Holiday rentals in Sharon

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Top-rated holiday rentals in Sharon

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Top guest favourite

A cozy living room is depicted with a gray sofa and a wooden coffee table resting on a patterned area rug. Natural light fills the space through large windows, highlighting the warm wood trim and the adjacent dining area featuring a wooden table and chairs.

Home in South Beloit

Spacious Craftsman 4BR Sleeps 9 Pet-Friendly Yard

Stay in a beautifully remodeled Craftsman Home with 4 bedrooms and space for up to 9 guests, with the 9th guest sleeping on the sofa. Enjoy rich woodwork and classic character throughout, plus a fenced yard, private parking, grill, laundry, fast Wi-Fi, and complimentary coffee & tea. Just minutes from downtown Beloit, restaurants, shops, the riverfront, and local attractions. Traveling with a larger group? Our second vacation home, 721 Roscoe, is right next door. Perfect for families and groups.

4.97 out of 5 average rating, 142 reviews

Guest favourite

A charming farmhouse is framed by a large, mature tree, with a pathway leading to a welcoming porch. Bright red chairs are positioned on the lawn, inviting relaxation. The white exterior of the home is complemented by green foliage, creating a harmonious outdoor setting.

Farm stay in Capron

4 BR farmhouse on 40 quiet acres

Get away from urban life and decompress at Boone Prairie Farm! This charming 1880s farmhouse is situated on 40 peaceful acres with stunning native prairie views, a winding creek, ancient oaks, and a lush organic garden to eat from. A well-maintained path allows easy access to everything. Great for quiet walks in nature, stargazing, campfires, and yard games. A great option for restorative peaceful retreats or family and friend getaways. Well situated between Chicago, Milwaukee, and Rockford.

4.94 out of 5 average rating, 51 reviews

Guest favourite

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

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.

4.93 out of 5 average rating, 189 reviews

Guest favourite

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

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.

4.95 out of 5 average rating, 219 reviews

Guest favourite

Home in Delavan

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.

4.99 out of 5 average rating, 107 reviews

Guest favourite

The exterior of the home is presented, featuring a spacious covered wrap-around patio. Large windows allow for ample natural light. Surrounding greenery enhances the setting, with a view of the nearby water visible in the background.

Home in Delavan

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.

4.96 out of 5 average rating, 53 reviews

Top guest favourite

Home in Rockton

HD Jameson House at River’s Edge

Nestled on the Rock River, the HD Jameson House, a National Historic Register gem, blends historic charm with modern amenities. Enjoy river views and with quaint shops and restaurants exploring the Village of Rockton is a perfect family-friendly retreat. This haven is surrounded by nature but close to numerous attritions, ideal for a romantic getaway or peaceful escape. The HD Jameson House offers a heavenly retreat, blending past beauty with present allure for everyone in the family.

4.97 out of 5 average rating, 117 reviews

Guest favourite

Home in Janesville

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

4.99 out of 5 average rating, 154 reviews

Guest favourite

A charming lakefront cottage is positioned amidst green lawns and vibrant foliage. A porch with seating is visible, while adirondack chairs in red and white add a pop of color. A flagpole with the American flag stands amongst the serene surroundings, enhancing the outdoor appeal.

Cottage in Delavan

Summer 2026 Lakefront Cottage on Delavan Lake

Escape to this lakefront cottage for your next “lake-cation”. The newly renovated Cottage on Willow Point would be the perfect destination. 3 bedroom, 1.5 bath and sleeps up to 9 comfortably. Beautiful outdoor deck and dining space. 15 steps from the lake and includes a private 120 foot pier, sun deck and ladder! We are a fully furnished rental. We also rent another cottage that can accommodate bigger groups. Please email for more info! Thecottageondelavanlake@gmail.com

4.94 out of 5 average rating, 101 reviews

Guest favourite

The striking A-frame exterior features large triangular windows that allow natural light to flood the interior. The patio area includes seating for relaxation and a hot tub, set against a backdrop of lush surrounding trees, enhancing the connection with nature.

Cabin in Bloomfield

Modern A-Frame Lake Cabin w/ Pickleball Ct.4Bd 3Ba

Escape to this stunning A-frame home in Genoa City, Wisconsin, where tranquility meets adventure. Just minutes away from Nippersink golf course, Lake Geneva and Wilmot Ski Resort. Nearby Cabin offers a range of amenities designed to enhance your stay. Including a private pickleball court, hot tub, kayaks, and many more. Providing private lake access, and a private pier, this spacious vacation rental is the perfect getaway for families and groups looking to unwind and explore.

4.95 out of 5 average rating, 88 reviews

Top guest favourite

Home in Janesville

Janesville Repose -Hot Tub, Sauna, Gym, and Games

Welcome to your home away from home, where relaxation and fun both get their own wing. Unwind: ○ Private Hot Tub ○ Sauna ○ Private Gym ○ Outdoor fire table ○ Outdoor fire pit Entertain: ○ Surround sound home theater (lower level) ○ Perfect setup for cheering on your team, drink in hand ○ Room to gather, celebrate, and make noise ○ Plenty of outdoor games and activities for the kiddos ○ Self-playing piano Perfect for a private retreat or for larger family gatherings!

5.0 out of 5 average rating, 23 reviews

Top guest favourite

The cottage features a charming facade with a combination of blue siding and stonework. Two sets of double doors are framed by large windows, allowing natural light to fill the entrance. Flower beds line the pathway leading to the front door, enhancing the welcoming appearance.

Home in Elkhorn

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.

4.98 out of 5 average rating, 165 reviews