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

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

LocationValueNearby

5.0 out of 5 average rating, 48 reviews

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

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

LocationValueKitchen

4.87 out of 5 average rating, 106 reviews

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

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.

LocationFamilyCheck-in

4.94 out of 5 average rating, 131 reviews

Top Guest favourite

Apartment in McHenry

Walk to downtown McHenry. Heart of the Fox River

NO PETS Entire 2nd. floor. < 2 blocks away from downtown, Fox River Riverwalk. Pokémon Gym across the street. Full stocked kitchen, books, games, toys & extra amenities to make your stay beyond relaxing. 4:20 allowed in backyard & not in view of under the age of 21. Private smoking area in front. Minutes from 2 State Parks, 1 with free boat/kayak launch. Several marinas, boat rentals, golf courses & other varieties of entertainment. Look at Bettye's Guidebook for more information.

LocationFamilySleep quality

5.0 out of 5 average rating, 193 reviews

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

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 !

LocationValueAccess

4.96 out of 5 average rating, 241 reviews

Top Guest favourite

Cottage in Wonder Lake

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!

FamilyValueNearby

4.94 out of 5 average rating, 177 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.

ValueFamilyTV

4.95 out of 5 average rating, 88 reviews

Top 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

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.

ValueLocationPets

4.98 out of 5 average rating, 140 reviews

Top Guest favourite

Home in Twin Lakes

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.

ValueFamilyCheckout

5.0 out of 5 average rating, 14 reviews

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

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!

LocationFamilyCondition

4.85 out of 5 average rating, 93 reviews

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

"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.

FamilyLocationNearby

4.96 out of 5 average rating, 212 reviews

Guest favourite

Apartment in Richmond

Richmond No. 267 Boutique Loft Apartment

Centrally located in charming downtown Richmond, Illinois and only 15 minutes from beautiful Lake Geneva, Wisconsin, Richmond No. 267 is the area's newest boutique loft lodging. This former union hall was completely renovated with attention to every detail: open industrial ceilings, refinished original pine flooring, and a comfortable vintage midcentury aesthetic.

FamilyValueParking

4.96 out of 5 average rating, 50 reviews