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Madison Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Madison holiday rentals

Coffee/tea maker, fridge, microwave, oven

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.
Waterfront Getaway with Dock
Outdoor dining

2. 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 HK$3,020
HK$3,785 total
includes taxes & fees
27 Sept - 28 Sept
Sunset Breezes - quiet waterfront retreat
Smart TV, books, printers

3. 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)
"Anne is a great host, always responded promptly regardless of time.Property is huge! Lots of patio space, and included kayaks for us to use. Next time in the area will definitely stay there"
United States
Ramon A.
The price is HK$3,303
HK$5,638 total
includes taxes & fees
6 Oct - 7 Oct
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Smart TV

4. 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 HK$2,610
HK$4,862 total
includes taxes & fees
21 Sept - 22 Sept
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Terrace/patio

5. Waterfront • Heated Decks • Workspace • EV Charging • Home Gym • Downtown

Waterfront • Heated Decks • Workspace • EV Charging • Home Gym • Downtown
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 HK$2,167
HK$4,489 total
includes taxes & fees
21 Sept - 22 Sept
Waterfront • Heated Decks • Workspace • EV Charging • Home Gym • Downtown
Private kitchen

6. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (39 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is HK$1,216
HK$1,996 total
includes taxes & fees
21 Sept - 22 Sept
Sailwinds Loft at Cambridge Creek
Marina

7. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (14 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is HK$1,491
HK$3,085 total
includes taxes & fees
29 Sept - 30 Sept
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Marina

8. 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 HK$1,373
HK$3,068 total
includes taxes & fees
12 Oct - 13 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Exterior

9. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (63 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is HK$1,177
HK$2,445 total
includes taxes & fees
30 Sept - 1 Oct
Soul Oasis - home on the Chesapeake Bay
Interior

10. 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 HK$3,648
HK$9,447 total
includes taxes & fees
21 Sept - 22 Sept
Lakefront Cabin Near Solomons Island w/ Hot Tub
Exterior

11. 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 HK$2,118
HK$2,570 total
includes taxes & fees
21 Sept - 22 Sept
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Interior

12. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is HK$4,299
HK$9,299 total
includes taxes & fees
21 Sept - 22 Sept
Lakefront Cabin Near Solomons Island w/ Hot Tub
Smart TV

13. 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 HK$2,920
HK$5,415 total
includes taxes & fees
21 Sept - 22 Sept
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
TV, fireplace

14. 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 HK$946
HK$1,959 total
includes taxes & fees
23 Sept - 24 Sept
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Property grounds

15. 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 HK$3,624
HK$6,461 total
includes taxes & fees
29 Sept - 30 Sept
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Smart TV, books

16. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is HK$2,353
HK$5,448 total
includes taxes & fees
22 Sept - 23 Sept
4-BR Waterfront Turret Home
Exterior

17. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is HK$2,138
HK$3,591 total
includes taxes & fees
21 Sept - 22 Sept
Plum Point Cottage #17
Exterior

18. 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 HK$2,118
HK$2,570 total
includes taxes & fees
21 Sept - 22 Sept
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Pool

19. 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 HK$1,130
HK$3,569 total
includes taxes & fees
21 Sept - 22 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
TV, fireplace, video games, books

20. 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 HK$3,624
HK$7,361 total
includes taxes & fees
1 Oct - 2 Oct
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.
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Top Madison Hotel Reviews

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"very clean"
Jolyn 2-night trip
Posted 5 hours ago
Rod 'N' Reel Resort

Find out more about Madison

Search for holiday rentals in Madison on Expedia! You can easily find your home rentals, villas, holiday apartments in Madison using one of the methods below:

  • View our selection of featured holiday rentals in Madison
  • Use the map to find apartments and other holiday homes in the Madison neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Madison while they last

Look no further and take a look at our great range of rental properties in Madison!

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?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: This holiday home rental outside of Madison is located on the waterfront, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

How many holiday rentals will I find in Madison?

Choose from 3 Expedia holiday rentals in Madison for a memorable holiday.

What’s there to see and do in Madison?

Explore the area and family-friendly sights such as Phillips Wharf Environmental Center, or get out into nature at a spot like Blackwater National Wildlife Refuge. Harriet Tubman Underground Railroad National Historical Park and Harriet Tubman Museum and Educational Center 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 kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public 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 is another reason why a holiday rental is an attractive option for family gatherings.