Madison Vacation Rentals

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Our top choices for Madison vacation rentals

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.
$309 nightly
The price is $328
Mar 9 - Mar 10
Total with taxes and fees
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
8.8 out of 10, Excellent, (10 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.
$583 nightly
The price is $618
Mar 9 - Mar 10
Total with taxes and fees
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Apartment in Cambridge

Sailwinds Loft at Cambridge Creek
10.0 out of 10, Exceptional, (24 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
$240 nightly
The price is $254
Mar 10 - Mar 11
Total with taxes and fees
Sailwinds Loft at Cambridge Creek

Vacation Home in Woolford

Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (53 reviews)
"Great place, will stay again"
United States
Matt S.
$255 nightly
The price is $270
Mar 9 - Mar 10
Total with taxes and fees
Waterfront Getaway with Dock
3.0 star property
$663 nightly
The price is $736
Mar 16 - Mar 17
Total with taxes and fees
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
10.0 out of 10, Exceptional, (42 reviews)
"House was very nice and tidy and exactly as described. The host had a small binder full of helpful info including local restaurants and attractions. There was so much to do and everything was close bye. "
United States
Mindy V.
$262 nightly
The price is $277
Mar 10 - Mar 11
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
$499 nightly
The price is $529
Mar 10 - Mar 11
Total with taxes and fees
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Vacation Home in Solomons

4-BR Waterfront Turret Home
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
$696 nightly
The price is $769
Mar 11 - Mar 12
Total with taxes and fees
4-BR Waterfront Turret Home
10.0 out of 10, Exceptional, (1 review)
"We stayed Sunday - Wednesday at Riverside Lodge. The Lodge was beautiful. Breakfast was absolutely fantastic and Hooper Island was breath taking. We were able to take a boat ride to tour around the island and grad a little history and enjoy the stories. If you looking for a place to relax and renew... this is the place. "
United States
Robin E.
$309 nightly
The price is $328
Mar 9 - Mar 10
Total with taxes and fees
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
10.0 out of 10, Exceptional, (7 reviews)
"The property was clean, accurate to the listing and to prior feedback from other visitors. We loved the area; very quaint and cute. We enjoyed our stay and would recommend it to anyone looking for a cozy place to stay. "
United States
Amanda S.
$338 nightly
The price is $358
Mar 9 - Mar 10
Total with taxes and fees
Station House East: Upscale Loft in the Historic District Cambridge, MD
9.6 out of 10, Exceptional, (5 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
$378 nightly
The price is $401
Mar 30 - Mar 31
Total with taxes and fees
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
$347 nightly
The price is $368
Mar 11 - Mar 12
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
10.0 out of 10, Exceptional, (10 reviews)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
$368 nightly
The price is $390
Mar 17 - Mar 18
Total with taxes and fees
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
10.0 out of 10, Exceptional, (8 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
$421 nightly
The price is $446
Mar 16 - Mar 17
Total with taxes and fees
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
9.8 out of 10, Exceptional, (12 reviews)
"Host was personally accessible during stay, responded quickly, and went the extra mile with wonderful touches left around the place."
United States
John S.
$347 nightly
The price is $368
Mar 17 - Mar 18
Total with taxes and fees
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Vacation Home in Dorchester County

Sunset Breezes - quiet waterfront retreat
10.0 out of 10, Exceptional, (43 reviews)
"Clean, quiet, comfy"
United Kingdom
Deborah V.
$310 nightly
The price is $342
Mar 30 - Mar 31
Total with taxes and fees
Sunset Breezes - quiet waterfront retreat
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
$823 nightly
The price is $829
Mar 10 - Mar 11
Total with taxes and fees
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
8.4 out of 10, Very Good, (6 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
$294 nightly
The price is $312
Mar 10 - Mar 11
Total with taxes and fees
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Vacation Home in Chesapeak beach

Family Beach House: Spacious Deck, Grill & Views
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
$417 nightly
The price is $439
Mar 15 - Mar 16
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views
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

Find out more about Madison

Everything you need to know about Madison vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Madison vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Madison vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Madison vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Madison. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Madison in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Madison rentals

At Expedia, we put the best Madison vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Madison rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Madison vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Madison. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 2 Acre Waterfront Family Retreat with Pool & Pier: This vacation home rental outside of Madison is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

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.