Vacation Rentals By Owner In Galena, IL

Modern hangout meets historical charm at this 3-bedroom, 1.5-bath home! Located blocks from downtown Galena, this vacation rental is ideal for those looking to see all the top sights while having a welcoming space to come home to. Bring your pooch along for a stroll down Main Street, have a picnic in Galena Grant Park, or spend the day on a wine tour. Chestnut Mountain offers year-round fun thanks to the ski slopes and Alpine Slide. For some chill time, hang out in the one-of-a-kind disco cave!br-- THE PROPERTY --br0.3 Mi to Main St | Modern & Stylish Interior | Pet Friendly w/ FeebrHere at ‘The FiveTen Federal,’ feel free to explore downtown at your leisure whether that be a relaxing day in the park, wine tour, or a visit to one of the historical sites for a refresher on local culture!brBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen BedbrKITCHEN: Fully equipped, kitchen island w/ seating, stainless steel appliances, dishware & flatware, knife set, Crock-Pot, tea kettle, toaster, Indoor Foreman Grill, popcorn maker, blender, drip and Keurig coffee makersINDOOR FEATURES: 2 flat-screen TVs w/ Netflix provided, disco cave, electric fireplace, laptop-friendly workspace, 6-person dining table, vanity, board games, books, Record player, Blue Tooth speakersGENERAL: Free WiFi (strong signal), washer/dryer, towels/linens, hair dryer, trash bags, ample dish rags, cleaning solution and air conditioningFAQ: Pet fee (paid pre-trip, 2 pet max), stairs required for bedroom accessPARKING: Driveway (2 vehicles), street parkingbr-- THE LOCATION --brHISTORICAL SITES: Market House State Historic (0.5 miles), Galena Jo-Daviess County Historical Society (0.6 miles), Dowling House (0.6 miles), Galena History Museum (0.6 miles), Belvedere Mansion (1.1 miles), Ulysses S Grant Home (1.4 miles)OUTDOOR RECREATION: Galena Grant Park (1.3 miles), Depot Park (1.4 miles), Horseshoe Mound Preserve (3.9 miles), Casper Bluff Land & Water Reserve (6.2 miles), Lake Galena (6.4 miles), Thunder Bay Falls (6.4 miles), Chestnut Mountain Resort (9.8 miles)LOCAL ATTRACTIONS: P.T. Murphy Magic Theater (0.5 miles), Linmar Gardens (0.8 miles), Chicago Athenaeum (1.0 mile), Galena Center for the Arts (1.2 miles), West Street Sculpture Park (1.4 miles), Galena Cellars Vineyard (6.8 miles)AIRPORT: Dubuque Regional Airport (22.6 miles)br-- REST EASY WITH US --brEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.br-- POLICIES --br- No smoking - Pet friendly with $85 fee (+ fees & taxes, dogs only, 2 pet max)- No events, parties or large gatherings - Additional fees and taxes may apply- Photo ID may be required upon check-in- NOTE: The bedrooms on this property require stairs and may be difficult for guests with limited mobility

'The FiveTen Federal' - Downtown Galena Gem!

Galena, Illinois, United States

Bed

Bath

Sleeps

$633.48

At The Galena Glen, days unfold with cozy, modern-heritage charm. Sip coffee on sunlit decks, unwind in the hot tub beneath quiet woods and starry skies, and gather by the wood-burning fireplace after exploring historic Galena. EMF-neutralizing technology adds calm, and access to the Owner's Club gym, pools, and amenities invites effortless play. With 3 bedrooms and space for 8, it’s a retreat where families and friends and drawn to linger + reconnect.brbrTucked near a quiet cul-de-sac in the rolling hills of the Galena Territory, The Galena Glen feels like the kind of place families talk about long after the suitcases are unpacked. It’s warm, refined, and crafted with playful elegance—where every corner invites you to slow down and reconnect with the people who matter most.brbrKey Features:br Firepit with Smores Sticksbr Indoor Wood-Burning Fireplacebr Private Hot Tub br Thoughtfully Stocked Kitchenbr Vintage bookshelf board games br Washer & Dryerbr 3 Decks + Screened Deckbr Aires® EMF Technologybr Smart TVs in Every Roombr Ample Parkingbr Basketball Hoopbr Owner’s Club Accessbr Four Award-Winning Golf Coursesbr 32 miles of hiking trailsbrbrBedrooms + Layout:br Beds 1 + 2: br• King bedsbr• Roku Smart TVsbr• Large Closetsbr• Full-Length Mirrorsbr Bed 3: br• Full-size floor level bunkbr• Roku Smart TVbr• Large Closetbr• Full-Length Mirrorbr• Kiddie size cozy reading nookbr• Kiddie games & karaoke machinebr♥ Family Friendly Extras: br• Highchair br• Kid’s dishesbr• Full bathtubbr• Pack ‘n play with sheetsbr• Lectro Fan white noise machinebrbrLocation Highlights:br• Downtown Galena (14 min)br• Chestnut Mountain (24 min)br• Stonedrift Spa (5 min)br• Country Store (4 min)br• Long Hollow Zip Lines (9 min)br• Lake Galena Marina + Bait Shop (7 min)br• Shenandoah Riding Center (4 min)br• Elizabeth’s Grand Antique Co. (12 min)br• Eagle Ridge Resort (6 min)br• Galena Cellars (10 min)br• Fergedaboudit Vineyard & Winery (18 min)br• Rocky Water Vineyard & Winery (20 min)br• Massbach Ridge Winery (27 min)br• Terrapin Orchards (15 min)br• Dry Creek Beekeeping (10 min)br• Hoof It Goat Treks (10 min)brbrThe Inside...brThe moment you arrive, the home feels like an exhale. Inside, sunlight pours through generous windows, tracing across exposed beams and a soaring custom bookshelf that rises nearly twenty feet. The living room blends nostalgia with modern ease: a wood-burning fireplace, vintage-style bookshelf games waiting for spontaneous tournaments, and a large smart TV for cozy movie nights.brThe main floor flows effortlessly—living, dining, and kitchen connected in an open layout ideal for families and groups. The fully equipped kitchen is a thoughtful blend of style and practicality: ceramic-coated cookware, an air fryer for quick snacks between adventures, and both a classic coffee pot and French press for slow, indulgent morning brews. Step through the dining room onto the screened-in deck, where morning sunlight filters through trees and evenings feel like a quiet, private retreat in the woods.brDownstairs, the lower level becomes a restful sanctuary. Two king bedrooms offer calming spaces with Roku TVs, full-length mirrors, and direct access to nature’s backdrop. The third bedroom is a child’s dream —floor-level full bunk beds, a reading nook that sparks imagination, toys for creative play, and thoughtful touches like a white noise machine and pack ’n play to make traveling with little ones easier. Two bathrooms—one with a tub for easy nighttime routines, the other with a walk-in shower—add comfort and convenience for groups of up to eight.brbrThe Outside…. brOutside, the experience deepens. The front porch beckons with brightly colored hanging swing chairs, the kind kids race to claim and adults secretly love even more. The upper deck off the living room offers multiple seating areas and a propane grill for effortless alfresco meals. From there, wander down to the lower deck, where one of the king bedrooms opens directly to the hot tub—perfect for stargazing soaks after exploring historic downtown Galena just fifteen minutes away. Beyond the deck, the backyard slopes gently enough for winter sledding and features a basketball hoop for friendly competitions when the driveway isn’t full (though it can welcome up to eight parked cars).brEvenings settle sweetly around the fire pit. Wrapped in blankets, you can bask in the surroundings while kids retell their favorite moments of the day. The property’s EMF-neutralizing technology quietly supports a sense of calm, helping guests truly unwind.brYour stay also includes access to the Owner’s Club amenities—indoor pool, gym, and more—expanding the possibilities for relaxation and play.brEvery detail at The Galena Glen was chosen to make life feel effortless and meaningful, whether you’re hosting a family movie night by the crackling fire, sharing stories in the hot tub, cooking comfort meals with loved ones, or simply savoring the quiet in a swing chair as the woods breathe around you.brIt’s the kind of place that feels instantly familiar, beautifully designed, and forever memorable—a retreat where modern comfort meets timeless moments…. And it’s waiting for you!brbrOther things to note:brNo pets allowed… as much as we love them, we do not allow them in our home in order to remain sensitive to other guests that may have allergies.brbrNon-smoking… No smoking in the home – we are family-friendly & desire to keep the property clear of any traces of cigarettes / other smoking devices.brbrNo parties of any kind… We ask this out of respect for our home and out of love for our wonderful neighbors.brbrDark Skies Policy... The Galena Territory is officially recognized as a Dark Sky Development of Distinction…. That means the stars are amazing here!!

Luxe Escape in Galena Territory / Sauna / Hot Tub / Fire Pit / Games!

Galena, Illinois, United States

Bed

Bath

Sleeps

$370.49

Discover serenity in the Galena Territory with this charming chalet surrounded by nature. The house features 3 bedrooms, each with a designated bathroom, along with a powder room. Walking into the open concept house with its large windows and natural light, you will find the main living area, dining area, and fully stocked kitchen, tastefully decorated in a minimalist design to reflect the simplicity and tranquility of the outdoors. The powder room and the master king bedroom suite are also located on the main level.brbrThe lower level consists of a walk-out family room with a pool table and a wet bar, one king bedroom, one queen bedroom, and 2 full bathrooms. In addition, each of the 3 bedrooms have a single sofa sleeper available for use that can comfortably accommodate a child or a teen (disclosure: the cushions on the sleeper sofas are on the firm side and no sheets provided).brbrThe house also features a screened porch, a main level deck, a lower level patio and a beautiful stone fire pit outside. You can have your morning coffee on the screened porch and a glass of wine by the fire pit while enjoying your time with family and friends.brbrAs part of your stay, you will also have access to the Owner’s Club facilities with both indoor and outdoor pools, gym, game room and business center.brbrBook now to experience all that Galena and its territory has to offer, and then retreat and relax to this amazing home away from home.brbrThings to note: Charcoal for the grill and wood for the firepit are the guests' responsibility. This house comes with 6 keycards to access the Owner's Club ($50 charge per card if lost). Additional daily passes can be purchased at the Owner's Club for $5 each. There is no garbage collection in the Territory. Guests will need to take all trash from the house to the refuse facility. There is a $75 fee if the garbage is not removed at check-out.br

Chalet

Rustic with a modern twist 3 bdr/3.5 bath chalet

Galena, Illinois, United States

Bed

Bath

Sleeps

$266.35

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!!!!brbrSituated 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(s) and high-speed Wi-Fi for streaming entertainment and all your work from home needs. brbrThe townhouse is a 2 bedroom, 2 bathroom loft-style home only minutes away from the historic downtown Galena with everything you need for your stay. As you walk in the front door, you will be greeted by two large skylight windows in the entryway. To the right in the entryway we have a closet for you to hang your coat or store your bags as well as a bench for you to sit on while you remove your shoes and get comfortable and ready. brbrOn this floor, you will find Bedroom 1. Bedroom 1 has a king size bed, high ceiling and great views of the wooded backyard. We have furnished the room with a large floor mirror, yoga mats, ceiling fans, extra throw blankets, and an alarm clock. As you walk past the closet, you will walk into your on-suite bathroom. This bathroom features a soaking tub for your self-care and enjoyment. With the bath tray, you can enjoy a book or your tablet while you soak all your worries away. brbrCome downstairs and you will find the kitchen, with everything you need for your morning coffee/tea and everything you need to prepare a quick meal. You will also find the laundry room if you ever need to clean something before heading home. brbrThe dining room table will seat four and we have two additional stools at the kitchen island for you to enjoy a meal or open up your laptop. brbrThe living room features a pull out sofa that can sleep 2, a few board games for those electronic-free nights, a smart tv (with Netflix) and a fireplace (please review instruction) for you to get cozy. We also have what we are calling 'The Reading Nook' - a small pink love seat next to the wood fireplace for you to enjoy a book or a laugh. Books are scattered throughout the house for your reading enjoyment. brbrPast the living room is the exterior doors that leads to the back patio with outdoor seating for four and a propane grill with an incredible peaceful wooded view. brbrNext to the living room is Bedroom 2 and Bathroom 2. Bedroom 2 also have a king size bed, so no need to fight over who gets the bigger bed. This bedroom also have a large floor mirror, yoga mats, ceiling fan, extra throw blankets and an alarm clock. Bathroom 2 is connected to Bedroom 2 and the kitchen. It features a rain shower, if you are not a bath person, and a shower hand wand. brbrAs our guest, you will also have access to the pools (indoor and outdoor), fitness center, basketball court and game room at the Galena Territory Owner's Club, a short three miles from the townhouse (2000 Territory Drive Galena, IL). You'll access this with the Owner's Club proximity cards that will be in the kitchen drawer when you arrive. Electric Vehicle charging stations are available on-site in the Owner's Club.

2 Bedroom Townhouse w/Soaking Tub + Rain Shower

Galena, Illinois, United States

Bed

Bath

Sleeps

$345.71

Welcome to Fox Wood Retreat @ A&D Rise Getaways!brbrUnwind in the private hot tub, gather around the outdoor fire tables, or cozy up by the wood-burning fireplace. Start your mornings on the screened-in porch surrounded by nature, then head into downtown Galena just minutes away for shopping, dining, and local charm.brbr ️ SLEEPING ARRANGEMENTSbr• Loft (Primary): King bed with projector and projector screenbr• Main Level Bedroom 1: Queen bed with Smart TVbr• Main Level Bedroom 2: Queen bed with Smart TVbrbr KITCHEN & DININGbrFully equipped kitchen with everything you need:br• Stove, oven, microwave & refrigeratorbr• Dual coffee maker (drip + Keurig, coffee provided ☕)br• Dining table seating for 6brbr LIVING & OUTDOOR SPACESbr• Wood-burning fireplace (bring your own firewood)br• Smart TVbr• Private hot tubbr• Screened-in porch + outdoor seatingbr• Fire tablesbr• Propane grill brbr LOCATIONbrCentrally located in The Galena Territory:br~7 minutes to Owner’s Clubbr~11 minutes to historic downtown Galenabr~25 minutes to Chestnut MountainbrVisit the Galena Tourism website for more detailsbrbr OWNER`S CLUB ACCESSbrEnjoy access to:br• Indoor & outdoor poolsbr• Fitness centerbr• Game room & arcadebr• Pickleball, tennis & basketball courtsbr• Trails, marina, boating & golfbr• Horseback riding + spa servicesbrCheck out the Galena Territory website for more detailsbrbrIncludes 4 proximity cards for accessbrAdditional cards available for $5/day at the Owner’s Club located at 2000 Territory DrivebrbrPlease note: Amenity availability is managed by the Territory and is not guaranteed. No refunds are provided for closures.brbr✨BEFORE YOU ARRIVEbrGuests receive a detailed digital guest guide filled with local recommendations, tips, and everything you need to plan your Galena getaway.brbr OPTIONAL ADD-ONSbrAvailable after booking in your Guest Portal:br• Grocery pickup servicebr• Birthday & anniversary packagesbr• Family game night packagebrbr GRILL INFO brGrill available for guest use. We do our best to provide at least 1/3 tank of propane, but additional refills are the guest’s responsibility. Please clean the grill after use.brbr STARTER SUPPLIESbr• 1 roll of toilet paper per bathroombr• 1 roll of paper towelsbr(We recommend bringing extras for longer stays.)brbr GOOD TO KNOWbr• Check-in: 12 PMbr• Check-out: 12 PMbr• Washer & dryer availablebr• Ample on-site parkingbr• High Speed Wifibr• No petsbrbr Save this listing by clicking the ♥ to easily find it later!brbrWe can`t wait to host you @ A&D Rise Getaway`s Fox Wood Retreatath!br** Exterior lights must be turned off by 1am. The Galena Territory charges $150 for lights left on overnight **brbr*An additional cleaning fee will be charged for any property left in an unusually dirty condition following a guest’s stay. *

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

Galena, Illinois, United States

Bed

Bath

Sleeps

$383.96

Cozying up to a fire or a soak in the hot tub next to a firepit is exactly what you need. Our fully renovated historical schoolhouse where the only lessons are relaxation, tranquility, and soul-deep rejuvenation is a perfect place for your getaway! From the moment you arrive, take in breathtaking views of three states including the Mississippi River bluffs of Iowa, Illinois farmland and the rolling hills of Wisconsin all from a single window, your first assignment in serenity. brThis unique getaway features two luxurious king bedrooms, two full bathrooms with oversized walkin showers, and a cozy living room with a queen sofa bed and electric fireplace offering comfort for every guest. Modern amenities ensure a seamless stay, including a fully stocked kitchen, WiFi, central air, laundry room, and indulgent extras like a hot tub and firepit for peaceful evenings under the stars.brPerfectly situated just minutes from downtown Galena, 12 minutes from Dubuque, IA, 2 minutes from Galena Golf Course and a beautiful 15 mile drive to Chestnut Mountain, and many other locations, Our schoolhouse provides the ideal balance of seclusion and convenience. Here, school is always out—so come, unwind, and experience the best of Galena with us.

Hot Tub 2-bedroom 2 full bath all comforts of home in Galena countryside

Galena, Illinois, United States

Bed

Bath

Sleeps

$460.69

Amazing views! Golf course views and distant panoramas abound from this stunning contemporary located on the South Course Hole #16 with amazing green and fairway location and a distant treed backdrop. Open and airy great room offers living room with stone surround fireplace and big windows offering lots of light and a great place to admire nature. Just steps away is an open dining area with convenient access to large rear deck and screened porch, as well as large kitchen with breakfast bar. Spacious main level master suite with vaulted ceiling and a master bathroom with double vanity, whirlpool tub with large picture window, and separate shower. Lower level has radiant in-floor heat, and offers two large guest bedrooms each with their own private bathrooms and a central family room with built-in desk area. Additionally, the family room has access to laundry area, and walks out to a aggregate rear patio and large backyard.

3 Bedroom, 3 1/2 bath house in The Galena Territory.

Galena, Illinois, United States

Bed

Bath

Sleeps

$427.39

Beautiful 3+ bedroom home located in the Galena Territory resort CORE between the North and South golf courses. This home has enter on the upper level, the main level requires access by stairs. This is the perfect home for golfers, a large family get-a-way, or a group of friends! Master bedroom, located on upper level, includes a king bed master bath with a large steam shower and a double whirlpool tub; while two bedrooms on the main level include one queen and two twin beds. Additional twin beds in the family room on the lower level makes for plenty of sleeping areas. Located close to amenities of the Galena Territory. Sleeps 8, Max. Occupancy 8.

3+ Bedroom, 3 bath house in The Galena Territory.

Galena, Illinois, United States

Bed

Bath

Sleeps

$283.19

Adorable cabin in the woods! This cabin has 2 bedrooms (both Queen) and 2 full baths. There are twin beds in the loft, so it is perfect getaway for 2 couples with children or a small family. It also has internet with a smart tv and YouTube channels, a fireplace and a deck with a gas grill. This unit is a short 1.8 miles to the Owners' Club where you will have access to the Indoor, Outdoor, and Kiddie Pools, Game Room, Fitness Center, Indoor/ Outdoor Basketball Courts, etc... Sleeps 6. Max. Occupancy 6.

2 Bedroom + Loft, 2 bath house in The Galena Territory.

Galena, Illinois, United States

Bed

Bath

Sleeps

$199.49

Located in the heart of the resort core you will find this lovely Long Bay Point Condo. It's located just a short distance to the North Course and the paved walking trails. Enjoy the open and airy living room with wood-burning fireplace, a spacious master bedroom and adjoining bathroom. Bathroom has a nice shower as well as a large jetted tub. Enjoy nature and wildlife without the bugs from the screened in porch. You have access to the Long Bay pool which you can enjoy in the heat of summer. This home is located only 3 minutes from the Owners' Club in the heart of the Galena Territory and comes with access to the Owners' Club where you can enjoy indoor/outdoor pools, fitness center, indoor/outdoor basketball courts, tennis courts, and Game Room. The Galena Territories offer many activities to choose from, including horseback riding, hiking, wine tours, fishing, shopping, skiing, and more. Sleeps 2, maximum occupancy 4.

Condo

1 Bedroom, 1 bath townhouse in The Galena Territory.

Galena, Illinois, United States

Bed

Bath

Sleeps

$237.5

2 bedroom, 2 bath townhome in the heart of the Galena Territory or Eagle Ridge Resort. Newly Remodeled with the lodge theme. Main floor has Living Room, Dining Room, and Kitchen (wide open concept), also 1 Queen bedroom and Bath. Upper level has Queen Bedroom and Bath. Deck, TV/DVD, Gas Fireplace in Main Floor Living Room, and WIFI. Access to the resort amenities. There is golf, indoor/outdoor pool, game room, tennis courts, exercise room, horseback riding, marina for boat rentals and fishing, walking trails, hiking trails, and much much more! Only a few miles to Galena for antique shopping, restaurants, winery tours, wine tasting, trolley tours, Grant's Home, historic tours, and whole lot more!

Beautiful Rustic Townhome - Lodge Theme

Galena, Illinois, United States

Bed

Bath

Sleeps

$239.28

ACTION NEEDED: Please send your Booking with -one- name (first & last) of the person who will be responsible for checking into your condo at the front desk as it appears on your/their ID. The front desk is required to view the ID at check-in and the name given by you must match the ID. ADDITIONALLY, please be aware that I need to know the person's name ON THE BOOKING REQUEST at the Time guest submits Booking, or Booking Request ( NOT on an inquiry ). PLEASE NOTE that; If no name is stated, the name on the VRBO Account that sends the Booking Request will be entered on the reservation -and- (name CANNOT be changed on the guest VRBO Account after the booking is accepted, in an attempt to avoid this requirement). PLEASE NOTE that there may be a fee involved for a name change once your Booking is accepted. Thank you!brbrIMPORTANT NOTICEbrTHIS WEBSITE'S AI HAS DEFAULTED SOME ENTRIES TO INCORRECT INFORMATION AND DOES NOT ALLOW ME TO MAKE CORRECTIONS. PLEASE CAREFULLY REVIEW ALL PROVIDED DATA AND DESCRIPTIONS BELOW.brbrTHIS CONDO IS LOCATED WITHIN A RESORT AND IN A MULTI-STORY BUILDING (AS SHOWN IN PHOTOS). THE FRONT DESK ASSIGNS THE CONDO AT CHECK-IN, SIMILAR TO A HOTEL, MEANING THE CONDO MAY BE ON ANY FLOOR. LISTINGS FOR COTTAGE, CASITA, OR SIMILAR ACCOMMODATIONS ARE NOT IN MULTI-STORY BUILDINGS.brbrTHIS RESORT IS FULLY HANDICAP COMPLIANT.brbrIf a pool is listed as an amenity, pool hours are typically 8 a.m. to 10 p.m. Outdoor pools may be seasonal in colder climates, and all pools/hot tubs require occasional maintenance.brbrStudio: Queen murphy bed in living area. Condo has partial kitchen that includes a two-burner stovetop, microwave, and small refrigerator, limited counter space. Jetted tub in bathroom. Maximum occupancy 2.brbr***Please review ALL details in each field***brbrThe Resort maintains a high standard through its maintenance, upgrade, and refurbishment program. As a result the unit characteristics may change from time to time and vary. brbrAt check-in, the resort Front Desk requires a $250 security deposit HOLD on a credit or debit card for potential damages. This HOLD will be released upon departure.brbrABSOLUTELY NO PETS ALLOWED! If you have a service animal, you must let us know in writing prior to booking.brbrUnit Amenitiesbrbr- Internet access (fee applicable) br- Air conditioningbr- Cable TVbr- DVD playerbr- Stereo with CD playerbr- Telephonebr- Fireplace br- Murphy bed br- Washer and dryer in 1- and 2-bdrm unitsbr- Iron and ironing board br- Hairdryerbr- Jetted TubbrbrbrResort Amenitiesbr- Indoor pool br- Indoor hot tubbr- Fitness centerbr- Arcade games br- Laundry facilitybr- Barbecue grills br- Movie rentalsbr- Shared computer with Internetbr- Elevatorbr- Basketball courtbrbrbrLocal Activitiesbr- Belvedere Mansion br- Ulysses S. Grant Home br- Dowling House br- Horseback riding at Shenandoah Riding Center - Galena Cellars Winery br- Chestnut Mountain Ski Area br- Vinegar Hill Lead Mine br- Golf at the spectacular General Course at Eagle Ridge Resortbr- Boone's Placebr- Civil War Daysbr- Country Fairbr- Great balloon racebr- Taste of Galenabr- Night of Luminariabr- Woodbine Bend Golfbr- WoodlandsbrbrbrbrbrbrAs you enter downtown Galena, you find a mining boomtown perfectly untouched by age since its mid-nineteenth century heyday. Old homes and buildings have been meticulously preserved, and much of Galena today is listed in the National Register of Historic Places. Tourism is now the city's main attraction, with specialty shops, boutiques, galleries and restaurants appealing to the more than a million visitors annually. And nearby, you'll find ample outdoor activities at Apple River Canyon State Park, four challenging world-class golf courses, equestrian trails and even some downhill ski runs.brbrbrbrWorldMark Galena is situated near Eagle Ridge Resort's General, the most challenging of the four world-class Galena territory golf courses. Each unit includes a fireplace, cable TV, dining area and a deck. One- and two-bedroom units include fully equipped kitchens. The resort features a glassed-in indoor pool, hot tub and game room.brbrbrPopular AttractionsbrApple River Fort State Historic SitebrJourney into the past at this reconstructed fort. Learn about the conflict between early settlers and local natives that escalated into the Black Hawk War. Open: 9 a.m.-5 p.m., Wed.-Sun. (Apr.-Oct.); 9 a.m.-4 p.m., Wed.-Sun. (Nov.-Mar.). 8.5 mi.brbrbrGalena/Jo Daviess County History MuseumbrLocated in the 1858 Daniel A. Barrows mansion, this museum features a variety of exhibits, including Civil War memorabilia, mining, steam boating, clothing, dolls and toys, as well as an original 1830s mineshaft. Open: 9 a.m. to 4:30 p.m. daily. 8 mi.brbrbrGalena Trolley ToursbrTake a trolley ride through Galena, one of the most historically preserved, 19th century towns in the United States. Galena Trolley Tours offers 1-hr nonstop and 2-hr, 2-stop tours daily. 8 mi.brbrbrAnnual FestivalsbrMarch: St. Paddy's Day ParadebrbrbrOctober: Halloween ParadebrbrbrDecember: Country Christmas

All the comforts of home!

Galena, Illinois, United States

Bed

Bath

Sleeps

$490.16

Escape the noise and step into your own secluded sanctuary. Tucked away on 1.8 acres of lush woodland, this beautifully designed modern cottage offers the perfect blend of privacy, comfort, and elevated style. Surrounded by nature and set back from the road, this home is ideal for those seeking a peaceful getaway without sacrificing modern conveniences.brbrFrom the moment you arrive, you’ll notice the charm—classic cottage architecture paired with clean, modern finishes. Inside, natural light pours through large windows, bringing the outdoors in and creating a warm, inviting atmosphere throughout the space. Thoughtfully designed interiors balance cozy textures with a fresh, updated feel, making it just as perfect for relaxing weekends as it is for longer stays.brbrStep outside and enjoy your own private retreat. Sip your morning coffee on the porch, unwind in the evening with the sounds of nature, or gather with friends and family in the serene outdoor setting. With plenty of space to breathe and no nearby distractions, this property offers a rare sense of calm and seclusion.brbrWhether you’re looking for a romantic escape, a quiet solo reset, or a peaceful place to reconnect with loved ones, this modern woodland cottage delivers a stay that feels both intimate and refreshing.brbrHighlights:br• Secluded 1.8-acre wooded propertybr• Private setting, set back from the roadbr• Modern cottage design with farmhouse touchesbr• Bright, airy interior with large windowsbr• Peaceful outdoor spaces for relaxing and entertainingbr• Perfect for couples, small groups, or quiet getawaysbrbrlarge Home with 4 ensuites and additional 1/2 bath just perfect large groups. brbrFeaturing hardwood floors W/open floor plan & massive staircase leading to a private third level en-suite with cathedral ceilings and an adjacent sunny loft space overlooking the Living-room and a wood burning Fireplace. The lower level has 2 more very large & private ensuites. brbrThis 3-story beauty is filled with comfort cozy and relaxing vibes. Located in the famous Eagle Ridge Gulf Resort with indoor/outdoor pool, spa, gym, basketball court, restaurant & arcade facilities located in the owner's club just 5 minutes from home. Smart and private setting off the road with limestone outdoor firepit. Home is just 12 minutes from the famous Galena town with magnificent ghost and boat tours, not to mention the buzzing restaurant/bar district. Beautiful stargazing skies! This is your perfect home in the perfect location for an any season getaway. There is so much to do all year around! Enjoy the summer Boating in the gorgeous Marina, the waterfall, Wine Vineyard, shopping, golfing, gliding, horseback riding and in the winter all you can ski! Let's not forget Hunting season. brbrGalena is considered one of the Country's coolest small towns. Gorgeous walking paths and look out points right at the end of the road!! You Will not regret your stay. Contact Margie Call or Text 773.699.1374

Cottage

4 private Ensuite Bedrooms -Dog friendly-Eagle Ridge Escape

Galena, Illinois, United States

Bed

Bath

Sleeps

$315.82

ACTION NEEDED: Please send your Booking with -one- name (first & last) of the person who will be responsible for checking into your condo at the front desk as it appears on your/their ID. The front desk is required to view the ID at check-in and the name given by you must match the ID. ADDITIONALLY, please be aware that I need to know the person's name ON THE BOOKING REQUEST at the Time guest submits Booking, or Booking Request ( NOT on an inquiry ). PLEASE NOTE that; If no name is stated, the name on the VRBO Account that sends the Booking Request will be entered on the reservation -and- (name CANNOT be changed on the guest VRBO Account after the booking is accepted, in an attempt to avoid this requirement). PLEASE NOTE that there may be a fee involved for a name change once your Booking is accepted. Thank you!brbrIMPORTANT NOTICEbrTHIS WEBSITE'S AI HAS DEFAULTED SOME ENTRIES TO INCORRECT INFORMATION AND DOES NOT ALLOW ME TO MAKE CORRECTIONS. PLEASE CAREFULLY REVIEW ALL PROVIDED DATA AND DESCRIPTIONS BELOW.brbrTHIS CONDO IS LOCATED WITHIN A RESORT AND IN A MULTI-STORY BUILDING (AS SHOWN IN PHOTOS). THE FRONT DESK ASSIGNS THE CONDO AT CHECK-IN, SIMILAR TO A HOTEL, MEANING THE CONDO MAY BE ON ANY FLOOR. LISTINGS FOR COTTAGE, CASITA, OR SIMILAR ACCOMMODATIONS ARE NOT IN MULTI-STORY BUILDINGS.brbrTHIS RESORT IS FULLY HANDICAP COMPLIANT.brbrIf a pool is listed as an amenity, pool hours are typically 8 a.m. to 10 p.m. Outdoor pools may be seasonal in colder climates, and all pools/hot tubs require occasional maintenance.brbrTwo Bedroom Queen: King in master, queen in second bedroom, queen murphy bed in living area. Jetted tub in master bathroom. Maximum occupancy 6.brbr***Please review ALL details in each field***brbrThe Resort maintains a high standard through its maintenance, upgrade, and refurbishment program. As a result the unit characteristics may change from time to time and vary. brbrAt check-in, the resort Front Desk requires a $250 security deposit HOLD on a credit or debit card for potential damages. This HOLD will be released upon departure.brbrABSOLUTELY NO PETS ALLOWED! If you have a service animal, you must let us know in writing prior to booking.brbrUnit Amenitiesbrbr- Internet access (fee applicable) br- Air conditioningbr- Cable TVbr- DVD playerbr- Stereo with CD playerbr- Telephonebr- Fireplace br- Murphy bed br- Washer and dryer in 1- and 2-bdrm unitsbr- Iron and ironing board br- Hairdryerbr- Jetted TubbrbrbrResort Amenitiesbr- Indoor pool br- Indoor hot tubbr- Fitness centerbr- Arcade games br- Laundry facilitybr- Barbecue grills br- Movie rentalsbr- Shared computer with Internetbr- Elevatorbr- Basketball courtbrbrbrLocal Activitiesbr- Belvedere Mansion br- Ulysses S. Grant Home br- Dowling House br- Horseback riding at Shenandoah Riding Center - Galena Cellars Winery br- Chestnut Mountain Ski Area br- Vinegar Hill Lead Mine br- Golf at the spectacular General Course at Eagle Ridge Resortbr- Boone's Placebr- Civil War Daysbr- Country Fairbr- Great balloon racebr- Taste of Galenabr- Night of Luminariabr- Woodbine Bend Golfbr- WoodlandsbrbrbrbrbrbrAs you enter downtown Galena, you find a mining boomtown perfectly untouched by age since its mid-nineteenth century heyday. Old homes and buildings have been meticulously preserved, and much of Galena today is listed in the National Register of Historic Places. Tourism is now the city's main attraction, with specialty shops, boutiques, galleries and restaurants appealing to the more than a million visitors annually. And nearby, you'll find ample outdoor activities at Apple River Canyon State Park, four challenging world-class golf courses, equestrian trails and even some downhill ski runs.brbrbrbrWorldMark Galena is situated near Eagle Ridge Resort's General, the most challenging of the four world-class Galena territory golf courses. Each unit includes a fireplace, cable TV, dining area and a deck. One- and two-bedroom units include fully equipped kitchens. The resort features a glassed-in indoor pool, hot tub and game room.brbrbrPopular AttractionsbrApple River Fort State Historic SitebrJourney into the past at this reconstructed fort. Learn about the conflict between early settlers and local natives that escalated into the Black Hawk War. Open: 9 a.m.-5 p.m., Wed.-Sun. (Apr.-Oct.); 9 a.m.-4 p.m., Wed.-Sun. (Nov.-Mar.). 8.5 mi.brbrbrGalena/Jo Daviess County History MuseumbrLocated in the 1858 Daniel A. Barrows mansion, this museum features a variety of exhibits, including Civil War memorabilia, mining, steam boating, clothing, dolls and toys, as well as an original 1830s mineshaft. Open: 9 a.m. to 4:30 p.m. daily. 8 mi.brbrbrGalena Trolley ToursbrTake a trolley ride through Galena, one of the most historically preserved, 19th century towns in the United States. Galena Trolley Tours offers 1-hr nonstop and 2-hr, 2-stop tours daily. 8 mi.brbrbrAnnual FestivalsbrMarch: St. Paddy's Day ParadebrbrbrOctober: Halloween ParadebrbrbrDecember: Country Christmas

Breathtaking in all directions!

Galena, Illinois, United States

Bed

Bath

Sleeps

$256.49

ACTION NEEDED: Please send your Booking with -one- name (first & last) of the person who will be responsible for checking into your condo at the front desk as it appears on your/their ID. The front desk is required to view the ID at check-in and the name given by you must match the ID. ADDITIONALLY, please be aware that I need to know the person's name ON THE BOOKING REQUEST at the Time guest submits Booking, or Booking Request ( NOT on an inquiry ). PLEASE NOTE that; If no name is stated, the name on the VRBO Account that sends the Booking Request will be entered on the reservation -and- (name CANNOT be changed on the guest VRBO Account after the booking is accepted, in an attempt to avoid this requirement). PLEASE NOTE that there may be a fee involved for a name change once your Booking is accepted. Thank you!brbrIMPORTANT NOTICEbrTHIS WEBSITE'S AI HAS DEFAULTED SOME ENTRIES TO INCORRECT INFORMATION AND DOES NOT ALLOW ME TO MAKE CORRECTIONS. PLEASE CAREFULLY REVIEW ALL PROVIDED DATA AND DESCRIPTIONS BELOW.brbrTHIS CONDO IS LOCATED WITHIN A RESORT AND IN A MULTI-STORY BUILDING (AS SHOWN IN PHOTOS). THE FRONT DESK ASSIGNS THE CONDO AT CHECK-IN, SIMILAR TO A HOTEL, MEANING THE CONDO MAY BE ON ANY FLOOR. LISTINGS FOR COTTAGE, CASITA, OR SIMILAR ACCOMMODATIONS ARE NOT IN MULTI-STORY BUILDINGS.brbrTHIS RESORT IS FULLY HANDICAP COMPLIANT.brbrIf a pool is listed as an amenity, pool hours are typically 8 a.m. to 10 p.m. Outdoor pools may be seasonal in colder climates, and all pools/hot tubs require occasional maintenance.brbrOne Bedroom: King in master, queen murphy bed in living area. Jetted Tub in bathroom. Maximum occupancy 4.brbr***Please review ALL details in each field***brbrThe Resort maintains a high standard through its maintenance, upgrade, and refurbishment program. As a result the unit characteristics may change from time to time and vary. brbrAt check-in, the resort Front Desk requires a $250 security deposit HOLD on a credit or debit card for potential damages. This HOLD will be released upon departure.brbrABSOLUTELY NO PETS ALLOWED! If you have a service animal, you must let us know in writing prior to booking.brbrUnit Amenitiesbrbr- Internet access (fee applicable) br- Air conditioningbr- Cable TVbr- DVD playerbr- Stereo with CD playerbr- Telephonebr- Fireplace br- Murphy bed br- Washer and dryer in 1- and 2-bdrm unitsbr- Iron and ironing board br- Hairdryerbr- Jetted TubbrbrbrResort Amenitiesbr- Indoor pool br- Indoor hot tubbr- Fitness centerbr- Arcade games br- Laundry facilitybr- Barbecue grills br- Movie rentalsbr- Shared computer with Internetbr- Elevatorbr- Basketball courtbrbrbrLocal Activitiesbr- Belvedere Mansion br- Ulysses S. Grant Home br- Dowling House br- Horseback riding at Shenandoah Riding Center - Galena Cellars Winery br- Chestnut Mountain Ski Area br- Vinegar Hill Lead Mine br- Golf at the spectacular General Course at Eagle Ridge Resortbr- Boone's Placebr- Civil War Daysbr- Country Fairbr- Great balloon racebr- Taste of Galenabr- Night of Luminariabr- Woodbine Bend Golfbr- WoodlandsbrbrbrbrbrbrAs you enter downtown Galena, you find a mining boomtown perfectly untouched by age since its mid-nineteenth century heyday. Old homes and buildings have been meticulously preserved, and much of Galena today is listed in the National Register of Historic Places. Tourism is now the city's main attraction, with specialty shops, boutiques, galleries and restaurants appealing to the more than a million visitors annually. And nearby, you'll find ample outdoor activities at Apple River Canyon State Park, four challenging world-class golf courses, equestrian trails and even some downhill ski runs.brbrbrbrWorldMark Galena is situated near Eagle Ridge Resort's General, the most challenging of the four world-class Galena territory golf courses. Each unit includes a fireplace, cable TV, dining area and a deck. One- and two-bedroom units include fully equipped kitchens. The resort features a glassed-in indoor pool, hot tub and game room.brbrbrPopular AttractionsbrApple River Fort State Historic SitebrJourney into the past at this reconstructed fort. Learn about the conflict between early settlers and local natives that escalated into the Black Hawk War. Open: 9 a.m.-5 p.m., Wed.-Sun. (Apr.-Oct.); 9 a.m.-4 p.m., Wed.-Sun. (Nov.-Mar.). 8.5 mi.brbrbrGalena/Jo Daviess County History MuseumbrLocated in the 1858 Daniel A. Barrows mansion, this museum features a variety of exhibits, including Civil War memorabilia, mining, steam boating, clothing, dolls and toys, as well as an original 1830s mineshaft. Open: 9 a.m. to 4:30 p.m. daily. 8 mi.brbrbrGalena Trolley ToursbrTake a trolley ride through Galena, one of the most historically preserved, 19th century towns in the United States. Galena Trolley Tours offers 1-hr nonstop and 2-hr, 2-stop tours daily. 8 mi.brbrbrAnnual FestivalsbrMarch: St. Paddy's Day ParadebrbrbrOctober: Halloween ParadebrbrbrDecember: Country Christmas

Breathtaking in all directions!

Galena, Illinois, United States

Bed

Bath

Sleeps

$239.28

ACTION NEEDED: Please send your Booking with -one- name (first & last) of the person who will be responsible for checking into your condo at the front desk as it appears on your/their ID. The front desk is required to view the ID at check-in and the name given by you must match the ID. ADDITIONALLY, please be aware that I need to know the person's name ON THE BOOKING REQUEST at the Time guest submits Booking, or Booking Request ( NOT on an inquiry ). PLEASE NOTE that; If no name is stated, the name on the VRBO Account that sends the Booking Request will be entered on the reservation -and- (name CANNOT be changed on the guest VRBO Account after the booking is accepted, in an attempt to avoid this requirement). PLEASE NOTE that there may be a fee involved for a name change once your Booking is accepted. Thank you!brbrIMPORTANT NOTICEbrTHIS WEBSITE'S AI HAS DEFAULTED SOME ENTRIES TO INCORRECT INFORMATION AND DOES NOT ALLOW ME TO MAKE CORRECTIONS. PLEASE CAREFULLY REVIEW ALL PROVIDED DATA AND DESCRIPTIONS BELOW.brbrTHIS CONDO IS LOCATED WITHIN A RESORT AND IN A MULTI-STORY BUILDING (AS SHOWN IN PHOTOS). THE FRONT DESK ASSIGNS THE CONDO AT CHECK-IN, SIMILAR TO A HOTEL, MEANING THE CONDO MAY BE ON ANY FLOOR. LISTINGS FOR COTTAGE, CASITA, OR SIMILAR ACCOMMODATIONS ARE NOT IN MULTI-STORY BUILDINGS.brbrTHIS RESORT IS FULLY HANDICAP COMPLIANT.brbrIf a pool is listed as an amenity, pool hours are typically 8 a.m. to 10 p.m. Outdoor pools may be seasonal in colder climates, and all pools/hot tubs require occasional maintenance.brbrStudio: Queen murphy bed in living area. Condo has partial kitchen that includes a two-burner stovetop, microwave, and small refrigerator, limited counter space. Jetted tub in bathroom. Maximum occupancy 2.brbr***Please review ALL details in each field***brbrThe Resort maintains a high standard through its maintenance, upgrade, and refurbishment program. As a result the unit characteristics may change from time to time and vary. brbrAt check-in, the resort Front Desk requires a $250 security deposit HOLD on a credit or debit card for potential damages. This HOLD will be released upon departure.brbrABSOLUTELY NO PETS ALLOWED! If you have a service animal, you must let us know in writing prior to booking.brbrUnit Amenitiesbrbr- Internet access (fee applicable) br- Air conditioningbr- Cable TVbr- DVD playerbr- Stereo with CD playerbr- Telephonebr- Fireplace br- Murphy bed br- Washer and dryer in 1- and 2-bdrm unitsbr- Iron and ironing board br- Hairdryerbr- Jetted TubbrbrbrResort Amenitiesbr- Indoor pool br- Indoor hot tubbr- Fitness centerbr- Arcade games br- Laundry facilitybr- Barbecue grills br- Movie rentalsbr- Shared computer with Internetbr- Elevatorbr- Basketball courtbrbrbrLocal Activitiesbr- Belvedere Mansion br- Ulysses S. Grant Home br- Dowling House br- Horseback riding at Shenandoah Riding Center - Galena Cellars Winery br- Chestnut Mountain Ski Area br- Vinegar Hill Lead Mine br- Golf at the spectacular General Course at Eagle Ridge Resortbr- Boone's Placebr- Civil War Daysbr- Country Fairbr- Great balloon racebr- Taste of Galenabr- Night of Luminariabr- Woodbine Bend Golfbr- WoodlandsbrbrbrbrbrbrAs you enter downtown Galena, you find a mining boomtown perfectly untouched by age since its mid-nineteenth century heyday. Old homes and buildings have been meticulously preserved, and much of Galena today is listed in the National Register of Historic Places. Tourism is now the city's main attraction, with specialty shops, boutiques, galleries and restaurants appealing to the more than a million visitors annually. And nearby, you'll find ample outdoor activities at Apple River Canyon State Park, four challenging world-class golf courses, equestrian trails and even some downhill ski runs.brbrbrbrWorldMark Galena is situated near Eagle Ridge Resort's General, the most challenging of the four world-class Galena territory golf courses. Each unit includes a fireplace, cable TV, dining area and a deck. One- and two-bedroom units include fully equipped kitchens. The resort features a glassed-in indoor pool, hot tub and game room.brbrbrPopular AttractionsbrApple River Fort State Historic SitebrJourney into the past at this reconstructed fort. Learn about the conflict between early settlers and local natives that escalated into the Black Hawk War. Open: 9 a.m.-5 p.m., Wed.-Sun. (Apr.-Oct.); 9 a.m.-4 p.m., Wed.-Sun. (Nov.-Mar.). 8.5 mi.brbrbrGalena/Jo Daviess County History MuseumbrLocated in the 1858 Daniel A. Barrows mansion, this museum features a variety of exhibits, including Civil War memorabilia, mining, steam boating, clothing, dolls and toys, as well as an original 1830s mineshaft. Open: 9 a.m. to 4:30 p.m. daily. 8 mi.brbrbrGalena Trolley ToursbrTake a trolley ride through Galena, one of the most historically preserved, 19th century towns in the United States. Galena Trolley Tours offers 1-hr nonstop and 2-hr, 2-stop tours daily. 8 mi.brbrbrAnnual FestivalsbrMarch: St. Paddy's Day ParadebrbrbrOctober: Halloween ParadebrbrbrDecember: Country Christmas

Breathtaking in all directions!

Galena, Illinois, United States

Bed

Bath

Sleeps

$764.29

New construction! Dog friendly! Up to 2 well-behaved dogs allowed. 100 dollar fee per dog applies. Brand new hot tub outside!! Stunning modern rustic house located in The Galena Territory. Enjoy panoramic views from multiple balconies. Each bedroom has its own bathroom! With 3 king beds, 1 queen bed, 1 queen sofa sleeper in lower living room, and 3 bunk beds--up to 12 guests will have plenty of space to relax. The property features 5.5 bathrooms with showers and hair dryers, Water is softened for a better shower/dishes experience. Relax in 2 cozy living rooms- lower with a sofa bed and a gas fireplace upstairs. Custom fire pit is stocked with wood and ready to enjoy! Whether you're looking for a charming getaway or a wonderful retreat, this gorgeous house is the perfect place to unwind. The horse riding/hiking trails to Shenendoah stables and Belden School go right by the backyard!

New construction! 5-bdrm Hot tub-Firepit-WiFi-Smart Tvs-In Shenendoah valley!!

Galena, Illinois, United States

Bed

Bath

Sleeps

$794.25

Located in the beautiful rolling hills of The Galena Territory. Awesome wooded lot on quiet Street. Prime location in the Resort Core near both the North/South Golf Courses & scenic hiking trails. This custom 3 level home offers 5 bedrooms (2 Master Suites with King beds and whirlpool tubs; main and upper level), 5.5 baths, two-story living area with floor to ceiling stone fireplace, flat screen TV's in each bedroom, and a large lower level family area with a pool table and wet bar! Also includes another king bed in the third upper level bedroom and two bedrooms on the lower level with queen beds. Off street parking available, garage is NOT included.

5 Bedroom, 5 1/2 bath house in The Galena Territory.

Galena, Illinois, United States

Bed

Bath

Sleeps

$363.89