Vacation rentals in Highwood

Pet-Friendly Slice of Heaven by Lake Geneva & Como

Experience the ultimate family retreat in this well-appointed getaway in Geneva, Wisconsin. Hilltop Haven provides the perfect blend of relaxation and access to adventure! Nestled near quaint Lake Como and a few miles from the renowned Geneva Lake, you can easily partake in water sports, stroll by the waterfront, or visit the plethora of shops, restaurants, activities, and attractions nearby. Or stay on the property to get a slice of nature and relax, it’s set up to be comfortable and enjoyable!

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Private Cozy Cottage Lake Geneva, WI

Come stay at our top rated Bed & Breakfast, located two blocks from the beautiful Lake Geneva. Relax in our California king suites, each contains a spa tub and shower, with heated floors and towel rails in the bathroom. Your complimentary breakfast basket is placed in your fridge prior to arrival, as well as complimentary gift of wine & cheese. Free WIFI is available on the property. No Pets, ADULTS over 21 ONLY. *NOTE all guests are required to pay a 8% Lake Geneva Bed Tax at check in.

The Clean Slate, Walk to down town, pet friendly

The Clean Slate is the latest offering from Lake Geneva luxury Rentals. Half mile walk to downtown. Pet friendly The house can accommodate 8 guests, but can be rented with its sister property, The White House, to accommodate larger groups. Contact host to inquire about renting both houses. This newly built home will surely delight. Tastefully decorated with all modern amenities. Easy access to downtown Lake Geneva’s shops, restaurants, Riviera Beach, and Geneva Lake Shore Path.

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!

1 block to the Lake, then 2 blocks to Downtown

Renovated vintage cottage is blocks from the lake, 4 blocks to Riviera Beach, and a short walk to downtown. Stunning cottage boasts original stained glass with gorgeous renovated kitchen including granite countertops and stainless steel appliances. Fully stocked kitchen with plates, utensils, pots, pans and mixing bowls. Cabinets and drawers clearly labeled. Child plates, bowls, cups and kid utensils. Many games, toys, puzzles and books for kids too! Patio table outside.

NEW! Cozy Downtown Farmhouse, 5BR 3 BA Sleeps 15!!

Our gorgeous home is set in the heart of downtown Lake Geneva. 5 bedroom, 3 bathroom home that is two blocks from the lake and a few blocks from downtown shopping and restaurants. We just completed an extensive renovation of the home and it is now ready for you to stay for your dream vacation. Our homes are fully licensed and legal for short term rentals. We also rent the home two doors down and another in nearby Williams Bay!

Modern Downtown Lake Geneva Charm - Sleeps 8

Beautiful 3 bedroom home located in the heart of Lake Geneva and walking distance to restaurants, bars, & the beach. This recently remodeled house is the perfect place for an escape. With an open kitchen concept, leading out to a large composite (Trex®) deck, there is no shortage of space for any activity or just to get back to a quieter more relaxing pace. *** This property is Licensed & Legal for weekend rentals ***

Lakefront Paradise

Relax and have fun with the family and friends at this unique getaway! We are situated directly on the lakefront with private access to our pier where you can enjoy world class sunset views. Jump in and go swimming, roast s'mores over a campfire right next to the water, grill up some burgers on the spacious deck or get some rest in our luxurious suites in this newly renovated (June 2021) home.