Holiday rentals in Hebron

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Top-rated holiday rentals in Hebron

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

A charming historic home is set within a lush landscape, framed by blooming white magnolia trees. The exterior features a welcoming porch with railings, large windows, and a gabled roof, surrounded by neatly maintained grass and flower beds, complemented by a clear blue sky.

Home in Richmond

5.0 out of 5 average rating, 48 reviews

Richmond Magnolia House

1850’s charming historic home in heart of Richmond. THE DISTRICT wedding/event venue is walkable(1/2 block away). Great for guests or wedding party. Local restaurants/bars, shops, and bike trail steps away. Only 15 minutes to Lake Geneva for summer fun or skiing. Only 15 minutes to Wilmot Skiing. Bedroom #1 Queen Bedroom #2 (2) Full beds Bedroom #3 Queen and Twin XL (2 ) FULL BATHROOMS GENERAL: Keyless entry, 2 parking spots on property and street parking, linens, washer/dryer provided

Top guest favourite

Home in Genoa City

5.0 out of 5 average rating, 80 reviews

Getaway near Lake Geneva, Orchards & Pumpkin Farms

TOP 5% GETAWAY✨ - Private backyard & fire table, ideal for s’mores & memories 🔥 - 15 min to Lake Geneva boutiques 🛍️ - 15 min to World’s Largest Corn Maze - Near ziplining, orchards, pumpkins & boating - Near skiing & tubing ⛷️ - Gameroom with Simpsons arcade game & more - Oversized heated pool (May-Sept) - Quiet neighborhood: baseball fields, basketball courts & walking trail ⚾️🏀🚶 - 25 min to Alpine Valley - 1 hour to ORD/MKE/RFD airport ✈️ - 40 min Six Flags & Great Lakes Navy Base 🇺🇸

Top guest favourite

The outdoor area features a spacious patio surrounded by decorative stone architecture. Comfortable seating arrangements are placed near the pool, which is bordered by lush greenery. A large umbrella and several lounge chairs add to the inviting atmosphere. The house showcases large windows and multiple levels.

Home in McHenry

5.0 out of 5 average rating, 61 reviews

Paradiso Vacation

Welcome to our home, a sanctuary of comfort, and unique design. This house it's a perfect blend of modern amenities and timeless elegance. The living area features a cozy fireplace, ideal for family gatherings. The kitchen is equipped with top-of-the-line appliances. The master suite is a private retreat, with walk-in closets, vanities, and a shower. A unique feature of this home is the outdoor living space, with a pool, jacuzzi and BBQ grill making it perfect for entertaining or relaxing.

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

4.93 out of 5 average rating, 189 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

A spacious living area features comfortable gray sectional sofas adorned with turquoise cushions. A light wooden coffee table is centered on a soft area rug. Soft lighting is provided by table lamps, and large sliding doors lead to an outdoor space with a view of greenery.

Home in Lake Geneva

4.95 out of 5 average rating, 122 reviews

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD

✔ 1000 Sq. Ft. Ground Level Condo ✔ Patio overlooking expansive lawn ✔ Resort-like community ✔ New community pool ✔ Tennis,v-ball Courts ✔K-cup & drip coffee, Big Screen TV, Cable, FAST wifi ✔Steps to the Ridge Hotel w/ restaurant, coffee/wine shop ✔ Direct lake access w/boat launch, kayak, SUP board rental ✔ 5 min drive to Shops and dining in DT Lake Geneva ✔ Fully equipped kitchen ✔ Close to summer fun: Lake, golf, zipline, hiking ✔Close to Winter fun: Ice Castle, skiing, snowshoeing

Guest favourite

The exterior of the house showcases a modern design with light blue siding and white trim. A wide paved driveway leads to two garage doors, framed by stone accents. Lush green grass surrounds the property, and trees can be seen in the background under a clear blue sky.

Home in Lake Geneva

4.94 out of 5 average rating, 48 reviews

Hillside House Lake Geneva

Privately located in Lake Geneva, Hillside House is the perfect summer getaway for you and your family and friends. Downtown Lake Geneva is a short 8 minute drive, with beaches, restaurants, and shopping for everyone. Bring your boat and drop in at the boat launch down the street, take in the beautiful Wisconsin sunsets from the front porch, and enjoy happy hour on your screened-in porch. With 3 bedrooms and 4 private bathrooms, plus a full basement, there is room for the whole crew.

Top guest favourite

A spacious living area is highlighted by large windows offering views of the water. Colorful seating options, including bean bags and patterned chairs, complement a wooden coffee table. Sleek ceiling fixtures and a soft rug define the gathering space, enhancing the open layout.

Home in Richmond

4.96 out of 5 average rating, 245 reviews

TheGlassCabin @ HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

Top guest favourite

Cottage in Wonder Lake

4.94 out of 5 average rating, 178 reviews

The Cozy Lake House, Dm me ?s Lake Front Property!

Welcome to The Cozy Lake House, your year-round haven for relaxation and celebration! Savor breathtaking sunsets, indulge in boating, watersports, and high-speed internet, and make special memories during holidays, bachelorette party's getaways, birthdays, family reunions, micro weddings, and more. With a fully equipped kitchen, spacious rooms, and the tranquil lakeside setting, every moment here is magical. Reserve your spot now and experience the ultimate in lakeside living!

Guest favourite

A modern house features an inviting front porch with landscaped gravel beds and well-maintained grass. A wooden garage door complements the green exterior walls. Surrounding trees and shrubs enhance the outdoor space, creating a welcoming entrance.

Home in Twin Lakes

4.98 out of 5 average rating, 140 reviews

4Bd 3.5ba Cozy New Construction! Close to lake!

Welcome to our cozy home! Twin Lakes is quintessential small town America situated surrounding lakes Elizabeth and Mary in Wisconsin. Less than 15 minutes from downtown Lake Geneva and less than 5 minutes from Richmond, Illinois. During your stay you can experience much of what the area has to offer including boating and fishing on Lakes Elizabeth and Mary, access to the community beach, local shopping, and peaceful country nights in this small family-oriented community.

Guest favourite

This charming Victorian farmhouse showcases a large, inviting porch with ample seating. The exterior features white siding and a steeply pitched roof, surrounded by a lush green lawn. Trees and landscaping enhance the tranquil atmosphere of the property.

Home in Hebron

4.96 out of 5 average rating, 48 reviews

The Farmhouse! 1905 Victorian, fits up to 16

A Charming Victorian Farmhouse that can fit up to 16 guests. Sit back and relax in this historical farmhouse. Enjoy coffee on the large front porch or a drink with friends in the eat-in kitchen or dining room. Easy driving to Richmond, Lake Geneva, Fontana or stay close and enjoy Hebron. You will find everything you need to settle in and stay for a few days. This home is all original with lots of awesome details, pocket doors, intricate carve work and period decor.

Top guest favourite

A spacious bathroom features large skylights that illuminate a freestanding tub, set beneath an arched window overlooking greenery. Two modern lounge chairs are situated nearby, enhancing the tranquil ambiance. The glass-enclosed shower and soft neutral tones create a serene and relaxing environment.

Farm stay in Harvard

4.95 out of 5 average rating, 179 reviews

Eden Farm: Family Stays & Intimate Moments

Unwind and find your inspiration just 1.5 hours from Chicago at the Ten Acre Farmhouse Retreat. Designed for families, intimate moments, and retreats. High-speed Wi-Fi, Smart TVs, and workspaces enhance your stay. This 5,000 sq ft estate blends modern comfort with rustic charm on 10 peaceful acres near Lake Geneva. Luxurious bedrooms, a Jacuzzi, and premium entertainment await. Two outdoor cameras monitor the front yard and driveway. No indoor cameras. Book now.

Guest favourite

Cottage in Lake Geneva

4.92 out of 5 average rating, 113 reviews

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.