Vacation rentals in Apple River

Updated Unit w/Panoramic Views

Escape to this fully updated 2-bedroom, 1-bath garden level apartment with private entrance. Embrace breathtaking panoramic countryside views just 15-20 minutes from downtown Galena, just 15 minutes from wedding venue Oak Hill Farm, and 35 minutes to downtown Dubuque, IA! The galley kitchen is stocked with all you need. Step outside to a stamped concrete patio, hammock, patio furniture, and fire pit, creating an idyllic outdoor space. Book now and experience the serenity of Galena's countryside.

Doe Meadow, a tiny house farm stay

Doe Meadow is my newest custom designed tiny house nestled along the drive to my family farm. Sharing my little slice of heaven with guests is something I have found great joy in. Rural tourism is my passion, & all the farm animals are anxiously awaiting your visit- treats in tow- of course! I wanted to create something unique, a place to make memories, & somewhere you'll want to come back to. Settle in the hammock, listen to the peaceful wind chimes, watch the goats & mini cows graze, unwind.

The Ho Hum East on Apple Canyon Lake

The Ho Hum East is a beautiful lake house with private dock on pristine Apple Canyon Lake! The house is named in honor of my grandparents who ran the Ho Hum Motel in Denison, Iowa :) A place to unwind, de-stress, and have some family fun! The house features all brand new mattresses in 3 bedrooms plus flex space; master bedroom with queen bed, guest bedroom with 1 queen and 1 twin, loft bedroom with 2 queens, pull out couch in living room, and 2 couches in the loft that pull out into twin beds.

Fast Wi-Fi | EV Charger | Fireplace | Hot Tub

Unwind in our comfortable Galena Territory cabin with 3 bedrooms, 3 full baths and sofa sleeper. EV Charging outlet in garage. Strong Eero boosted Wi-Fi; Roku streaming on every floor. Stone wood burning fireplace. Three-season room with scenic sunrise and wooded views. Lower-level walkout to patio with hot tub, fire pit and beautiful stargazing. Minutes away from the Lake Galena Marina, golf, tennis, pool, and fitness center. 15 mins from Chestnut Mountain and historic downtown Galena.

Hot Tub+ Firepit+ "Tiny"house+ Views+ Near Galena

Tucked away in the countryside of Galena, our charming A-frame cabin is the perfect escape for those seeking peace, nature, and a touch of nostalgia. This intimate retreat blends mid-century modern charm with cozy modern comforts, creating an unforgettable getaway. Whether you’re sipping coffee on the deck at sunrise, soaking in the brand-new hot tub under a canopy of stars, or unwinding by the fire with a vinyl record spinning in the background, every moment here is designed for relaxation.

Octagon treehouse Hottub-pool-fireplace-firepit

Unique "tree house" - an octagon tiny house, surrounded by the woods! 2 bedroom, 2 bathroom home you can enjoy the views of nature all around, with floor to ceiling windows. One king bed, one queen bed. Modern comforts with fun flash blacks. Private hot tub and firepit look into serene woods! Sit by the indoor gas fireplace and enjoy our record collection. Soak in a Japanese soaking tub. Enjoy fall colors or watch snow fall! Community indoor poor, seasonal outdoor pool, gym access

Lake Retreat - Hot Tub, Game Room & Two-Tier Deck

Welcome to our modern lake retreat! This 4BR, 3BA home sleeps 12 and is perfect for families and groups. Enjoy a 2-tier deck with loungers, seating, and a propane grill on a live gas line. The lower deck offers a private 7-seat hot tub, lounge area, and firepit with Adirondack chairs. Inside, the basement features a TV, arcade basketball, pool/air hockey, wet bar, and fridge. A 5th room is a kids’ playroom. Bright kitchen skylight and a master suite w/ walk-in closet complete the stay.

Peaceful, Cozy Home w/ Club Amenities in Galena.

Welcome to the Toasted Marshmallow; your cozy escape from reality. Enjoy the peace and quiet of this charming three bedroom, two bath home in The Galena Territories. Kitchen is fully equipped to meet your needs. Enjoy the additional lower level family room w/ 2nd fireplace so your group may spread out. Deck with ample room for dining outside and enjoying your coffee or wine. Home includes six access passes to the GTA Owner's Club and pools. Strong Wi-Fi for remote work, if needed.

Apple Canyon - Galena Getaway

Enjoy this spacious home near the peaceful lake in Apple River IL. Apple Canyon Lake, Galena country/Jo Daviess County. Enjoy the large living areas indoor & out. Features 2 kitchen areas, 2 decks, rec. room & peaceful views. There are several options for local entertainment perfect for families & friends. Just some of the local options - beach, swimming pool, fishing, hunting, boating or just a simple relaxation while taking in all nature has to offer. There's something for all!

Ulysses Suites, Suite 203

Ulysses Suites has just been completed inside the historic J. G. Schmohl building in the heart of downtown Galena, located at 213 to 217 S. Main Street. The location is walking distance to all the best restaurants and shops. We have 7 suites and a beautiful lobby that are modern and luxurious, with lots of historical character and texture as a nod to its previous existence as the Grant Hotel from 1895 to 1933. Suite 203 is almost 1400 square feet and is located on the 2nd floor.

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

Farm Stay | ATV Trails | Large Yard | Near Galena

Escape to this cozy 4-bedroom, 1-bath farmhouse on the Wisconsin–Illinois state line—perfect for relaxing, reconnecting, and enjoying a peaceful countryside getaway. ✨ HIGHLIGHTS • Located on ATV/UTV + near snowmobile trails 🏍️ • Spacious yard + country views • Classic farmhouse charm + natural light • Large dining space for groups • Smart TVs in every bedroom • 12pm check-in & check-out • ~30 minutes to downtown Galena • Ample parking for trailers + gear