Madison Holiday Rentals

Start date: Check-in selected.
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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Madison

New Madison beach house - Ocean front- Great views- booking Summer 2025

10.0 out of 10, Exceptional, (66)
"Delightful to be on the water, spacious house for a family, responsive owner, a worthwhile trip! "
New Madison beach house - Ocean front- Great views- booking Summer 2025

Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

10.0 out of 10, Exceptional, (33)
"Very much enjoyed our stay!"
The price is AU$455
includes taxes & fees
11 Sept - 12 Sept
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Waterfront Estate Home - Beach and Shared Pool - East

9.8 out of 10, Exceptional, (43)
"Perfect home for a big family gathering!"
Waterfront Estate Home - Beach and Shared Pool - East

Postcard Cabins Machimoodus

2.0 star property
9.6 out of 10, Exceptional, (63)
"Great stay"
The price is AU$253
includes taxes & fees
21 Sept - 22 Sept
Postcard Cabins Machimoodus

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (240)
"Great view of the water and nice amenities with the beach and pool."
The price is AU$640
includes taxes & fees
11 Sept - 12 Sept
Cliffside Resort Condominiums

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is AU$276
includes taxes & fees
23 Sept - 24 Sept
The Stern at Soundview · Beach+Ocean+Sunrise

Rustic Lakeside Cabin at White Gate Farm

10.0 out of 10, Exceptional, (117)
"Just amazing!"
Rustic Lakeside Cabin at White Gate Farm

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

10.0 out of 10, Exceptional, (13)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is AU$565
includes taxes & fees
1 Oct - 2 Oct
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (54)
"Loved the property and we will surely be coming back."
Luxury Furnished Apartments by Hyatus Downtown at Yale

Shoreline Oasis

9.2 out of 10, Wonderful, (7)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is AU$399
includes taxes & fees
11 Sept - 12 Sept
Shoreline Oasis

4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres

4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

10.0 out of 10, Exceptional, (99)
"Our multigenerational long weekend loved our stay. Fab manager. House so well kitted out. "
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

The Mast at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.4 out of 10, Exceptional, (3)
"Perfect spot for my stay! I loved being able to walk down to the beach and enjoyed the quiet neighborhood. Check in directions were straightforward and I had no issues getting into my room or finding the place. Host was very responsive! "
The price is AU$297
includes taxes & fees
23 Sept - 24 Sept
The Mast at Soundview · Beach+Ocean+Sunrise

Freeboard at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.2 out of 10, Wonderful, (5)
"It was very close to the beach , quiet, parking on property room had everything you would need i enjoyed my stay didnt want to leave so soon wouldve liked at least 1 more day maybe next year thank you. "
The price is AU$265
includes taxes & fees
11 Sept - 12 Sept
Freeboard at Soundview · Beach+Ocean+Sunrise

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

10.0 out of 10, Exceptional, (44)
"Amazing property, we loved everything about it, highly recommended, will stay again "
The price is AU$1,070
includes taxes & fees
14 Sept - 15 Sept
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

9.4 out of 10, Exceptional, (13)
"Beautiful area, close to the beach, with a wonderfully kept house."
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

The Bridge at Soundview · Beach+OceanView+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (1)
"The space was much larger than expected and was perfect for a group of 4 adults and 3 kids under 3! We had a great time, being a 5 minute walk from the beach and having a comfortable space to come back to. We'll definitely be coming back."
The price is AU$915
includes taxes & fees
16 Sept - 17 Sept
The Bridge at Soundview · Beach+OceanView+Sunrise

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (144)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (29)
"Always a pleasure staying here!"
The price is AU$354
includes taxes & fees
30 Sept - 1 Oct
1-bedroom cottage with Grove Beach 🏖️ access.

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (97)
"We loved being by the beach."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Madison Hotel Reviews

Find out more about Madison

Find out more about Madison

Everything you need to know about Madison holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Madison holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Madison holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Madison holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Madison. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Madison holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Madison holiday rentals we have selected for you start as low as AU$253 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Madison rentals

At Expedia, we put the best Madison holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Madison rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Madison holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Madison. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Madison?

Yes, there are holiday rentals in Madison close to RJ Julia Booksellers, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Madison. Make sure you have time to check out the aquarium and waterfront during your trip.

What are some of the best holiday rentals that Madison has to offer?

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food: This holiday home rental outside of Madison is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Madison?

With 32 Expedia holiday rentals, you're guaranteed to find just the right place for your Madison stay.

What’s there to see and do in Madison?

Family-friendly attractions include RJ Julia Booksellers and Anna Mia's, whereas Hammonasset Beach and Meigs Point Nature Center are a couple of great spots to enjoy the outdoors. Hammonasset Beach State Park and North Madison Shopping Center are other places to visit while you're in town.

What’s a holiday rental in Madison like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Madison. Holiday rentals offer extras such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.