Vacation rentals with a kayak in Jo Daviess County

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Top-rated kayak rentals in Jo Daviess County

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Guest favorite

Home in Galena

4.93 out of 5 average rating, 194 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. )

Guest favorite

Cabin in Galena

4.97 out of 5 average rating, 31 reviews

Beautiful Cabin with World Class Amenities

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.

Guest favorite

Home in Elizabeth

5 out of 5 average rating, 23 reviews

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.

Guest favorite

Home in Galena

4.89 out of 5 average rating, 115 reviews

Cozy Retreat | Hot Tub | Firepit | Dog-friendly

New for 2024 - Golf Packages -- inquire for(e) more details! 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.

Cabin in Bellevue

4.95 out of 5 average rating, 58 reviews

Historic 1800s Cabin Retreat on prairie w/3 ponds

Historic 1800s Rustic Cabin Escape/Retreat Acreage w/3 Spring-fed, Stocked Ponds & Acres of Restored prairie/wildflowers, Walking paths behind cabin, Paddle boat, Kayak, Basic 3 adult life jackets, Napping hammocks, Several outdoor cooking/eating options, Fire pit, Raised garden beds w/veggies, Fruit trees. Various outdoor seating options to read/relax. Ponds stocked w/bass, bluegill, catfish, trout when restocked, for you & kids to enjoy (typically bite quickly!), Catch & release policy.

Guest favorite

Townhouse in Galena

4.97 out of 5 average rating, 34 reviews

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.

Guest favorite

Treehouse in Galena

4.98 out of 5 average rating, 110 reviews

Retro octagon house in woods- Hot tub, fireplace,

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 favorite

Cabin in East Dubuque

4.96 out of 5 average rating, 213 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.

Guest favorite

Home in Galena

4.95 out of 5 average rating, 43 reviews

Galena Fox Wood Path Getaway

Come & unwind in The Beautiful Galena Territory! Our getaway is the perfect place to relax - featuring a hot tub, outdoor propane fire tables, fireplace, and screened in porch. A short drive to downtown Galena for fine dining & shopping. As a guest, you'll have access to the Owner's Club where you can take a dip in the indoor or outdoor pool, challenge friends to a game pool or shoot some hoops in the basketball court. Pamper yourself with an unforgettable getaway.

Guest favorite

Home in Galena

4.98 out of 5 average rating, 54 reviews

Inviting & Bright | Firepit Sauna Hot Tub & Games!

NEW AMENITY: Hot tub available after November 1! 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, or challenge your friends to Pac-Man or foosball. Perfect for families and couples alike. Oh, and dog-friendly.

Guest favorite

Home in Scales Mound

5 out of 5 average rating, 28 reviews

Mirror Lake, Rare, private lake!

Stunning, private location on 40 plus acres of land. Enjoy your own private beach and 3 acre lake. On the beach you have access to 2 kayaks, 2 paddle boards, and one peddle boat which are included in your rental! Beautiful wooded surroundings with manicured walking paths. On the grounds you will find a separate cottage with many fun activities including, a pool table, shuffle board, dart board, and the list goes on!