Holiday houses in Richmond

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Top-rated holiday rentals in Richmond

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

LocationFamilyAccess

Guest favourite

A charming two-story house is set within a lush green lawn, featuring large trees that provide shade. The front porch is approachable and includes a railing, while an American flag gently waves. A fence encloses the backyard, creating a private outdoor space.

Home in Twin Lakes

4.87 out of 5 average rating, 106 reviews

walk to beach, dog friendly yard hot tub sleeps 12

4,000 sq ft 5 bedroom, 3.5 bath home. Short walk to small beach and boat launch (Musial Beach) on Lake Elizabeth. Perfect for large families with multiple living areas. Island Kitchen with fireplace & den. 3 season room. Master bedrm with walkin shower. Large 2nd floor family room with tv, vinyl records and shuffle board! Outdoor natural gas grill, fire pit, free firewood. Close to Grand Geneva, Lake Geneva and Wilmot Mtn. Turnkey boat rental available. hot tub, beach chairs & bags available

LocationFamilyCheck-in

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 🇺🇸

ValueFamilyOutdoor spaces

Top Guest favourite

A cozy seating area is presented with two sofas adorned with decorative pillows. A large lamp with a blue shade complements the space, while light filters through the large windows, enhancing the bright atmosphere. A piece of wall art and natural accents are also visible.

Home in Salem

4.94 out of 5 average rating, 133 reviews

Center Lake View Cottage, near Camp&Silver Lakes

Relax & enjoy your stay in this peaceful home in quiet, friendly neighborhood. Launch boat in Center Lake at end of street or several nearby lakes. Camp Lake is 2 mins away, close to Silver Lake and many others. This home has an awesome sled hill, fire pit with seating area, and a relaxing deck with lake views. Close to Lake Geneva, & Renaissance Faire. Ski at Alpine Valley or Wilmot Mountain. 25 mins to Six Flags or Lake Geneva, 1 hr to Chgo or Milwaukee. 35 mins to Great Lakes Naval Base.

ValueFamilyNearby

Top Guest favourite

A serene lake view captures a sunset with warm colors reflected on the water's surface. The sun descends behind distant trees, creating a peaceful ambiance. The shoreline is faintly visible, providing a glimpse of the surrounding nature.

Home in Twin Lakes

4.96 out of 5 average rating, 55 reviews

Lake view! Steps to beach and close to Lake Geneva

Sunset Lakehouse is a serene, year-round retreat steps away from Lake Elizabeth's Sunset Beach. With a lake view, Sunset Lakehouse is perfect for boating, swimming, and fishing! In the summer, enjoy the nearby sandbar where boats and swimmers gather. In the winter, take advantage of one the nation's premiere ice fishing lakes. With a windowed sunroom for rainy days and a large backyard, Sunset offers a peaceful place to land after a day by the water. In the evening, cozy up by a campfire.

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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, 244 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 !

LocationFamilyParks

Superhost

A modern living area features a sleek fireplace and large glass doors opening to a deck with lounge chairs overlooking the water. Sunlight shines through, creating a bright and airy feel, while the serene lake and surrounding greenery are visible outside.

Home in Twin Lakes

4.87 out of 5 average rating, 186 reviews

Cove at 420: Modern Lake Front Home near Chicago

Welcome to the Cove at 420. A modern vacation paradise where indoor and outdoor lines blur. Every space is designed for enjoyment. A short 75 minute drive from Chicago, this is a true retreat. Wake up to beautiful sunrise views or enjoy them from a kayak on the water. We offer kayaks, paddle boards, hot tub & sauna, Sonos sound system, a fire pit and plenty of yard games for our guests. Hidden on a cul-de-sac between Lake Mary and Lake Elizabeth, enjoy the best of lake life!

LocationFamilyWalkability

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!

LocationValueCheck-in

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.

FamilyValueComfort

Top Guest favourite

Home in Twin Lakes

5.0 out of 5 average rating, 14 reviews

Modern Lake Escape 3BR/2BA

Welcome to your modern lake escape in Twin Lakes, WI! Just blocks from Lake Elizabeth, enjoy a short stroll to a public sandy beach for swimming, fishing, or boating fun. This 3BR/2BA home is freshly remodeled with stylish finishes, an open layout, and cozy spaces to relax. Whether you’re sipping coffee on the porch or winding down after a lake day, this getaway offers comfort, charm, and the best of lake life.

FamilyValueAccess

Guest favourite

The exterior of Richmond Café is captured from street level, showcasing its historic brick façade and tall windows. A prominent sign featuring the café's name hangs above the entrance. Warm sunlight illuminates the scene, highlighting the inviting atmosphere of the vibrant downtown area.

Apartment in Richmond

4.85 out of 5 average rating, 93 reviews

2000 sqft bnb in Historic DT. Near Lake Geneva WI

Get ready for a genuinely unique getaway! Spacious apartment in historic downtown Richmond 20 min from downtown Lake Geneva WI. This hidden gem offers the best of both worlds with hiking trails and a lively downtown feel. Experience some of the best restaurants and shopping steps from your door! The best part is your above a trendy hot spot for some of the best coffee around!

LocationFamilyQuiet

Top Guest favourite

A historic stone home built in 1911 is prominently featured, showcasing its grand architectural details. The façade includes a porch supported by strong columns. A group of individuals stands in front, illustrating the home's welcoming presence in its early days amidst a natural landscape.

Guesthouse in McHenry

4.96 out of 5 average rating, 213 reviews

"The Apartment" in the heart of downtown McHenry

We welcome you to be our guest in this charming, historic home built in 1911 by German mason Nicholas Bohr. This upper unit apartment is a spacious 1,100 square feet, restored in 2018. The private entrance to "The Apartment" will lead you to 2 cozy bedrooms, 1 bathroom with a walk in shower, a large living room, and bright clean kitchen will make you feel right at home.

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