Holiday rentals with a kayak in Lake Galena

4.96 out of 5 average rating, 112 reviews

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.

4.91 out of 5 average rating, 22 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.

5 out of 5 average rating, 26 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.

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, 159 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

Place to stay in East Dubuque

4.96 out of 5 average rating, 272 reviews

Custom Floating Suite-HOT TUB!

Enjoy a stay directly on the backwaters of the Mississippi River. This custom cabin is floating right on the water, and you won't find anything like it! Grab your loved one or friend and surround yourself in nature, while soaking in the hot tub on the floating patio, or in the beautiful tub inside. Relax in the king size bed thats in front of one of the two fireplaces. The cabin has everything you need, including a small kitchen. This floating oasis is located at Millennium Marina.

5 out of 5 average rating, 3 reviews

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

Escape to Arbor View, a beautifully updated 4 BR (all King beds!) vacation home nestled in the heart of the Galena Territory. This inviting retreat offers modern comforts, making it the perfect destination for family gatherings, friend getaways, or a relaxing escape accommodating up to 10 guests. Enjoy the hot tub, pool table, and access to resort amenities including pools, hiking trails, & more. Hey Golfers! Inquire for(e) more details about our discounted golf packages!

4.89 out of 5 average rating, 383 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.

Holiday rentals for every style

Get the amount of space that is right for you

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Kick off your hiking boots at these rustic lodgings

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Popular amenities for Lake Galena kayak rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

Mike & KatherineRating, 5 stars1 week ago

New place to stay

The Tree House

Really just a wonderful place. Thoughtfully decorated and designed. Stunning refuge in nature. What a pleasure

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, 201 reviews

Home in East Dubuque

2 Bedroom Lakefront Cabin W/ Deck, Boats & Dock

EricRating, 5 stars3 weeks ago

We enjoyed our stay, beautiful home and pleasant stay near lake. No issues at all and must note, very comfortable bed!

4.99 out of 5 average rating, 72 reviews

Inviting & Bright | Firepit Sauna Hot Tub & Games!

CherylRating, 5 stars3 weeks ago

Johnny was extremely accommodating and was there within 20 minutes when I needed him. Very personable and friendly, made me felt like I knew him all my life. Will definitely book again in the future!

4.78 out of 5 average rating, 27 reviews

Best on Bayward! All King Beds, Pool Table, Hot Tu

EthanRating, 5 stars3 weeks ago

We had a great stay in a beautiful home. Very relaxing environment and both the hot tub and fireplace was extremely convenient for use. Kitchen utensils left something to be desired (sharper knives, etc) but otherwise the place was well equipped. We really enjoyed this location and were happy with how close it was to both downtown Galena and the amenities of the territories. It would be kind to have the parking permits available on entry (rather than requiring that we get them).

4.74 out of 5 average rating, 27 reviews

Amazing 6 BR Home! Whiskey Room! Pool Table! Karao

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 stars2 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!

5 out of 5 average rating, 8 reviews

Cozy up @ Driftless Haus HotTub*Firepit*Fireplace

TanyaRating, 5 stars3 weeks ago

Beautiful tranquil home with lots of amenities. Brian was terrific and so close to downtown Galena! Will definitely book again!

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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 stars2 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 stars1 day 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.

Cabin in Dubuque

4.86 out of 5 average rating, 7 reviews

The Edelweiss Cabin

ChristopherRating, 5 stars1 week ago

The cabin was relaxing and a nice weekend getaway. We highly recommend staying here. We look forward to staying again. Thank you!

5 out of 5 average rating, 8 reviews

Cabin in Dubuque

The Aster Cabin

JenniferRating, 5 stars3 weeks ago

The property is beautiful! Well kept trails to walk, great yard for lawn games, large fire pit to sit around and lots of wildlife, especially birds! Cottage was cozy, beds comfortable and hot tub clean and well kept. Short drive to Dubuque. We would definitely stay here again 😀

Cabin in Bellevue

4.95 out of 5 average rating, 58 reviews

Historic 1800s Cabin Retreat on prairie w/3 ponds

KathrynRating, 5 stars24 months ago

We had the BEST time. The cabin and acreage were breathtaking. Our kids had a blast playing, fishing, catching frogs and more. The cabin was small but perfect for our needs, we loved the porch overlooking the view. The kitchen/bathroom are very small (historic property!) but well equipped. Cabin stayed pretty cool even in the heat of the day, but A/C is there if you need it. We would totally visit again! Hosts were very responsive and friendly!