Book Holiday Homes in Watertown

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Featured Holiday Homes in Watertown

A Pleasant Retreat- No Cleaning Fee & New Discounts

A Pleasant Retreat- No Cleaning Fee & New Discounts

Sun Prairie WI
The price is AU$528 per night from 1 Jan to 2 Jan
AU$528
1 Jan - 2 Jan 2026
includes taxes & fees
With a stay at this vacation home in Sun Prairie, you'll be within a 10-minute walk of Sun Prairie Historical Library and Museum and Angell Park Speedway.
Opens in a new windowA Pleasant Retreat- No Cleaning Fee & New Discounts
NEW! Experience the Serene & Unique Blue Tree House – Hike, Relax & Lake Nearby

NEW! Experience the Serene & Unique Blue Tree House – Hike, Relax & Lake Nearby

Richfield WI
Located in Hubertus, this vacation home is on a lake, a 2-minute drive from Heiliger Huegel Ski Club and 6 minutes from Holy Hill.
Opens in a new windowNEW! Experience the Serene & Unique Blue Tree House – Hike, Relax & Lake Nearby
Sunset Lake House w Hot Tub, 4 fireplaces & kids bunkroom!

Sunset Lake House w Hot Tub, 4 fireplaces & kids bunkroom!

Oconomowoc WI
Located in Oconomowoc, this vacation home is on the waterfront, a 3-minute drive from Aurora Medical Center Summit and 6 minutes from Oconomowoc Memorial ...
Opens in a new windowSunset Lake House w Hot Tub, 4 fireplaces & kids bunkroom!
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Private Pool - HOT TUB - Sauna - Game Room - Pets

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

Sun Prairie Wisconsin
Located in Sun Prairie, this vacation home is within a 5-minute drive of Sun Prairie Historical Library and Museum and Sun Prairie Family Aquatic Center.
Opens in a new windowPrivate Pool - HOT TUB - Sauna - Game Room - Pets
Serene 4-bedroom Lake House in Pewaukee-Hot Tub!

Serene 4-bedroom Lake House in Pewaukee-Hot Tub!

2 out of 5
Pewaukee WI
With a stay at this vacation home in Pewaukee (Starke Peninsula), you'll be a 1-minute drive from Pewaukee Lake and 5 minutes from Two Brothers Wines.
Opens in a new windowSerene 4-bedroom Lake House in Pewaukee-Hot Tub!
Erin Hills Area Perfect Getaway - NEW Fall Color and Winter Pricing!

Erin Hills Area Perfect Getaway - NEW Fall Color and Winter Pricing!

Rubicon WI
Located in Rubicon, this vacation home is in a rural location, within a 15-minute drive of Erin Hills Golf Course and Heiliger Huegel Ski Club.
Opens in a new windowErin Hills Area Perfect Getaway - NEW Fall Color and Winter Pricing!
Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars

Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars

Hartford WI
The price is AU$1,391 per night from 26 Jan to 27 Jan
AU$1,391
26 Jan - 27 Jan 2026
includes taxes & fees
With a stay at this vacation home in Hartford, you'll be within a 5-minute drive of Hartford City Hall and Wisconsin Automotive Museum.
Opens in a new windowLuxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars
4 Bdrm 4 Bath Lake front Lake Sinissippi home

4 Bdrm 4 Bath Lake front Lake Sinissippi home

Juneau WI
Located in Juneau, this vacation home is on the waterfront, within a 15-minute drive of Sinissippi Lake and Neider Park.
Opens in a new window4 Bdrm 4 Bath Lake front Lake Sinissippi home
4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!

4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!

Hubertus WI
Located in Hubertus, this vacation home is on a lake, a 4-minute drive from Heiliger Huegel Ski Club and 8 minutes from Holy Hill.
Opens in a new window4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!
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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.

Watertown 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 Watertown vacation homes are the perfect way for you to wing it.

Holiday houses in Watertown 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 Watertown 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 Watertown adventures, obvs.

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

Watertown Holiday Homes essential information

Accommodation
133 Holiday Homes
Lowest Price
AU$102
Highest Price
AU$1,391
Popular accommodation
A Pleasant Retreat- No Cleaning Fee & New Discounts, NEW! Experience the Serene & Unique Blue Tree House – Hike, Relax & Lake Nearby, Sunset Lake House w Hot Tub, 4 fireplaces & kids bunkroom!, Private Pool - HOT TUB - Sauna - Game Room - Pets, Serene 4-bedroom Lake House in Pewaukee-Hot Tub!, Erin Hills Area Perfect Getaway - NEW Fall Color and Winter Pricing!, Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars, 4 Bdrm 4 Bath Lake front Lake Sinissippi home , 4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!

Top trending hotels in Watertown

Best Western Watertown

Best Western Watertown

2.5 out of 5
101 Aviation Way Watertown WI
Fully refundableReserve now, pay when you stay
The price is AU$118 per night from 4 Jan to 5 Jan
AU$118
4 Jan - 5 Jan 2026
includes taxes & fees
Located in Watertown, Best Western Watertown is in a rural location, within a 5-minute drive of Maranatha Baptist University and The Octagon House.
Opens in a new windowBest Western Watertown
Super 8 by Wyndham Watertown WI

Super 8 by Wyndham Watertown WI

2 out of 5
1730 S Church St Watertown WI
Fully refundableReserve now, pay when you stay
The price is AU$102 per night from 4 Jan to 5 Jan
AU$102
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at Super 8 by Wyndham Watertown WI in Watertown, you'll be within a 5-minute drive of Maranatha Baptist University and Riverside Park.
Opens in a new windowSuper 8 by Wyndham Watertown WI
Heritage inn

Heritage inn

2.5 out of 5
700 E Main St Watertown WI
Fully refundableReserve now, pay when you stay
The price is AU$117 per night from 4 Jan to 5 Jan
AU$117
4 Jan - 5 Jan 2026
includes taxes & fees
A stay at Heritage inn places you in the heart of Watertown, within a 5-minute drive of Tivoli Island Park and Maranatha Baptist University.
Opens in a new windowHeritage inn
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The Ingleside Hotel

The Ingleside Hotel

4 out of 5
2810 Golf Road Pewaukee WI
Fully refundableReserve now, pay when you stay
The price is AU$180 per night from 5 Jan to 6 Jan
AU$180
5 Jan - 6 Jan 2026
includes taxes & fees
Located in Pewaukee, The Ingleside Hotel is within a 10-minute drive of Waukesha County Expo Center and The Corners of Brookfield.
Opens in a new windowThe Ingleside Hotel
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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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^Subject to availability and chosen travel dates.