A mural of a boat with people and a quote about praying to God.

Madison Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Madison vacation rentals

Coffee/tea maker, fridge, microwave, oven

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (62 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is ￥37,352
￥43,208 total
includes taxes & fees
Aug 18 - Aug 19
Waterfront Getaway with Dock
Outdoor dining

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is ￥72,642
￥91,313 total
includes taxes & fees
Jul 29 - Jul 30
Sunset Breezes - quiet waterfront retreat
Private kitchen

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (37 reviews)
"Can’t wait to come back!"
United States
Tiffany K.
The price is ￥25,172
￥41,315 total
includes taxes & fees
Jul 27 - Jul 28
Sailwinds Loft at Cambridge Creek
Smart TV

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (15 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is ￥72,171
￥122,635 total
includes taxes & fees
Aug 5 - Aug 6
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
House (3 Bedrooms) | Interior

Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is ￥82,986
￥185,834 total
includes taxes & fees
Aug 11 - Aug 12
Lakefront Cabin Near Solomons Island w/ Hot Tub
Marina

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Downtown Cambridge
10.0 out of 10, Exceptional, (12 reviews)
"Great space. Great location for exploring Cambridge on foot. Check-in easy. Everything clean. Everything works."
United States
Peter G.
The price is ￥44,690
￥81,134 total
includes taxes & fees
Jul 28 - Jul 29
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Marina

Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8

Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our weekend getaway at the beautiful gated community. Great water views and a walkable community. The townhouse met all our needs. Fully stocked with essential items. The added bonus is a the workout room with top of the line equipment. A nice touch! Two great decks overlooking the marina. The owners are very responsive."
United States
Melissa
The price is ￥52,816
￥107,622 total
includes taxes & fees
Jul 22 - Jul 23
Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8
Marina

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (13 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is ￥42,253
￥80,791 total
includes taxes & fees
Jul 28 - Jul 29
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Marina

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
8.0 out of 10, Very Good, (8 reviews)
The price is ￥34,104
￥65,759 total
includes taxes & fees
Jul 29 - Jul 30
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Smart TV

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
9.0 out of 10, Wonderful, (13 reviews)
"Clean, cozy, and lovely - a winter cabin stay to remember. Kids already wanted to go back 5 days later. 10 out of 10 stars! "
United States
Mr.
The price is ￥56,149
￥106,889 total
includes taxes & fees
Jul 22 - Jul 23
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
1 bedroom, iron/ironing board, WiFi, bed sheets

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Downtown Cambridge
The price is ￥23,401
￥43,237 total
includes taxes & fees
Jul 22 - Jul 23
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (23 reviews)
The price is ￥43,065
￥81,651 total
includes taxes & fees
Jul 28 - Jul 29
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (55 reviews)
"It was a nice small A-frame just like the picture. Great quiet location I would recommend it to anyone."
United States
Bobby H.
The price is ￥23,694
￥49,060 total
includes taxes & fees
Aug 20 - Aug 21
Soul Oasis - home on the Chesapeake Bay
Property grounds

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (13 reviews)
"The home was lovely and very quiet location. My sister and I were caring for our mom after discharge from hospital and it was very convenient. Would stay there again. "
United States
Tova A.
The price is ￥67,526
￥129,246 total
includes taxes & fees
Aug 19 - Aug 20
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
House (6 Bedrooms) | Front of property

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
The price is ￥74,054
￥148,355 total
includes taxes & fees
Jul 29 - Jul 30
'the Bayside Escape' Remote Chesapeake Bay Estate
TV, fireplace

3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (2 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is ￥14,031
￥34,669 total
includes taxes & fees
Aug 19 - Aug 20
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Beach

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

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (13 reviews)
"Listing was accurate; communication with host was great and helpful. We had a wonderful family time."
United States
Melissa D.
The price is ￥63,336
￥104,836 total
includes taxes & fees
Jul 24 - Jul 25
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Interior

Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"
United States
Tanya S.
The price is ￥70,319
￥186,696 total
includes taxes & fees
Jul 27 - Jul 28
Lakefront Cabin Near Solomons Island w/ Hot Tub
Exterior

'The Bayside Escape' Remote Chesapeake Bay Estate

'The Bayside Escape' Remote Chesapeake Bay Estate
Fishing Creek
'The Bayside Escape' Remote Chesapeake Bay Estate
Exterior

Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fishing Creek
10.0 out of 10, Exceptional, (11 reviews)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
The price is ￥43,848
￥53,192 total
includes taxes & fees
Jul 25 - Jul 26
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Madison Hotel Reviews

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Beautiful property, very well maintained. Dinner and Brunch at Stars were both very good. We loved being by the boats. Staff was accommodating when I had to do a zoom call on the morning of departure and found me a quiet private spot. Short walk to the Maritime Museum which was worth going to learn about the Eastern Shore. Short walk to town to pick up some needed items at the local pharmacy and on the way back stopped at the olive oil store and bought a couple of interesting bottles. Would have like to check out the SPA, but we decided on Friday to spend Saturday and Sunday nights and they were booked. The staff was generally friendly. It was expensive per night. But for clean and beautiful grounds, a clean room, friendly staff, and views from our room and from the restaurants that included water and boats, I felt it was worth it for our spontaneous road trip from the Philly suburb. We would come back and this time book a sailing activity and a massage. Notes: The big Samsung TV was nice but doesn't allow streaming from my phones and so we had to watch our show on my laptop. Room #2 was great in that it was in the main lodge next to the restaurant and a across from the bar which was very noisy at times. We didn't mind for 2 days, we enjoyed the convenience and drowned at noisy with a sound machine. If we were there for longer, the noise may have gotten old. In summary, we liked it and would visit again."
Greg 2-night trip
Posted 11 hours ago
Inn at Perry Cabin

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:

  • View our selection of featured holiday rentals in Madison
  • Use the map to find apartments and other holiday homes in the Madison neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Madison while they last

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

Frequently asked questions

Are there vacation rentals in Madison?

Yes, we offer vacation rentals near top attractions in Madison, or you can go with a more secluded option if you want a relaxing place to stay.

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

Private Chesapeake Bay Beach community…love to feel the sand between your toes?: This vacation home rental outside of Madison is located on the waterfront and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and an oven, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Madison?

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

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 larger area.

What’s a vacation rental in Madison like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Madison. Vacation rentals feature extras like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for family trips.