Watertown Vacation Rentals

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Our top choices for Watertown vacation rentals

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.
$170 nightly
The price is $179
Jan 11 - Jan 12, 2026
Total with taxes and fees
Log Cabin at Lake Koshkonong - “The Overlook”

SUNNY! Convenient to Holy Hill, NFL Draft, Harley Reunion, Hiking+Skiing + Golf

SUNNY! Convenient to Holy Hill, NFL Draft, Harley Reunion, Hiking+Skiing + Golf
Hartford
10.0 out of 10, Exceptional, (4)
"Gorgeous interior, responsive host, clear instructions. Enjoyed proximity to hiking, cafe, and arcade. "
United States
M. M.
$328 nightly
The price is $369
Jan 2 - Jan 3, 2026
Total with taxes and fees
SUNNY! Convenient to Holy Hill, NFL Draft, Harley Reunion, Hiking+Skiing + Golf

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.
$401 nightly
The price is $455
Jan 11 - Jan 12, 2026
Total with taxes and fees
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove

Hot Tub - Private Pool - Game Room - 20 min DT

Hot Tub - Private Pool - Game Room - 20 min DT
2.0 star property
Sun Prairie
10.0 out of 10, Exceptional, (1)
"The house was clean, large, and nicely decorated. It felt welcoming and homey. The host was friendly and responsive to our questions. "
United States
Ellen M.
$709 nightly
The price is $781
Dec 28 - Dec 29
Total with taxes and fees
Hot Tub - Private Pool - Game Room - 20 min DT

Hot Tub - King Suite - Game Room - Large Groups

Hot Tub - King Suite - Game Room - Large Groups
Sun Prairie
10.0 out of 10, Exceptional, (16)
"We had a great visit "
United States
Jennifer D.
$564 nightly
The price is $671
Dec 28 - Dec 29
Total with taxes and fees
Hot Tub - King Suite - Game Room - Large Groups

Historic Downtown-Old World Charm-Dining-Coffee

Historic Downtown-Old World Charm-Dining-Coffee
Delafield
10.0 out of 10, Exceptional, (5)
"Great place to rest and relax on a fun weekend getaway. "
United States
Jeffrey C.
$246 nightly
The price is $278
Jan 5 - Jan 6, 2026
Total with taxes and fees
Historic Downtown-Old World Charm-Dining-Coffee

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.
$279 nightly
The price is $314
Jan 4 - Jan 5, 2026
Total with taxes and fees
2 Bedroom - Main Street Sun Prairie WI

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
$284 nightly
The price is $320
Dec 31 - Jan 1, 2026
Total with taxes and fees
Cannery Square Unit - 106 by Patriot Properties

Cannery Square Short Term Rentals -104 by Patriot

Cannery Square Short Term Rentals -104 by Patriot
Sun Prairie
9.6 out of 10, Exceptional, (44)
"Roomy. Kitchen had basics. Good beds and pillows. "
United States
Susan
$284 nightly
The price is $320
Dec 29 - Dec 30
Total with taxes and fees
Cannery Square Short Term Rentals -104 by Patriot

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.
$312 nightly
The price is $351
Jan 1 - Jan 2, 2026
Total with taxes and fees
A Pleasant Retreat- No Cleaning Fee & New Discounts

✨ Stylish Home with Fire Pit: Near Downtown & Weddings Venues ✨

✨ Stylish Home with Fire Pit: Near Downtown & Weddings Venues ✨
Oconomowoc
10.0 out of 10, Exceptional, (20)
"Clean, cozy and convenient for walks dowtown! Stayed a week- Loved all of the special touches- including lots of towels, keurig pods and the smores basket! Thank you for a liovely stay in Oconomowoc."
United States
sk k.
$431 nightly
The price is $487
Dec 29 - Dec 30
Total with taxes and fees
✨ Stylish Home with Fire Pit: Near Downtown & Weddings Venues ✨

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.
$471 nightly
The price is $522
Jan 13 - Jan 14, 2026
Total with taxes and fees
The Gatsby Getaway - A Charming 100-Year-Old Lakeside Retreat in Beaver Dam!

Historic Downtown- King Bed-St Johns Acad-Shopping

Historic Downtown- King Bed-St Johns Acad-Shopping
Delafield
9.4 out of 10, Exceptional, (6)
"Needed a low cost option for staying downtown for a business meeting. Super convenient and very nice."
United States
Eric B.
$269 nightly
The price is $304
Dec 30 - Dec 31
Total with taxes and fees
Historic Downtown- King Bed-St Johns Acad-Shopping

Bright, cozy 3BR ranch in Lake Country with fenced yard and covered patio.

Bright, cozy 3BR ranch in Lake Country with fenced yard and covered patio.
2.0 star property
Oconomowoc
$204 nightly
The price is $231
Jan 4 - Jan 5, 2026
Total with taxes and fees
Bright, cozy 3BR ranch in Lake Country with fenced yard and covered patio.

Studio | Free Breakfast. Pool. Gym

Studio | Free Breakfast. Pool. Gym
Oconomowoc
$119 nightly
The price is $133
Dec 29 - Dec 30
Total with taxes and fees
Studio | Free Breakfast. Pool. Gym

Free Breakfast. Suite Near Aurora Medical Center!

Free Breakfast. Suite Near Aurora Medical Center!
Oconomowoc
$222 nightly
The price is $247
Dec 29 - Dec 30
Total with taxes and fees
Free Breakfast. Suite Near Aurora Medical Center!

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
10.0 out of 10, Exceptional, (5)
"This is a nice place to stay. The bedrooms are all spacious, clean and very comfy. The communication with the host was great. I would stay here again. "
United States
Nicole D.
$783 nightly
The price is $881
Jan 5 - Jan 6, 2026
Total with taxes and fees
Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars

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

Hot Tub - Game Room - 20 min to Downtown - Pets
2.0 star property
Sun Prairie
$576 nightly
The price is $636
Dec 28 - Dec 29
Total with taxes and fees
Hot Tub - Game Room - 20 min to Downtown - Pets

DElafield Rivers Gateway Luxurious Condo

DElafield Rivers Gateway Luxurious Condo
Delafield
$485 nightly
The price is $548
Dec 31 - Jan 1, 2026
Total with taxes and fees
DElafield Rivers Gateway Luxurious Condo

1 Bedroom - 1220 Canterbury Ct

1 Bedroom - 1220 Canterbury Ct
Sun Prairie
$251 nightly
The price is $282
Dec 27 - Dec 28
Total with taxes and fees
1 Bedroom - 1220 Canterbury Ct
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 Watertown Hotel Reviews

Find out more about Watertown

Everything you need to know about Watertown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Watertown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Watertown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Watertown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Watertown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Watertown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $179 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Watertown rentals

At Expedia, we put the best Watertown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Watertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Watertown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Watertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Watertown?

Yes, we have vacation rentals near well known points of interest in Watertown, or you can go with a more secluded option if you're looking for a relaxing stay. Our travelers say Watertown has a good selection of restaurants. Make sure you have time to check out the university setting and gardens during your trip.

What are some of the best vacation rentals in Watertown?

A Pleasant Retreat- No Cleaning Fee & New Discounts: Visitors like this Watertown vacation home rental. It offers a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Watertown?

Expedia has 4 vacation rentals for your stay in Watertown.

What’s there to see and do in Watertown?

Tivoli Island Park and Riverside Park are a couple of scenic spots to enjoy the outdoors, whereas The Octagon House is one of the cultural attractions. Maranatha Baptist University and Johnson Creek Premium Outlets are a couple of places you'll find in the larger area.

What’s a vacation rental in Watertown like?

A vacation rental is a private property you can stay in for a couple of days or more in Watertown. Vacation rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for family trips or small group gatherings.