Search Madison Cottage Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec

Featured Cottages in Madison

Our top choices for Madison cottages

Guilford Carriage House at Granite Lodge!
Interior

Guilford Carriage House at Granite Lodge!

3.0 star property
9.0 out of 10, Wonderful, (2)
"I’m normally not one to leave reviews but I had to for The Carriage House! Everything from the homey, relaxing feel to the great views was amazing! My friends and I wanted to extend our stay lol. We’re already planning another stay here for a summer trip! Also appreciated the host’s friendliness and ensuring we had an enjoyable experience. 10/10"
Guilford Carriage House at Granite Lodge!
New Haven Gem w/ Private Pool, Walk to Beach!
Interior

New Haven Gem w/ Private Pool, Walk to Beach!

3.0 star property
New Haven Gem w/ Private Pool, Walk to Beach!
Elegant Middlefield Getaway w/ Game Room!
Interior

Elegant Middlefield Getaway w/ Game Room!

3.0 star property
Elegant Middlefield Getaway w/ Game Room!
Charming Old Lyme Cottage, Steps to Private Beach!
Interior

Charming Old Lyme Cottage, Steps to Private Beach!

2.0 star property
10.0 out of 10, Exceptional, (1)
Charming Old Lyme Cottage, Steps to Private Beach!
Upscale Waterbury Retreat w/ Indoor Hot Tub!
Interior

Upscale Waterbury Retreat w/ Indoor Hot Tub!

3.0 star property
Upscale Waterbury Retreat w/ Indoor Hot Tub!
Shelter Island Retreat w/ Outdoor Pool!
Interior

Shelter Island Retreat w/ Outdoor Pool!

3.0 star property
Shelter Island Retreat w/ Outdoor Pool!
Walk to Beach: Long Island Wine Country Home!
Interior

Walk to Beach: Long Island Wine Country Home!

3.0 star property
Walk to Beach: Long Island Wine Country Home!
Walkable New Haven Retreat w/ Ocean Views!
Interior

Walkable New Haven Retreat w/ Ocean Views!

3.0 star property
Walkable New Haven Retreat w/ Ocean Views!
Dreamy Waterfront Westbrook Home on Private Beach
Front of property

Dreamy Waterfront Westbrook Home on Private Beach

3.0 star property
Dreamy Waterfront Westbrook Home on Private Beach
Mattituck Home w/ Fireplaces - Near Wineries
Interior

Mattituck Home w/ Fireplaces - Near Wineries

3.0 star property
Mattituck Home w/ Fireplaces - Near Wineries
Westbrook Home w/ Ocean Views - Walk to Beach
Interior

Westbrook Home w/ Ocean Views - Walk to Beach

3.0 star property
Westbrook Home w/ Ocean Views - Walk to Beach
Waterfront Cottage w/ Sunroom + Patio & Grill
Interior

Waterfront Cottage w/ Sunroom + Patio & Grill

3.0 star property
Waterfront Cottage w/ Sunroom + Patio & Grill
Cozy Westbrook Vacation Rental - Walk to Beach!
Front of property

Cozy Westbrook Vacation Rental - Walk to Beach!

3.0 star property
4.0 out of 10, (1)
"The property was clean. The pictures in the ads made it clear that it was supposed to be a waterfront property. It was not. The pictures were taken on a neighbors private property that actually does sit on the water. The fireplace did not work. The only beach access was through a public park which was immediately next to the house. There were several slats missing from the blinds in the bedroom facing the parking lot which was about 8 feet away. Very disappointing for what was supposed to be a...
Cozy Westbrook Vacation Rental - Walk to Beach!
Lakefront Home, Close to Mt Southington!
Interior

Lakefront Home, Close to Mt Southington!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful house with great views of the lake. "
Lakefront Home, Close to Mt Southington!
Historic Essex Home w/ Large Yard Near Downtown!
Interior

Historic Essex Home w/ Large Yard Near Downtown!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Amazing Host. Fantastic trip "
Historic Essex Home w/ Large Yard Near Downtown!
Charming Old Saybrook Home: Half-mi to Sand & Sea!
Terrace/patio

Charming Old Saybrook Home: Half-mi to Sand & Sea!

3.0 star property
Charming Old Saybrook Home: Half-mi to Sand & Sea!
Wolcott Home w/ Deck: Near Connecticut Attractions
Interior

Wolcott Home w/ Deck: Near Connecticut Attractions

3.0 star property
Wolcott Home w/ Deck: Near Connecticut Attractions
1/2 Mi to Beach: Family Retreat in Old Lyme!
Interior

1/2 Mi to Beach: Family Retreat in Old Lyme!

3.0 star property
1/2 Mi to Beach: Family Retreat in Old Lyme!
3 Mi to Dtwn: Gem w/ Patio & Fire Pit in New Haven
Interior

3 Mi to Dtwn: Gem w/ Patio & Fire Pit in New Haven

3.0 star property
3 Mi to Dtwn: Gem w/ Patio & Fire Pit in New Haven
Cottage-chic Retreat < 1 Mi to Connecticut River!
Interior

Cottage-chic Retreat < 1 Mi to Connecticut River!

3.0 star property
Cottage-chic Retreat < 1 Mi to Connecticut River!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Madison Hotel Reviews

Madison Beach Hotel

Madison Beach Hotel

10/10 Excellent
"Always a great time at the Madison Beach Hotel."
John 1-night trip
Posted 2 days ago
Madison Beach Hotel

Find out more about Madison

Find out more about Madison

Madison Cottages information

Number of reviews
5
Accommodation
43 Cottages
Lowest Price
Highest Price

Frequently asked questions

Why book your cottage in Madison with Expedia?
Expedia has some superb cottages in Madison, so get ready for a memorable stay on nature's doorstep. If you're on a budget, click on how much you'd like to spend and the star rating of your property. Or, make use of our filters to search for cottages with free WiFi or a pool. We'll help you find the right digs whatever your style of travel or plans.
How can I find cheap cottages in Madison?
Expedia is here to help you look for cheap cottages in Madison. To find your special stay in a matter of clicks, try out our handy filter tool to refine your search results by amenities, budget and star rating.
What is there to do in Madison near my cottage?
Madison has enough experiences to keep you on the go for weeks (or months!), starting with Meigs Point Nature Centre. Allis-Bushnell House and Museum, Scranton Memorial Library and Hammonasset Beach State Park are other wonderful attractions. If you're in town for longer, Hammonasset Beach and RJ Julia Booksellers are great additions to your itinerary.

Explore a world of travel with Expedia

Explore a world of travel with Expedia