Vacation rentals with a kayak in Lake Galena

A tranquil vacation home is set in a lush green landscape. The house features a screened-in porch and multiple balconies, surrounded by a wooden fence. Mature trees provide shade, and the inviting lawn enhances the serene outdoor environment.

4.93 out of 5 average rating, 221 reviews

Galena Getaway

Peaceful, pet-friendly ($50 fee per reservation) vacation home in the Galena Territory. 3 bedrooms, 3 bathrooms, two living rooms, 2 wood fireplaces, screened in porch, upper level porch, deck, firepit, access to owner's club (pool, exercise room and game room), marina and 24 miles of hiking trails. Sleeps up to ten people. (Please ensure your guest count is accurate when you make your reservation. The guest count can be updated if needed. Inaccurate reservations will be charged accordingly. )

ValueLocationHiking

4.96 out of 5 average rating, 147 reviews

A cozy cabin is nestled on a grassy hillside, surrounded by trees. A wooden deck wraps around the cabin, providing outdoor space. Stone steps, lined with potted flowers, lead up to the cabin entrance, enhancing the natural setting.

Cabin in Benton

Our cabin's a win-win

In 1834, it was a chicken coop nestled between the house and barn. Today, it's a cozy cabin just a stone's throw away from the villa and venue. From the private, rural setting to the rustic decor, you'll feel as though you've traveled back to simpler times. It's unique, refreshing and oh-so tranquil. If you're looking for a little hush and a lot less rush, you're going to fall in love with this little home away from home. While you're visiting, get the scoop on how we transformed this coop.

LocationValueCheckout

4.78 out of 5 average rating, 87 reviews

Townhouse in Galena

Getaway - Indoor Pool, Arcade, Hiking, Skiing

Come and relax in our 3 level townhome. There are 2 large living rooms for conversation and entertaining (give the children their own space to enjoy). Lower level living room has private arcade machines, foosball, and a big screen television. Multi-level decks to enjoy your morning coffee in peace. Walking distance to Stone Drift Spa and Eagle Ridge Resort. Short drive to everything: - Eagle Ridge Resort: 1 min - The Galena Territory Owners' Club: 5 mins - Downtown Galena: 15 mins - Chestnut

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A modern living room features a comfortable seating arrangement with a light gray sofa and armchair. A large window allows natural light to fill the space, while a flat-screen TV is mounted above a cozy fireplace. Built-in shelves are neatly arranged with books and decorative items.

4.98 out of 5 average rating, 109 reviews

Inviting & Bright | Firepit Sauna Hot Tub & Games!

Golfer? Inquire for(e) for details on our Golf Packages. Welcome to The Overlook, your perfect home away from home during the upcoming summer season in the Galena Territory. This contemporary three-bedroom, two-and-a-half-bathroom home is the ideal retreat for a relaxing and fun-filled vacation. Enjoy the firepit under starry skies, sweat it out in the sauna, soak in the hot tub, or challenge your friends to Pac-Man or foosball. Perfect for families and couples alike. Dog-friendly with a fee.

LocationValueWalkability

5.0 out of 5 average rating, 47 reviews

Home in Elizabeth

Family Friendly Modern Farmhouse 42 Private Acres

PRIVATE FARM FOR YOU! 42 acres of woods, prairie and pastures surround a renovated 1880s farmhouse nestled in a private valley outside Elizabeth, IL. Breathtaking views, fishing pond, canoe, hiking trails, fire pits, screened in porch and acres of rolling prairie make for the perfect getaway. Pets welcome (add. fee applies). 20 min. from Galena & 2 hrs from Chicago. Family friendly, we provide everything for kids of all ages including pack-n-play, height chair, games, activities and more.

Outdoor spacesLocationGetting around

4.9 out of 5 average rating, 67 reviews

Townhouse in Galena

Charming 3B3B | Access to indoor and outdoor pools

Discover comfort and charm in our inviting 3-bedroom, 3-bathroom home nestled in the heart of the Galena Territory. Immerse yourself in the tranquility of nature while enjoying modern amenities. This spacious retreat features a fully-equipped kitchen and cozy living areas with a fireplace and arcade. Explore nearby hiking trails, golf courses, and historic downtown Galena. Whether you're seeking relaxation or adventure, our Galena getaway is the perfect home base for an unforgettable escape.

Outdoor spacesValueCleanliness

Place to stay in East Dubuque

A hot tub is positioned on a private deck, surrounded by scenic views of the Mississippi River backwaters. The calm water reflects greenery from the banks, while a seating area with dark outdoor furniture is visible nearby.

4.95 out of 5 average rating, 226 reviews

Retro themed floating river cabin with a HOT TUB!

Our unique floating cabin features retro vibes and beautiful views of the Mississippi River backwaters. This cabin sits DIRECTLY in the water and has amazing views of the water You can even fish right off your deck! Enjoy the nature around you while sitting on your private floating deck, or snuggle up inside in front of the electric fireplace and Smart TV. This cabin features 2 bedrooms with queen beds, and a pull out couch in the living room. Our rental is located at Millennium Marina.

Outdoor spacesLocationRiver

4.99 out of 5 average rating, 239 reviews

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

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

ValueLocationHiking

5.0 out of 5 average rating, 8 reviews

Hideaway Cove, woodland serenity + modern comfort

Escape to Hideaway Cove, a stunning end-unit townhouse in The Galena Territory, where woodland serenity meets modern comfort. This 3-bedroom, 3-bath gem is perfect for family adventures, golf getaways, or romantic escapes. Dive into summer fun or cozy up year-round—your Galena story starts here. Relax with your favorite people at this peaceful home. Includes 6 passes to the Owners Club with access to the indoor/outdoor pools, basketball court, fitness center, game room, and more!

LocationAmenitiesCleanliness

5.0 out of 5 average rating, 60 reviews

The living area features a cozy sofa and a reclining chair, complemented by a wooden coffee table. A kitchen with light wooden cabinets and a stainless steel refrigerator is visible in the background. Natural light enters through a window, enhancing the inviting atmosphere.

Home in East Dubuque

C&R Lake Lacoma

Keep it simple at this peaceful and centrally-located home on Lake Lacoma in East Dubuque. Sleeps up to 4 . Has 2 bedrooms, 1 with king size bed and the other has a queen size bed. Each bedroom has a TV. 1 bathroom with tub, shower, washer and dryer. Enjoy the outdoor scenery on the 800 sq. ft. wraparound deck. Spend time fishing, playing horseshoes or relaxing by the fire pit. Galena, IL approx. 10 miles and Dubuque is approx. 1 mile. No indoor smoking. No pets.

Outdoor spacesLocationAccuracy

4.91 out of 5 average rating, 147 reviews

A modern soaking tub is centered against a natural wood accent wall. A wooden bath tray rests across the tub, holding a glass of red wine and a book. Soft blue water adds a serene touch to the inviting space.

Townhouse in Galena

2 Bedroom Townhouse w/Soaking Tub + Rain Shower

Welcome to Dear Galena, a modern Zen retreat on a corner-unit townhouse golf villa with a wooded view. It's the perfect getaway for couples, friends, family or just you! Situated within The Galena Territory and near Eagle Ridge South Golf Course, this townhouse has two bedrooms - each with a king size bed and two bathroom. A pull out sofa bed for additional guest and high-speed Wi-Fi for streaming and all of your work from home needs.

ValueOutdoor spacesFamily