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Top Holiday Rentals in Madison

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (177)
"The views are fantastic. Very quiet neighborhood. "
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

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

10.0 out of 10, Exceptional, (49)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

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

9.8 out of 10, Exceptional, (129)
"Great house, host and location. Stayed with a larger group and plenty of room!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (75)
"We had a very nice stay and enjoyed the quiet environment and the amenities of the property. Lots of great area for walking. "
Waterfront Cottage in Beautiful Hoopers Island

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (121)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (7)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Maryland Vacation Rental w/ Private Pool & Dock

9.2 out of 10, Wonderful, (12)
"Had a great time fishing from the dock while we got out of the city for a weekend."
Maryland Vacation Rental w/ Private Pool & Dock

Studio in Downtown – Walk to Everything!

10.0 out of 10, Exceptional, (22)
"This was the perfect spot for a long weekend. Excellent location and the unit itself was more than we expected. "
Studio in Downtown – Walk to Everything!

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (184)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Heated pool, sandy beach, pier, and playground set punch point apart!

10.0 out of 10, Exceptional, (9)
"Beautifully decorated, peaceful, well appointed home for our girls bday celebration. Highly recommend."
Heated pool, sandy beach, pier, and playground set punch point apart!

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (253)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier

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

10.0 out of 10, Exceptional, (120)
"Clean and spacious. Great views! Loved the beach! Found a bunch of fossils. Enjoyed kayaking. Overall outstanding!"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

9.6 out of 10, Exceptional, (29)
"Very roomy and lots of amenities. Superb location and private. Easy check-in and check-out. Guest contact was awesome - very responsive! Thanks so much!"
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (167)
"The Waterfront Retreat on the Patuxent River is better than advertised. Our whole family stayed -- everyone loved it! It was clean, comfortable, with everything needed to stay comfortably, sleep, eat, relax and use as a home base for exploring. Solomons Island and the surrounding area was filled with lots of fun things to do (restaurant's, museums, history, boating, walking, etc.). "
Waterfront Wildlife Retreat on the Patuxent River

Waterfront Solomons Apartment

9.4 out of 10, Exceptional, (10)
"The location is great with amazing views of the docks and very walkable to the boardwalk, restaurants, and the Solomon museum. Apartment was cozy with great communication from the hosts. Would recommend to anyone! "
The price is £220
includes taxes & fees
6 Sept - 7 Sept
Waterfront Solomons Apartment

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.8 out of 10, Exceptional, (11)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is £380
includes taxes & fees
8 Sept - 9 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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

9.8 out of 10, Exceptional, (40)
"Property was perfect for our family stay. House was clean and well stocked."
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Terrace Suite · Terrace Suite - Private Flat in Historic Manor.

9.8 out of 10, Exceptional, (31)
"Great stay, clean & owner gave great local suggestions!"
Terrace Suite · Terrace Suite - Private Flat in Historic Manor.

Waterfront property with private boat ramp and new dock!

9.4 out of 10, Exceptional, (13)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!

St. Michaels Waterfront Home

9.8 out of 10, Exceptional, (31)
"We had a wonderful stay. Check in and out was very easy. The place was clean and well maintained. Very peaceful spot on the water. "
St. Michaels Waterfront Home
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.
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Top Madison Hotel Reviews

Frequently asked questions

Are there holiday rentals in Madison?

Yes, there are holiday rentals close to the most popular sights in Madison, or you can select a more secluded option if you're looking for a relaxing stay.

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

Bay view from Calvert Cliffs, Solomons Island & State Park nearby: This holiday home rental outside of Madison is located on a lake, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Madison?

Choose from 3 Expedia holiday rentals in Madison for a memorable holiday.

What’s there to see and do in Madison?

Explore the area and family-friendly sights such as Richardson Maritime Museum, or get out into nature at a spot like Blackwater National Wildlife Refuge. Harriet Tubman Underground Railroad National Historical Park and Harriet Tubman Museum and Educational Center are a couple of places you'll find in the wider area.

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 provide amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and bustling concierge desks 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 an attractive option for family gatherings.