Vacation rentals in Dorchester

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Top-rated vacation rentals in Dorchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

The cabin's exterior showcases a blue wooden facade with a metal roof, set against a backdrop of lush greenery. A stone base supports the structure, enhancing its rustic charm. In the foreground, a grassy area is complemented by a few trees, creating a peaceful outdoor environment.

Farm stay in Decorah

Footbridge Farm Cabin

Footbridge Farm is a quiet country get-away located on 90 wooded acres, 15 miles NE of Decorah. We are close to the mouth of Canoe Creek, the Upper Iowa River and adjacent to state DNR land. The cozy owner-built cabin has an open ceiling with exposed beams and rafters giving a sense of spaciousness. Local stone was used in the exterior walls and the floor-to-ceiling fire back behind the wood-burning stove. The floors are oak and slate. Detailed craftsmanship can be found throughout the cabin.

4.99 out of 5 average rating, 148 reviews

Top guest favorite

The exterior of the cabin is presented, featuring a modern, blue façade complemented by large windows. A gravel path leads to a patio area with outdoor seating and a grill. Green grass surrounds the structure, enhancing its connection to the lush landscape.

Cabin in Spring Grove

Modern Country Cabin

Clear your mind at this modern, fully furnished cabin in heart of the Driftless region of MN, WI, and IA. Built in 2016, this truly unique space has everything you need for a relaxing getaway. There is plenty of space inside the cabin. The cabin contains two private rooms, one with a king size bed and the other with a queen bed. In the summer months there is also opportunity to camp, with 4 acres of luscious green space + some woodlands! Indoor fireplace, outdoor fire pit, and Traeger grill!

4.97 out of 5 average rating, 533 reviews

Top guest favorite

A cozy bedroom is presented with a spacious bed featuring a metal headboard. Natural light filters through two windows, enhancing the rustic log walls. A wooden chair is situated in the corner, adding functionality to the space.

Home in Decorah

Glenwood Getaway

1860's log cabin, remodeled into a modern house. Located 8 miles east of Decorah on 5 acres of woods. Cell service is weak (Verizon, US Cell) or not available (others). WiFi is available. TV with local BluRay/DVD/VHS only - No TV channel service. Come here to get away. The last mile to the house is a gravel road. Main entry is on the 1st (lowest) floor. One bedroom on the 2nd floor. Two bedrooms on the 3rd floor. There is one bathroom on each floor. Stairs to the 3rd floor are steep.

4.98 out of 5 average rating, 179 reviews

Guest favorite

A restored caboose sits on a gravel base, showcasing wooden steps leading up to a porch with a railing. The evening sky displays warm sunset colors, while the surrounding landscape features open fields and sparse trees, emphasizing the tranquil rural setting.

Train in Decorah

CR Station Train Caboose

Enjoy the restoration of our charming and cozy caboose! Complete with all the amenities you'll need and more! Linens and towels, refrigerator, microwave, a double burner hot plate, dishes for cooking, barware for cocktailing, and even the original conductor's chairs to watch the sunset over the horse pasture. We also offer guided trail rides on our horses for up to 3 guests. You can book through Airbnb Experiences here: https://www.airbnb.com/experiences/6860469?viralityEntryPoint=2&s=7

4.85 out of 5 average rating, 508 reviews

Top guest favorite

Barn in Dorchester

The Barn Loft

The Barn Loft, located in NE Iowa, is just a short drive from some of the best trout fishing in this part of the state! It is a full Loft Space (1500 square feet) above this Timber Framed Barn built by Wally and Traci. Here you have access to your own rooms, kitchen, and more. Whether you're a large family, or a couple just trying to get away for a few days, The Barn Loft is perfect for you and your loved ones. There are miles of hiking trails and private streams. Ask about hunting.

4.99 out of 5 average rating, 168 reviews

Guest favorite

Cabin in Waukon

Little Red School House

The Little Red Schoolhouse is located in a remote and serene area of Allamakee County. It is steps away from one of Iowa’s natural trout streams Patterson Creek, the recreational playground of the Upper Iowa River, and over 1,000 acres of wild prairie and woodlands managed by the Iowa Natural Heritage Foundation. The Little Red Schoolhouse is surrounded by natural beauty and can provide a quiet refuge free from all distractions. We are excited for your stay!

4.83 out of 5 average rating, 140 reviews

Top guest favorite

The interior of the silo guesthouse features a circular design with wooden beams overhead. A cozy seating area includes a large sectional sofa and a stylish ottoman. Natural light enters through multiple windows, enhancing the space, while a staircase leads to a loft area.

Farm stay in Caledonia

Silo Loft Guesthouse

Our silo guesthouse provides a beautiful country retreat surrounded by hundreds of acres of woods and farm land. This working dairy farm is the perfect stay for a tranquil get away or the full dairy farm experience. If you’re looking for a CLEAN, peaceful & unique stay, this is the place for you! Recent guests say it’s the “hidden gem” of MN! Just 10-30 minutes from local coffee shops, restaurants, and many outdoor activities, this getaway has something for everyone!

4.99 out of 5 average rating, 129 reviews

Superhost

A hot tub is positioned on a wooden deck, featuring bubbling water and jets. The surrounding landscape displays a scenic view of the Upper Iowa River and hills in the distance beneath a clear blue sky.

Tiny home in Dorchester

River run Tiny house w/ hot tub

This cute and modern 340 sqft tiny house is an unique Airbnb experience . With all custom work inside and out it’s a must see ! Located on the beautiful Upper Iowa river in dorchester Iowa . For a romantic couples getaway , fishing trip or small family retreat, it will make your trip a special one . It features 2 open loft bedrooms ( one on each side ) 1 room with a queen bed and the other with 2 single beds. Downstairs futon can sleep 1 more adult or 2 children .

4.71 out of 5 average rating, 213 reviews

Top guest favorite

A park model home is positioned on a stone terrace, surrounded by lush greenery. Large windows offer expansive views of the surrounding landscape. A wooden deck with seating is visible, extending the living space outdoors, with a tranquil atmosphere conveyed by the scenic backdrop.

Cabin in De Soto

Paradise Point sleeps 2 Hot Tub

1 bedroom 1 bath with loft. Cozy home where you can see Paradise. This memorable place is anything but ordinary. Views for miles of the Mississippi River, bluff tops and you can soar with the Eagles. What a place to relax in the newly added hot tub while you enjoy the view in what is call "God's Country". This is promised to be a one of a kind view. The Deck with comfortable outdoor seating Located in the heart of WIsconsin's Driftless Region.

4.96 out of 5 average rating, 162 reviews

Guest favorite

Cabin in Dorchester

Paddle Cove @UpperIowaResort

Paddle Cove offers a modern cabin vibe. It is the perfect place to unplug, slow down, and enjoy the outdoors. Located at Upper Iowa Resort, Paddle Cove, has a stunning view of the Upper Iowa River valley and access to resort amenities. 15 min drive to Waukon 30 min drive to Decorah 30 min drive to Lansing Experience Paddle Cove with us and learn more below! This cabin is pet friendly - $50 per stay for up to two pets.

4.8 out of 5 average rating, 5 reviews

Guest favorite

The exterior of a two-story house is presented, featuring a sloped roof and warm wooden accents. A spacious balcony showcases ample seating and is illuminated by recessed lighting, creating a welcoming entryway. The surrounding trees hint at a serene natural setting.

Home in Decorah

Hill Top House

Located .5 miles from the Upper Iowa River, Hilltop house has the most perfect view. The house sleeps 8, but we welcome and encourage smaller groups as well. This location has 2 bathrooms, a relaxing loft and the most dreamy porch. *WARNING* When booking in the winter be aware of our driveway shown in the picture. We highly recommend 4 wheel drive. We also have a pack n play and high chair available upon request.

4.91 out of 5 average rating, 312 reviews

Top guest favorite

A wooden porch swing is featured, adorned with blue and yellow decorative pillows. The swing is positioned on a spacious deck, with a yellow door and a window visible in the background, allowing for ample natural light.

Farm stay in Spring Grove

Black Hammer Hus | Modern Driftless Farmhouse

Escape to Black Hammer Hus, a bright and peaceful farmhouse surrounded by rolling Driftless farmland. Enjoy sunrise coffee, sunset views, stargazing, and quiet country living just minutes from small-town food, trails, and attractions. With natural light, cozy gathering spaces, a well-stocked kitchen, and room for families and friends, this home is the perfect retreat to rest, reconnect, and recharge year-round.

4.98 out of 5 average rating, 131 reviews