Madison Holiday Rentals

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Madison

The Cabbage on Olive Street, overlooking Hayden Brook
Property grounds

The Cabbage on Olive Street, overlooking Hayden Brook

9.0 out of 10, Wonderful, (11)
"If you, dear reader, and I have anything in common, then you're reading this at 1am after a long work day and you've reached this listing by googling "places to stay in Maine under $100." You're also probably saying to yourself "What a quaint little cabin in the heart of Stephen King country! I wonder if anything Stephen King-related would happen to me if I stayed there?" Dear reader, let me put your fears to rest: book the dang cabin!!! I went here on my first solo vacation and could not have...
The Cabbage on Olive Street, overlooking Hayden Brook
2-bedroom cabin just 19 minutes from Skowhegan State Fairgrounds
Fridge, microwave, oven, stovetop

2-bedroom cabin just 19 minutes from Skowhegan State Fairgrounds

10.0 out of 10, Exceptional, (33)
"Quiet, cozy cabin in the woods- just what we were looking for!! We had everything we needed for our vacation especially in the kitchen as we did lots and lots of cooking. We had a great time! "
The price is AU$551
includes taxes & fees
26 Nov - 27 Nov
2-bedroom cabin just 19 minutes from Skowhegan State Fairgrounds
the Corner cottage: Overlooking Hayden Brook, Steps to Lakewood Summer Theater
Exterior

the Corner cottage: Overlooking Hayden Brook, Steps to Lakewood Summer Theater

9.0 out of 10, Wonderful, (12)
"My brother and I were traveling for our Uncle's funeral. We were thrilled to find the Perkins House was available. The house reminded us of our grandparents house in Harrison, ME. It brought us back in time to days of our childhood. I definitely want to return with my family to enjoy the Lakewood Theatre and the lake."
the Corner cottage: Overlooking Hayden Brook, Steps to Lakewood Summer Theater
Quiet rural cabin in Maine near Bigelow Preserve, Flagstaff Lake and Sugarloaf
Property grounds

Quiet rural cabin in Maine near Bigelow Preserve, Flagstaff Lake and Sugarloaf

10.0 out of 10, Exceptional, (79)
"Spent a few nights for a quick hunting trip. Cut the trip short because I filled my tag! Looking forward to next year!"
The price is AU$282
includes taxes & fees
1 Dec - 2 Dec
Quiet rural cabin in Maine near Bigelow Preserve, Flagstaff Lake and Sugarloaf
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.

Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.

9.4 out of 10, Exceptional, (124)
"Cabin was amazing. My second time staying at this place. Amazing host. Clean cabin with all the amendities. "
The price is AU$204
includes taxes & fees
1 Dec - 2 Dec
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
The Cabin Skowhegan
Terrace/patio

The Cabin Skowhegan

9.8 out of 10, Exceptional, (36)
"Larry hosted us for a week with our dogs while we were on a house-hunting expedition. Larry was a perfect host; very attentive but allowed us our space. The Cabin is very cozy and while there is no kitchen sink, the property details disclose this so we were prepared. It was a wonderful stay!"
The price is AU$290
includes taxes & fees
26 Nov - 27 Nov
The Cabin Skowhegan
Private three season cabin nestled in woods on shore of pristine Maine lake
Exterior

Private three season cabin nestled in woods on shore of pristine Maine lake

9.8 out of 10, Exceptional, (110)
"We come to this cabin twice a year and always love it! Spring summer and fall are beautiful months to be on clearwater pond. The perfect getaway! "
Private three season cabin nestled in woods on shore of pristine Maine lake
Lakefront, Stunning Home only 30 min to Sugarloaf!
Miscellaneous

Lakefront, Stunning Home only 30 min to Sugarloaf!

10.0 out of 10, Exceptional, (25)
"Beautiful peaceful spot on the pond/lake. We could not have enjoyed our stay more! Clean, well equipped and tremendous view of the pond and mountains. We are already discussing going back next year. Special place!"
Lakefront, Stunning Home only 30 min to Sugarloaf!
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Interior

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

8.6 out of 10, Excellent, (14)
"We were traveling through New England and were looking forward to spending some time exploring the pond. We’d already been at the coast and were headed to more mountains and hiking inland over the rest of the week. We arrived and found they had put the paddleboards and kayaks away for the season. The neighbors on the cove still had lots of water toys set up. When we called, we were told that they put the Paddleboards and kayaks away October 1st. There was no mention of that in the listing and...
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
5BED HOUSE-HOT TUB, SAUNA, POOL TABLE, FIRE PIT, 3+ LG TV, PRIVATE LAKE FRONTAGE
Property grounds

5BED HOUSE-HOT TUB, SAUNA, POOL TABLE, FIRE PIT, 3+ LG TV, PRIVATE LAKE FRONTAGE

10.0 out of 10, Exceptional, (4)
"The house had a lot of room. This would be a great family getaway place. The host was available and very attentive. I would recommend this house. "
5BED HOUSE-HOT TUB, SAUNA, POOL TABLE, FIRE PIT, 3+ LG TV, PRIVATE LAKE FRONTAGE
Central Maine Apartment offering 4 Seasons of Fun.
Miscellaneous

Central Maine Apartment offering 4 Seasons of Fun.

10.0 out of 10, Exceptional, (32)
"This clean, spacious, comfortable place was just what we needed for our time spent in Maine. Gary and Irma thought of everything! "
The price is AU$390
includes taxes & fees
7 Dec - 8 Dec
Central Maine Apartment offering 4 Seasons of Fun.
Cozy Winter Getaway on North Pond - Hidden Harlow Lane Retreat
On the beach, sun-loungers

Cozy Winter Getaway on North Pond - Hidden Harlow Lane Retreat

9.6 out of 10, Exceptional, (25)
"The view of the lake is beautiful and the loon was perfect, but we did not have drinkable water and for the price of cleaning and using only the Loon it was overpriced for the stay. "
Cozy Winter Getaway on North Pond - Hidden Harlow Lane Retreat
Cozy & Peaceful Waterfront Cabin on Porter Lake!
Fridge, microwave, stovetop, dishwasher

Cozy & Peaceful Waterfront Cabin on Porter Lake!

10.0 out of 10, Exceptional, (16)
"Looked exactly like the photos, was truly a cabin-resort like experience with beautiful views and all the amenities you could need. Super peaceful and my family is already talking about returning again! "
Cozy & Peaceful Waterfront Cabin on Porter Lake!
3bed -1 bathApartment in town mins to UMF or Hospital
Fridge, microwave, oven, stovetop

3bed -1 bathApartment in town mins to UMF or Hospital

9.8 out of 10, Exceptional, (31)
"Aside from the obvious benefits of cleanliness and comfort, it is in a great location close to all things in Farmington. The only thing missing is a washer/dryer but there is a convenient laundromat 5 minutes away. I look forward to returning!"
3bed -1 bathApartment in town mins to UMF or Hospital
Beautiful Embden Pond Cabin w/ Dock & Kayaks!
Miscellaneous

Beautiful Embden Pond Cabin w/ Dock & Kayaks!

9.8 out of 10, Exceptional, (13)
"Look no further! This place has everything you need and then some. The location is absolutely perfect. It is off the beaten path and so serene, but still close enough to activities and food places to make it well worth a bit of extra driving. There is a Japanese soaker tub which was very cool and a steamer shower which is like a combination of a sauna and shower. Such a treat!! If you're into stargazing, you're in luck. The sky puts on a show nightly. We were lucky enough to see the ATLAS...
Beautiful Embden Pond Cabin w/ Dock & Kayaks!
Little Beans Cottage on Great Pond, Belgrade ME
Smart TV

Little Beans Cottage on Great Pond, Belgrade ME

10.0 out of 10, Exceptional, (38)
"It was a delight, with beautiful Great Pond and inlet close by. The house itself is rustic, spacious and comfortable. Its L.L. Bean history added to the charm. The space heaters were welcome. The location, on a spit of land near the end of a long dirt road, but convenient to the Belgrade Lakes town center, was most enjoyable. We'd definitely recommend it."
Little Beans Cottage on Great Pond, Belgrade ME
Classy AF Home Steps from Colby and Trails
Fridge, oven, stovetop, dishwasher

Classy AF Home Steps from Colby and Trails

10.0 out of 10, Exceptional, (39)
"Lovely house. Only thing was just one bathroom bit otherwise recommend. "
Classy AF Home Steps from Colby and Trails
Central Maine Waterfront
Property grounds

Central Maine Waterfront

9.6 out of 10, Exceptional, (5)
"This property was full off character with barn wood lined walls and cute fixtures. John was incredibly hospitable and made us feel like family. "
Central Maine Waterfront
Cozy cabin with 200’ of waterfront on Whites Pond
Exterior

Cozy cabin with 200’ of waterfront on Whites Pond

9.6 out of 10, Exceptional, (31)
"The cabin on Whites pond is a very nice cozy cabin on a beautiful pond. It was clean and very comfortable. You can tell it is a cabin that family enjoys. Loved the Indian looking out over the water. Truly a lovely cabin. So sorry about the floor. I am glad that the charge was applied for the repair. "
Cozy cabin with 200’ of waterfront on Whites Pond
Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 kayaks
Property grounds

Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 kayaks

7.6 out of 10, Good, (22)
"The camp was quaint, great kitchen! Unfortunately there was confusion & communication issues with our host not being notified that we had booked property. We received a refund from the host for the nights we didn't stay due to propane running out. The host had intended to have camp closed up the week we had booked."
Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 kayaks
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.
Don't see what you're looking for?
See all available properties in Madison
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Madison you may be interested in

The Cabbage on Olive Street, overlooking Hayden Brook
Property grounds

The Cabbage on Olive Street, overlooking Hayden Brook

9.0 out of 10, Wonderful, (11)
"If you, dear reader, and I have anything in common, then you're reading this at 1am after a long work day and you've reached this listing by googling "places to stay in Maine under $100." You're also probably saying to yourself "What a quaint little cabin in the heart of Stephen King country! I wonder if anything Stephen King-related would happen to me if I stayed there?" Dear reader, let me put your fears to rest: book the dang cabin!!! I went here on my first solo vacation and could not have...
The Cabbage on Olive Street, overlooking Hayden Brook
2-bedroom cabin just 19 minutes from Skowhegan State Fairgrounds
Fridge, microwave, oven, stovetop

2-bedroom cabin just 19 minutes from Skowhegan State Fairgrounds

10.0 out of 10, Exceptional, (33)
"Quiet, cozy cabin in the woods- just what we were looking for!! We had everything we needed for our vacation especially in the kitchen as we did lots and lots of cooking. We had a great time! "
The price is AU$551
includes taxes & fees
26 Nov - 27 Nov
2-bedroom cabin just 19 minutes from Skowhegan State Fairgrounds
Holiday Inn Express & Suites Waterville - North, an IHG Hotel
Exterior

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

2.5 star property
8.6 out of 10, Excellent, (670)
"Everyone was very polite "
The price is AU$173
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Express & Suites Waterville - North, an IHG Hotel
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Frequently asked questions

Are there holiday rentals in Madison?

Yes, there are holiday rentals close to the most popular sights in Madison, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Madison has to offer?

Lakefront, Stunning Home only 30 min to Sugarloaf!: This holiday home rental outside of Madison is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Madison?

With 8 Expedia holiday rentals, you're guaranteed to find just the right place for your Madison stay.

What’s there to see and do in Madison?

While you're exploring the area, Kennebec River and Belgrade Lakes Chain are a couple of picturesque spots to get outside and enjoy nature. Skowhegan State Fairgrounds and University of Maine - Farmington are a couple of places you'll find in the wider area.

What’s a holiday rental in Madison like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Madison. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for families.