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Madison Vacation Rentals

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Our top choices for Madison vacation rentals

1. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
3.0 star property
Cambridge
10.0 out of 10, Exceptional, (1 review)
"This apt was built in the 50’s, or back when fewer outlets were needed, and it has window air conditioners. It was just what we were looking for as we visited the ste for family reunions"
United States
LOIS
The price is CA $133
CA $451 total
includes taxes & fees
Nov 6 - Nov 7
Cambridge Apt in Walkable Neighborhood

2. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
Cambridge
8.0 out of 10, Very good, (4 reviews)
"great location."
United States
Anonymous traveller
The price is CA $92
CA $440 total
includes taxes & fees
Nov 6 - Nov 7
Cambridge Apt in Walkable Neighborhood

3. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is CA $217
CA $338 total
includes taxes & fees
Nov 8 - Nov 9
Sailwinds Loft at Cambridge Creek

4. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
Cambridge
The price is CA $314
CA $363 total
includes taxes & fees
Nov 6 - Nov 7
2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

5. 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, (26 reviews)
"Pet friendly!"
United States
Mary Beth S.
The price is CA $238
CA $517 total
includes taxes & fees
Nov 17 - Nov 18
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

6. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (69 reviews)
"Excellent stay! Just as described! Very quiet, private location."
United States
Mills Family A.
The price is CA $308
CA $355 total
includes taxes & fees
Nov 8 - Nov 9
Waterfront Getaway with Dock

7. 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, (15 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is CA $252
CA $533 total
includes taxes & fees
Dec 1 - Dec 2
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

8. 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, (17 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is CA $395
CA $694 total
includes taxes & fees
Nov 8 - Nov 9
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

9. Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym

Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym
Cambridge
10.0 out of 10, Exceptional, (2 reviews)
"We only stayed one night but wouldn't hesitate to come back and stay for a few days. Beautiful home overlooking the docks."
United States
mike
The price is CA $339
CA $691 total
includes taxes & fees
Nov 9 - Nov 10
Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym

10. 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, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is CA $213
CA $399 total
includes taxes & fees
Nov 17 - Nov 18
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

11. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (67 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is CA $189
CA $395 total
includes taxes & fees
Dec 1 - Dec 2
Soul Oasis - home on the Chesapeake Bay

12. More, than just a place to sleep - welcome home!

More, than just a place to sleep - welcome home!
Cambridge
The price is CA $416
CA $543 total
includes taxes & fees
Nov 6 - Nov 7
More, than just a place to sleep - welcome home!

13. 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, (15 reviews)
"Very spacious home. 4 bedrooms and 4 baths. Great basement for watching TV with a large group. Home is about 15 minutes from downtown Cambridge."
United States
Anonymous traveller
The price is CA $389
CA $704 total
includes taxes & fees
Nov 9 - Nov 10
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

14. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Very clean and nice property"
United States
Ben W.
The price is CA $198
CA $561 total
includes taxes & fees
Dec 2 - Dec 3
Family Beach House: Spacious Deck, Grill & Views

15. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.2 out of 10, Wonderful, (12 reviews)
"A great place to crash and explore the area."
United States
Sean B.
The price is CA $272
CA $555 total
includes taxes & fees
Nov 20 - Nov 21
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

16. 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, (15 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is CA $646
CA $1,145 total
includes taxes & fees
Nov 8 - Nov 9
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

17. 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 CA $384
CA $422 total
includes taxes & fees
Nov 9 - Nov 10
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

18. 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 CA $605
CA $1,514 total
includes taxes & fees
Nov 8 - Nov 9
Lakefront Cabin Near Solomons Island w/ Hot Tub

19. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (4 reviews)
"Dude. This is what I always hope a rental property will be. Comfy beds, best stocked kitchen, working hot tub, beautiful waterfront area with kayaks and a dock. And our mini golden doodle could come too?! It was absolute perfection."
United States
Dani B.
The price is CA $492
CA $1,235 total
includes taxes & fees
Nov 11 - Nov 12
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

20. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (10 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is CA $478
CA $754 total
includes taxes & fees
Nov 9 - Nov 10
Plum Point Cottage #14
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Madison. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.