Holiday rentals with a kayak in Kenosha County

4.83 out of 5 average rating, 18 reviews

Steps to the Lake- Cozy 2 Bedroom Retreat

Welcome to your home away from home! Experience the best of Wisconsin in our serene 2-bedroom home located just steps from the lake. This inviting space features a fully equipped kitchen, spacious living room, comfortable bedrooms, & backyard firepit for evening gatherings. Enjoy outdoor adventures during the day & cozy nights around the fire. Perfect for families/friends looking to unwind & enjoy nature. Create lasting memories in this charming retreat. Book your perfect lakeside escape today!

4.93 out of 5 average rating, 156 reviews

Home in Richmond

"About Time" You will love it! -12 beds

We are SUPERHOSTS !!!- Look for all inclusive boat and wave runner packages through Twin Lakes Boat Rental. Swimming at the Sand Bar in the middle of the lake or at Lake Mary’s beach in Twin Lakes is best for kids. About Time has a spacious yard for corn hole/wiffleball, basketball, Kayaks & SUP's. There’s a large playfield is just 200 yards East too. Visit the Sand Bar Restaurant also, a must! The spring fed clear water is great for fishing & skiing. We love this place and know you will too.

4.94 out of 5 average rating, 16 reviews

Waterfront Stay, Optional Pontoon Rental, Sauna

Welcome to Lake Shangrila Haven, your ultimate wellness escape. This spacious lakeside retreat is designed with health enthusiasts in mind. Unwind in the built-in sauna, stay active with a gym featuring a Peloton, and recharge with endless outdoor activities. Whether you’re savoring a relaxing night by the fire pit, or enjoying the game room with ping pong and foosball. With direct lake access, you can indulge in boating, fishing, kayaking, and swimming. Embrace true serenity and wellness here!

5 out of 5 average rating, 24 reviews

2BR Lake House | Lake Toys | Views | Dog Friendly

Escape to Rock Lake! Enjoy our cozy lake house on a peaceful electric motor-only lake with 3 kayaks, 2 paddle boards, a pedal boat, swim raft & private pier for fun in the sun. Relax on the spacious deck or screened-in porch (steps to public beach & playground), enjoy beautiful sunsets, fire pit, or explore Antioch shops (under 10 min). Grill delicious meals lakeside with stunning views, or check out nearby restaurants. Your ultimate lakeside retreat! Ask about 4-6 night deals! @RockLakeEscape

5 out of 5 average rating, 32 reviews

Home in Salem

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.

4.89 out of 5 average rating, 71 reviews

Home in Burlington

Lake Home - Private Beach, Near Lake Geneva

Lakefront! Gorgeous views! Freshly renovated and charming, this Lily Lake three bedroom, two full bath beach house practically hangs over water, so you can enjoy the beautiful views of the lake from the living room and upper deck. Relax in the sun outside while sitting lakeside on the private sandy beach, kayaking, fishing from the pier, and at night enjoy evening conversations around the wood fire pit. The public beach is just steps away, allowing access to the another sandy beach area.

4.97 out of 5 average rating, 34 reviews

Home in Burlington

Lilly Lake Life-Golden Getaway

Come unwind at this roomy, cozy home on the shores of Lilly Lake. With updated kitchen and baths, this 4 bedroom, 2 full bath home is situated on flat frontage mere steps to the wide, private beach. Close to Chicago and Milwaukee makes it easy to plan an escape any time of year. In Summer, enjoy morning coffee on the deck with lake views and evenings stargazing by the fire pit. In Winter, nearby Wilmot and Lake Geneva offer skiing, shopping and the renowned Lake Geneva Winterfest.

4.95 out of 5 average rating, 39 reviews

Cottage in Twin Lakes

Twin Lakes Bungalow

Cute 1930’s bungalow with a cabin feel and many modern updates, just blocks away from Lake Mary in the adorable Twin Lakes Manor neighborhood of Twin Lakes, WI! Relax in this 2 bedroom, one bath cabin with a full tub and shower, fully-stocked kitchen, and a HUGE fully fenced-in backyard you can bring your dogs to! Patio with table and a fire pit surrounded by Adirondack chairs to relax in! 2 kayaks and 2 sets of golf clubs included! You don’t want to miss this adorable and cozy place!

4.94 out of 5 average rating, 64 reviews

Home in Salem

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!

4.9 out of 5 average rating, 166 reviews

Home in Twin Lakes

Cove at 420: Modern Lake Front Home near Chicago

Welcome to the Cove at 420. A modern vacation paradise where indoor and outdoor lines blur. Every space is designed for enjoyment. A short 75 minute drive from Chicago, this is a true retreat. Wake up to beautiful sunrise views or enjoy them from a kayak on the water. We offer kayaks, paddle boards, hot tub & sauna, Sonos sound system, a fire pit and plenty of yard games for our guests. Hidden on a cul-de-sac between Lake Mary and Lake Elizabeth, enjoy the best of lake life!

Campervan/Motorhome in Salem

4.84 out of 5 average rating, 19 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.

4.78 out of 5 average rating, 9 reviews

Lakefront Family Retreat Hot Tub, Dock

Escape to this stunning lakefront retreat on Cross Lake, perfect for up to 10 guests. Enjoy a private hot tub with panoramic lake views, direct lake access with a boat slip, and spacious living areas designed for family and friend gatherings. Just 3 minutes to Cross Lake Beach, with dining and outdoor adventures nearby — the perfect place to relax, recharge, and make memories. No pets allowed to maintain an allergy-friendly, clean environment.

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House rentals with a kayak

4.95 out of 5 average rating, 105 reviews

Home in Burlington

Relaxing Lakeview Getaway: Steps to Beach, Dogs ok

JoshuaRating, 5 stars11 months ago

Being directly across from the beach was amazing but what was better is there was enough gear, kayaks, paddle boards, life jackets, chairs, and so on, available for our use we were able to enjoy the beach and water all day together.

5 out of 5 average rating, 41 reviews

Charming lake front home w/paddle boards & kayaks!

SébastienRating, 5 stars9 months ago

This is the second time that we enjoy this house on the lake Shangrila and as the first time we enjoyed it a lot. Our kids have grown up and they had even more fun that the last time kayaking on the lake. The house was perfect for us and we will absolutely come back a third time. Jaime is very helpful and all was super easy. I highly recommend.

4.93 out of 5 average rating, 44 reviews

Light-Filled Lake Retreat - 5th night free!

RobertRating, 5 stars3 days ago

FANTASTIC place on the lake! Lily and Arun's home couldn't have been better. Well appointed, right on the water, with a huge yard for the kids to play. Communication was spectacular and they were even accommodating to send a pack and play for our baby to sleep in. My highest recommendation!!

4.83 out of 5 average rating, 35 reviews

Lakefront Oasis w/ Boat Dock, Fire Pit, Grill

MonicaRating, 5 stars6 months ago

We had an amazing thanksgiving experience at this beautiful house. When it is cold outside we are very cozy inside. The house provided many board games which was awesome because it gave us much to do! The view was breathtaking on our last day we even saw Swans. Very close to many grocery stores. Brenda was amazing! She let us check in early and out late and whenever we had any issues she was super quick to help us. Would definitely stay again. The only part we did not like about the house was there was no bedroom with a bathroom inside and the stairs to go up and downstairs are together and we had a toddler who loves to go up and down so we ended up using the foldable table as a gate. Overall I would recommend this place to everyone!

5 out of 5 average rating, 8 reviews

Lakefront w/ incredible views- Summer Availability

SyedRating, 5 stars2 months ago

Great place for a peaceful weekend getaway. There are a lot of things to do nearby with good food recommendations by the host.

4.86 out of 5 average rating, 50 reviews

Huge Lake Retreat Spa near Lake Geneva, Wilmot

AngelikaRating, 5 stars2 months ago

I can’t say enough wonderful things about this lake house! From the moment we arrived, everything surpassed our expectations. The home was spotless, beautifully decorated, and equipped with everything we needed for a relaxing and memorable stay. Waking up to the view of the lake every morning was absolutely magical. The hosts were incredibly thoughtful and responsive, providing clear instructions and delightful little touches throughout the home that made us feel welcome and comfortable. I highly recommend this place to anyone looking for a lovely lakeside retreat!

5 out of 5 average rating, 8 reviews

Home in Salem

Lake House ON the Water! Hot tub! Amazing Views!

DannielleRating, 5 stars2 days ago

We rented this house as a large family to attend my daughter’s wedding and it definitely made the trip even better! Everyone was very comfortable. The space was open enough for all of us to be in there and communicate with each other and really reconnect. We absolutely loved it.!