Madison Holiday Homes
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^
Featured Holiday Homes in Madison

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Shewell's A-Frame on Mill Creek

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Discover tranquility near Calvert Cliffs

Midcentury Modern Lake House, gorgeous views, deck, 4-bedrooms in Lusby/Solomons

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Heart of Tilghman Island | Pet Friendly | Perfect for Weddings Guests & Families
Holiday Accommodation Madison
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Madison are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Madison itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Madison holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Madison, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Madison with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
Madison Holiday Homes essential information
Accommodation | 255 Holiday Homes |
|---|---|
Lowest Price | NZ$160 |
Highest Price | NZ$1,082 |
Popular accommodation | Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock, The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!, Shewell's A-Frame on Mill Creek, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, Discover tranquility near Calvert Cliffs , Midcentury Modern Lake House, gorgeous views, deck, 4-bedrooms in Lusby/Solomons, Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space., Heart of Tilghman Island | Pet Friendly | Perfect for Weddings Guests & Families, Woodwind Manor on the Tred Avon minutes to St Michaels and Easton. |
Top trending hotels in Madison

Hyatt Regency Chesapeake Bay
More accommodations in Madison
^Eligibility requirements and conditions apply








