Vacation rentals in Darien

Red Lodge|Hot Tub, Game Room, 5 Min to Lake, Yard!

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, a hot tub, a fire 🔥 pit, and a BBQ pit. Rent a boat right in the neighborhood at Lauderdale Lakes. Bike and hike at Kettle Moraine State Forest. Visit Lake Geneva for golfing and shopping—a quick 20-25 min drive away. Alpine Valley is minutes away!

Pet-Friendly Industrial 2 Bedroom Near UWW Campus!

This newly renovated two bedroom unit is conveniently located near UWW, Starin Park, and the Kettle Moraine! We are pet friendly! We are within walking distance to sports fields and UWW. Explore all that Whitewater has to offer with our personalized guidebook! Hike the Kettle Moraine, enjoy many local dining options and events, or shop your heart out. We are local hosts and strive to provide a five star experience! If your group is larger than 4, we have two other units in the same building.

Exquisite Modern A-frame all WithInnReach

An amazing space that truly caters to the guest experience. We've built this art piece to have our guests immerse themselves in all the amenities, from heated floors to in-ceiling speakers - all whilst losing yourself in the wood burning fireplace. At WithInnReach the attention to detail was paramount - with an emphasis of what we enjoy...amazing food through a well balanced kitchen, beautiful sound through Klipsch speakers and relaxation with floor to ceiling showers...enjoy to the fullest.

Sanctuary Woodland Guest House!

Our guest house is located on a picturesque 5 acres, next to a woodland forest. We also run a bird sanctuary on the property, Georgia's Place Bird Sanctuary, which makes this a paradise for an animal lover! We are happy to give guests a tour of our sanctuary. There is a large deck and fire pit for an enjoyable evening, and a walking trail for wildlife enthusiasts! We kindly ask guests not to bring meat onto the property as we are running a sanctuary that promotes compassion for all animals.

Adults-only Red Room retreat with hot tub

Adults-only private getaway on the Rock River with a hot tub, patio, and one-of-a-kind Red Room experience. Perfect for couples wanting privacy, comfort, and something more adventurous than a typical stay. Relax with a scenic river view, enjoy the hot tub, then explore a playful adult-themed space with a St. Andrews Cross, swing, Sybian, and more. Designed for birthdays, anniversaries, date nights, or a private weekend that feels secluded, romantic, unforgettable, and anything but ordinary.

House on 5 acres - Walk to Alpine Valley

Valley Oasis is a private 3 bedroom 2 bath home located on 5 acres next to the entrance of Alpine Valley Resort. Far enough off the road to enjoy the quiet beauty of nature. Woods located behind the house and a field next to it. Enjoy the outdoors on the deck, have dinner in the screened in porch, enjoy a fire in the fire pit, or warm up by the fireplace. You will have access to the entire house and immediate yard. The garage is not accessible. No smoking in the home. No parties allowed.

Fully Renovated 2BR 1BA Gorgeous Exec Home #8ma-R

Enjoy your stay in Janesville, WI in this fully renovated two-bedroom cozy executive home Professionally Managed by Kevin Bush! The location is central to dining, shopping, and popular Janesville spots like the Rotary Botanical Gardens. This home will truly feel like your home away from home. Located just minutes from I39 giving you easy access for day trips to Madison, Milwaukee, Chicago, and surrounding. Please check out our listing on St. George Lane for more dates. Kevin, Host

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 !

Bungalow in Delavan Lake

Simple, Upgraded, Quiet, with Some Fun & Thoughtful Touches Shh…we’re on the quiet side of the lake… yet you’re minutes from golf, fishing, bunches of restaurants & Belfry Music Theatre…Updated & Upgraded the kitchen is outfitted with a full complement of pots & pans. and plenty of dishes & silverware. Large Patio…which overlooks ¼ Acre backyard with a cool tree swing and large grilling area, plus a fire pit conversation area. *We are not on the lake nor do we have lake access.

The Oasis, 7 bed, hot tub 1/2 acre by Lake Geneva

Do you love the Lake Geneva and Delavan area, but also like your own private oasis? Kick back and relax in this calm, stylish private home and enjoy outdoor dining, 1/2 acre living area and hot tub? This is a 5 bedroom/ 7 bed 3-level home. It offers a peaceful retreat near all the fun. The property is perfect for couples, families & friends looking to make special memories or reconnect. This home was built in 2021, features modern style decor and includes modern conveniences.

Summer 2026 Lakefront Cottage on Delavan Lake

Escape to this lakefront cottage for your next “lake-cation”. The newly renovated Cottage on Willow Point would be the perfect destination. 3 bedroom, 1.5 bath and sleeps up to 9 comfortably. Beautiful outdoor deck and dining space. 15 steps from the lake and includes a private 120 foot pier, sun deck and ladder! We are a fully furnished rental. We also rent another cottage that can accommodate bigger groups. Please email for more info! Thecottageondelavanlake@gmail.com

Charming Farm View Retreat

Welcome to a tranquil getaway in the heart of Southeastern Wisconsin! Located just 20 minutes from the vibrant Lake Geneva, our remodeled 2-bedroom ranch-style home is perfect for families, couples, and friends seeking a peaceful retreat. Start your day with a cup of coffee in the three-season room, soaking in the serene morning light and beautiful sunrise and enjoy the scenic beauty of the countryside with views of frolicking cattle and lush woods right next door.