Holiday rentals in Paddock Lake

4.98 out of 5 average rating, 104 reviews

Cottage in Castle Manor

The Lakehouse-3bdr/Lakefront/Wi-Fi

Enjoy your stay at this cozy cottage just steps away from beautiful Cross Lake. This 3bdr, 1bath house features a 4 seasons porch so you can relax and unwind all year. Our large yard provides you additional space to enjoy the stunning view. From the first weekend of May-Sept 30th, you will also have access to our shared pier. Enjoy swimming, boating, fishing or other nearby activities: skiing, golfing and ziplining. Beach chairs/toys, fire pit, grill, games and folding chairs are also provided.

4.89 out of 5 average rating, 200 reviews

Guest suite in Zion

Non-smoking, attached mother-in-law suite.

25 minutes away from the Naval Station 5 minutes away from the beach. 10 minutes to Wisconsin. 1 hour 40 minutes to O’Hare Airport and downtown Chicago. 40 minutes to Milwaukee Airport 25 minutes to Six Flags and Great Wolf Lodge. Safe and quiet neighborhood with plenty of wildlife right in the back yard. This Mother in Law suite has tons of natural light. For nature lover’s this unit is close to the beach and there are walking trails nearby. Small children maybe heard from 7AM to 7PM.

4.98 out of 5 average rating, 132 reviews

Cabin in Castle Manor

A Frame Log Cabin Near Multiple Local Lakes

Experience the allure of Salem Lakes Chalet, featuring modern comforts nestled within a quaint 3-story log cabin. Relax in a fenced yard offering picturesque vistas of woods, and relish in the variety of recreational options at nearby lakes. Your ideal retreat beckons! Enjoy the northern ambiance without the lengthy journey—be amazed by our expansive wall of windows! Whether you are in town to visit family or looking for a retrieve from the city we are conveniently located 10 mins from I-94.

5 out of 5 average rating, 32 reviews

Lago Amore - Channel house, pier, kayaks

A recently updated family home awaits you. Unwind with breathtaking views in the quaint Village of Paddock Lake. Kayak, go to the beach, fish with the family, or ice fish and snowmobile during the winter. Bring your boat with launch access and a private pier. No matter the season, this home offers wonderful views of Paddock Lake. Centrally located between Milwaukee and Chicago, as well as Lake Geneva and Kenosha, there is always something happening just a short drive in any direction.

4.94 out of 5 average rating, 63 reviews

Beautiful Lakehouse w/Sunset Views, Kayaks, Pier

Conveniently located one hour north of Chicago on Paddock Lake, our newly renovated lake cottage offers a peaceful, four season waterfront retreat. This split level home comes with a large waterfront deck with views of the entire lake and gorgeous sunsets(west facing!) Enjoy swimming, kayaking, paddle boarding, and roasting marshmallows over the fire pit in the summer. Plan the perfect winter vacation filled with skiing (10 mi to Wilmot Ski Resort) ice fishing, snowmobiling and more!

4.98 out of 5 average rating, 235 reviews

Flat in Kenosha

Kenosha! Enjoy your stay as you work or play!

Soft towels, fluffy pillows, complimentary breakfast, soft drinks, and more in a safe and secure environment. Only children over 13 allowed and must be accompanied by an adult. This n-smoking, pet-free 1-bedroom w/king bed, twin mattress daybed and cot, furnished kitchen and bath apartment is on the 2nd floor of an office building. Free HI-SPD Wi-Fi and big screen Smart TV. Access to museums, universities, shopping, Chicago’s METRO train and only 37 miles from downtown Milwaukee!

4.99 out of 5 average rating, 150 reviews

Home in Round Lake Beach

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Holiday home in Castle Manor

4.98 out of 5 average rating, 140 reviews

Lake Home w/View, Private Pier, + Indoor Hot Tub

Welcome to our home on Lake Shangri-La. Our home offers stunning lake views throughout the house. The house is a beautiful 3 bedroom / 2 bathroom ranch property with nearly 200+ feet of lake frontage and a private pier. Our four-season room allows you to enjoy incredible sunrises and sunsets, all from the hot tub or while enjoying a game of pool. Then you can step outside to easily access your private pier, perfect for swimming, fishing, or boating in the two provided kayaks!

Campervan/Motorhome in Salem

4.88 out of 5 average rating, 16 reviews

Paddock Lake RV Carriage House

Enjoy the Paddock Lake RV carriage house, an 8-person RV comfortably situated in our carriage house garage. We are within walking distance to many beaches and parks around Paddock Lake, and provide easy access to Kenosha, Lake Geneva, Wilmot Mtn, Milwaukee, and Chicago. You will have your own separate living area, but are welcome to enjoy our cozy fire pit, kayaks and waterfront access. It is perfect for a year round glamping experience with all the extra conveniences.

4.99 out of 5 average rating, 102 reviews

Cabin in Twin Lakes

Secluded in the Woods, Hot Tub

Owl's Rest Cabin is nestled in acres of fully wooded, peaceful forest. This is a cozy couple's retreat or small family getaway with a fireplace, hot tub, full kitchen, washer/dryer, located 4 minutes from Lake Mary and 15 min to Lake Geneva. Many activities nearby - festivals, hiking, boat rentals, golf, beach, downhill skiing, tubing, and snow shoeing. Eco conscious cabin, including Level 2 electric vehicle charging & more. Please message us with any questions.

4.97 out of 5 average rating, 31 reviews

Lake it Easy at this beautiful 2 bedroom lake home

Step inside to discover a cozy haven adorned with tasteful furnishings and modern comforts. The spacious living area invites relaxation with its plush sofas and inviting ambiance, perfect for unwinding after a day of fun. Outside, the expansive yard beckons with its promise of outdoor adventure just steps from the lake. Escape the hustle and bustle of everyday life and immerse yourself in the serenity of lakeside living at Lake It Easy.

4.95 out of 5 average rating, 404 reviews

Flat in Elkhorn

FarmWise Country Stay by Alpine Valley/Lake Geneva

Retreat to a quiet countryside experience at this all organic farm, where you can sit back, relax, and enjoy the country charm of your private space inside the main farm house. Optional for you are joining us for early morning chores in the barn. If you tell me the night before, you can try milking Carmel, the cow by hand, feeding the pig, collecting eggs from the chicken coop and more. Most loved of all are our friendly cats!

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Popular amenities for Paddock Lake holiday rentals

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Free parking on premises

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Other great holiday rentals in Paddock Lake

5 out of 5 average rating, 9 reviews

Home in Twin Lakes

Cozy Cabin in Town | Walk to Lake Mary

DavidRating, 5 stars1 day ago

We had a great stay. The house was perfect for a quick weekend getaway. We enjoyed some of the local spots in Twin Lakes and made the short drive for dinner in Lake Geneva. Highly recommend!

5 out of 5 average rating, 4 reviews

Salem Vacation Home w/ Dock: Steps to Paddock Lake

ChrisRating, 5 stars8 months ago

Very quiet and beautiful place

Place to stay in Racine

4.86 out of 5 average rating, 720 reviews

Wisconsin Treehouse Getaway!

ArielRating, 5 stars1 week ago

Beautiful space and property. Had a great stay and made wonderful memories. Main thing I’d say to be aware of is it is connected to the hosts’ actual home so keep that in mind. While the space is private, it’s not isolated. You may interact or hear the hosts’ family along the way. It wasn’t a big deal for us, but something to think about if you’re not fond of or used to it. Overall, great stay and recommend!

5 out of 5 average rating, 16 reviews

Home in Burlington

Comfortable Cabin on Lake and 20 min from Ski Hill

KendraRating, 5 stars1 week ago

We stayed for a wedding weekend and had a great time! Sean really went above and beyond as a host. He was incredibly responsive and helpful. He checked in on us multiple times during the trip! High recommend this stay.

4.95 out of 5 average rating, 182 reviews

Home in Richmond

TheGlassCabin @ HackmatackRetreat

JayRating, 5 stars1 day ago

What a beautiful rustic setting. So many wonderful Buddhist / mindfulness reminders to disconnect and slow down. We would love to come back to this getaway location again!

4.96 out of 5 average rating, 26 reviews

Farm stay in Burlington

Beautiful Farmstay Experience in S/E Wisconsin

NicoleRating, 5 stars3 weeks ago

We absolutely adored our stay! It is so peaceful and beautiful on the farm, which I love! The space itself is beautiful and has everything you could ask for! Marisa is kind, responsive, and a very welcoming host. I only wish I had more time to explore the farm more and see more animals. I definitely hope to return!

4.92 out of 5 average rating, 229 reviews

Apartment in Kenosha

Spacious 2-BDRM Apt, Great location, near lake

VeotaRating, 5 stars2 weeks ago

Simon greeted us upon arrival. Simon is friendly and responsive. The neighborhood is peaceful and safe. The place looks like the pictures, spacious and is very clean. Has amenities you need such as a blow dryer, microwave, coffee maker, tea maker, shampoo, soap, etc. A comfortable and lovely stay.