hosts were very responsive, and the only issue (which they acknowledged in advance) was that a portion of the fence was missing, due to a recent storm. That said, they were up front and apologetic, knowing that I'd booked because my dogs were along....
The price is $292
$507 total
includes taxes & fees
11 Jun - 12 Jun
Luxury Cottage near Saybrook Point Marina- Dog Friendly!
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (81)
"Beautiful house in a beautiful location! We hope to return soon!"
Waterfront Cottage in Branford
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Peconic Sound Beach Home: Backyard & Vineyards
9.8 out of 10, Exceptional, (6)
"Tucked away near the sound….a piece of paradise ! Truly a beautiful place to unwind and enjoy all the North Fork has to offer . Centrally located on the North Fork, but easy access to a spectacular beach . You will leave refreshed & trying to figure out how soon you can return ."
Peconic Sound Beach Home: Backyard & Vineyards
Beach Bungalow, large porch, 1/2 mile to the water.
Beach Bungalow, large porch, 1/2 mile to the water.
The Carriage House at Rose Hill - Minutes to Yale! Dog Friendly!
10.0 out of 10, Exceptional, (3)
"My mother and i were so happy to check into this beautiful and relaxing place after a long day of travel. Abigails attention to detail and artistic flare in decor creates a unique experience. She was also extremely responsive and kind. It was moms first time at a vbro and so safety was key- this fit the bill. The beds were very comfy. Absoutely perfect stay , i would go back again!"
The Carriage House at Rose Hill - Minutes to Yale! Dog Friendly!
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, (8)
"We were there for a family event in Glastonbury for just a couple of days, and so we didn't go to the lake. However, the cottage was perfect for our needs -- quiet, allowed for contemplation, and privacy that we needed. We hope to perhaps and experience the beautiful lake."
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
70 Year old cottage on 2.8 acres, stunning views and sunsets
70 Year old cottage on 2.8 acres, stunning views and sunsets
The Bay Cottage · Rocky Neck Park, Beach & Niantic
10.0 out of 10, Exceptional, (5)
"I booked this for a sister weekend. It was perfect for what we needed. It appears that the house was built to be a summer getaway, so it is pretty basic and no frills and comes with all the creaks and quicks of an older house. The living room is perfect for hanging out and the four chairs make it easy to rearrange to suit your needs. The kitchen is nicely stocked with everything you would need to stay with a family and the dining room is spacious enough to easily accommodate everyone staying...
The price is $284
$554 total
includes taxes & fees
17 Jun - 18 Jun
The Bay Cottage · Rocky Neck Park, Beach & Niantic
"Salt 'n' Lyme" - Walk to everything !
9.2 out of 10, Wonderful, (21)
"This cottage is so adorable and just a short walk to the beach and a local convenience store. This makes it easy to park the car and just walk to get coffee and such. We stayed in October so not much open this time of year, but we were in the area for a family wedding so not much time to hang out anyway. This was the first time I've rented on Vrbo, so I wasn't sure what to expect as have read a lot about obnoxious owners with tons of rules, but Brett is super-chill with only a couple of things...
"Salt 'n' Lyme" - Walk to everything !
Fabulous Waterfront Property in the Heart of Wine Country
10.0 out of 10, Exceptional, (154)
"What a beautiful relaxing weekend getaway with friends. The view was beautiful and the place was clean and comfortable. We would stay here again!"
Fabulous Waterfront Property in the Heart of Wine Country
Waterfront Cottage w/ Sunroom + Patio & Grill
6.8 out of 10, (3)
"Relaxing and beautiful sunset views , Clean and floor plan one floor plan was perfect ! Spacious and so nice to relax on this vacation ! Close to everything we needed !"
Waterfront Cottage w/ Sunroom + Patio & Grill
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
10.0 out of 10, Exceptional, (56)
"The cottage was quite wonderful with a large kitchen and comfy porched living-room. Scott was very quick regarding any communication. The only thing in the description that I would add is that " you'll need to bring your own towels and bed linens". It wasn't a problem, but our airplane carry-on bags only were already packed. We made our adjustments and ended up checking a bag, no worries. Just a thought. We thoroughly enjoyed its quiet and relaxing location."
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
Charming Old Lyme Cottage, Steps to Private Beach!
7.4 out of 10, Good, (3)
"Very intimate cottage setting, lovely beach scenery, walking distance to the beach, feet away from hearing the crash of the waves. Short drive to grab whatever you have forgotten or need to enhance your stay in this tiny home. Great location to unplug, energize, and bond with your family. You can create the quality time you miss out on in the world today, you will not have the distractions of television, internet, or gaming."
Charming Old Lyme Cottage, Steps to Private Beach!
Walk to Love Lane! Immaculately renovated private cottage.
10.0 out of 10, Exceptional, (10)
"This is beautiful cottage, and the location is perfect for all the vineyards. The house was VERY clean, and the garage is a great place to hang out and relax too. My Husband and I will be booking again very soon for another getaway. Thank you so much."
Walk to Love Lane! Immaculately renovated private cottage.
The Island Sound: Ocean View Cottage near Yale, Beach, Downtown, Hikes
10.0 out of 10, Exceptional, (1)
"The owner is super helpful "
The Island Sound: Ocean View Cottage near Yale, Beach, Downtown, Hikes
Walk to Breakwater Beach in Heart of Wine Country
9.8 out of 10, Exceptional, (7)
"Returning to this property with our dog. Love being near the water and still close to everything. Brunch at Love Land is minutes away. My dog loves wineries and there are many dog friendly options near by. Dinner at North Fork Table is not far away. Highly recommend!"
Walk to Breakwater Beach in Heart of Wine Country
Beach access Cozy Cottage
10.0 out of 10, Exceptional, (3)
"My friends and I had a great time staying at this adorable cottage! The beach is so close and the parking pass is a lifesaver! We also loved making a fire and relaxing in the backyard. There was plenty of room in the kitchen to cook while spending time together. Will definitely book again!"
Beach access Cozy Cottage
Southold Cottage w/ Patio & Grill - Walk to Beach!
Southold Cottage w/ Patio & Grill - Walk to Beach!
Resting on an 18 acre farm, this historic cottage is the retreat of your dreams
10.0 out of 10, Exceptional, (1)
"Immaculate and cozy one bedroom cottage next to numerous trails at Devils Hopyard and protected lands right from the door step. Very quiet and rural if that is what you're looking for. Restaurants about 5-10 miles away. Looking to stay again maybe next year for our Anniversary or another special occasion. Am going to recommend to family that I know would love this spot."
Resting on an 18 acre farm, this historic cottage is the retreat of your dreams
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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

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!
New Haven Village Suites
3.0 star property
7.6 out of 10, Good, (1842)
"Comfortable beds and clean for the most part. Rooms are good size. More like a studio apartment. Will stay again sometime 👍 👍 ✌️. "
The price is $104
$120 total
includes taxes & fees
9 Jul - 10 Jul
New Haven Village Suites
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (183)
"Wonderful stay and super clean! Can’t wait to come back. "
The price is $312
$399 total
includes taxes & fees
27 Jun - 28 Jun
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.

Madison Cottages information

Number of reviews
375
Accommodation
135 Cottages
Lowest Price
Highest Price

Frequently asked questions

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We think that vacations should be simple, so if you’re chasing cottages in Madison at an affordable price, Expedia is here to help. Keep the budget under control and choose an inexpensive option far from the downtown buzz, or book a 5-star cottage to really spoil your favorite people.
How can I find cheap cottages in Madison?
With Expedia’s handy filter tool, sourcing cheap cottages in Madison couldn’t be simpler. To view properties that’ll make your hip pocket happy, refine your search by amenities, budget and star rating.
What is there to do in Madison near my cottage?
Madison has enough experiences and activities to keep you amused for weeks (or months!), starting with Hammonasset Beach State Park. Hammonasset Beach, Bishops Orchard and Winery and Allis-Bushnell House and Museum are other well-known attractions. If you have more time, Henry Whitfield State Museum and Hyland House Museum are nice finishing touches to your itinerary.

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