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

Family · Location · Kitchen

The Hideaway: 8 Acre Resort

Welcome to The Hideaway, an eight-acre luxury log retreat near Whitewater Lake and Kettle Moraine State Park, offering year-round access to scenic parks and hiking. Outdoor amenities include a hot tub, fire pit with oversized Adirondack seating, and lighted pickleball and beach volleyball courts. Inside, enjoy a 16-foot shuffleboard table, foosball, air hockey, ping pong, and a private home theater. Six bedrooms, including a primary suite with jetted soaking bath, provide exceptional comfort.

Location · Family · Getting around

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!

Family · Location · Decor

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.

Family · Value · Access

Newly Remodeled Rustic Lakehouse Cabin

We are lovers of "Lake Life" and want to share our experiences of Turtle Lake with others who love tranquility and time to reflect, but also want to hike at the Kettle Morraine State Forest, enjoy camp fires, tour local historic towns such as Lake Geneva and other sites, fish (including the best ice fishing in the area!), canoeing, paddle boarding, swimming, reading, and simply enjoying conversations with friends and family. We recently remodeled the kitchen, bathroom and 2 lower bedrooms.

Family · Location · Pets

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.

Location · Value · Nearby

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

Family · Value · Hospitality

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.

Family · Location · Bathroom

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.

Value · Location · Getting around

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.

Location · Family · Sleep quality

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 our cattle herd and lush woods right next door.

Location · Family · Indoor spaces

The Peacock Cottage

Cozy, quiet, accessible Lake Geneva home with large open living area, vaulted ceilings, large 1-acre wooded lot. 3 minutes from beach, 5 minutes to both Lake Geneva and Williams Bay, 2 minutes to a local Wisconsin-style convenience store. Welcome to the Peacock Cottage! Located on a deep, private lot surrounded by woods, so it's great to let loose without any nearby traffic. We are super into cozy homes, and love creating spaces that are restful and fun.

Location · Value · Grill