Pet-friendly holiday rentals in Williams Bay

3BR Home w/ Hot Tub 1.5 blocks from Lake Como

Fully equipped 3 bedroom 1 bathroom home in the great neighborhood of Lake Como. Basement has a separate door and is considered the 3rd BR. House is located 1.5 blocks from the lake and is less than a 10 minute drive to Lake Geneva. Featuring an outdoor hot tub, gated backyard and an amazing basement bar. Spend the afternoon shopping and enjoying the many activities the area has to offer. Spend the evening with a cocktail in the 4 person hot tub on the deck or have some s'mores by the firepit.

Fall in love with our Sweet Retreat

It’s fall! Come spend the weekend with friends and family or have a much needed vacation. Lake Geneva has something for everyone. Our Sweet Retreat is a perfect location for fall activities and is a short drive to downtown Lake Geneva. Tons of bars and restaurants to enjoy and explore . After enjoying your day, come home and relax in our spacious backyard. Enjoy a glass of wine or games with friends and family, we have a quaint retreat to unwind and relax. We’re just waiting for you!

Fall Specials at the Red Lodge-Game Room, Hot Tub!

Conveniently located amidst Southeast Wisconsin's best attractions, The Red Lodge is a contemporary-styled retreat that offers the space and family-friendly amenities to keep everyone entertained for hours. Enjoy an 👾 room, a secondary game room, hot tub, fire 🔥 pit, BBQ area, and more! Rent a boat right in the neighborhood at Lauderdale Lakes. Bike and hike Kettle Moraine State Forest. Visit Lake Geneva for golfing and shopping-a quick 20-25 min drive. Alpine Valley is minutes away!

TheGlassCabin @ HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

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!

Charming A-Frame - Dog Friendly!

FEATURED IN Madison Magazine's, December 2021 issue, "Wisconsin Winter Cabin Getaway"....The River Birch Cabin is a 900 sq ft A-Frame nestled in a partially wooded lot and is the perfect couples retreat or family escape from the city. Just 2 blocks from Lake Como, there are many activities & restaurants nearby including kayak & boat rentals. It is also located within minutes of downtown Lake Geneva, plus fishing, hunting, hiking, zip lining, snow skiing, boating & much more.

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.

Eden Farm: Family Stays & Intimate Moments

Unwind and find your inspiration just 1.5 hours from Chicago at our Elite Farm Retreat. Designed for executives, families, and intimate weddings. High-speed Wi-Fi, Smart TVs, and workspaces enhance your stay. This 5,000 sq ft estate blends modern comfort with rustic charm on 10 peaceful acres near Lake Geneva. Luxurious bedrooms, a Jacuzzi, and premium entertainment await. Two outdoor cameras monitor the front yard and driveway. No indoor cameras. Book now.

Pedal Inn II

The Pedal II is located just off the beaten path, yet still walking distance to downtown Lake Geneva and many fabulous restaurants. Back yard is private and not shared, perfect for a getaway with your pets. Parking available for up to 3 cars. This unit offers 2 bedrooms each with a king size bed. In the living room there is a queen size fold out sofa sleeper. The kitchen has all the amenities including a coffee maker, pots, pans and cooking utensils.