Book Holiday Homes in Madison

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Madison

Peaceful Maine Home with Mountain Views

Peaceful Maine Home with Mountain Views

2 out of 5
Kingfield
With a stay at this vacation home in Kingfield, you'll be within a 10-minute drive of Stanley Museum and Ski Museum of Maine.
Peaceful Maine Home with Mountain Views
Lakefront, Stunning Home only 30 min to Sugarloaf!

Lakefront, Stunning Home only 30 min to Sugarloaf!

Strong
When you stay at this vacation home in Strong, you'll be on the waterfront and 11 minutes by foot from Porter Lake.
Lakefront, Stunning Home only 30 min to Sugarloaf!
5 BED HOUSE + HOT TUB, SAUNA AND 600’ OF PRIVATE SHORELINE.

5 BED HOUSE + HOT TUB, SAUNA AND 600’ OF PRIVATE SHORELINE.

Belgrade
With a stay at this vacation home in Belgrade, you'll be within a 15-minute drive of Belgrade Lakes Chain and Belgrade Lakes Golf.
5 BED HOUSE + HOT TUB, SAUNA AND 600’ OF PRIVATE SHORELINE.
Save an average of 15% on thousands of hotels when you're signed in
Cozy Long Pond cottage, private mooring at the community beach. Bring your boat!

Cozy Long Pond cottage, private mooring at the community beach. Bring your boat!

Rome
Located in Oakland, this vacation home is on a lake, within a 15-minute drive of Belgrade Lakes Chain and Belgrade Lakes Golf.
Cozy Long Pond cottage, private mooring at the community beach. Bring your boat!
Cozy, NEW log cabin on Fahi Pond! Right on ATV trail through Kennebec Valley.

Cozy, NEW log cabin on Fahi Pond! Right on ATV trail through Kennebec Valley.

Embden
Located in Embden, this vacation home is on the waterfront, within a 15-minute drive of Kennebec River and Embden Pond.
Cozy, NEW log cabin on Fahi Pond! Right on ATV trail through Kennebec Valley.
Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH

Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH

New Vineyard
When you stay at this vacation home in New Vineyard, you'll be on a lake and within a 5-minute drive of Porter Lake.
Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH
Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach

Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach

Madison
Located in Madison, this vacation home is on a lake, a 4-minute drive from Inland Hospital and 8 minutes from Skowhegan State Fairgrounds.
Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach
Lake Front with Amazing Sunsets on McGrath Pond

Lake Front with Amazing Sunsets on McGrath Pond

Oakland
Located in Oakland, this vacation home is on the waterfront, within a 15-minute drive of Belgrade Lakes Chain and Tree Spirits.
Lake Front with Amazing Sunsets on McGrath Pond
Nature Enthusiast's Haven:Cabin with Scenic Trails

Nature Enthusiast's Haven:Cabin with Scenic Trails

2 out of 5
Starks
With a stay at this vacation home in Anson, you'll be 6.6 mi (10.7 km) from Kennebec River and 11.3 mi (18.1 km) from Inland Hospital.
Nature Enthusiast's Haven:Cabin with Scenic Trails
Don't see what you're looking for?
See all available properties in Madison
View all properties
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.

Madison Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Madison vacation homes are the perfect way for you to wing it.

Holiday houses in Madison let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Madison in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Madison adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Madison with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Madison vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Madison Holiday Homes essential information

Accommodation
65 Holiday Homes
Lowest Price
AU$172
Highest Price
AU$548
Popular accommodation
Peaceful Maine Home with Mountain Views, Lakefront, Stunning Home only 30 min to Sugarloaf!, 5 BED HOUSE + HOT TUB, SAUNA AND 600’ OF PRIVATE SHORELINE. , Cozy Long Pond cottage, private mooring at the community beach. Bring your boat!, Cozy, NEW log cabin on Fahi Pond! Right on ATV trail through Kennebec Valley. , Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH, Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach, Lake Front with Amazing Sunsets on McGrath Pond, Nature Enthusiast's Haven:Cabin with Scenic Trails

Top trending hotels in Madison

The Cabbage on Olive Street, overlooking Hayden Brook

The Cabbage on Olive Street, overlooking Hayden Brook

Madison
Located in Madison, this cottage is a 4-minute drive from Inland Hospital and 8 minutes from Skowhegan State Fairgrounds.
The Cabbage on Olive Street, overlooking Hayden Brook
Lovely Family& pet friendly cabin retreat, PRIVATE, Trails, parking,fire pit,BBQ

Lovely Family& pet friendly cabin retreat, PRIVATE, Trails, parking,fire pit,BBQ

Madison
The price is AU$548 per night from 22 Nov to 23 Nov
AU$548
includes taxes & fees
22 Nov - 23 Nov
With a stay at this cabin, you'll be centrally located in Madison, within a 15-minute drive of Kennebec River and Inland Hospital.
Lovely Family& pet friendly cabin retreat, PRIVATE, Trails, parking,fire pit,BBQ
Holiday Inn Express & Suites Waterville - North, an IHG Hotel

Holiday Inn Express & Suites Waterville - North, an IHG Hotel

2.5 out of 5
332 Main St, Waterville, ME
Fully refundable
The price is AU$172 per night from 1 Dec to 2 Dec
AU$172
includes taxes & fees
1 Dec - 2 Dec
With a stay at Holiday Inn Express & Suites Waterville - North, an IHG Hotel in Waterville, you'll be within a 5-minute drive of First Congregational Church ...
Holiday Inn Express & Suites Waterville - North, an IHG Hotel
Save an average of 15% on thousands of hotels when you're signed in
The Elmwood

The Elmwood

2.5 out of 5
455 Kennedy Memorial Dr, Waterville, ME
Fully refundableReserve now, pay when you stay
The price is AU$226 per night from 22 Nov to 23 Nov
AU$226
includes taxes & fees
22 Nov - 23 Nov
When you stay at The Elmwood in Waterville, you'll be on the Strip, within a 5-minute drive of Inland Hospital Diabetes and Redington Museum.
The Elmwood
Don't see what you're looking for?
See all available properties in Madison
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.