Holiday rentals in Watertown

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Top-rated holiday rentals in Watertown

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Natural wood accents are featured throughout the entryway, highlighting a stone fireplace and a warmly lit chandelier. A decorative area rug provides contrast against the light wooden floor, while a cozy armchair invites relaxation near the staircase leading to the upper level.
Home in Lake Mills
4.95 out of 5 average rating, 228 reviews

The Treehouse

Welcome to the Treehouse. This is our home away from home—and hopefully yours too. We love coming to the treehouse just off clear Rock Lake. The Treehouse is a getaway, although there are neighbors, you feel as if you are nestled in a grove of trees. The house itself provides places where guests can linger, relax, sip a glass of wine or a cup of java or simply just be. One of my favorite features is the glass windows that wrap up around the ceiling so that it feels like the outside is coming in.

Top guest favourite
A cozy cottage is framed by vibrant autumn foliage, with golden and orange leaves carpeting the ground. The structure features large windows and a welcoming front door, while a small flower arrangement adds a pop of color. Tall trees create a serene and private setting.
Cottage in Watertown
4.98 out of 5 average rating, 43 reviews

Maple Cottage Retreat

Come discover the tranquility of our charming Maple Cottage Retreat. Nestled among tall mature trees, this spacious retreat offers ample room to breathe in the fresh, crisp country air and unwind in a setting that feels like a true haven. With tall mature trees surrounding the property, you'll have all the space you need to explore and take leisurely strolls. The interior exudes warmth and comfort. Adorned with tasteful decor, it strikes the perfect balance between modern convenience and charm.

Top guest favourite
A two-story home with a mix of stone and wood siding sits on a grassy lot. Large windows allow natural light inside. A paved driveway leads to the garage, with trees and a view of open land in the background.
Guest suite in Sun Prairie
4.89 out of 5 average rating, 386 reviews

Entire Lower Level, Countryside Garden Suite

Welcome to our home! We have upgraded our Garden (lower) Level to host travelers much like ourselves and long-term guests. The view of our backyard is incredible! You will find yourself lost in the country, yet less than ten minutes from all the excitement that Madison has to offer. Along with a private drive and entrance, you will have 1,000 square feet of comfort all to yourselves. This property is perfect for a quiet getaway we all need from time to time. All designed with you in mind.

Top guest favourite
A historic home features a multi-gabled roof and intricate architectural details. The exterior showcases a blend of light and dark hues, complemented by well-maintained landscaping and a spacious lawn. A charming porch wraps around the front, providing an inviting entrance with rocking chairs nestled on one side.
Home in Wales
4.94 out of 5 average rating, 192 reviews

Beautifully Restored Historic Victorian

Whether this is for a single, couple, or small group, your stay at this historic home will truly be memorable. You’ll love the MBR suite featuring a gas fireplace, whirlpool tub, and double walk-in custom tile shower. There is an additional very nice full bath/shower on the main floor. The finished lower level has two separate rooms, each with a quality double futon with bedding available for your guests. For this attractive price, the upper 4 bedrooms are locked but may be opened for more

Guest favourite
A charming home is set among lush greenery, showcasing large windows that allow plenty of natural light. A stone wall supports a decorative patio area with several outdoor chairs and potted plants, creating a serene outdoor space. Tall trees frame the scene.
Home in Nashotah
4.92 out of 5 average rating, 102 reviews

Beautiful home on Okauchee Lake, WI

I have a beautiful home on a fun lake. It is just 25 mins from Milwaukee and 50 mins from Madison. There are several bars and restaurants on&off the water; you can either walk, drive or boat to. I have a boat slip available if you want to bring your own 18' or smaller boat. There is a fire-table on the patio for those quiet nights sitting out under the stars. Winter is spectacular here too. Nearby is the Nashotah Park, with a dog park and hiking trails. Lions park has an area for parties.

Top guest favourite
The cozy sitting area features a mix of patterned sofas and an armchair, with warm ambient lighting from two table lamps. Rich green walls create a comfortable environment, while a view into the dining area is visible through an open doorway, adding to the home's vintage charm.
Home in Watertown
4.93 out of 5 average rating, 179 reviews

Beautiful Victorian in Historic District

My Victorian home, "Belle Maison" (beautiful house), is waiting just for you. Newly restored, with 2 bedrooms, 2 baths - one with its original claw foot tub!- and a queen size sofa bed in the TV room. It is located in historic, downtown Watertown. Just a block from Main Street - with lots of shops and restaurants within walking distance - and the beautiful Rock River. The location is perfect - whether you're visiting Jefferson County or looking for a home base between Madison and Milwaukee.

Top guest favourite
A wooden deck sits beside a serene lake, surrounded by lily pads. Two lounge chairs are positioned on the grass, offering a peaceful spot to relax. Nearby, trees provide natural shade, enhancing the tranquil outdoor setting.
Yurt in Cambridge
4.98 out of 5 average rating, 618 reviews

YurtCation

YurtCation is a relaxing getaway with lake frontage and nature trails. There is another yurt about 300ft up the same driveway. There are a total of two yurts and two homes that have access to the same 17 acre lake. Each yurt is off the grid and has their own queen-sized comfy bed, wood stove, Weber grill w/charcoal, fire pit, firewood, fresh water, canoe, and clean Porto Potty. Pet Policy: Max two - Must be in your sight and supervised at all times or $500 fine and check out immediately.

Top guest favourite
Tall sunflowers bloom vibrantly in a garden, displaying bright yellow and orange petals. A wooden gazebo with hanging lights stands in the background, surrounded by lush greenery. Soft sunlight filters through the trees, enhancing the serene outdoor setting.
Guest suite in Sussex
4.99 out of 5 average rating, 148 reviews

Garden Retreat in law Suite

Welcome to our in-law suite apartment featuring a full eat-in kitchen, living room, queen bed in large bedroom, walk in closet and full bathroom with walk-in shower. Our beautiful two acre yard has many areas to relax in, including a hammock and fire pit for the evenings. Twenty mins. to Erin Hills and Holy Hill and a half hour to most downtown Milwaukee attractions, as well as the RNC activities taking place this summer. Lots of city tips and suggestions for our guests.

Top guest favourite
The image depicts a charming three-building arrangement situated on a cul-de-sac. The structures feature varying architectural styles with a mix of siding colors. Lush greenery is visible in the surrounding landscape, and an American flag is displayed on one of the buildings under a blue sky with scattered clouds.
Guest suite in Deerfield
4.95 out of 5 average rating, 153 reviews

Studio on the Prairie Fen

Kick back and relax at the Studio! The Studio is a 400 sq ft unique suite in the lower level of our home. A private locked entrance opens up to a sunny space with great views of a wetland beyond the backyard. Private patio to enjoy morning coffee and the sunrise. A great place to unwind and enjoy nature's beauty! We have binoculars if you love bird watching, and bikes to ride or hike the Glacial Drumlin Trail just 0.1 mile from the front door. Lic LICHMD-2021-00621.

Top guest favourite
An open-concept kitchen showcases modern appliances, including a stainless steel refrigerator and a sleek range with an island. Two bar stools are positioned at the island, and a wall-mounted television is visible. Natural light fills the space through the window, highlighting the blue accent wall.
Home in Watertown
4.93 out of 5 average rating, 40 reviews

Modern Comfort in the Heart of Watertown

SPRING FLASH PROMO: Book your stay by March 30 & Get a FREE Late Checkout! Relax a little longer – we’re rushing winter out, but you can stay! This exclusive offer ends soon. Book now for stay anytime in 2025 to grab this bonus. Charming farm house on the Rock River in Watertown, Wisconsin.  Old world architecture with modern kitchen and bathroom.  Living and dining room, two bedrooms and a loft, screened porches and a relaxing patio set up.

Top guest favourite
A spacious living room features natural light flowing through large windows. A comfortable gray sofa is positioned alongside two armchairs, creating a cozy seating area. A light-colored area rug covers the hardwood floor, and a lamp provides additional illumination in the corner.
Home in Watertown
5 out of 5 average rating, 75 reviews

Watertown Family Retreat

The perfect peaceful place for families, couples, or individuals to relax during their stay. You will find places for a quiet cup of coffee in the morning, family meals together, and even toasting marshmallows for s'mores at the fire pit as the sun sets and the stars come out. Before turning in, maybe you might want to take a short ten-minute walk down to the bridge over the Rock River and see the moon reflected over the water.

Top guest favourite
A charming three-story building features rich brown exterior walls and a welcoming front porch adorned with potted plants. Strings of warm lights enhance the inviting atmosphere. An American flag is displayed prominently, while lush greenery surrounds the property, providing a sense of tranquility.
Flat in Fort Atkinson
4.96 out of 5 average rating, 268 reviews

‘The Part Time Local’ - A boho small town retreat.

A cozy, comfortable 1 bedroom apartment with eat in kitchen and separate living room. Newly remodeled bathroom with tiled shower. Mahogany floors and all the charm you'd expect in a 1907 Arts & Crafts. Stylish, boho décor to make anyone feel right at home. Private balcony with Rock River views. Laundry available. Downtown Fort Atkinson, walking distance to everything!

Popular amenities for Watertown holiday rentals

When is the best time to visit Watertown?

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Frequently Asked Questions

  • How much does it cost to stay in house rentals in Watertown?

    Experience the best of Watertown with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Watertown?

    Yes! Work meets play with ease at over 10 vacation rentals in Watertown featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Watertown have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Watertown. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Watertown have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Watertown. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Watertown?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Watertown have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Watertown. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Watertown

  • Total holiday rentals

    Explore 10 holiday rentals in Watertown

  • Nightly prices starting at

    Watertown holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 650 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Watertown holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Watertown rentals

  • 4.9 Average rating

    Watertown stays are highly rated by guests – averaging 4.9 out of 5!

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