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Waterloo Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Waterloo holiday rentals

Private kitchen
Charming 2-bedroom cottage near Lake Koshkonong - The Overlook Too!

Charming 2-bedroom cottage near Lake Koshkonong - The Overlook Too!

Charming 2-bedroom cottage near Lake Koshkonong - The Overlook Too!
2.0 star property
Milton
9.6 out of 10, Exceptional, (5)
"Cute! Near winery and a supper club! "
United States
Juanita W.
Charming 2-bedroom cottage near Lake Koshkonong - The Overlook Too!
Property grounds
Log Cabin at Lake Koshkonong - “The Overlook”

Log Cabin at Lake Koshkonong - “The Overlook”

Log Cabin at Lake Koshkonong - “The Overlook”
Edgerton
9.2 out of 10, Wonderful, (48)
"Checkin was super easy, great amenities, and cozy cabin atmosphere."
United States
Nicholas R.
The price is HK$700
HK$1,436 total
includes taxes & fees
24 Dec - 25 Dec
Log Cabin at Lake Koshkonong - “The Overlook”
Interior
Spacious Condo: Historic Boutique Rental in Downtown Edgerton

Spacious Condo: Historic Boutique Rental in Downtown Edgerton

Spacious Condo: Historic Boutique Rental in Downtown Edgerton
2.0 star property
Edgerton
10.0 out of 10, Exceptional, (5)
"Beautiful and interesting stay!! Comfortable and spacious accommodations for our visit to over the vines wedding venue.. "
United States
Amy S.
The price is HK$778
HK$1,978 total
includes taxes & fees
6 Jan - 7 Jan 2026
Spacious Condo: Historic Boutique Rental in Downtown Edgerton
Interior entrance
The Dylin by Mint House

The Dylin by Mint House

The Dylin by Mint House
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (122)
"Great stay at the Dylin"
United States
Lauri
The price is HK$885
HK$1,023 total
includes taxes & fees
29 Dec - 30 Dec
The Dylin by Mint House
Exterior
Cannery Square Unit - 106 by Patriot Properties

Cannery Square Unit - 106 by Patriot Properties

Cannery Square Unit - 106 by Patriot Properties
Sun Prairie
9.4 out of 10, Exceptional, (26)
"Great place "
United States
Armando
The price is HK$988
HK$2,486 total
includes taxes & fees
11 Jan - 12 Jan 2026
Cannery Square Unit - 106 by Patriot Properties
Fridge, microwave, oven, stovetop
2 Bedroom - Main Street Sun Prairie WI

2 Bedroom - Main Street Sun Prairie WI

2 Bedroom - Main Street Sun Prairie WI
Sun Prairie
9.6 out of 10, Exceptional, (36)
"Clean and quiet. Nice neighborhood amenities. "
United States
Mark L.
The price is HK$949
HK$2,442 total
includes taxes & fees
8 Jan - 9 Jan 2026
2 Bedroom - Main Street Sun Prairie WI
Exterior
Cannery Square Short Term Rentals -104 by Patriot

Cannery Square Short Term Rentals -104 by Patriot

Cannery Square Short Term Rentals -104 by Patriot
Sun Prairie
9.6 out of 10, Exceptional, (43)
"Walkable restaurants. "
United States
Mike H.
The price is HK$988
HK$2,486 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cannery Square Short Term Rentals -104 by Patriot
Interior
HotTub/Kayaks/Arcade Your Dream Vacay Starts Here

HotTub/Kayaks/Arcade Your Dream Vacay Starts Here

HotTub/Kayaks/Arcade Your Dream Vacay Starts Here
Milton
10.0 out of 10, Exceptional, (17)
"We had the best VRBO experience at Harbor House. The hosts are absolutely fabulous. The house was perfect, just as presented online. 6 of us adults and a little French bulldog spent a long weekend there so we could cheer on our son (one of the visitors) as he ran the half Ironman in Madison. He LOVED the hot tub afterward. Great visit. Would definitely stay again if in the area."
United States
Karrie S.
HotTub/Kayaks/Arcade Your Dream Vacay Starts Here
Terrace/patio
The Gatsby Getaway - A Charming 100-Year-Old Lakeside Retreat in Beaver Dam!

The Gatsby Getaway - A Charming 100-Year-Old Lakeside Retreat in Beaver Dam!

The Gatsby Getaway - A Charming 100-Year-Old Lakeside Retreat in Beaver Dam!
2.0 star property
Beaver Dam
9.8 out of 10, Exceptional, (19)
"A beautiful home in a peaceful setting. Well appointed, everything we needed and more for a stress free relaxing getaway. Thank you Doug for the wonderful experience."
United States
Marjean P.
The price is HK$1,533
HK$4,023 total
includes taxes & fees
13 Jan - 14 Jan 2026
The Gatsby Getaway - A Charming 100-Year-Old Lakeside Retreat in Beaver Dam!
Fridge, microwave, oven, stovetop
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove

Charming 3-bedroom Duplex unit with WiFi in Cottage Grove

Charming 3-bedroom Duplex unit with WiFi in Cottage Grove
Village of Cottage Grove
10.0 out of 10, Exceptional, (7)
"Stayed with friends for the weekend and really enjoyed the home. It was comfortable and had great amenities for our group!"
United States
Anakin F.
The price is HK$1,186
HK$3,615 total
includes taxes & fees
21 Jan - 22 Jan 2026
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove
Exterior
One Bedroom Queen in the heart of downtown.

One Bedroom Queen in the heart of downtown.

One Bedroom Queen in the heart of downtown.
2.0 star property
Downtown Madison
10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay and the close location to the capital. Great modern style and very functional "
United States
Alexandrines H.
The price is HK$1,315
HK$1,734 total
includes taxes & fees
18 Jan - 19 Jan 2026
One Bedroom Queen in the heart of downtown.
Pool
Private Pool - HOT TUB - Sauna - Game Room - Pets

Private Pool - HOT TUB - Sauna - Game Room - Pets

Private Pool - HOT TUB - Sauna - Game Room - Pets
Sun Prairie
10.0 out of 10, Exceptional, (8)
"The house is great and the facilities in the house were well-functioning, and the dish washer saved us much time. The neighborhood is quiet and great views. We enjoyed our stay."
United States
Patti M.
Private Pool - HOT TUB - Sauna - Game Room - Pets
Terrace/patio
Free Breakfast Pool & Hot Tub. Near UW-Madison

Free Breakfast Pool & Hot Tub. Near UW-Madison

Free Breakfast Pool & Hot Tub. Near UW-Madison
Madison
10.0 out of 10, Exceptional, (1)
"It was comfortable and clean and the staff was so nice. It was well located and the pool and hot tub were lovely as well."
United States
Joy E.
The price is HK$1,755
HK$2,314 total
includes taxes & fees
24 Dec - 25 Dec
Free Breakfast Pool & Hot Tub. Near UW-Madison
Exterior
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Monona
9.8 out of 10, Exceptional, (47)
"We had a great time on our weekend trip to Madison. Location was super quick to get to downtown, house was clean, and we really enjoyed taking the canoe out on the lakes to explore."
United States
Molly S.
The price is HK$1,857
HK$3,812 total
includes taxes & fees
1 Jan - 2 Jan 2026
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Exterior detail
A Pleasant Retreat- No Cleaning Fee & New Discounts

A Pleasant Retreat- No Cleaning Fee & New Discounts

A Pleasant Retreat- No Cleaning Fee & New Discounts
Sun Prairie
10.0 out of 10, Exceptional, (262)
"Great place and the hosts were great!"
United States
Drew M.
The price is HK$2,140
HK$2,757 total
includes taxes & fees
1 Jan - 2 Jan 2026
A Pleasant Retreat- No Cleaning Fee & New Discounts
Sauna
1 Bedroom - 1220 Canterbury Ct

1 Bedroom - 1220 Canterbury Ct

1 Bedroom - 1220 Canterbury Ct
Sun Prairie
The price is HK$1,144
HK$2,197 total
includes taxes & fees
20 Jan - 21 Jan 2026
1 Bedroom - 1220 Canterbury Ct
Smart TV, fireplace, printers
Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
9.8 out of 10, Exceptional, (15)
"Plenty of blankets pillows bed were great"
United States
Kimberly P.
The price is HK$2,723
HK$4,665 total
includes taxes & fees
24 Dec - 25 Dec
Entire 3 Bedroom with Fireplace - sleeps 12
Interior
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Sun Prairie
10.0 out of 10, Exceptional, (13)
"Everything was great !"
United States
Beth V.
The price is HK$2,567
HK$4,473 total
includes taxes & fees
26 Dec - 27 Dec
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
TV, fireplace, offices
Hot Tub - Game Room - 20 min to Downtown - Pets

Hot Tub - Game Room - 20 min to Downtown - Pets

Hot Tub - Game Room - 20 min to Downtown - Pets
2.0 star property
Sun Prairie
Hot Tub - Game Room - 20 min to Downtown - Pets
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 Waterloo Hotel Reviews

Comfort Inn & Suites Madison East Interstate I-90

Comfort Inn & Suites Madison East Interstate I-90

10/10 Excellent
"The room was lovely and newly renovated. However, there was no chair in the room other than the one at the desk.Enjoyed the stay. "
Rebecca 1-night trip
Posted 3 days ago
Comfort Inn & Suites Madison East Interstate I-90

Find out more about Waterloo

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

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

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

Frequently asked questions

Can I find holiday rentals in Waterloo?

Yes, there are holiday rentals close to the most popular sights in Waterloo, 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 Waterloo has to offer?

A Pleasant Retreat- No Cleaning Fee & New Discounts: This holiday home rental outside of Waterloo offers a patio, a garden and a BBQ to help you feel perfectly comfortable 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Waterloo?

While exploring the area, visit family-friendly sights like Little Amerricka, or get outside and enjoy nature at Lake Ripley Park Beach. In the wider area, you’ll find Holzhueter Farm State Park and Sun Prairie Ice Arena.

What are holiday rentals like in Waterloo?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Waterloo. Holiday rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety 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 a great option for a family trip.