Vacation rentals in Darien

Modern New Build Near Ski & Snowboarding Lifts

Escape to our new, beautiful 4-bedroom home! Perfect for families and groups of friends seeking a refreshing change of scenery. Our home provides ample space, modern amenities, and access to a shared beach space with a swim pier on lake Delavan. Quickly get to Delavan, Lake Lawn, nearby Lake Geneva & Alpine Valley Resort. Highlights: - Brand new modern amenities - Dedicated office with a view. High-speed Wi-Fi - Fully equipped chef's kitchen - <30 minutes to Alpine or Grand Geneva ski resorts

Peaceful retreat by the lake.

**Welcome to Inlet Shores Retreat!** Escape to our spacious and inviting Lake Delavan home, ideal for families and friends. With 5 bedrooms (4 queen beds and 1 king bed) and 3 bathrooms, you'll enjoy comfort and convenience throughout your stay. Our beautifully updated kitchen is fully equipped for all your culinary needs. Situated at the northernmost point of Lake Delavan, the water is just across the street. You're also conveniently close to shopping and dining. Book your stay today!

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.

Modern & Relaxing South Shore Lake Retreat

Lake Lifestyle! Modern home a block from beautiful Delavan Lake. You are also 5 min. to Geneva Lake - Fontana & Williams Bay. This home is ready for you to enjoy summer at the lake. Luxe decor and curated local touches are reflected in this airy and bright, open concept home. A large deck, covered front porch and large green space, make this the perfect lake getaway. Close to multiple lakes, Williams Bay, Fontana, Lake Geneva, Farmer’s Markets, Coffee Shops, Golf, Nightlife & Restaurants.

Delavan Lake Retreat HotTub Pvt Pickleball Ct

New for 2026 Private Pickleball Court ! Pet friendly Centrally located on Delavans north shore and within walking distance of multiple bars including the world famous Inn Between Bar/ Grill. Within 1 mile of the Lake Lawn resort which offers golf, dining, and boat rentals. Short drive to Lake Geneva shops and restaurants. Enjoy ample outdoor space which includes a covered wrap around patio with a private hot tub. Our home is on a large lot with plenty of room to relax and enjoy.

Updated Waterfront Home & Pier on Northshore

Welcome to the Lake! This fully renovated 4 bed 2 bath waterfront home was completed in 2025 and sits just feet away from Delavan Lake, this home comes with a new pier and the option to rent a boat or bring and dock your own. The house is located on Delavan's north shore and is the perfect gathering place for family and friends. Views of the water from every room in the house give way to amazing sun rises and natural light throughout. Private Chef available for booking @eclecticcooking

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.

Cozy Country Cottage near Lake Geneva, WI

Our Cozy Cottage features 3 comfortable bedrooms and nightly magnificent sunsets. Nestled on a country road, the house offers plenty of space to rest after visiting Lake Geneva, Lauderdale lakes, biking at Kettle Moraine or site seeing in the area. It’s close to Walworth County fair grounds where the flea market, Das Fest and Rib Fest are held. This is country living with plenty of opportunity to enjoy the beautiful outdoors or the peace and quiet of the countryside.

A-Frame Retreat w/ Hot Tub, Sauna & Cold Plunge

Tucked in the woods near Lake Geneva, The Cozy Cardinal is a dreamy A-frame retreat with a hot tub, panoramic sauna, cold plunge, fire pit, and private forest trail. Watch birds and wildlife from the deck—this is a Certified Wildlife Habitat! Cozy up by the fireplace, sway in hammock swings, or enjoy s’mores under the stars. Dog-friendly and sleeps 4. Just minutes from downtown, hiking, and the lake—yet it feels a world away. Perfect for fall color and snowy escapes.

Eden Farm: Family Stays & Intimate Moments

Unwind and find your inspiration just 1.5 hours from Chicago at the Ten Acre Farmhouse Retreat. Designed for families, intimate moments, and retreats. 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.

The Bay House - cottage 1 block to Geneva Lake

Best location in Williams Bay — walk to everything! Beach passes included! The Bay House embodies the history, charm, and character of Williams Bay. Walk to the beach, shops, restaurants, trails, and the park. Enjoy slow, small-town lake life — rock on the front porch, play games in the backyard, gather around the fire pit, and relax with modern comforts throughout the home. SPRING DISCOUNT - 25% off 3-night stays!

The Little Farm Fontana 5 min from Geneva Lake!

Cozy cottage less than 2 miles from Fontana Beach and the sought after Geneva Lake! Minutes away from The Abbey Resort and just across the street from Abbey Springs Golf course, relax in this beautifully located home away from home out in the country with the luxury of quick and easy access to shopping and dining. We are within 15 minutes of downtown Lake Geneva if you are planning a day trip or a night on the town.