Madison Vacation Rentals from ￥39,179: Search Short-Term Rentals

Q: 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.

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Our top choices for Madison vacation rentals

Coffee/tea maker, fridge, microwave, oven

1. Waterfront Getaway with Dock

Woolford

Meagan G.

￥42,072 total

includes taxes & fees

Oct 4 - Oct 5

2. Sunset Breezes - quiet waterfront retreat

Dorchester County

John C.

3. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford

Ramon A.

￥112,746 total

includes taxes & fees

Oct 6 - Oct 7

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

Cambridge

Jill C.

￥99,694 total

includes taxes & fees

Sep 22 - Sep 23

5. Waterfront • Heated Decks • Workspace • EV Charging • Home Gym • Downtown

Cambridge

mike

￥89,760 total

includes taxes & fees

Sep 21 - Sep 22

6. Sailwinds Loft at Cambridge Creek

Cambridge

Sharon D.

￥39,910 total

includes taxes & fees

Sep 21 - Sep 22

7. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Downtown Cambridge

Kristen S.

￥61,694 total

includes taxes & fees

Sep 28 - Sep 29

8. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge

Robert

￥61,362 total

includes taxes & fees

Oct 12 - Oct 13

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Top Madison Hotel Reviews

Rod 'N' Reel Resort

10/10 Excellent

"very clean"

Wylder Tilghman Island

8/10 Good

"Property is well maintained and clean. The rooms are small but adequate. Our only fault was the restaurant pricing. Dishes are at least 25 to 40 percent upvharged. For example, a bowl of gazpacho was priced at $18 . If crab eas added it would have been $15 more for a grand total of $33 for a bowl of soup. Outrageous. I’ve been to 5 star restaurants and never paid that much for a bowl of soup. The chicken entree was $30 and the chicken consisted of 2 small chicken finger type pieces. No full breast or thigh/leg. Drinks definitely upcheged. Drive a bit down the road and eat at Chesapeake seafood or drive into town. If you don’t feel comfortable driving at night, go in and have a late lunch or get takeout."

Find out more about Madison

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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.

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 Phillips Wharf Environmental Center, 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.

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