Holiday rentals in Apple River

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Top-rated holiday rentals in Apple River

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

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Guest favourite

A cozy living area is highlighted by a sectional sofa adorned with yellow accent pillows. A wall-mounted television is positioned above a dark furniture unit that features decorative items. Soft carpet covers the flooring, contributing to a welcoming atmosphere.

Flat in Scales Mound

4.95 out of 5 average rating, 66 reviews

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.

Guest favourite

The lake house is situated on a sloping hillside, surrounded by trees. A stone pathway leads down to the water's edge, where a private dock can be seen. The calm lake reflects the blue sky and scattered clouds, creating a serene setting.

Home in Apple River

4.93 out of 5 average rating, 103 reviews

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.

Superhost

A stone fire pit is depicted in the foreground, with flames brightly rising as the sun sets in the background. The calm water reflects the evening light, and several leafless trees are visible, adding a serene ambiance to the scene.

Home in Thompson Township

4.91 out of 5 average rating, 11 reviews

Lakefront cabin in the woods.

This stylish place has Wifi /Wood Fireplaces, Fully Stocked Kitchen, Coffee Maker, Washer/Dryer, Rear deck w/charcoal grill. 204 feet of lakefront property. Safe swimming off the pier & hunting for crawfish along the shoreline. Acres of woods to explore on property as well as 13 mile trail system around the Lake. Outdoor fire pit & With your stay is access to the swimming pool/tennis court, work out room, golf course (fees not included), Marina/Nixon beach. Don't forget to visit the waterfall!

Top guest favourite

A custom log cabin is framed by lush greenery and manicured landscaping. The warm wooden exterior features multiple gabled roofs and large windows. A stone pathway leads through the vibrant garden, creating an inviting approach to the entrance.

Cabin in Galena

4.96 out of 5 average rating, 139 reviews

Private, Galena Log Cabin

This custom log cabin is the perfect getaway for friends & family seeking the solitude of the Galena Territory and fine dining and shops just 10 minutes away on Galena's Main Street. Each of the 3-levels offers an owner's suite with bath. Cozy up to 2 fireplaces, grill on the deck, or make 'smores at the firepit. The cabin has high speed, fiber internet and the lower-level walkout features a 55” flat screen TV. Guests can access swimming pools & pool tables at the Owner's Club 7 minutes away.

Guest favourite

A tri-level house with a muted gray exterior features multiple large windows. A front porch with railings is visible, inviting relaxation. Surrounding greenery and a neatly maintained yard contribute to the peaceful setting. The sloped roof adds character to the home.

Home in Galena

4.9 out of 5 average rating, 123 reviews

Cozy Wooded Tri-Level In Galena Territory

Relax with friends or the whole family at this wooded and peaceful place to stay in the Galena Territory.Cozy Tri-Level with 3 comfortable bedrooms and 3 baths. Tvs in 2 bedrooms as well as large tvs in the living room and downstairs rec room.Fireplace in living room area.Sit outside and enjoy the scenery on the front porch or back screened patio.Only 6 miles to Downtown Galena .Guests are welcome at Lake Galena,the Owners Club,Restaurants,Pools and Trails.Six Free passes are included.

Top guest favourite

The exterior of the cabin is framed by trees, with warm lights glowing from within. A covered entrance leads to the front porch, which features wooden steps and stone accents. Fallen leaves cover the ground, enhancing the rustic appeal against a dramatic sunset sky.

Cabin in Galena

4.97 out of 5 average rating, 199 reviews

Family Fall! Hot Tub•Fire In/Out•Game Room•3 Kings

Relax, unwind, & explore at this Fall Retreat in Galena Territory! Escape to this cozy, spacious cabin for a peaceful winter getaway. Sip morning coffee as snow falls through the trees, then unwind in the hot tub or by the fireplace. Roast marshmallows around the fire or enjoy arcade games, air hockey, darts, and more indoors. Stay active with access to the owner's club—indoor pool, fitness center, and pickleball (8 amenity cards included). Perfect for relaxation and fall/winter adventure!

Superhost

The living area features mid-century modern furniture with vibrant green and orange chairs surrounding a coffee table. A gas fireplace is centered under a unique light fixture, and large windows allow views of the surrounding woods. A dining area is visible in the background.

Treehouse in Galena

4.99 out of 5 average rating, 239 reviews

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

Guest favourite

Home in Thompson Township

4.93 out of 5 average rating, 15 reviews

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.

Guest favourite

Home in Galena

4.94 out of 5 average rating, 280 reviews

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.

Guest favourite

An indoor recreational space is visible, featuring a ping pong table set between two high-top tables with stools. Exposed wood paneling lines the walls, and various amenities, including a television and a grill area, can be seen in the background.

Home in Thompson Township

4.95 out of 5 average rating, 39 reviews

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!

Guest favourite

A historic two-story house constructed with light-colored stone is showcased under a bright blue sky. The entryway features a wooden porch with seating, complemented by a neatly maintained grassy yard and surrounding trees.

Home in Darlington

4.94 out of 5 average rating, 109 reviews

Hamilton Goebel House

This house is a historic home that was built in 1833 on land owned by Jamison Hamilton, the founder of Darlington. It is not known if he actually lived in the house,but could be assumed. During your stay you will find bits of history and pictures that have been gathered along the way.It has all the comforts of home. A beautiful four bedroom home that has been completely renovated to reflect the old and new times. This home was on the list to be torn down by the city.

Guest favourite

Farm stay in Shullsburg

5.0 out of 5 average rating, 6 reviews

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