Madison Holiday Homes from £175: Search Holiday Homes in Madison

Change your mind
Book hotels with free cancellation
Treat yourself
Save instantly and earn perks with One Key
Learn about One Key
Be picky
Search almost a million properties worldwide

Find holiday rentals that suit your style

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

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

Woolford

Mills Family A.

includes taxes & fees

15 Nov - 16 Nov

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

Cambridge

Mary Beth S.

includes taxes & fees

30 Nov - 1 Dec

A fire pit surrounded by Adirondack chairs in an outdoor setting.

3. Lusby 3BD Family Beach House - Steps to the Sand!

Lusby

includes taxes & fees

16 Nov - 17 Nov

A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

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

Cambridge

Jill C.

includes taxes & fees

2 Dec - 3 Dec

A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

5. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

Nancy P.

includes taxes & fees

16 Nov - 17 Nov

A marina with boats docked, a water tower, and residential buildings with balconies.

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

Cambridge

mike

includes taxes & fees

12 Nov - 13 Nov

A covered patio area with a table and chairs, large windows, and a ceiling fan.

7. Covenant Cove - Cove Point Beach

Lusby

includes taxes & fees

17 Nov - 18 Nov

A dining area with a round table, chairs, and a decorative table runner.

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

Cambridge

includes taxes & fees

12 Nov - 13 Nov

A wooden interior with a dining area, sofas, and a table.

9. WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Cambridge

Anonymous traveller

includes taxes & fees

12 Nov - 13 Nov

A laundry area with two washing machines and a shelf above containing cleaning supplies.

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

Prince Frederick

Sean B.

includes taxes & fees

20 Nov - 21 Nov

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

Chesapeak beach

Ben W.

includes taxes & fees

2 Dec - 3 Dec

A pathway lined with trees and lights leading to a wooden building with a visible window.

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

Lusby

Anonymous traveller

includes taxes & fees

12 Nov - 13 Nov

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.

13. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lusby

Tanya S.

includes taxes & fees

12 Nov - 13 Nov

A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

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

Lusby

Dani B.

includes taxes & fees

17 Nov - 18 Nov

A house with a large lawn and a dock extending into a calm lake.

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

Fishing Creek

Thomas S.

includes taxes & fees

12 Nov - 13 Nov

A spacious living room with a large sofa, a television, and a view of the ocean.

16. 4-BR Waterfront Turret Home

Solomons

Thomas S.

includes taxes & fees

12 Nov - 13 Nov

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

Fishing Creek

Robin E.

includes taxes & fees

12 Nov - 13 Nov

View all properties

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 marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.

Knapps Narrows Marina & Inn

Sherwood

10/10 Excellent

Anonymous traveller

A breakfast buffet with various food items and a sign indicating complimentary breakfast hours.

Holiday Inn Express Cambridge by IHG

Cambridge

10/10 Excellent

Colin

A spacious lobby with a reception desk, seating area, and a television screen.

Comfort Inn & Suites Cambridge

Cambridge

8/10 Good

I don't travel very often however I had thought that the Comfort Inn & Suites Cambridge would be a no thrills stay however I was warmly welcomed by a member of staff when I arrived who broke into conversation and showed interest in the reason for my visit (wedding). Upon reaching my room I was greeting with a reasonable size and space to spread out in and the beds and pillows were extremely comfortable easing away any aches from the stern Virgin Atlantic seats. The bathroom was clean and tidy...

Nirav

A sunlit room with a checkered sofa, wicker chairs, a glass table, and large windows offering a view of greenery.

Marvel's on the Creek

East New Market

10/10 Excellent

Mike

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

Downtown St. Michaels

10/10 Excellent

Robert

A Holiday Inn Express hotel with a central entrance, two flagpoles, and a well-lit facade.

Holiday Inn Express Prince Frederick by IHG

Prince Frederick

8/10 Good

We were visiting Chesapeake Beach & Bay in Maryland & opted to stay here. The reception staff were lovely; do take their recommendation of visiting Jerry's for dinner - the food is amazing! Breakfast was pretty good, once we'd convinced the breakfast staff to re-stock everything. The pool was a little disappointing. There were towels strewn everywhere & no fresh ones when I went to use the pool. That having been said they did deal with the issue promptly when I raised it. The water for the pool...

RiaG