Holiday rentals in Shannon

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Top-rated holiday rentals in Shannon

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

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Top guest favourite

Loft in Monroe

4.99 out of 5 average rating, 175 reviews

Loft 3 - On The Historic Monroe Square

Loft 3 is 40 steps (2 flights of stairs) above the Monroe Square. It's a climb, but the view is totally worth it! Newly remodeled in 2021, and reminiscent of the 1859 character of the building, this space is cute, cozy, and truly one of a kind. Literally a couple steps away from your entryway is Sunrise Donut Cafe, featuring customized donuts and a full menu of excellent coffee items. From there, explore the rest of the Square for food, drinks, and shopping in a quaint Main Street atmosphere.

Top guest favourite

Loft in Morrison

4.97 out of 5 average rating, 260 reviews

The Tailor

Beautifully restored 1892 apartment in the heart of Morrison's national historic district offers Victorian elegance with many modern conveniences. Amenities include a full kitchen, washer/dryer, luxurious queen bed, Roku Smart TV, and high speed wi-fi. The 800 sq ft apartment includes original Doug Fir flooring, 10 ft high ceilings, pocket doors, claw-foot tub, custom cabinets and cherry island. Perched above an art gallery, this is the perfect clean and quiet retreat for work or leisure.

Top guest favourite

Place to stay in Brodhead

4.98 out of 5 average rating, 161 reviews

Historic Randall Schoolhouse

You'll love this beautifully redone Historic One-room Schoolhouse. Situated on the edge of the Driftless area 5 miles from the Sugar River Trailhead. An easy 30 minutes to Monroe, Beloit & Janesville and just an hour outside Madison. Relax in comfort with all new appliances including a full kitchen, washer/dryer, dishwasher and fireplace. Fenced yard. Just a mile down the road from a working homestead where you can milk a cow, pet a goat, harvest fresh produce and eggs and so much more.

Top guest favourite

Tiny home in Darlington

4.98 out of 5 average rating, 758 reviews

Arbor Crest Cottage

Thank you for checking out Arbor Crest Cottage! Jeremiah and I would be happy to host you. We are entering our 5th year of hosting and have been enjoying the experience. The farmette is conveniently located 2 miles from town, set off the road, and through the woods. The cottage is located on the edge of our woodland area. We invite you to explore our property and enjoy the animals. The west end of our land over looks town and is a great place to watch the sunset and the goats graze.

Top guest favourite

Tiny home in Savanna

4.96 out of 5 average rating, 113 reviews

"Tiny House" Cabin at Spring Lake Campground

The excitement of camping with all the comforts! Outdoor grilling area with picnic table, queen size bed in the loft, 2 recliners & TV/dvd on main level, AC/heat, sink, microwave & mini fridge. Kitchen service for 2, basic cooking essentials & bedding. Well kept private port-a-john outside cabin and outdoor shower is close by (no bathroom inside cabin) Bring bikes to ride the “Great River Trail”. Camp store & kayak/canoe rentals (through Oct 1st) on site! No pets No smoking please.

Top guest favourite

Cabin in Savanna

4.96 out of 5 average rating, 302 reviews

Cozy, Secluded Cabin -A Peaceful Getaway Location!

Located just a half mile from town, but secluded enough to be a private hilltop house retreat. The deck overlooks downtown with a backdrop of the Mississippi River! Enjoy the outdoors hiking at the Palisades State Park with miles of trails just a short drive away, kayak or fish one of the many rivers or lakes, stroll through downtown for antique and gift shopping, or visit a nearby winery. After a day of adventures, relax in the spa tub or enjoy a glass of wine on the private deck.

Top guest favourite

Chalet in Elizabeth

4.92 out of 5 average rating, 347 reviews

Galena Country Getaway

Brick walkway leads to the cedar deck with Adirondack chairs overlooking the large backyard. Enjoy dinner out on the deck and roast marshmallows over a bonfire at the firepit. The dark sky provides excellent stargazing. Kitchen features full-sized refrigerator, cooking utensils and a variety of spices. Spacious bathroom with a waterfall-style shower. Carpeted loft includes a sleep number queen sized bed and two twin beds. Close to Historic Galena & Apple Canyon State Park

Guest favourite

Cottage in Savanna

4.9 out of 5 average rating, 206 reviews

Cozy Cottage getaway close to River, Casino,antiq

Owners are next door. River and marina short block away within walking distance. Grocery store half a block away within walking distance. Downtown less than a mile. Galena about half hour. Iowa 5 min away and casino in Iowa 20-25 min. Palisades State Park 5 min away. This is a cozy cottage with use of deck and grill, and full amenities to cook in house if you like. Check out C-Savanna for other great, adventurous, and scenic things to do while visiting. Great Getaway

Guest favourite

Cabin in Oregon

4.96 out of 5 average rating, 182 reviews

GOOSE ISLAND CABIN -Secluded Riverside Eco-Retreat

Nestled along the banks of the Rock River under tall oaks, ye ol cabin was built by early settlers in 1907. Legit rustic charm. Secluded yet only 10 mins from the fun town of Oregon. 100 acres of private property, bordering Lowden-Miller State Forest. Includes use of canoes/kayaks, large riverfront yard, grills, hammocks, deck, porch and firewood. $35/night/person/pet after first 2 people. Message Tim about accomodating big groups and events.

Top guest favourite

Guest suite in Freeport

5 out of 5 average rating, 101 reviews

Lower Level Suite in Home-Private Entrance!

Large lower level walk out apartment for up to 7 people, separate entrance in single family home in a quiet upscale neighborhood. The apartment has a lighted sidewalk. Gas in wall heater supplements heating needs in winter. Sleeps up to 7 guest with 1 king bed (heated mattress pad) in master, common area has 2 Twin XL that JOINS TO MAKE A 2nd KING both w/memory foam mattresses and 3 additional Twin XL beds. Free Washer/Dryer in apt.

Guest favourite

Tiny home in Thomson

4.87 out of 5 average rating, 438 reviews

Cozy Cabin on the Mississippi River

This cabin is located on the serene backwaters of the Mississippi. It is the perfect destination for a weekend getaway, or ideal spot to rent for fishing tournament‘s or duck hunting. This cabin is situated next to pool 13, and there is plenty of space for multiple vehicles and boats to park. Only half a mile away from the loading dock and close by to an Illinois State Park, our cabin allows Guests to enjoy nature in a relaxed setting.

Guest favourite

Cabin in Oregon

4.96 out of 5 average rating, 214 reviews

Hidden Gem - Rock River

The Eagle’s Nest: A Cozy Family Escape! Unplug and unwind at The Eagle’s Nest, a renovated cabin on stilts nestled on 5 private wooded acres with stunning views of the Rock River and Kyte Creek—just 5 minutes from Oregon, IL! Hike, fish, kayak, or relax by the firepit under the stars. Perfect for families and outdoor lovers, this peaceful retreat offers adventure and tranquility. Book now and escape the city hustle!

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Other great holiday rentals in Shannon

Top guest favourite

Cottage in Saint Donatus

4.99 out of 5 average rating, 96 reviews

Gorgeous Views, Sweeping Valley, Amazing Sunsets

CarolynRating, 5 stars2 weeks ago

This was the nicest rental I have ever stayed in! The quality of everything was top of the line, and Joe and Kelly spared absolutely NO expense to make this space truly fabulous. From the quality of the appliances and furniture, to the beautiful details in every room, to the handwritten card welcoming us and local chocolate and wine (which were delicious)...there was absolutely not a thing that could have made our stay better (other than staying longer!). We saw rabbits, tons of birds, turkey vultures, hawks, deer, chipmunks, and squirrels, and enjoyed seeing the animals in their natural environment. What a spectacular view! My boyfriend (whose birthday we were celebrating) said it was the nicest house he's ever been in, period. If you're a fan of FL Wright, you will adore this house and all the details that show the love and appreciation for his work. We will most definitely come back, it was worth every penny! Thank you, Joe and Kelly, for being as amazing as your cabin! :)

Guest favourite

Guest house in Rockford

4.73 out of 5 average rating, 11 reviews

1 Cozy and peaceful place

MelissaRating, 5 stars2 days ago

The listing photos don’t do it justice—this studio was more spacious than expected! Great spot for a couple of nights and close to downtown. Just a quick note: I missed this in the listing, but the fridge was unplugged, so if you’re bringing perishables, you might want to have a cooler handy. Overall, it was a clean, comfortable stay and I’d definitely recommend it!

Guest favourite

Loft in Clinton

4.98 out of 5 average rating, 49 reviews

The Java Loft

AmyRating, 5 stars3 days ago

Very spacious for two people. I loved the dressing and make-up table in the bathroom for getting ready. The kitchen was well stocked and the water pressure in the shower was really good. Easy access to what we needed in the area and Deanna was very responsive. We would rent here again.

Top guest favourite

Flat in Sabula

5 out of 5 average rating, 40 reviews

The Pearl, Full Loft Apartment

JulieRating, 5 stars2 weeks ago

This apartment is so nice! It had everything that I needed and I loved the location. I also really enjoyed the little coffee shop below the apartment!

Guest favourite

Boat in Sabula

4.92 out of 5 average rating, 53 reviews

The "Lily Pad" Boatel Houseboat

NIcoleRating, 5 stars1 week ago

The Lily Pad was perfect for a mini college-reunion. We loved sitting on the deck at night and listening to the fish jump, and the hiking and outdoor activities in the surrounding areas were top-notch.

Top guest favourite

Cottage in Oregon

4.94 out of 5 average rating, 64 reviews

Spacious Hillside Home Overlooking Private Woods

IrinaRating, 5 stars1 month ago

This was our second time staying at the Fuller House. We had a magical trip with highlights including getting cozy by the fireplace and listening to records, setting up our tent in the backyard and roasting marshmallows over the fire, reading and napping in the hammock, and spending hours running around the property with our toddler and finding wild flowers, walnut shells, bugs, and swinging on the tree swing. We love this home and Krista and Jeff are very thoughtful and responsive hosts. We had a minor plumbing issue and Jeff came over the fixed it right away. Love this place and will definitely come back!

Top guest favourite

Place to stay in Savanna

5 out of 5 average rating, 7 reviews

Saints and Sinners Hideaway

JosephRating, 5 stars2 weeks ago

Amazing place to stay. The owner has really gone the extra mile to make this spot something truly spectacular. If this looks like something you’d be interested in, rest assured it will be time worth spent!

Guest favourite