Vacation rentals in Whittemore

Lula & Bill Legacy Inn-Cozy Vintage Charm in Iowa

Welcome to the Lula & Bill Legacy Inn - cozy historic home with vintage charm in the lakeside town of Emmetsburg. Just minutes from beautiful Five Island Lake, local shops, the family splash park, golf course, and Wild Rose Casino. Perfect for road trippers and families looking for a relaxing stop to rest and recharge. Traveling professionals working in the area are also welcome to contact us about extended stay options. ❤️We care about our guests and are always happy to help.❤️

Lost Island Getaway: Hiking, Hunting & Fishing!

Welcome to Lost Island Getaway! This acreage is a walk to Lost Island Lake and Barringer Slough with direct access to public hunting ground. Lost Islands west boat ramp is just down the road for boating and fishing. Perfect getaway if you want to relax or if you are up for an adventure. Fire pit outside. We are a country home and will have farm fresh eggs ready for you. There is dining located at the highway corner. We are dog friendly. We are just 30 minutes from Okoboji!

Hunters Paradise Cabin

This property is located in the perfect location for every hunter, fisherman and boater. We are on the North end of Trumble lake surrounded by thousands of acres of public hunting. We are only 5 miles from Lost Island and 20 miles to the Okoboji area. We have a heated garage for the pets to stay with some kennels provided. Pets are welcome to run the yard and play. No hunting is allowed on the property. There is 300 acres just across the creek to hunt.

Headwaters Hideaway

Headwaters Hideaway is the perfect place for you to unwind for a quick getaway, a week long stay, or an extended stay. Our cabin sits at the edge of our seasonal site campground on the shores of Crystal Lake (264 acres). Public access is within walking distance if you choose to enjoy boating or fishing on your stay. We also have 2 kayaks available. The kids will stay entertained with a playground and basketball hoops just across the campground access road.

The River View at Evergreen Hill

Relax with the whole family at this peaceful place to stay. Or book a longer stay while working on the area. River View is a 2100 sq. ft duplex. Originally built in the 50’s, the architecture will take you back in time and has been updated to keep the mid century charm! The BEST part is the amazing view. This River View sits on top of a bluff overlooking the Des Moines river and is beautiful all year round! **Fireplace DOES NOT operate**

3Bedroom 3bath 1870s house for getaway or events

Relax and enjoy this unique getaway. Built in 1870s with Italianate architecture this beautiful stately brick house has large French windows and original wood floors The house is a step into history with modern updates to make guests feel right at home. Relax upstairs in a large jacuzzi tub. Enjoy grilling on the front porch area and enjoy the park a block away and downtown just three blocks with eateries and shopping downtown.

Split Pine | Updated Cottage w/ W/D | Near Hunting

Experience modern comfort at Split Pine, a freshly remodeled cottage in the heart of Thompson. Whether you’re here for a night or an extended stay, enjoy a brand-new bathroom with a tiled walk-in shower, in-home laundry, and a cozy layout that sleeps six. Perfectly situated just one block from Thompson’s famous steakhouse and local grill—your ideal home base in Winnebago County.

Union Suite #1

A quiet small town getaway close to the grotto, town pool, shops, parks, and more. This suite includes 2 bedrooms, 1 bath, full kitchen & living room. The second bedroom has a set of bunk beds with a twin on the top and a full on the bottom. Just a note, we do not have a TV but do offer free WIFI. **There are quite a few stairs going up to the apartment.

The Shady Rest

Welcome to Shady Rest—a cozy one-bedroom cottage just steps from your hosts’ home. Enjoy a king bed, full-size pull-out, country kitchen, spacious bath, and shady yard. Includes Wi-Fi, ,washer/dryer, and free parking. Family-friendly with pack-and-play available. Your hosts are next door if needed, but you’ll have full privacy to relax and enjoy your stay.

The Hometown BNB: Fully Renovated Cozy Home

Bring the whole family to this cozy home with lots of room for fun. Our house includes a fully stocked kitchen, 4 queen beds, games, a toy room, screened in porch, outdoor patio, propane grill and fire pit area. One block away from a large park and the city pool! Only a few minutes away from the Grotto of Redemption and fun shopping on Broadway!

New construction home sleeps 6.

Brand-new construction home located near the heart of town, offering convenience and modern living. Equipped with all-new appliances, this home also features a washer and dryer, along with TVs in both bedrooms and the living room for added comfort and entertainment. 2 New Queen beds Pullout couch with Queen Bed.

Aunt Martha’s Cottage -Pet Friendly

Welcome to Aunt Martha’s Cottage, a cozy retreat with the charm of yesteryear. Step into a simpler time, where the air is fresh, the pace is slow, and every corner holds warmth and nostalgia. With its cheerful kitchen and a bedroom dressed in soft quilts, this little cottage feels like home the moment you arrive.