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Vacation rentals in Darien

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Top-rated vacation rentals in Darien

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Guest favorite
A welcoming living area is presented, featuring a spacious black sectional sofa and a cozy round chair. Natural light floods in through sliding glass doors, leading to an outside view. A subtle decor with plants and a table lamp adds to the inviting ambiance.
Home in Lake Geneva
4.93 out of 5 average rating, 160 reviews

Lake Geneva cottage with private beach access

This cute cottage for 6 is located just down the street from beautiful Lake Como that offers fishing, boating, and water sports. It is also just a short drive to Lake Geneva and all that it has to offer with its beautiful lake, shopping, historic buildings, and delicious restaurants. Along with the house you get access to the HOA covered private beaches and playgrounds nearby. There is also a bar and grill down the street with live music. Bring your family or your friends and welcome to my home.

Top guest favorite
The spacious living area is illuminated by natural light from large windows. A leather sofa is paired with an accent chair, while a round rug centers the space. A modern coffee table sits atop the rug, and a dining counter with two bar stools is positioned nearby.
Condo in Lake Geneva
5 out of 5 average rating, 41 reviews

Chic Condo in Lake Geneva.

Discover the freshly renovated one-bedroom condo at the charming Hayloft Lodge, located a few miles from downtown Lake Geneva. Unwind on the comfy couch, enjoy a restful night on the cozy queen bed, or head downstairs for a fun game of pool. This end unit features a kitchen with a mini fridge & freezer, a two-burner stove, a Keurig coffee maker, & more! The fitness area is available year-round, while the pool is open seasonally. A washer & dryer are conveniently located just outside your unit.

Guest favorite
A welcoming living area features a comfortable sectional sofa facing a gas fireplace and a 65" Smart TV mounted on the wall. Sliding glass doors provide access to the outdoor patio, allowing natural light to fill the space. A decorative wreath adorns the door.
Condo in Lake Geneva
4.93 out of 5 average rating, 104 reviews

Lake Geneva Retreat! Fireplace! WiFi!

Your cozy getaway begins in a newly redesigned condo with patio (there are stairs to get to villa), conveniently located between Lake Como and Lake Geneva in Interlaken Resort! Just a short peaceful walk to lake, restaurants, pool, tennis, volleyball, boat launch, small craft rentals, & more! The resort community is located by Lodge Geneva National, which adds additional restaurants and available amenities at an additional charge. Many local areas to explore & visit will await your arrival.

Top guest favorite
A spacious outdoor area features a fire pit surrounded by seating. In the background, a large barn with a green and white exterior is visible, set against a serene landscape of lush grass and trees.
Farm stay in Cherry Valley
4.98 out of 5 average rating, 402 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 favorite
The kitchen features dark cabinetry against a brick wall, complemented by a large island with seating for six. Pendant lights hang above, illuminating the cooking area which includes modern appliances and tasteful decor. A dining table is positioned in the background, promoting an open-concept feel.
Condo in Fontana-on-Geneva Lake
4.88 out of 5 average rating, 17 reviews

Luxurious Condo Experience at Lakeside Villa |Pool

Vacation memories await at this 2 bedroom, 2 full bathroom Abbey Villa at the West end of Geneva Lake. A true standout within the association, Lakeside Villa has been finished with thought and detail to deliver a luxurious condo experience. Walk-able to everything Fontana has to offer, including restaurants, boat rentals, and the beach- not to mention, the fantastic Abbey Villa pool that is just steps away! Book today to discover why guests return to the Abbey Villas year-after-year!

Guest favorite
A comfortable seating area is featured with a mix of armchairs and a stylish lounge chair. A coffee table is placed centrally, while natural light enters through a large window. A doorway leads to additional living space, providing a cozy gathering spot.
Cottage in Lake Geneva
4.94 out of 5 average rating, 47 reviews

Quaint and cozy cottage

Get a break from the hustle and bustle of city life. We're located 3 miles from downtown Lake Geneva, so you're super close to the action, but far enough away that you can easily put your feet up and completely get away from it all. 5 miles to Geneva National, a short .5 mile walk to Lake Como, 12 miles to Alpine Valley Resort and plenty of friendly local restaurants close by. We have a large yard for the kids (or adults) to run around in with a fire pit to chill out by out back.

Guest favorite
The exterior of the tiny house features a welcoming porch with two chairs, surrounded by greenery. A neatly trimmed lawn and colorful shrubbery enhance the inviting entrance. The white siding and simple design contribute to a calming presence amidst the natural surroundings.
Home in Williams Bay
5 out of 5 average rating, 19 reviews

The Valley House

Welcome to our cozy 2- bedroom haven, where simplicity meets comfort in our cute tiny house. Unwind in this basic yet charming space. Embrace the simplicity of small living and make the most of the inviting atmosphere. spacious front porch and backyard. Our home is walking distance to the local coffee shop and grocer. Even better, our home is located within walking distance of Williams Bay public beach and pier. Ice fishing, boating, kayaking, and swimming all within a short walk!

Top guest favorite
A comfortable living area showcases a sectional sofa in a warm brown hue, accompanied by a decorative throw. Neutral wall art is displayed above, while a glass-top coffee table stands in front. A desk and chair are positioned nearby, with natural light filtering through a window.
Apartment in Janesville
4.97 out of 5 average rating, 202 reviews

Cozy Apartment Close to Downtown Janesville

This welcoming 1 bedroom apartment is located close to downtown Janesville, the city of parks. It has been updated throughout and has all the amenities necessary for a very comfortable stay, including a gas grill in the wooded back yard. It even has off street parking. You can easily walk to the Janesville Performing Arts Center and continue downtown and enjoy the Saturday morning Farmer's Market, shopping, restaurants and bars. Access to the Bike Trail is only a few minutes away.

Guest favorite
The exterior of the home reveals a spacious backyard featuring a green lawn and a fenced area. Several Adirondack chairs are arranged around a firepit, inviting relaxation. A patio with outdoor seating and a gazebo are visible, set against a clear blue sky.
Home in Delavan
5 out of 5 average rating, 5 reviews

The Oasis! 5 bedroom on 1/2 acre near 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 and 1/2 acre living areas. This is a 5 bedroom, 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 a modern industrial style decor and includes modern conveniences.

Guest favorite
A spacious suite is shown with a comfortable bed against the wall, accompanied by a cozy seating area featuring a gray couch. A decorative wall art piece adds character, while natural light filters in through the window, illuminating the warm wood flooring.
Guest suite in Waukesha
4.93 out of 5 average rating, 14 reviews

Inlaw Suite with Downtown Charm

Unbeatable Historic Downtown location. Duplex-like entry to your key-access 300sf downstairs suite, full kitchen/bath. Walk a quiet neighborhood to the park, or two blocks over for Mexican food! <1 mile to the art hub of downtown - enjoy the summer farmer's market, or walk along Fox River! Minutes from convenience/department stores/more parks, 10 mins to I-94, <20 min to Pewaukee lake, <30 mins to Milwaukee/the airport/Lake Michigan. *NOTE: Ceiling is 6ft 7 inches.*

Top guest favorite
A cozy living area features a dark sofa set against a textured wall, with a small decorative pillow. An open kitchen bar with four modern black stools invites gatherings, while greenery enhances the room's decor. Natural light is filtered through large windows.
Condo in Lake Geneva
4.97 out of 5 average rating, 212 reviews

Relaxing Villa with Amazing Amenities!

Resort day passes included with booking! Hot tub, indoor and outdoor pool, outdoor bar and fire pit, sauna, the list goes on! Only five minutes from downtown Lake Geneva, this second floor condo offers the best of both worlds. Enjoy the laid back Lake Como attractions, or have a blast in Lake Geneva! This hidden gem is perfect from golfers (only 5 minutes from Geneva National) to families. Give us a try, and enjoy a discount on your second stay!

Top guest favorite
Condo in Lake Geneva
4.96 out of 5 average rating, 114 reviews

The Landis, in charming Lake Geneva

Kick back and relax in this calm, elegant One bedroom Villa with a KING size bed. This vacation rental is in a quiet area of Lake Geneva, but just minutes from all the vibrancy of downtown Lake Geneva or Williams Bay. It is within walking distance to Mars Resort, The Getaway or The Ridge. This is a perfect spot for couples looking for a relaxing getaway. Local laws require all guests names and address be provided prior to check in.

Popular amenities for Darien vacation rentals

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  2. United States
  3. Wisconsin
  4. Walworth County
  5. Darien