Madison holiday rentals

We found 135 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Madison to find one that's perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the amenities that you need and want for your stay, such as air conditioning and Wi-Fi. You're sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Madison

Showing deals for:25 Dec - 1 Jan

Living area
Dining
Exterior
Terrace/patio
Exceptional
(5 reviews)

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Lusby

8% off
AU$6,866
for 7 nights, 1 home
AU$981 per night
includes taxes & fees
Beach House w/TheaterRm, GameRm, Outdoor Shwr
Dining
Outdoor dining
Living area
Private kitchen
Exceptional
(13 reviews)

High Water Guest House<br>

Cambridge

8% off
AU$4,042
for 7 nights, 1 home
AU$577 per night
includes taxes & fees
High Water Guest House<br>
Kitchen/dining
Foyer into Living Room
Kitchen with peak into living room
Living Room into Kitchen/Dining
Exceptional
(92 reviews)

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Taylors Island

8% off
AU$6,048
for 7 nights, 1 home
AU$864 per night
includes taxes & fees
Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball
Living area
Marina
Property grounds
Exterior
Exceptional
(14 reviews)

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Cambridge

8% off
AU$2,824
for 7 nights, 1 apartment
AU$403 per night
includes taxes & fees
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Private kitchen
The beautiful marina is just 4 blocks away
Boutiques and vintage shops are right outside your door
Marina
Exceptional
(11 reviews)

Station House East: Upscale Loft in the Historic District Cambridge, MD

Cambridge

8% off
AU$1,608
for 7 nights, 1 apartment
AU$230 per night
includes taxes & fees
Station House East: Upscale Loft in the Historic District Cambridge, MD
Private kitchen
Exterior
Living area
Dining
Exceptional
(28 reviews)

Spacious waterfront home with amazing views, private pier, fishing and crabbing.

Cambridge

8% off
AU$6,670
for 7 nights, 1 home
AU$953 per night
includes taxes & fees
Spacious waterfront home with amazing views, private pier, fishing and crabbing.

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    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Madison getaway

Learn about the unique charm of Madison with a stay in a holiday home rental. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Madison

Are you looking for attractions to see while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Madison a one-of-a-kind holiday spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Phillips Wharf Environmental Center (15.6 mi / 25.1 km)
  • Layton's Chance Vineyard and Winery (17 mi / 27.4 km)
  • Bay Country Shop (9.5 mi / 15.2 km)
  • Chesapeake Hills Golf Course (14.1 mi / 22.6 km)
  • Perigeaux Vineyards and Winery (16.6 mi / 26.8 km)

Exploring the natural features in Madison

Whether you're an outdoor enthusiast or just want to take in the scenery, Madison is a great place to get outside. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Blackwater National Wildlife Refuge (8 mi / 13 km)
  • Long Wharf Park (9.3 mi / 15 km)
  • Gerry Boyle Park at Great Marsh (9.3 mi / 15 km)
  • Cove Point Beach (12.5 mi / 20.1 km)
  • Breezy Point Beach (17.6 mi / 28.4 km)
  • Flag Ponds Nature Park (13.6 mi / 21.9 km)

Transport to and around Madison

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 22.7 mi (36.5 km) from the city centre.

Frequently asked questions

Where are the best areas for renting a beach house in Madison?
For renting a beach house in Madison, Maryland, the area along the Chesapeake Bay is particularly appealing. The waterfront properties near the Madison Wharf are ideal, as they offer stunning views of the bay and easy access to sandy beaches. Many of these rentals come equipped with amenities such as spacious decks for outdoor dining, private docks for boating or fishing, and fully equipped kitchens, making them great for families or groups looking to enjoy a seaside getaway.Additionally, the nearby Easton area provides further options, where you can find charming houses set in a picturesque environment. These rentals often feature amenities like fire pits, outdoor showers, and garden spaces that enhance the beach experience. The proximity to local shops and restaurants in Easton adds convenience, allowing guests to enjoy both relaxation and local cuisine.For those interested in outdoor activities, the nearby Blackwater National Wildlife Refuge offers excellent opportunities for hiking and birdwatching, with rentals in this area often highlighting easy access to nature trails.
What is the most popular type of holiday rental accomodation in Madison?
In Madison, holiday rentals primarily consist of holiday houses and cottages, with several options available in the area. These types of accommodations are typically situated in peaceful neighbourhoods, providing a serene setting for relaxation. Most holiday houses come equipped with multiple bedrooms, spacious living areas, and fully equipped kitchens, allowing guests to enjoy a home-away-from-home experience. Cottages, on the other hand, often offer quaint charm and may feature outdoor spaces such as decks or gardens, great for enjoying the natural surroundings.
Are there any family house rentals in Madison?
In Madison, Maryland, there are several family-friendly house rentals available, making it a suitable destination for groups looking to enjoy a getaway. Properties in this area typically offer spacious living rooms and fully equipped kitchens, great for preparing family meals together. Many homes also feature outdoor spaces where children can play and adults can relax.Nearby attractions enhance the family experience, with parks and waterfront areas providing opportunities for outdoor activities. Visitors can explore the natural beauty of the Chesapeake Bay, enjoy picnics at local parks, or take leisurely walks along scenic trails.
Are there any remote work holiday rentals in Madison?
In Madison, Maryland, there are several holiday rentals available that cater to remote workers. These accommodations often come equipped with essential amenities such as free Wi-Fi, both in the rooms and common areas, ensuring a reliable internet connection for work. Many properties also offer dedicated office spaces, allowing for a comfortable and productive work environment.The picturesque surroundings of Madison, with its charming waterfront views and proximity to local attractions, make it an appealing location for those looking to combine work and leisure. Additionally, the area is home to lovely parks and scenic spots ideal for a break after hours of working remotely. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Madison?
In Madison, popular holiday rental amenities include well-equipped kitchens, superb for preparing meals with local ingredients. Many properties come with cosy fireplaces, adding a warm touch for those cooler evenings. Travellers can also expect convenient appliances such as blenders and coffee or tea makers, ideal for a quick breakfast or a relaxing afternoon drink. Additionally, some rentals offer a selection of books, providing entertainment and a chance to unwind after a day of exploring the area.
When is the best time to visit Madison for a holiday rental?
The best time to visit Madison for a holiday rental is during the peak season from July to September. This vibrant period attracts a variety of travellers eager to immerse themselves in the region's outdoor activities, including kayaking, hiking, and exploring local parks. The warm summer months provide ideal conditions, with temperatures typically ranging from 20 to 30 degrees Celsius, making it great for enjoying the beautiful landscapes and waterfront.August is particularly popular, as it offers a lively option with plenty of events and activities. Visitors can revel in the local culture, partake in seasonal festivals, and indulge in the area's culinary delights, all while soaking up the sun.For those looking for a more budget-friendly option, November presents a wonderful opportunity to visit Madison. While this month is considered the low season, it offers a chance to enjoy the area's tranquillity and natural beauty without the crowds. The cooler temperatures, usually between 5 and 15 degrees Celsius, allow for peaceful walks along the shoreline and the chance to witness the stunning autumn scenery.
What are the top attractions in Madison?
In Madison, Maryland, visitors can enjoy a variety of attractions that showcase the area's natural beauty and historical significance. The nearby Blackwater National Wildlife Refuge is a prime spot for birdwatching and hiking, featuring scenic trails and diverse wildlife. This expansive refuge is a great destination for nature lovers and those looking to explore the Chesapeake Bay area's ecosystems.Another top attraction is the historic town of Easton, just a short drive away, where visitors can stroll through charming streets lined with boutique shops and art galleries. The Academy Art Museum in Easton offers rotating exhibitions and educational programmes, making it a cultural highlight in the region.For a taste of local history, the nearby sites of St. Michaels, known for its maritime heritage and picturesque waterfront, provide opportunities for boat tours and exploring the Chesapeake Bay Maritime Museum.
Are all fees included in the Madison holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Madison holiday homes with parking?
Stayz offers a wide selection of holiday homes in Madison with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Madison holiday homes?
You can find great discounts on holiday homes in Madison on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Madison holiday home booking on Stayz?
To find Madison holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Madison?
A long-stay holiday home in Madison is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Madison holiday home?
Book your Madison holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Madison?
Prices for holiday homes in Madison vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Madison to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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