Holiday rentals in Olin

Lake House • Kayaking Fishing, Sunrises, Bonfires

Little House on the Lake is a peaceful, cozy lake home retreat surrounded by nature and quiet beauty. Wake up to striking sunrises over the lake through large picture windows, and settle into slow, unhurried days. Spend your days relaxing on the deck, kayaking, paddleboarding, or simply enjoying the quiet rhythm of the water and woods. Unwind or gather around the fire pit and enjoy our timeless lake house getaway feel -perfect for families, couples, and anyone looking to slow down and reconnect.

Creekside Cottage farm stay nice for two to six.

Relax and enjoy time together at Creekside. The cottage is a picturesque spot for one or two guests or for groups up to 6. Extra guest charge is $20 per person after 2. Located on our farm only 15 minutes from downtown Dubuque and the Mississippi Riverfront. Explore the woods, fields, and creek on our farm. Visit the animals. A short drive to Mines of Spain, EB Lyons Nature Center, Eagle Point Park, Galena, Bellevue, Chestnut and Sundown ski areas, two monasteries, craft breweries, wineries.

Cozy Cabin by the Pond

Quiet, private country location to relax and unwind. 9 miles west of Dubuque, close to Wineries, Heritage Trail, Sundown Mountain Resort. Cozy cabin and quarter acre pond. Sun yourself on the patio, or nap in the shade of the covered porch. We're sure you will love this space as much as we do. Not suitable for children under 12, we strictly enforce no children and no pets. Outdoor relaxing space, gas grill. Fully stocked cabin, with breakfast items included for you to enjoy at your leisure.

Main Street Suite

Enjoy a stylish stay at this centrally located, solar powered airbnb. All the amenities of home in a rustic setting. Real barn wood wall and tin ceiling. Electric fireplace, 65" smart tv, washer/dryer, dishwasher, stove, refrigerator,AC and more. Sleep on the comfortable Nectar queen mattress. Couch is a sleeper sofa with full size bed for extra sleeping space. Bars, restaurant, grocery store and gas stations nearby. Minutes away from Dubuque, Field of Dreams and Sundown mountain ski resort.

Private & Modern. Near river and wildlife refuge!

Experience the outdoors in comfort from this modern cabin, situated next to the 2200 acre Princeton Wildlife Management Area, and the nearby Mississippi River. It is ranked as the most “Wish Listed” Iowa listing of 2025 on Airbnb. Are you into hiking, biking, fishing, hunting, boating, or other water, winter, and summer sports? This cabin can support it all! Sit back and relax on the large deck while enjoying a coffee & the local wildlife, flora, & fauna of the Mississippi Valley Region.

Cozy Cottage

Our place is close to everything! A 5-10 minute drive to just about anything in town. Newbo District and downtown are 5 min by car and 15 min on a bike. The bike path is 1/2 mile from the house and easily accessible. You will enjoy the quiet wooded location of this completely renovated "cozy" 500 Sq. Ft. one bedroom cottage. There is a fire pit and wood for a nice relaxing night, if you choose to stay in. Check out my other listing next door. 3 bed 2 bath if you need more space.

Custom Floating Suite-HOT TUB!

Enjoy a stay directly on the backwaters of the Mississippi River. This custom cabin is floating right on the water, and you won't find anything like it! Grab your loved one or friend and surround yourself in nature, while soaking in the hot tub on the floating patio, or in the beautiful tub inside. Relax in the king size bed thats in front of one of the two fireplaces. The cabin has everything you need, including a small kitchen. This floating oasis is located at Millennium Marina.

Location Location Location

When they say location is everything, they were talking about Sandstone Haus. Located just a few steps from all the action of Main Street. Wineries, Brewery, eateries, bakery, and boutique shopping are waiting for you in Amana Colonies. Book your stay in this spacious one bedroom (queen size bed) and oversized living room suite that includes a queen pull out couch for additional guests, large eat in kitchen for four people. If you need a workspace, this suite has one! Book today.

The Milk House at Lucky Star Farm

The Milk House is a unique space located in the countryside, between Iowa City and Kalona. This 700 square foot home has ample parking and room for four adults. The house is well appointed with a full kitchen, two luxurious queen beds, wifi and a Smart TV. Guests are invited to explore our 20-acre working farm with lots of livestock and two friendly dogs. It's a perfect blend of rural living with the perks of beautiful Iowa City 15 minutes away. Come unwind at Lucky Star Farm!

La Grande Dame - Cozy & Historic

Large home in a local historic district, boasting plenty of space & amenities. Large spaces inside & out, fine finishes & comfortable provisions. Unique décor & historic charm of a 1913 American Foursquare home, lovingly maintained & updated. Centrally located with simple, quick access to all areas of town, interstate, shopping, entertainment, medical district, & more. Comfortable, peaceful, quiet, cozy! Christmas decor (3 full size trees!) throughout the home Nov/Dec/Jan!

The Uptown B - Uptown Marion

Welcome to The Uptown B! This beautifully renovated upstairs duplex blends historic charm with modern comforts. Enjoy a brand-new kitchen and a luxurious rainfall shower for a spa-like experience. Just a few blocks from Marion Town Square, this quiet retreat offers easy access to shops, dining, and attractions. ✔ Private Entrance & Outdoor Staircase ✔ Free Street Parking ✔ Walkable to Downtown Book your stay at The Uptown B today! ** Brand new washer/dryer unit in 2025

Deer Trail Cabin

🌿 Cozy cabin tucked in the quiet Wisconsin woods—your perfect spring retreat. Enjoy fresh air, blooming trees, and peaceful forest trails right outside your door. Relax in the outdoor hot tub under the stars, gather around the fire pit in the evening (bring your own wood or collect from the property), and watch the free-range goats and chickens roaming the property. A peaceful, private getaway for couples, small families, or anyone looking to unwind in nature. 🌿