Holiday houses in Howards Grove

Shoreline Serenity

Welcome to ''Shoreline Serenity''! 200 ft of Lake Michigan frontage w/unobstructed views that go on for miles and tucked away on a 2-acre lot offering peace & privacy. Inside the home, you will be drawn to the beautiful views through the full wall of east facing windows & patio doors. The interior is cozy, clean, and comfortable. Fully equipped kitchen w/coffee bar. Main level has (2) bedrooms including the primary bedroom w/fantastic views. The spacious upper level loft has a king & twin bed.

Hospitality · Sleep quality · Kitchen

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

Value · Family · Heating

Relaxing Sheboygan/Kohler Getaway

Newly remodeled townhouse with all the comforts to make you feel at home in quiet neighborhood, boasting a spacious backyard w/patio, fire pit & free parking. Amenities include well-equipped kitchen, 2 BR & 2 BA, washer/dryer, wi-fi, & smart TV. Conveniently located within minutes to Village of Kohler, Downtown Sheboygan & Lakefront, Black Wolf Run, Whistling Straits (14 min), Road America (18 min), Kohler-Andrae State Park (16 min), grocery stores, restaurants, shopping & local entertainment.

Location · Value · Bathroom

Spacious lower level priv entrance no cleaning fee

Not set up for babies or toddlers. Entire basement is for rent with a separate entrance. Kitchen area includes refrigerator, microwave, coffee pot, toaster, sink, dining table and chairs. NO STOVE OR OVEN IS AVAILABLE. Free Wifi and Cable TV. Air conditioning. Plenty of parking, keyless entry. 14 min to Road America, 13 min to Kohler, 9 min to Whistling Straits, 5 min to Lakeland University, 1 hr to Milwaukee, 1 hr to Green Bay. Lots of nice amenities, clean, spacious. No cleaning fee.

Family · Value · Heating

Boutique Wellness Retreat - Hot Tub and Fireplace

Celebrate your special occasion in Sheboygan at this beautiful boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom w/King size bed. Secondary bedroom has 2 twin beds. The beautiful fireplace in the living room is perfect for a relaxing couples evening. Enjoy a glass of wine or local brew on the patio while you grill out. EV Charger and E-Bikes to explore the area. Let us impress you and help make it a memory.

Location · Family · Decor

Quiet Country Charm

Cozy barn loft with rustic charm. This newly renovated private loft sleeps 4 with the possibility of 1 or 2 more if you don’t mind sleeping on an air mattress. This room includes a bathroom with shower and small efficiency kitchen with microwave, coffee maker, and small refrigerator. The futon pulls out to a double bed. This relaxing local comes complete with barnyard animals for an authentic Wisconsin experience! You won’t forget the peaceful surroundings of this rustic destination.

Value · Family · Nearby

hot tub and sauna on 5 private acres

Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!

Value · Location · Skiing

Lovely modern two bedroom home with fire pit

Newly renovated two bedroom home just a mile from the beach and five star restaurants. Enjoy a game of golf at world class Whistling Straight. Car enthusiasts will love Elkhart Lake Road America. Salmon fishing the Great Lake Michigan or just have a relaxing time around the fire pit. There is a laundry with washer/dryer, steamer and folding table. Dogs under 30 pounds. No cats sorry. No smoking in the house. Ample street parking at the front door. Fire pit in back yard.

Family · Value · Parking

Sunset Vista- cozy two bedroom retreat

This cozy vacation rental is the perfect place to relax and unwind! Enjoy a warm and inviting fireplace, comfy furnishings, soft lighting, and a fully equipped kitchen ready for your favorite meals. Step outside to a peaceful garden and scenic views — an ideal backdrop for morning coffee or quiet evenings. Whether you’re vacationing with family or friends, this space offers a home-like feel where beautiful memories come naturally. ❌🐾 We currently are not pet friendly.

Family · Location · Accuracy

Church Street Romance & Retreats-Village of Kohler

“A well-appointed, cozy and stylish retreat close to everything in Kohler.” -Kim Take the stairs to my secluded 2nd floor tree view retreat! A private side entrance and open floor plan flanked by two bedrooms makes this unit perfect for couples or a girl's getaway spa weekend. Romantic turn-of-the-century touches meet modern convenience & comfort. Baker furniture, previously a Kohler Company, can be found throughout the apartment enhancing your Village of Kohler stay.

Family · Value · Hospitality

Clean, Comfy Stay Near Parks, Downtown & Lake!

Enjoy a peaceful stay near Sheboygan’s lakefront, family parks, and downtown eats. This clean, cozy 2BR unit offers everything you need—walkable location, garage parking, full kitchen, and thoughtful touches like old-school Nintendo and local recommendations. ⭐ “Clean, comfy, quiet—close to everything. We’ll definitely stay again!” – Roger ✓ Minutes to downtown & Lake Michigan ✓ Family park across the street ✓ Garage + easy onsite parking

Family · Location · Decor

Guest Favorite | Super Host + Clean & Modern Stay!

Unwind in this modern retreat just minutes from Whistling Straits Golf, Road America, Lake Michigan, and year-round outdoor adventures. The bright, open living spaces feature high ceilings, skylights, and stylish furnishings, with thoughtful comforts like heated bathroom floors. Enjoy the spacious outdoor living area for relaxing after a day out. Ideal for golfers, couples, families, wedding groups, business travelers, and traveling nurses.

Location · Value · Backyard