Holiday rentals in Howards Grove

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Top-rated holiday rentals in Howards Grove

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Top guest favourite
A serene lakeshore scene is captured at sunset, with the sun dipping below the horizon, casting warm hues across the sky. Gentle waves are visible in the foreground, while smooth stones line the water's edge.
Guest house in Oostburg
4.91 out of 5 average rating, 393 reviews

Beach House

This guesthouse is detached from the main house, comes with garage parking and has all the amenities you need including a wood-burning fire place! Towels, bath tissue, soaps & travel items. AC Window Unit. Kitchen includes pots/pans, dishes, mugs/glasses, coffee pot, toaster & microwave. Paper goods. New appliances/new water heater in 2020. Stairs to the apartment are on the northeast corner of the garage. The beach is steps away with a fire pit, boat house lounge, kayaks, beach toys & bicycles.

Top guest favourite
The A-frame cabin is framed by lush greenery and colorful landscaping. A welcoming pathway leads to the entrance, featuring a spacious deck. The cabin's dark exterior contrasts with the surrounding trees, creating a serene and private atmosphere.
Cabin in Elkhart Lake
4.99 out of 5 average rating, 330 reviews

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.

Top guest favourite
The cottage is surrounded by trees, featuring a well-maintained exterior with a shingled roof and a welcoming front path. Colorful flowers and greenery adorn the entrance, while large windows allow for ample natural light. A cozy sitting area is visible near the front door.
Cottage in Oostburg
4.97 out of 5 average rating, 324 reviews

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

Top guest favourite
A bright living area showcases a spacious dining table with place settings, and a cozy red armchair positioned nearby. Large sliding doors reveal an inviting patio space, while a television stands against the wall opposite, enhancing the relaxing atmosphere.
Home in Sheboygan
4.97 out of 5 average rating, 111 reviews

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.

Guest favourite
A wooden shelf is mounted on a gray wall, displaying a collection of colorful ceramic mugs hanging from hooks. Above the mugs, a white container holds green plants, while a coffee bag is placed alongside framed artwork.
Home in Sheboygan
4.94 out of 5 average rating, 279 reviews

Dog Friendly Blue Door Cottage / Fully Fenced Yard

Nobody should have to leave their fur baby behind while on vacation. This is exactly why we created this comfortable home with your family & puppy in mind. You'll be at ease knowing that your pooch will be having just as much fun as you are. Modern hints are complemented by the cozy, welcoming decor found throughout. The coffee bar is a fav for any morning person, and the "take-a-wine leave-a-wine" wine bar offers evening excitement! The huge yard features a fire pit, gas grill, & cornhole.

Top guest favourite
A single-story house with a neatly maintained lawn and vibrant flower beds welcomes visitors. An American flag is displayed at the entrance. The driveway leads to a garage on the left side of the house, and ample green space surrounds the property.
Home in Howards Grove
4.96 out of 5 average rating, 195 reviews

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.

Guest favourite
The kitchen area offers light wood cabinetry and a breakfast bar, with a dining table that seats four. Large sliding glass doors provide views of the lake, while ample counter space accompanies a full-size refrigerator and modern appliances.
Home in Sheboygan
4.86 out of 5 average rating, 219 reviews

Dog Friendly Cozy Cottage Rental on Lake Michigan!

Kohler Design Center Rentals, Kohler Andrae State Park Rentals, Whistling Straits Rentals, Blue Harbor Rentals, Road America Rentals, Kohler Art Center Rentals, Black Wolf Run Rentals, Lake Michigan Fishing Charters Rentals, Green Bay Packer Rentals, Door County Rentals, Honeymoon Rentals, Women's Weekend Rentals, Lake Michigan Sunrise Rentals, Dog Friendly Rentals, Winter Rentals. Dog Friendly Rentals, Sheboygan, Wisconsin Rentals, Saugatuck, Michigan Rentals, New Buffalo, Michigan Rentals

Guest favourite
An aerial view captures the layout of the property, showcasing a cluster of buildings surrounded by lush greenery and a small pond. Farm fields extend in all directions, while trees add a touch of vibrant color to the landscape.
Barn in Sheboygan Falls
4.72 out of 5 average rating, 139 reviews

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.

Top guest favourite
Cabin in Cascade
5 out of 5 average rating, 234 reviews

sauna and hot tub 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!

Top guest favourite
A cozy two-story home nestled among tall trees, featuring a spacious front porch and a gravel driveway leading to a two-car garage. Lush greenery surrounds the property, providing a serene and inviting woodland atmosphere.
Home in Sheboygan
5 out of 5 average rating, 231 reviews

Woodland Creek Retreat: explore & relax!

Lovely home nestled in 9 acres of peaceful woodland. 1.5 miles off I-43. Enjoy a walk in the woods or enjoy the dunes and wonderful views of Lake Michigan from Terry Andrae State Park only .2 miles away! Enjoy relaxing on the front porch or taking in the view of the woods from the spacious back deck. Be on the lookout for turkeys and deer. Wonderful wood burning fireplace and extensive game collection(500+) for staying in! We love the cozy and open cabin feel and hope you will too!

Top guest favourite
A well-lit living area features a neutral-colored sofa adorned with a soft throw. A glass coffee table sits on a patterned rug, complemented by a wicker basket. Natural light filters through the window, illuminating the space and the nearby armchair.
Flat in Sheboygan
4.98 out of 5 average rating, 190 reviews

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.

Top guest favourite
The exterior of a charming house is depicted, showcasing a welcoming front porch with steps leading up. The porch features a small seating area and decorative plants, while lush green grass frames the path, adding to the inviting ambiance.
Home in Sheboygan
4.97 out of 5 average rating, 215 reviews

Logan's Guest Nest

Logan's Guest Nest is located in a nice small town feel area. With a small look on the outside your Nest has a big feel on the inside. Spacious rooms and quiet area to rest after a day at the many beaches lining Lake Michigan. Or coming back from the races at Road America. Not to mention a day of golf at the many area courses, Whistling Straits maybe. All these wonderful outings are just minutes from the Nest. Plenty of local dinning or delivery for a nice ending of the day.

Popular amenities for Howards Grove holiday rentals