Holiday rentals in Darien

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Top-rated holiday rentals in Darien

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Guest favourite

Cabin in Lake Geneva

4.98 out of 5 average rating, 194 reviews

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 Lake Geneva Ice Castles/Winter Realms, plus fishing, hunting, hiking, ziplining, snow skiing, boating & much more.

Guest favourite

Home in Whitewater

4.97 out of 5 average rating, 191 reviews

Mid-Century Masterpiece on Secluded 18-Acre Woods

Built in 1968, this impressive house was designed with the utmost care and thought to ensure that it would stand the test of time. We made sure to preserve its timeless look and feel to provide a one-of-a-kind experience for our guests. Located on 18 acres, this house is hidden amongst the trees in an otherwise farm-centric town. This change in scenery is just one of the ways that this house sets itself apart from any other place in Whitewater. We can't wait for you to see it for yourself!

Guest favourite

Apartment in Lake Geneva

4.98 out of 5 average rating, 195 reviews

Lake Geneva Cloud 9

A resort community with outdoor pool (open during the summer season only) boat launch, tennis courts and small craft rentals on the premises. Beautiful views of Lake Como from the patio. Five minute drive to Downtown Lake Geneva. Free parking and keypad entry. Walk to The Ridge Hotel Resort and enjoy the use of their amenities for a small user fee which includes indoor and outdoor pools, spa, whirlpool, fitness center and restaurant. The condo is comfy and ready to make your stay memorable.

Guest favourite

Cabin in Fontana-on-Geneva Lake

4.92 out of 5 average rating, 119 reviews

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.

Guest favourite

Rental unit in Lake Geneva

4.98 out of 5 average rating, 882 reviews

Geneva Street Inn in Maple Park Historic District

Geneva Street Inn is located one block away from the heart of Lake Geneva. This beautiful 1890's home is appealing to everybody whether your stay is a business trip, family, or even a couples getaway. A huge backyard and a front porch that will make you never want to leave. We strive to make your stay your "home away from home" with unique decor and it's timeless charm! Our price is inclusive cleaning fees (unless extenuating circumstances warrants a fee). We meet our guests at check-in.

Guest favourite

Apartment in Lake Geneva

4.93 out of 5 average rating, 487 reviews

Charming, Cozy & Eclectic Condo in Lake Geneva!

Quaint 1 BD 1 BA Condo by Lake Como. Neighborhood pool is newly remodeled. Launch your boat, stroll the woods, rent kayaks, play tennis, or chill. The hotel next door has pools to use for a fee. Dine at many local places or right next door, check out the Hotel’s options … plus their outdoor bar and fire pit. We have towels, toiletries, games, WiFi, basic cable, Roku, electric grill, a fireplace, and full kitchen. Don’t expect the Taj Mahal. DO expect to kick back and make great memories!

Guest favourite

Home in Roscoe

4.99 out of 5 average rating, 293 reviews

* Travelers Sanctuary 2/2, deck, native garden.

Two bedroom, two bath home, residential street. 1400 sq ft. Self check-in. Central Air. Parking in driveway. 1-acre, wooded backyard. 4 mi to I90/39-Exit Rockton Rd. 11 mi N of Rockford 7-8 minute drive to forest preserves, grocery. Ideal for biz class guests, couples, families with children over 8 yr. Share a bit about yourself, why in the area, who you are traveling with & that you read & agree to "House Rules". NOTE: The host lives in lower unit, uses separate, private entrance

Guest favourite

Farm stay in Cherry Valley

4.97 out of 5 average rating, 326 reviews

Bed and Breakfast with Horse Hotel at VRR

Victory Reigns Ranch Horse Hotel and Bed and Breakfast boasts a beautiful ranch setting close to Deer Run Forest Preserve, Oak Ridge Forest Preserve and other equestrian trails. *Come with or without your horse. We also have an RV hookup if needed along with spacious trailer and RV parking. *If interested in horse boarding during your stay a 12 x 12 barn stall is $35 per night. Private pasture turn out available for $25 per horse per night. Trailer hook up is $35 per night per trailer.

Guest favourite

Place to stay in Brodhead

4.98 out of 5 average rating, 119 reviews

Historic Randall Schoolhouse

You'll love this beautifully redone Historic One-room Schoolhouse. Situated on the edge of the Driftless area 5 miles from the Sugar River Trailhead. An easy 30 minutes to Monroe, Beloit & Janesville and just an hour outside Madison. Relax in comfort with all new appliances including a full kitchen, washer/dryer, dishwasher and fireplace. Fenced yard. Just a mile down the road from a working homestead where you can milk a cow, pet a goat, harvest fresh produce and eggs and so much more.

Guest favourite

Apartment in Lake Geneva

4.97 out of 5 average rating, 117 reviews

Magnificient views in a Lakefront condo, Fireplace

Welcome to this serene waterfront villa in Lake Geneva, Wisconsin, a haven for relaxation. This elegantly designed one-bedroom retreat is perfectly nestled on the shores of Lake Como, offering a blend of rustic charm and modern comfort. The real brick walls and cozy fireplace create a warm and inviting atmosphere. Your stay promises a perfect balance of peaceful relaxation and recreational activities creating unforgettable memories in this beautiful Wisconsin setting.

Superhost

Cabin in Delavan

4.88 out of 5 average rating, 176 reviews

Cabin Outdoor HotTub Sleeps 7 Pet Friendly

Renovated cottage that includes all the comforts of home. Featuring a full bath, hot tub, stone stacked fireplace and much more. Bedrooms are bright and cozy , tastefully decorated with hand crafted log furniture & accessories, the master suite has a queen size bed and guest bedroom has full size. 2 sofa sleepers upstairs in the loft area. The kitchen includes all kitchen tools needed for your stay. We have stocked the house with family friendly movies, games, books..

Guest favourite

Home in Elkhorn

4.98 out of 5 average rating, 120 reviews

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.