Madison Holiday Rentals

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Check prices for these dates

Tonight
27 Oct - 28 Oct
Tomorrow
28 Oct - 29 Oct
This weekend
31 Oct - 2 Nov
Next weekend
7 Nov - 9 Nov

Holiday Rentals in Madison

Dining
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
10.0 out of 10, Exceptional, (180)
"First, Brett is an exceptional host. Very helpful and responsive. This is a very special place in a wonderful community with incredible views. Rustic, warm and the perfect place to relax. We didn’t want to leave! Highly recommend."
United States
Dee D.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (121)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
United States
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Exterior
Family and Pet-Friendly, Waterfront with Pier
Family and Pet-Friendly, Waterfront with Pier
10.0 out of 10, Exceptional, (262)
"This was an extension of our original 4-day stay. We had so much wonderful and fun time that we stayed an extra day. The owners Rob and Clarissa were the best host!"
United States
Alicia J.
Family and Pet-Friendly, Waterfront with Pier
Outdoor pool, a heated pool
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (74)
"We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we...
United States
Ronald S.
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Exterior detail
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, (13)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
United States
Dara M.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (144)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Interior
Waterfront Solomons Apartment
Waterfront Solomons Apartment
9.2 out of 10, Wonderful, (13)
"Very clean, awesome location and amazing hosts!! "
United States
Jeff R.
The price is HK$1,049
HK$2,092 total
includes taxes & fees
30 Oct - 31 Oct
Waterfront Solomons Apartment
Outdoor pool
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
9.8 out of 10, Exceptional, (7)
"Great House "
United States
Conrad L.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (80)
"Beautiful location, so peaceful and quiet, we loved our stay! "
United States
Janna C.
Waterfront Cottage in Beautiful Hoopers Island
Beach
Belle of the Chesapeake Bay
Belle of the Chesapeake Bay
9.2 out of 10, Wonderful, (16)
"Excellent communication from the owner, Julie and the property manager. Our family (newborn to adults) stayed at this property while in town for a wedding at Rousby Hall. We were a quick and easy 15 minute drive away from the venue. The house was very clean and nicely set up to accommodate our group. We only wish we had more time to spend at the house than we did. The pictures are exactly what you see when you check in - no unhappy surprises. Thank you for hosting us and being so flexible...
United States
eileen b.
Belle of the Chesapeake Bay
Outdoor dining
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (191)
"Very clean perfect location for St. Michael’s everything is walking distance from the house looking forward to coming back. "
United States
Frank G.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (44)
"Wonderful home in excellent location!!"
United States
Sydney S.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Marina
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (124)
"We had a wonderful stay. This was our second time staying here and we loved it. Very quay, cozy and clean. Everything as advertised. Location is perfect as it is a very walkable town. This place is right in the middle. The owner was very friendly, open and communicative. And I had a big surprise when we returned. My neck pillow I had forgotten and left it 2 years ago was still there sitting in a closet. We hope to return next year. "
United States
David W.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Private beach
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
10.0 out of 10, Exceptional, (18)
"House was great and the golf cart excellent"
United States
Bradley E.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Smart TV, books, printers
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
9.4 out of 10, Exceptional, (20)
"This property is beautiful and perfect for large groups. There is plenty of room and very inviting. We had a great time!"
United States
Shannon T.
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Outdoor pool
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
10.0 out of 10, Exceptional, (137)
"Great home! Has everything you need, especially if you're traveling with children. Will def consider staying here again if we're in the area!"
United States
Ajiab R.
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (59)
"Such a beautiful place to stay. Had absolutely everything you could need. Comfy beds and tons of space. Definitely recommend staying here!"
United States
Whitney H.
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Sun-loungers, beach towels
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
10.0 out of 10, Exceptional, (37)
"This is a beautiful property, well appointed, but not too formal for families wanting to be in the pool or on the water all day. We were a party of 12 including six grandchildren. There was plenty to do for the adults and the grandchildren and plenty of space in the home to not feel like you were on top of each other. The sunsets were spectacular. Marissa is an extremely responsive host, and all our questions were answered in a timely fashion. Saint Michaels is very close by and an absolutely...
United States
helen w.
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Terrace/patio
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
9.8 out of 10, Exceptional, (132)
"Great location with lots of privacy. The dock and the kayaks were a great hit with the family. Really no need to go anywhere. The house was really nice and very spacious. Some of the amenities like the grill and kitchen supplies could use some updating. A nice place to unwind with family and friends."
United States
Lisa T.
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
9.6 out of 10, Exceptional, (17)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
United States
Aaron N.
The price is HK$1,165
HK$2,792 total
includes taxes & fees
28 Oct - 29 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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

Holiday Inn Express Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG

10/10 Excellent
"The front desk ladies are very sweet and personable. Very nice welcome. Clean rooms. Awesome water pressure and super hot water. Love the Dove products. "
Lori 1-night trip
Posted 7 days ago
Holiday Inn Express Prince Frederick by IHG

Find out more about Madison

Search for holiday rentals in Madison on Expedia! You can easily find your home rentals, villas, holiday apartments in Madison using one of the methods below:

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Look no further and take a look at our great range of rental properties in Madison!

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?

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access: This holiday home rental outside of Madison is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 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 garden, a selection of games and 1 hot tub so that you can immerse yourself in your 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.