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

Holiday Homes in Madison

  • 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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 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, (66 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is AU$355
includes taxes & fees
4 Oct - 5 Oct
Waterfront Getaway with Dock
A spacious living room with a large TV, blue sofa, and a ceiling fan.

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

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
9.6 out of 10, Exceptional, (35 reviews)
"Great house for a large group! Very well equipped kitchen and comfortable home. Extra pillows and black out curtains would be the only thing I would add."
United States
Ximena G.
The price is AU$1,007
includes taxes & fees
5 Oct - 6 Oct
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

3. 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, (25 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is AU$605
includes taxes & fees
12 Oct - 13 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

4. 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 AU$621
includes taxes & fees
27 Sept - 28 Sept
Sunset Breezes - quiet waterfront retreat
A living room with two brown leather sofas, a wooden coffee table, a blue and white patterned rug, a black leather armchair, and a painting of a tree on the wall.

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

More, than just a place to sleep - welcome home!
Cambridge
The price is AU$552
includes taxes & fees
6 Oct - 7 Oct
More, than just a place to sleep - welcome home!
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$364
includes taxes & fees
30 Sept - 1 Oct
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

7. 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, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is AU$851
includes taxes & fees
7 Oct - 8 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A wooden interior with a dining area, sofas, and a table.

8. 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, (14 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$977
includes taxes & fees
30 Sept - 1 Oct
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

9. 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)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is AU$656
includes taxes & fees
20 Oct - 21 Oct
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
A house with a large lawn and a dock extending into a calm lake.

10. 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$460
includes taxes & fees
28 Sept - 29 Sept
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

11. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is AU$634
includes taxes & fees
25 Sept - 26 Sept
Plum Point Cottage #17
A house with a large lawn and a dock extending into a calm lake.

12. 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$414
includes taxes & fees
6 Oct - 7 Oct
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa, and a dining table.

13. 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$1,650
includes taxes & fees
7 Oct - 8 Oct
Lakefront Cabin Near Solomons Island w/ Hot Tub
A pathway lined with trees and lights leading to a wooden building with a visible window.

14. 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, (14 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is AU$1,193
includes taxes & fees
29 Sept - 30 Sept
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
A spacious living room with a large sofa, a television, and a view of the ocean.

15. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is AU$997
includes taxes & fees
7 Oct - 8 Oct
4-BR Waterfront Turret Home
A lakeside property with a large house, a shed, and a dense forest in the background.

16. 'The Bayside Escape' Remote Chesapeake Bay Estate

'The Bayside Escape' Remote Chesapeake Bay Estate
Fishing Creek
10.0 out of 10, Exceptional, (2 reviews)
"We absolutely loved our stay. They house was beautiful, the amenities were excellent, and we loved the crabs!! We went for a family weekend (mix of 18 kids and adults) and it was very spacious and comfortable for everyone. The pergola in the back was an especially big hit! We highly recommend and would stay again."
United States
Bridget C.
The price is AU$1,289
includes taxes & fees
27 Sept - 28 Sept
'The Bayside Escape' Remote Chesapeake Bay Estate
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

17. 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, (2 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is AU$1,331
includes taxes & fees
29 Sept - 30 Sept
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
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

Wylder Tilghman Island

Wylder Tilghman Island

10/10 Excellent
"Everything exceeded expectations — particularly the staff — but the breakfast offering, which fell below."
Kendrick 3-night trip
Posted 17 hours ago
Wylder Tilghman Island

Find out more about Madison

Madison Holiday Homes information

Number of reviews
183
Accommodation
289 Holiday Homes
Lowest Price
AU$364
Highest Price
AU$1,650