Holiday rentals with a kayak in Jo Daviess County

4.91 out of 5 average rating, 23 reviews

Townhouse in Galena

Townhome - 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

4.93 out of 5 average rating, 199 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. )

4.95 out of 5 average rating, 43 reviews

Cabin in Galena

Beautiful Winter Retreat with Hot Tub and Firepit

Experience the ultimate family vacation, friends gathering, or romantic escape in our beautiful cabin! With 4 elegant bedrooms, each boasting an ensuite, and 4 patios (3 accessible from bedrooms), plus a spacious 3-season room, privacy and comfort are paramount. The cabin has been tastefully renovated to ensure an unforgettable stay. Nestled in the picturesque, resort-like Galena Territory, enjoy many amenities (pools, tennis courts, gym, game room, etc.) while only a 12 min drive to downtown.

4.99 out of 5 average rating, 73 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.

5 out of 5 average rating, 27 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.

4.92 out of 5 average rating, 49 reviews

Townhouse in Galena

Charming 3B3B|Walk to Lake|Fireplace|Arcade|Games

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.

Place to stay in East Dubuque

4.95 out of 5 average rating, 176 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.

4.89 out of 5 average rating, 127 reviews

Cozy Retreat | Hot Tub | Firepit | Dog-friendly

Golfer? Inquire for(e) for details on our Golf Packages. Welcome to The Nest, a beautifully updated and dog-friendly home in The Galena Territory. This spacious home features 3 BR & 3 full bathrooms all on different levels, each with a Smart TV. Enjoy the large kitchen and dining room, multiple patios, & two cozy living rooms with fireplaces. Soak in the hot tub after a long day of adventures in Galena. The Nest has a max occupancy of 8 guests. Access to Owner's Club amenities included.

4.98 out of 5 average rating, 160 reviews

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

4.93 out of 5 average rating, 27 reviews

Home in Apple River

The Lake Place at Apple Canyon Lake

Amazing location! Spend a long weekend away with family and friends at Apple Canyon Lake! Our A-frame has 5 bedrooms, 3 full baths, a 3-season room plus a hangout/gaming area with a pool table, dart board, and Golden Tee video game suite. We are close to the pool, marina, golf course/Pro Shop and The Cove restaurant. We're ready for whatever you're planning including golfing, hiking, biking, swimming, boating, basketball, tennis, pickleball or just relaxing or watching the game.

4.89 out of 5 average rating, 384 reviews

Home in East Dubuque

A MUST SEE! 2BR Lakefront Home w/ Boats & More!

Welcome to our cozy lakefront home located in East Dubuque, Il which is only minutes away from Galena, IL and Dubuque, IA. This two bedroom home with sleeps 4-5. We provide canoe's, and lifejackets. This home also has a large garage, a private deck overlooking the lake, and large yard. Other amenities include central air, comfy mattresses, all kitchen appliances, washer/dryer, Smart TVs with sound bar, and cable Internet. Don't miss out book now.

4.94 out of 5 average rating, 67 reviews

Fox Wood Path l HOT TUB l A&D Rise Getaways

Welcome to A&D Rise Getaways @ Fox Wood Path, your cozy escape in The Galena Territory. This charming 2-bedroom, 2-bathroom retreat is perfect for a romantic getaway, a family trip, or a relaxing weekend with friends. Unwind in the private hot tub, gather around the outdoor propane fire tables, or curl up by the wood-burning fireplace for a cozy evening in. Sip your morning coffee on the screened-in porch, surrounded by nature.

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Kick off your hiking boots at these rustic lodgings

Popular amenities for kayak rentals in Jo Daviess County

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House rentals with a kayak

DanielleRating, 5 starstoday

New place to stay

The Tree House

This was exactly the quiet getaway we needed. The cabin is private, quiet, and the surroundings are so peaceful. We brought our two dogs and Katherine made sure to have a dog bed, dog dishes, & lots of treats. Plenty to do in the Galena Territory and downtown Galena.

4.98 out of 5 average rating, 80 reviews

Inviting Home on Golf Course | Hot Tub & Fire Pit

ScottRating, 5 stars1 month ago

This was a fantastic place to stay. The house was clean, comfy and inviting. Bryan's instructions were clear and precise. We would totally stay here again.

4.85 out of 5 average rating, 202 reviews

Home in East Dubuque

2 Bedroom Lakefront Cabin W/ Deck, Boats & Dock

JamieRating, 5 stars1 week ago

We had a great stay here and loved that it was pet friendly. I would highly recommend :)

4.94 out of 5 average rating, 51 reviews

Summer @ your Private Hideaway on Basswood - Fire

MarkRating, 5 stars3 weeks ago

Exceeded our expectations. Having 2 toddlers with our group, the kids' playroom along with the nursery was a blessing. We also took advantage of our access to the Owners Club and swam in the pools, played ping pong, etc. We cooked most of our meals, and the kitchen was very well stocked with what we needed. We used the grill, the hot tub, the firepit, the gameroom, and the movie room. Everything worked well and was clean. Many of our group mentioned how comfortable the beds were. A very enjoyable time and we hope to return.

5 out of 5 average rating, 3 reviews

Arbor View: 4BR | Hot Tub | King Beds | Pool Table

AmyRating, 5 stars1 week ago

This was our first Airbnb experience and was by far the best birthday my daughter had. We definitely want to come back to this same place in the future.

4.74 out of 5 average rating, 27 reviews

Amazing 6BR! Whiskey Room, pool table & hot tub-su

ThomasRating, 5 stars3 weeks ago

This was a great spot. The surrounding area is really beautiful, especially when I visited (in the late spring), and lots of the house layout helps you appreciate this, whether it’s inside or out. The home is spacious, the fire pit was lovely at night (and well stocked), and the host was plenty responsive. Would stay again.

5 out of 5 average rating, 4 reviews

Longwood Hideaway in Galena!

MeganRating, 5 stars6 days ago

The house was even more beautiful in person! The kitchen was very well stocked as were the bathroom and laundry room. We had such a good time having a bonfire at night in the firepit and the supplied wood was perfect for burning! The decor was beautiful, with each bedroom having it's own style. Only minor suggestion is to provide a portable fan for each bedroom since only one bedroom has a ceiling fan and we only found one box fan. We hope to come back again!

4.96 out of 5 average rating, 24 reviews

Summer Starts Here: Talisman Getaway w/Hot Tub, Pe

DianeRating, 5 stars2 months ago

This house was amazing. It had everything you could need. Four bathrooms was a plus. Hot tub, pool table, fireplace and pit. it was rural but not far fromots of things to do. We had 4 turkeys in our backyard, someone horseback riding next to our house (right on a trail) and the last day, 2 deer walked across the front yard.

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Cabin rentals with a kayak

4.96 out of 5 average rating, 79 reviews

Cabin in East Dubuque

Gorgeous Custom Floating Cabin-HOT TUB!-Fun theme!

NicoleRating, 5 stars6 days ago

Great location to visit friends in DuBuque. Very cute and no complaints. Hosts were responsive when I asked a question.

4.99 out of 5 average rating, 72 reviews

Cabin in Galena

Secret Room-Fireplace-Hot Tub-Pool/Marina,Patio

ClayRating, 5 stars5 days ago

Beth’s place had everything we could think of for our family vacation. There were so many things to do and all of the rooms were extremely comfortable. Would definitely stay here again.

5 out of 5 average rating, 157 reviews

Cabin in Galena

Hot tub,Fireplace,Pool/Marina Access,Games, Space!

RobynRating, 5 stars1 week ago

Beth was very communicative before and during our stay. The house was nicely decorated, and furnished clean and exactly as we expected. I appreciated that we were able to leave without starting laundry, dishwashers, etc. The kitchen had a lot of useful utensils and supplies. We didn't do much cooking, but we could have easily prepared most anything we wanted. The beds and furniture was very comfortable. There were plenty of games and activities to do at the house; we did not utilize the community rec areas, but that was only due to our own agenda and time limitations. My only recommendation would be that blackout curtains in the bedrooms would have been greatly appreciated. I was up at 5:30am some mornings because of light pouring into the bedroom on the main floor.