Vacation rentals in Darien

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Top-rated vacation rentals in Darien

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Superhost

Two glass pendant lights hang from the ceiling, showcasing exposed bulbs. Below, a circular mirror with a black frame reflects the soft light and surrounding shiplap wall, adding a contemporary touch to the space.

Bungalow in Lake Geneva

4.78 out of 5 average rating, 262 reviews

Bungalow by the lake ~ 1 block to lake

Come stay in our calming bungalow by the lake. A comfortable, charming and recently updated two bedroom house with nautical touches throughout. We are a block from the lake, a quick 10 minute drive (or $8 Lyft) to downtown Lake Geneva. Located on private Lake Como, a fun, up and coming lake front community that boasts great restaurants and bars all within walking distance. We are an easy two hour drive from Chicago and only an hour from Milwaukee. Clean beach, boat launch and parks blocks away.

Superhost

An A-frame structure is nestled among lush green trees, showcasing large glass windows that allow for ample natural light. The contrasting wood siding complements the surrounding foliage, creating a harmonious blend with nature. A raised deck leads to the entrance, enhancing accessibility to the home.

Cabin in Fontana-on-Geneva Lake

4.92 out of 5 average rating, 139 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.

Superhost

An aerial view captures a sprawling five-acre property surrounded by a lush woodland forest. The landscape features a well-maintained green lawn with several trees and pathways, along with multiple buildings nestled together, offering a sense of tranquility in nature.

Home in Harvard

4.95 out of 5 average rating, 191 reviews

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.

Superhost

A well-lit bathroom features a spacious vanity with multiple drawers and a sink. A frosted glass shower stall is positioned in the corner, while decorative toiletries are placed on the countertop. Neutral-colored tiles cover the floor, and a mirror reflects the room's light.

Farm stay in Cherry Valley

4.97 out of 5 average rating, 364 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.

Superhost

The exterior of the home features a grey facade with two garage doors and a paved driveway. Soft landscaping is visible, with patches of grass and remnants of snow in the yard, contributing to a neat and welcoming appearance.

Home in Janesville

5 out of 5 average rating, 132 reviews

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

Superhost

Home in Delavan

4.9 out of 5 average rating, 117 reviews

Victorian in Delavan, near Lake Geneva & Alpine

Family & friends will be close to all Delavan offers staying at this beautiful historical 1901 Victorian home. One block from charming brick-paved downtown Delavan, you'll have shopping, music, parks & great restaurants at your fingertips! Your private gazebo w/ fireplace provides an ideal retreat, while the bandstand livens things up across the street! Playgrounds, sledding hill, beach, lake & arboretums are all within 4 blocks; skiing & Lake Geneva are just a 15-minute drive away!

Superhost

A cozy seating area features a gray sofa and a small table with decorative items. Natural wood walls add warmth, while large sliding glass doors frame the serene lake view, leading to an outdoor deck overlooking the water.

Home in Round Lake Beach

4.99 out of 5 average rating, 150 reviews

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Superhost

A welcoming outdoor space features a wooden deck with black Adirondack chairs surrounding a fire pit. Cozy blankets and colorful cushions are arranged on the chairs. Green trees and flowers in pots provide a natural backdrop, enhancing the retreat atmosphere.

Cabin in Twin Lakes

4.99 out of 5 average rating, 102 reviews

Secluded in the Woods, Hot Tub

Owl's Rest Cabin is nestled in acres of fully wooded, peaceful forest. This is a cozy couple's retreat or small family getaway with a fireplace, hot tub, full kitchen, washer/dryer, located 4 minutes from Lake Mary and 15 min to Lake Geneva. Many activities nearby - festivals, hiking, boat rentals, golf, beach, downhill skiing, tubing, and snow shoeing. Eco conscious cabin, including Level 2 electric vehicle charging & more. Please message us with any questions.

Superhost

Condo in Lake Geneva

4.97 out of 5 average rating, 156 reviews

Magnificent waterfront views & cozy 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, providing unforgettable memories in this beautiful Wisconsin setting. Local laws require all guests names and address be provided prior to check in.

Superhost

A bright living area showcases a stone fireplace as its focal point. Natural light filters through multiple windows arranged in an inviting layout. Comfortable seating options include a spacious sofa and two armchairs, complemented by a soft area rug and a cozy bean bag.

Farm stay in Harvard

4.97 out of 5 average rating, 119 reviews

Eden Farm: Family Stays & Intimate Moments

Unwind and find your inspiration just 1.5 hours from Chicago at our Elite Farm Retreat. Designed for executives, weddings, and families. High-speed Wi-Fi, Smart TVs, and workspaces enhance your stay. Our 5000 sq ft estate is a blend of comfort and rustic charm, set on 10 acres near Lake Geneva. Luxurious bedrooms, Jacuzzi, and premium entertainment await. Ideal for top-level meetings or intimate family events. Elevate your retreat experience with us. Book now.

Superhost

Cabin in Whitewater

4.95 out of 5 average rating, 338 reviews

Glamping Cabin on Cold SpringTree Farm

Unfortunately we can't accommodate same day bookings as we don't have enough lead time to prep the cabin for your stay. Glamping on a working Christmas tree farm. Beautiful single room stone cabin with loft and wood burning stove. Two small beds in loft and futon on main floor folds out into full bed. Lots of room around to pitch tents as well. Situated on 40 acres of land with a pond, barn with basketball court, creek and Christmas tree fields.

Superhost

A red barn is depicted with a backdrop of blue skies and scattered clouds. A tractor is positioned in front, carrying bales of hay towards the barn. Lush green grass surrounds the area, creating a vibrant rural scene.

Apartment in Elkhorn

4.95 out of 5 average rating, 402 reviews

FarmWise Country Stay by Alpine Valley/Lake Geneva

Retreat to a quiet countryside experience at this all organic farm, where you can sit back, relax, and enjoy the country charm of your private space inside the main farm house. Optional for you are joining us for early morning chores in the barn. If you tell me the night before, you can try milking Carmel, the cow by hand, feeding the pig, collecting eggs from the chicken coop and more. Most loved of all are our friendly cats!

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Other great vacation rentals in Darien

Superhost

A living room features a comfortable recliner and a smart TV positioned near a cozy fireplace. A large sliding glass door provides access to outdoor space, while the adjacent dining area is furnished with a wooden table and four chairs, complemented by a decorative rug.

Condo in Lake Geneva

5 out of 5 average rating, 4 reviews

Cozy Condo at Interlaken! Stay & Play on Lake Como

HeidiRating, 5 stars4 days ago

Such a great place! It was in a perfect location, quiet but close to Lake Geneva, Williams Bay and Delavan. The photos and description were accurate. We had everything we needed and the host was responsive. We will definitely be back when we are in the area and in need of an Airbnb.

Guest favorite

A brightly designed ukulele featuring a floral pattern hangs on a wall, accompanied by a beginner's guide titled 'How to Play Ukulele Level 1.' The wall surface is textured and light in color, providing a subtle backdrop to the musical items.

Apartment in Harvard

4.87 out of 5 average rating, 39 reviews

one bedroom apartment- self check-in

CassandraRating, 5 stars3 weeks ago

Lori's place was absolutely fantastic! It was so cozy and I loved staying in as much as I did going out. Lori's check in and check out was an introverts dream but Lori was responsive and just a text away if I needed anything. I absolutely would stay here again!

Guest favorite

A serene indoor space is showcased, featuring a large table surrounded by floor cushions in calming hues. Natural light filters through expansive windows, revealing a snow-covered landscape and a tranquil water view beyond. An elegant plant adds a touch of greenery to the setting.

Home in Richmond

4.94 out of 5 average rating, 181 reviews

TheGlassCabin @ HackmatackRetreat

KrisRating, 5 stars1 week ago

Our Glass Cabin stay was absolutely perfect! It was beautiful and peaceful inside and out, a destination in itself. All communication was clear and questions were answered practically instantly. If you get an opportunity to stay here, you will consider yourself lucky when you leave!

Superhost

A covered outdoor porch features several white Adirondack chairs and a matching bench, overlooking Lake Delavan. Surrounding trees provide shade, and the serene lake view is visible in the distance, framed by clear sky, creating a peaceful setting for relaxation.

Home in Delavan

5 out of 5 average rating, 10 reviews

Brand New Custom Home on Lake Delevan's Northshore

JenniferRating, 5 stars10 months ago

Beautiful home with such a quaint nautical vibe. Saw so many deer and got to enjoy picturesque sunsets each night. Really close to a marina to rent a boat for the day (highly recommend!) and centrally located to so many local spots for dinner. Loved being only 15 minutes from Lake Geneva’s shops and the Frosty Moose in Williams Bay. Would recommend bunk beds in the room downstairs for larger families but beyond that- this was perfectly designed and decorated! Thanks for sharing your home!

Guest favorite

The exterior of the Ole Bistro Inn is displayed, featuring a charming facade with white railings on the upper level. A paved pathway leads to the entrance, flanked by greenery and landscaped flower beds, creating a welcoming atmosphere for guests.

Condo in Lake Geneva

4.88 out of 5 average rating, 98 reviews

Top location, no cleaning fee, everthings close M

CarsonRating, 5 stars1 month ago

Great Airbnb for a weekend getaway. Top location, very walkable. Close proximity to the lake, shops and local restaurants. Very clean, spacious unit. Balcony was great to use with amble seating. Overall would recommend.

An inviting loft space showcases natural wood beams and large triangular windows that allow ample light to fill the room. Two comfortable sofas provide seating, complemented by a rustic wooden coffee table and a decorative storage trunk.

Cabin in Delavan

4.86 out of 5 average rating, 196 reviews

Cabin Outdoor HotTub Sleeps 7 Pet Friendly

ElizabethRating, 5 stars2 weeks ago

LOVED the cabin, it was family friendly. Exactly as the listing, well stocked kitchen with useful items. Very much enjoyed our time, will be back!

Top guest favorite

Home in Palmyra

4.98 out of 5 average rating, 50 reviews

A-Frame in forest on bike trail!

JaneRating, 5 stars2 weeks ago

Really a special place. It felt as though I was 100 miles away from civilization. Very quiet and peaceful. Lots and lots of migrating songbirds. 😍 The fenced yard was a real plus for me - traveling with two large dogs. Everything was super easy and very comfortable. Would definitely recommend!

Guest favorite

A modern kitchen features white cabinetry, a large island with seating for two, and stainless steel appliances. A decorative light fixture hangs above the island, while a window allows natural light to brighten the space. A vase with flowers adds a touch of color to the countertop.

Home in Crystal Lake

5 out of 5 average rating, 6 reviews

In Ground Pool, Full Ranch Home

MarkRating, 5 stars2 days ago

Great place and easy to work with.

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Vacation rentals in Darien

Top-rated vacation rentals in Darien

Vacation rentals for every style

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