Vacation Homes in Madison, MD
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Top Vacation Homes in Madison

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

Charming 2-bedroom Cap Cod style cottage

4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick

Dollhouse in Central Historic St Michaels

"Endless Summer" Waterfront on the Chesapeake Bay!

Beautiful 3 Bedroom Retreat walking distance to Downtown St. Michaels

Cottage with Private Water Access | Pet-Friendly | Near St. Michaels
Top hotels in Madison

The Wildset
Find the Best Vacation Homes in Madison
Why book a vacation home in Madison?
Vacation homes in Madison make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.
How much is a vacation home in Madison?
Private Madison rental homes range between $101 - $663 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.
What are the cancellation and flexibility options on Travelocity?
To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.
What amenities should I look out for in a vacation home?
There are some exciting amenities available in Madison vacation home rentals. You might look for Madison rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room.
Vacation rentals in Madison offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.
When is the best time to rent a vacation home in Madison?
You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.
Why book a vacation home with Travelocity?
Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Madison. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Madison hotels and vacation homes that best suit your stay. We also have deals for flights, and Madison car rentals. You’ll save even more when you bundle your items into a Madison vacation package!
How many vacation homes are available to book in Madison?
There are 259 rental homes in Madison. Enter your travel dates to check availability.
How do I find the best price for a vacation home in Madison?
Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.
Madison Vacation Homes essential information
Accommodation | 259 Vacation Homes |
|---|---|
Lowest Price | $101 |
Highest Price | $663 |
Popular accommodation | Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets, Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, Bay view from Calvert Cliffs, Solomons Island & State Park nearby, Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock, Back Creek Villa Covered Deck, Charming 2-bedroom Cap Cod style cottage, 4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick, Dollhouse in Central Historic St Michaels, "Endless Summer" Waterfront on the Chesapeake Bay!, Beautiful 3 Bedroom Retreat walking distance to Downtown St. Michaels, Cottage with Private Water Access | Pet-Friendly | Near St. Michaels, Plum Point Cottage #14 |







