Holiday Homes in Madison

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Find holiday rentals that suit your style

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Apartments
Apartments
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Cabins
Cabins

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Madison holiday homes

A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

1. 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 AU$363
includes taxes & fees
11 Nov - 12 Nov
Waterfront Getaway with Dock
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

2. 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 AU$541
includes taxes & fees
10 Dec - 11 Dec
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

3. 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 AU$709
includes taxes & fees
2 Dec - 3 Dec
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A dining area with a round table, chairs, and a decorative table runner.

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

More, than just a place to sleep - welcome home!
Cambridge
The price is AU$556
includes taxes & fees
24 Nov - 25 Nov
More, than just a place to sleep - welcome home!
A marina with boats docked, a water tower, and residential buildings with balconies.

5. 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 AU$709
includes taxes & fees
11 Nov - 12 Nov
Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

6. 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 AU$340
includes taxes & fees
16 Nov - 17 Nov
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A wooden interior with a dining area, sofas, and a table.

7. 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 AU$680
includes taxes & fees
11 Nov - 12 Nov
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

8. 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 AU$570
includes taxes & fees
20 Nov - 21 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
A pathway lined with trees and lights leading to a wooden building with a visible window.

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

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.8 out of 10, Exceptional, (16 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is AU$1,154
includes taxes & fees
24 Nov - 25 Nov
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Pool

10. Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Very clean and nice property"
United States
Ben W.
The price is AU$568
includes taxes & fees
7 Dec - 8 Dec
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

11. 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 AU$1,527
includes taxes & fees
23 Nov - 24 Nov
Lakefront Cabin Near Solomons Island w/ Hot Tub
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

12. 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 AU$1,307
includes taxes & fees
24 Nov - 25 Nov
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
A house with a large lawn and a dock extending into a calm lake.

13. 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 AU$448
includes taxes & fees
11 Nov - 12 Nov
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
A spacious living room with a large sofa, a television, and a view of the ocean.

14. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is AU$1,002
includes taxes & fees
22 Nov - 23 Nov
4-BR Waterfront Turret Home
A house with a large lawn and a dock extending into a calm lake.

15. Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
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.
The price is AU$406
includes taxes & fees
11 Nov - 12 Nov
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
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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Learn more about Madison

Venture to sights like Harriet Tubman Underground Railroad National Historical Park and Blackwater National Wildlife Refuge as you discover Madison.

See all hotels in Madison
A mural of a boat with people and a quote about praying to God.

Top reviews in Madison

A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.
Inn at Perry Cabin

Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels

10/10 Excellent

The Inn at Perry Cabin is a beautiful, luxurious hotel in a lovely setting. Our room was elegant and comfortable we had turn down service each night with cookies and slippers left for us. The staff is helpful and friendly. There are fresh flowers and plants throughout the hotel and the grounds are beautifully landscaped. The only negative is that they charge $50 a day to use the fitness facilities! Surprising at a very expensive hotel.
Australia
2revs
Reviewed April 17, 2015
Inn at Perry Cabin