Vacation Home Rentals By Owner In Galena, IL

30 Day Min Stay Right off Main St with Parking, Pet Friendly.brbrThis is the perfect spot to take some time away from the city and slow down to work from home. We've got top of the line wifi, Smart TVs in every room and the peace and quiet of a small town. Grab your coffee at Galena Roasters on Main St. to start your day. brbrBuilding a home nearby Got a work assignment or project in the region This is your perfect home away from home. All you need is your bags. Pets are welcome, too.brbrYou couldn't ask for a better location. Walk to all shops and restaurants on Main Street. The kitchen is fully stocked with all you'll need to cook a family dinner. brbrFind the living room, kitchen, dining room half bath and a bedroom on the main level. There are two bedrooms upstairs with a full bath. The bath features a soaking tub and hand shower.brOn the lowest level--don't miss the washer and dryer as well as a stand up shower for your convenience. brbrParking can be a challenge in Galena, but we've got you covered with private parking for up to two cars behind the house. brbrAlong with all there is to do on Main Street, Galena is full of other activities. Stroll along the levee to the pedestrian bridge and check out the East side of town featuring Grant Park. Visit the historical sites like the home of President US Grant and the Dowling House. 85% of Galena is an historic district, so the charm of the 1800s is evident everywhere you look. Take a Trolley Tour to learn more about Galena's history or stop by the Galena History Museum down the street. brbrThose looking for outdoor activities also have lots of options. There is kayaking on the Galena River, hiking on the Galena River Trail, skiing at Chestnut Mountain in the winter and the Alpine Slide in the Summer and Fall. brbrLove Anitquing You have to visit Elizabeth's Great Antique Company. What has to be the best antique mall in the region is just 15 miles away in Elizabeth, IL.brbrbr

30+ Day 3BR Home One Blk off Historic Main St. Galena w/Pking and W/D

Galena, Illinois, United States

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$513.78

Welcome to your family's ultimate getaway nestled in the serene beauty of the Galena Territory! Imagine waking up to the gentle rustle of leaves outside your window, the scent of fresh pine in the air, and the delightful chirping of birds welcoming the morning. Spend your days exploring the historic shops of Galena, indulging in unique treasures and delightful treats. Pamper yourself with a luxurious facial or massage at the renowned Snowdrift Spa, rejuvenating body and soul. After an exhilarating day of shopping and pampering, return to your retreat to unwind by the crackling fireplace under the starry night sky, where you can roast marshmallows and share stories with your loved ones. Whether you're savoring gourmet meals prepared in the fully-equipped kitchen or sharing stories on the spacious deck overlooking breathtaking vistas, your stay here is sure to create cherished memories that will last a lifetime. Welcome to your Galena getaway, where every moment is filled with joy and adventure!

3 Bedroom - 3 Bath in the Heart of the Galena Territory Amenity Accessibility

Galena, Illinois, United States

Bed

Bath

8

Sleeps

$276.89

You'll find all of the modern updates to the kitchen and baths in this 2BR 1.5 Bth home but the 1840s charm remains! brbrAlong with the two bedrooms, there is an additional space to sleep on a fold down couch in Den. brbrWe stocked the kitchen with a Thanksgiving meal in mind, so bring your culinary skills!brbrThe porches are the perfect place to watch the world go by with a cup of coffee or a glass of wine. brbrThe location is ideal for making your way to the shops and restaurants on Main Street. Leave your car and walk 8-10 minutes and you are in the heart of the fun! brbrGrant Park is just across the pedestrian bridge from downtown. brbrIf you are looking to enjoy the outdoors, The river trail is just below Grant Park and you can kayak on the Galena River. There are kayak rental locations near the river. In the winter, there's skiing or hiking at Chestnut Mountain. We've got some brochures in our Welcome Book as well. brbrHistory is front and center in Galena-- so whether you check out the homes of President Grant, hop onbrthe Trolley Tour, visit the Galena History Museum or just walk around the Historic District, you'll feel like a step back in time. brbrThere is never a shortage of things to do in Galena, no matter the season. We are happy to welcome you to this beautiful part of the world.brbrNOTE: The house is on a hill and there are a lot of stairs.

10 Min Walk to Main St., Updated 1840s Historic Home, Stocked Kitchen, W/D,

Galena, Illinois, United States

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Bath

Sleeps

$1304.76

This beautiful modern 3000 sq ft Eco-Friendly home is nestled in the woods in a private setting with gorgeous, peaceful views. Located in the highly sought after Galena Territory, this getaway is under 1 mile from the Owner’s Clubhouse. This gives you full access to indoor/outdoor pools, indoor basketball court, fitness center, tennis courts, kid’s room, arcade, pool, ping pong and much more. brbrIn the summer you and your guests can relax on the screened in porch with a Weber gas grill or enjoy a cool summer night in the brand new hot tub (2019). In winter, enjoy several outdoor activities including cross country or downhill skiing at nearby Chestnut Mountain, or simply cozy up to the gas fireplace in the home.brbrThe home is located close to 4 professionally designed championship golf courses, 38 miles of hiking trails, Lake Galena, the Marina, the Owner's Club, General Store and Woodstone Restaurant. brbrAlso located close by the Shenandoah Riding Center, Chestnut Mountain Ski Resort, and downtown Galena with many shopping and dining experiences.brbrThis home has 5 bedrooms, 4.5 bathrooms, and can sleep 10-12 (there is a full size bed with twin trundle and a pull out sleeping pad in one of the bedrooms). The Master Bedroom is located on the main floor complete with a large bathroom including a gorgeous tiled shower and corner bath tub with private picture windows.brbrThe downstairs floor offers 2 bedrooms, laundry room and game room. One bedroom zen themed, offers a king bed with private bathroom, whirlpool tub and rain shower head. The other bedroom offers a queen bed and a private bathroom with shower. The game room has a bar, 60” smart TV and an old school arcade with over 600 games in an original Asteroids cabinet. brbrThe upstairs floor offers 2 bedrooms sharing a large bathroom with skylights and a huge tiled rain shower. The beach themed king bedroom has large windows and beautiful views of the private woods. The 2nd bedroom includes a full bed with a twin size trundle underneath. There is also a chair that folds out to a twin size sleeping pad. There is a 50” Smart TV along with an Xbox 1 and games making this the perfect hangout for kids!brbrThe main floor offers a newly remodeled kitchen with custom cabinets and the kitchen island offers seating for 5. The kitchen opens up into a living/dining room area with vaulted ceilings, and skylights, reclining leather couches, 50” smart TV, a large fireplace and dining area with seating for 8 (more with additional leaf). Just outside the kitchen is the 3 Seasons porch with covered sitting area, a wraparound deck with a Weber grill and hot tub in a very private wooded setting. brbrThis home is fully remodeled and eco-friendly. All bedding and towels are made from 100% organic cotton. All mattresses and pillows are made from earth-friendly materials. All cleaning supplies, laundry detergent and soaps are all natural, plant based and non-toxic. We only stock earth-friendly toilet paper, paper towels and napkins. Light bulbs are LED energy saving. All appliances and entry doors are energy star rated. The furnace, air conditioning unit and hot water heaters are all high efficiency models. The hot tub is the highest efficiency model you can purchase (We know there is nothing earth-friendly about a hot tub but we did our best here). All toilets and shower heads are water saving models. We have a 7 Step Reverse Osmosis Water Filter w/ Added Minerals so you can enjoy top quality water during your stay and avoid plastic water bottles. brbrThis home is ideal for family/friend gatherings and has a terrific set-up with privacy for everyone having 5 bedrooms on 3 separate floors.

Beautiful Private Eco-Friendly 3 Level Home Nestled in Woods Hot Tub Galena

Galena, Illinois, United States

5

Bed

4

Bath

12

Sleeps

$407.25

Pine Hollow is just a quick half mile drive to the town of Galena. When you turn into our driveway you will find your wonderful home nicely tucked into the hillside, located on 120 wooded acres, and a spectacular park like setting. A beautiful stream flows past your rental and pure relaxation will begin. Put your feet up on a large wrap around porch, and take in one of the best natural settings in the Galena area. Secluded and so close to Galena. brWe offer 3 large bedrooms. Two king size beds and one queen bed. Each bedroom has a private bath room. As you travel through the house, downstairs there is a cozy bedroom with pine floors, stain glass window, vaulted beamed ceiling and a locally crafted, queen size four postered bed. The bath room includes a wonderful claw foot tub for soaking and relaxing.brUpstairs you will find two bedrooms, each with private bath/shower combination. Each bedroom is a spacious 400 square foot. There is a wood burning fireplace in each bedroom for those chilly evenings, vaulted wood beamed ceilings, king beds, television, skylights in each bedroom and bath, and an adjoining sitting area with couch and wing back chairs. brThe house offers a fully equipped country kitchen. This is a well equipped kitchen with a built in, counter top range and stove. The kitchen and dining area overlook the gorgeous park like setting. Located on the side of the home we provide a Weber gas grill. brbrThere are two large living rooms with local art work, wood mantels and fireplaces. These are great places for gathering together, playing games or just hanging out having good times. One living space has two large couches, winged backed chair, wood flooring and floor to ceiling windows. The second living area, includes two couches, a smart TV, and two winged back chairs.. There is also an additional bathroom off one of the living areas. So your rental has a total of four bathrooms and three bedrooms.brbrOutside, many guests take advantage of our fire pit for evening gatherings. This is located just a short walk from the front porch. We do provide fire wood for your enjoyment. There is also a weber gas grill for your enjoyment. Did we mention the wonderful stream that runs in front of the guest house. This is the most wonderful therapy for relaxing that you’ll find anywhere. Close to nature, close to Galena, close to perfect.br Explore beyond Galena’s Main Street and delve into the natural wonders that surround this charming, historic setting . At Pine Hollow we offer lush forests, rolling hills, and meandering rivers that paint a picturesque backdrop for outdoor enthusiasts. Keep watch for native wildlife as you explore, with opportunities for birdwatching and wildlife spotting around every corner. Whether relaxing on the front porch, or simply soaking in the natural splendor, you will love Pine Hollow Cottage. br br This beautiful home far surpassed our expectations. the furnishings were lovely and comfortable, and the surroundings were magical. We loved sitting on the porch, watching the sun glance through the tree tops at sunset, and later in the evening, watching the fireflies dance along the forest's edge. Kathy of Chicagobr . .

Close to Galena, close to perfect. Premier get away. Three beautiful suites.

Galena, Illinois, United States

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Bath

Sleeps

$225.01

Welcome Bottle of Wine & Snacks | Gas Fireplace | Resort-Style Amenities | On-Site Golf CoursebrbrThis townhome boasts 2 bedrooms, 2 baths, Smart TVs, a loft with an arcade game, a deck with golf course views, and access to the Galena Territories Owners Club — ideal for a family getaway, couple's retreat, or girl's trip! Enjoy shopping and dining in downtown Galena or take in the spectacular scenery and watch the sunset views, golfers teeing off, and birds and wildlife off of the deck.brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 queen bedbr- Loft: 1 full sleeper sofabr brCOMMUNITY AMENITIES br- 4 golf courses (additional fee paid on-site)br- Fitness center, tennis/pickleball/basketball courts, hiking trailsbr- Indoor & outdoor community pools, kids' splash poolbr- Lake access, boating, kayaking, fishing, bikingbr- Clubhouse, business centerbr- Game room, restaurantbr brOUTDOOR LIVINGbr- Deckbr- Gas grillbr- Outdoor dining areabr brINDOOR LIVINGbr- Smart TVs, recliners, laptop-friendly deskbr- Pac-Man arcade game, Bluetooth speaker, record player, board gamesbr brKITCHENbr- Granite countertops, stove/oven, refrigerator, microwave, dishwasherbr- Keurig duel pod/drip coffee maker, pods & drip coffee packet, creamers & sugar, teabr- Kettle, toaster, welcome snacks (popcorn, hot chocolate, & snack bars)br- Cooking basics, dishware & flatwarebr- Dining table w/ chairs, breakfast bar w/ stoolsbr brGENERALbr- Free WiFi, keyless entrybr- Central heating & A/C, ceiling fansbr- Linens & towels, pool & beach towelsbr- Washer & dryer, laundry detergentbr- Complimentary toiletries, 2 hair dryersbr brACCESSIBILITYbr- 2-story homebr- 2 steps to enterbr- Interior stairs to access main and upper floorsbr brPARKINGbr- Designated parking spaces (2 vehicles)br- Free street parking (first-come, first-served)brbr-- THE LOCATION --brbr- Golf course viewbr- Located in a quiet neighborhoodbr- 7 miles to Downtown Galenabr- 12 miles to Chestnut Mountain Ski Areabr- 22 miles to National Mississippi River Museum & Aquariumbr- 29 miles to Dubuque Regional Airportbrbr-- REST EASY WITH US --brbrEvolve 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.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr brADDITIONAL INFORMATIONbr- This 2-story home requires 2 steps to enter and requires interior stairs to access the main and upper floorsbr- Winter activities offered at Eagle Ridge Nordic Center: Snowshoeing, ice skating, sledding, cross-country skiing, and toboggan. Rentals are offered at the center (except cross county skies)

Galena Retreat: Shopping, Owners Club & Skiing!

Galena, Illinois, United States

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Bath

Sleeps

$230.77

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. Base price is for 2 people. The rate increases after two people. br 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. brThe spacebrThe lower living room has a wood burning fireplace and a 55 inch smart TV with a blue- ray player. The sectional in this room has a queen-sized sleeper sofa inside. The lower level also has a bedroom with a queen-size bed, end table, closet, full bathroom, washer/dryer, direct access to screened in porch, and a TV with a DVD player and an Amazon Firestick.brbrThe upper level has two bedrooms. One with a king sized bed, full bathroom, two closets, and flat screen tv with Roku. The other bedroom has a twin bed and a twin over full bunk bed, one closet, and a TV with roku, WII, and a DVD player. The upper twin can support adults up to 250 lbs. The 3rd bathroom is a full bath in the hallway between the two bedrooms.brbrThe upper level of the house includes another living room with a wood burning fireplace, direct access to the upper level wrap-around deck and an open kitchen.brbrOff the kitchen is a door which exits to the wrap-around deck and down to a full sized deck with a gas grill and seating for ten. The kitchen has a stainless steel refrigerator, stove/oven, microwave, dishwasher, coffee maker, toaster, crock pot, blender, and a counter for two people.brbrPlease note, there is no dining room. We have a cabinet that opens up to a full size dining table if desired. (see pics)brbrFor your convenience we've provided bath towels and beach towels that can be used for your visit to the pool. Please remember to bring back your beach towels.brbrThe bookshelves in the upper living room have some games, puzzles and children's books. The cabinet next to the counter seating has markers, coloring books, play-dough, paint, and small canvases. Please take care to put these items aware before your departure.brbrOur house sits on 1 1/2 acres. It is the middle house off a cul-de-sac. We have a firepit and four adirondack chairs at the front of our side yard.brbrBoth upper and lower covered decks have two rocking chairs, a glider for two and a coffee table. The lower deck also has a hanging chair. The deck has a patio table that seats six, a conversation set for four, and a gas grill. Additional indoor/outdoor folding chairs are available in the garage, if needed.brbrSome wood for the firepit and fireplaces is located in the garage. If you use the fireplaces, OPEN THE FLUE by reaching up and pulling the handle towards you. Please clean up the ashes into the steel bucket. You will probably need to open the window to allow proper ventilation. If the smoke detector goes off, open the window more and it should prevent it from going off again. PLEASE ONLY USE THE FIREPLACES IF YOU KNOW HOW TO PROPERLY USE THEM.brbrThe garage door is manual, and we don't use it for parking. You'll find a foosball table, firewood, and outdoor activity items in the garage.brGuest accessbrGuests have access to the entire house.brbr• INTERNETbrFree high speed fiber wireless internet (WiFi) is included and there are three flat screen TVs with Roku or a Prime Firestick.brbr• GROCERIESbrIf you plan to eat in during your stay, we suggest stopping at one of the grocery stores on your way to Galena. From Chicago we stop at Sullivan's Foods in Stockton.brFrom Dubuque you can stop at the Walmart or the Piggly Wiggly. Otherwise, there is a General Store right in the territory (6 minute drive).brbr• FREE USE OF OWNER'S CLUBbrSix (6) proximity cards are available in the house for guests to use to gain access into the Owner's Club located a short 3 minute drive away. It includes a full fitness center with Nautilus-style equipment, indoor olympic-size swimming pool with accessible ramp, outdoor swimming pool, indoor basketball court (not regulation size), and a game room with pool tables, ping-pong tables, TV, and video games. You can also sign up to use one of several tennis courts or play on the beautiful 63-hole golf course. The Business Center offers three computer stations with internet access. There is also a computer bar located outside the Business Center, plus the entire complex offers free wireless internet connectivity. There is a $50 fee per lost/damaged card.brbr• GALENA TERRITORYbrThe Galena Territory is a semi-private, residential, recreational and resort community located in the northeast corner of Illinois, near the historic city of Galena. The territory boasts 6,800 acres of spectacular vistas, valleys, prairies and woodlands. The Territory has set aside 1,500 acres of protected recreational land. The remainder is filled with low-density residential development and Eagle Ridge Resort & Spa. The Galena Territory was designated a Community Wildlife Habitat™ by the National Wildlife Federation in 2010. There are 1,900 acres of recreational amenities and Lake Galena for boating and fishing.brbrIf you love walking, there are about 24 miles of trails. Some of them go up in the hills and lead to wood deck lookouts with beautiful views. Some go right along the water of Lake Galena.brActivities in the Galena Territory include zipping thru the canopies of The Galena Territory on Long Hollow Canopy Tour’s new zipline course, or a leisurely horseback ride at the Shenandoah Riding Center. Or enjoy 63-holes of championship golf and award-winning restaurants at Eagle Ridge Resort & Spa.brbr• SPAbrNeed the next level of relaxation, you can make an appointment at the Stonedrift Spa located in the Eagle Ridge Resort main building. The 6,000 -square foot facility has certified and experienced spa professionals and 10 treatment rooms where therapies include couple’s massages, facials, and reflexology, energy therapies, teen and men’s services. The men’s and women’s locker rooms also feature state-of-the-art steam rooms. The relaxation room is a great place to unwind while awaiting treatment and the Spa Boutique offers the deluxe organic products for purchase which can be used during your treatment.brbr• LAKE GALENA & MARINAbrOne of The Galena Territory’s most cherished amenities is Lake Galena, a scenic 225-acre man-made lake perfect for anglers and boaters who enjoy observing nature on leisurely cruises. It boasts some of the best fishing in the area, with an abundance of smallmouth and largemouth bass, walleye, bluegill, channel catfish, perch and tiger muskie.brbrThe shoreline is designated Green space – land owned collectively by members of The Galena Territory Association – that cannot be purchased or developed. To protect the shoreline from erosion and keep the lake quiet, peaceful and attractive to wildlife, the lake is restricted to 10-horsepower motors. There is no swimming or water skiing.brbrTwo other special locations on Lake Galena are North Cove and Thunder Bay Falls Park. North Cove includes a picnic area, a small pavilion and barbecue grills. Thunder Bay Falls Park is located opposite Lake Galena’s spillway and dam. Hiking trails are available and fishing is allowed in the stream below the spillway. Two paths traverse the top and the base of the 17-foot-tall by 400-foot-long limestone retaining wall that leads to a popular observation point for a view of Lake Galena’s spillway.brbrThe Galena Territory Association’s Marina is located on Marina Drive and offers boat rentals and sells fuel and fishing licenses. The Marina features a well-stocked Bait & Tackle Shop for fishermen in need of live bait, extra lures, bobbers or perhaps a new rod and reel, and also sells pop, bottled water, chips, snacks and ice cream. The shop is open April through October.brbrOn the shoreline of Lake Galena, next to the Marina, you’ll find a number of recreational opportunities for family members of all ages to enjoy including a playground, picnic area, fish-cleaning shed as well three pickleball courts, a tennis court and volleyball courts. Other seasonal recreation opportunities include a badminton net and two horseshoe pits.brbr• HISTORIC DOWNTOWN GALENAbrThe house is about a 12-minute drive to downtown historic Galena. This New England-style town was recently rated #1 in 2017 by Architectural Digest for “Most Beautiful Main Street in America”. It was also listed as one of “America’s Prettiest Towns” by Forbes Magazine in 2013. You will love the quaint, mile-long downtown area with unique gift shops, ice cream parlors, artist galleries, craft stores, specialty food shops, and restaurants. There are also many vineyards to explore outside of Galena. See the Visit Galena website for more detailed information including a calendar of events.brbr• DININGbrIn Galena, there are many options ranging from pub-style burger places to high end dining. One of our favorites is a French/German restaurant called Fritz and Frittes. It has one of the best steaks we’ve had. The Log Cabin is known for great steaks as well (although at higher prices). One Eleven Main is a great restaurant that creates their dishes with food from local farmers. Durty Gurt's is known for their burgers. If you don’t want to leave the resort, there are four restaurants on the grounds. The Woodlands restaurant in the Eagle Ridge Resort & Spa has a good breakfast buffet and a stunning view from the bluff overlooking Lake Galena. There is an adjacent pub-style restaurant with a bar and large screen TV if you want to catch up on a game. Paisano's serves pizza and Italian sandwiches. There is another restaurant near the entrance of the Galena Territory called Highlands with 2 1/2 story windows facing a beautiful view of the valley.br

Galena Getaway

Galena, Illinois, United States

Bed

Bath

Sleeps

$280.19

Set on twenty-two acres of beautiful rolling hills, Bird Cottage at Sorriso Vineyard offers you a unique opportunity to relax and unwind. Located just ten miles from Galena, Illinois, our charming cottage overlooks a private vineyard with long views from every room. Beautifully decorated in modern farmhouse style, stay in and enjoy the wrap-around front porch and deck with plenty of seating and dining options for entertaining. Or enjoy Galena's restaurants, wineries, shopping and golf. Share a bottle of wine around the firepit and view the awesome sunsets and huge night sky. We offer internet, satellite TV, Google Assistant speaker system and a fantastic pool table for a fun vacation at your home away from home.

Minutes to Galena. Bird Cottage @ Sorriso Vineyard Galena Illinois

Galena, Illinois, United States

Bed

Bath

Sleeps

$284.11

Relax, Recharge, and Explore in Galena TerritorybrbrWelcome to your perfect getaway in the heart of the scenic Galena Territory—where relaxation meets recreation. This beautifully furnished 3-bedroom, 2-bath retreat offers the ideal blend of comfort, privacy, and access to world-class amenities, making it a favorite for families, couples, and adventure seekers alike.brbrStep inside and experience the inviting warmth of vaulted ceilings, a cozy fireplace, and an open-concept layout that connects the living room, dining room, and fully equipped kitchen. The kitchen features quartz countertops, a farm sink, soft-close drawers, a pantry, and both drip and Keurig coffee makers—ideal for casual breakfasts or evening gatherings.brbrThe main-level primary suite offers a peaceful sanctuary with a smart TV and easy access to the main living spaces. Enjoy stunning sunsets and serene forest views from the expansive back porch, or unwind in the vaulted-ceiling 3-season room with a comfortable couch, dining table, and TV.brbrDownstairs, the fully exposed lower level includes two additional bedrooms, a second living area with a smart TV, a sofa sleeper, laundry room, and direct access to a second covered porch. It’s the perfect space for kids, extended family, or friends traveling together.brbrThe fun continues in the detached 2-car garage, converted into a recreation space complete with a second fridge, ping pong table, foosball, and plenty of games.brbrGalena Territory AmenitiesbrAs guests, you’ll have access to the Owners Club, which features year-round enjoyment with indoor and outdoor pools, basketball courts, tennis courts, pickleball, and a fully equipped game room with pool tables, ping pong, cornhole, and more.brbrExplore the nearby Lake Galena with pontoon, kayak, and paddleboard rentals—or bring the kids to the lakeside playground. For equestrian lovers, the Shenandoah Riding Center offers horseback riding trails and experiences for all ages.brbrGolfers will appreciate four nearby championship golf courses, and for winter or summer thrills, Chestnut Mountain Resort is just 25 minutes away with skiing, alpine slides, and river cruises.brbrJust 15 minutes from the home, historic downtown Galena awaits with charming boutiques, local wineries, cozy cafes, and walking tours rich in 19th-century architecture. Or take a day trip to downtown Dubuque—just 30 minutes away—for casino entertainment, museums, and panoramic views of the Mississippi River.brbrWhether you’re looking for peaceful forest views or a launchpad for year-round adventure, this Galena Territory escape is the perfect place to call home during your stay.

Getaway on Wheatstrand. Ski, Fish, Golf, Horseback ride, Hike, Swim and more!

Galena, Illinois, United States

Bed

Bath

Sleeps

$437.86

Golfer Inquire for(e) for details on our Golf Packages.brbrWelcome to Rock Cove Villa -- hosted by The Collection Vacation Homes! Rock Cove is a lux and stylish Townhome on a quiet cul-de-sac overlooking beautiful Lake Galena. brbrWith three bedrooms and three full bathrooms, this spacious townhome is perfect for families and friends and accommodates up to 8. The open living and dining area, complete with a floor-to-ceiling wood-burning fireplace and large patio, offers stunning views and ample space to relax and unwind. The bedrooms are all outfitted with comfortable king-sized beds and Smart televisions, with ensuite bathrooms, and a bonus living room on the lower level - the perfect place to send the kids. The lower level also features a sleeper sofa for an additional spot to rest. brbrAs our guest, you'll have access to the Galena Territory Owners Club, with all its fantastic amenities, including an indoor/outdoor pool, fitness center, tennis and basketball courts, and a game room. Plus, with complimentary access cards for up to six guests, you can enjoy all the resort has to offer. Additional guest passes may be purchased for $5 per person/day.brbrGolf enthusiasts will love this location, the East Golf Course is just a short walk from the condo, and the other three courses are nearby. And when it's time to head into town, downtown Galena is only a 12-minute drive, and Piggly Wiggly and Walmart are just 15 minutes away.brbrPlease note that some amenities may require reservations due to COVID-19 restrictions, but the HOA maintains the facilities well for guests to enjoy. And while we don't have a specific COVID or weather Cancellation Policy, we strongly suggest getting travel insurance to protect your plans.brbrCheck-in details are sent to your email the day before your arrival, including the home's address, access code, and other important information.

Modern Spacious Lake View Villa | 3BR | King Beds | Amenity Access | Foosball!

Galena, Illinois, United States

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Bath

Sleeps

$1333.88

Welcome to Casa de Galena – A Luxury 6BR/6.5BA Retreat in the Heart of NaturebrbrExperience the ultimate getaway at Casa de Galena, a newly built 6-bedroom, 6.5-bath luxury estate designed for unforgettable group vacations, family gatherings, and retreats with friends. Nestled on 4.4 private acres in the scenic Galena Territory and just 14 minutes from historic downtown Galena, this home offers an unmatched blend of modern comfort, upscale amenities, and natural beauty.brbr✨ What You'll Lovebr Private Indoor Movie Theater – Enjoy cinema-quality evenings with surround sound and plush seating.brbr ️ Golf Simulator – Practice your swing or challenge friends to a virtual round with our state-of-the-art indoor golf simulator. We provide basic golf clubs for both adults and kids, but we encourage guests to bring their own clubs for the best fit and performance.brbr 8-Person Hot Tub – Soak under the stars in our spacious outdoor hot tub, surrounded by peaceful woods and fresh country air.brbr Fire Pit with Complimentary Firewood – Gather around for s’mores, stargazing, and late-night conversations. We provide firewood to keep the flames going throughout your stay.brbr Recreation Room – Pool/ping pong table, shuffleboard, queen sleeper sofa, and plenty of space to hang out.brbr Expansive Yard with Outdoor Games – Enjoy cornhole, giant Connect 4, and axe throwing for friendly competition and backyard fun.brbr ️ Comfort Meets PrivacybrEach of the six spacious bedrooms features an ensuite bathroom and Smart TV:brbrMaster Suite – King bed, spa bathroom with soaking tub and walk-in shower, private patio, office desk.brbr4 King Bedrooms – Plush king beds, premium linens, private baths.brbrBunk Room – Full-over-full bunk bed, great for kids or extra guests.brbr ️ Living & Dining SpacesbrOpen-Concept Living Room – Relax with ample seating, a large Smart TV, electric fireplace, and access to the expansive deck.brbrOutdoor Deck – Shared with the junior master suite, features a gas grill and dining for 10 with scenic wooded views.brbrDining Area – Indoor dining table comfortably seats 10, plus bar seating at the kitchen island for casual meals.brbr ️ Gourmet KitchenbrFully equipped with brand-new appliances including refrigerator, oven, dishwasher, and microwave.brbrStocked with everything you need to cook and serve, including a crockpot, Keurig, blender, and toaster.brbr Entertainment & AmenitiesbrSmart TVs – In every bedroom and common area.brbrEV Charger – Charge your electric vehicle right at the house.brbrHigh-Speed Wi-Fi – 1000 Mbps upload/download speeds for seamless streaming and remote work.brbrLaundry Room – Full-size washer and dryer for your convenience.brbrAmple Parking – Space for multiple vehicles.brbr ‍ ‍ ‍ Family- & Dog-FriendlybrChild Amenities – Pack-and-play and highchair provided.brbrPet Policy – Up to 2 well-behaved dogs welcome (pet fee applies). No cats or other pets, please.brbrBook your stay at Casa de Galena and enjoy a luxury home where relaxation, recreation, and connection come naturally.brbrCasa de Galena is perfectly positioned for guests eager to explore the best of the Galena area and beyond. brbrWithin the Galena Territory:br Galena Territory Owner’s Club – 0.9 milesbrbr Lake Galena & Marina – 1.9 milesbrbr Shenandoah Riding Center – 3.5 milebrbr Thunder Bay Falls – 4.2 milesbrbr Hoof It Goat Treks – 6.3 milesbrbr⛳ Championship Golf brCasa de Galena is just minutes from four stunning golf courses nestled in the heart of The Galena Territory:brbrThe General - 4 milesbr The crown jewel of Galena golf. Challenging, scenic, and unforgettable with 250 feet of elevation change.brbrThe North Course - 2.7 milesbr Tree-lined fairways, panoramic views, and a classic test of skill near Lake Galena.brbrThe South Course – 3.8 milesbr A secluded, wooded course with rolling hills and water features on most holes.brbrThe East Course – 2.1 milesbr A relaxed 9-hole course that’s great for families, beginners, or a quick round.brbrHistoric Sites & Downtown Galena:brbr Downtown Galena and restaurants- 8.2 milesbrbr ️ U.S. President Grant Home State Historic Site – 8.7 milesbrbr Washburne House State Historic Site – 8.7 milesbrbr ️ Galena History Museum – 8.3 milesbrbr ️ Belvidere Mansion – 8.8 milesbrbr Grant Park – 8.9 milesbrbr Galena Trolley Tours – 8.4 milesbrbr ️ Dowling House – 8.4 milesbrbr Galena Brewing Company and restaurant– 8.4 milesbrbr ️ Old Market House State Historic Site – 8.2 milesbrbr P.T. Murphy Magic Theatre – 8.3 milesbrbr ️ Galena-Jo Daviess County Historical Society & Museum – 8.3 milesbrbrNature & Outdoor Adventures:br⛷️ Chestnut Mountain Ski Resort – 14 milesbrbr Horseshoe Mound Preserve – 11 milesbrbr Casper Bluff Land & Water Reserve – 13 milesbrbrLocal Wineries, Distilleries & Farms:br Blaum Bros. Distilling Co. – 7.7 milesbrbr Galena Cellars Vineyard – 4 milesbrbr Galena Cellars Winery – 8.3 milesbrbrBeyond Galena:br Apple River Canyon State Park – 19.9 milesbr Berning Acres Dairy Farm

Just a Few Summer Gaps Left / Designer 6BR Getaway/Golf Sim + Theater

Galena, Illinois, United States

Bed

Bath

Sleeps

$1075.82

Picture 14 people settled around a fire pit as the valley goes golden — someone's already claimed a massage chair in the theater, the hot tub is warming up outside. This is Hurry Knot Hideaway: 5,500+ sq ft on three hillside floors with a private theater, full arcade, hot tub, six ensuite bedrooms, and valley views that greet you every morning. Built for groups who want more than a place to sleep. The adventure starts here.brbr Over 5,500 sq ft across 3 stories with sweeping valley viewsbr ️ 6 Bedrooms | 6 Ensuite Bathrooms (no bunk beds!)br ‍ ‍ ‍ Sleeps up to 14 comfortablybr No waiting for hot showers — 6 showers (2 double showers) + commercial water heaterbrbr ️ Chef’s Kitchen:brbr Brand-new 6-burner stovebr ️ Trash compactorbr Three refrigerators with ample fridge/freezer spacebr Everything you need for group meals and entertainingbrbr Entertainment for Every Seasonbrbr Private Theater Room — perfect for rainy days and movie nightsbr Pool & Ping Pong Tablebr ️ Arcade Roombr 2 Jetted Tubs for ultimate relaxationbrbr Bonus Amenitiesbrbr GTA Owner’s Club-5 min drivebrIncludes indoor pool, gym, café, and arcadebr ️ 6 complimentary amenity passes includedbr➕ Additional passes available for $5/day/personbrbrbr ️ Sleeping Arrangements brbrHurry Knot Hideaway features 6 bedrooms, each with ensuite or private bathroom access (one basement bedroom has a semi-private bath). No bunk beds — just comfortable, adult-friendly sleeping spaces for everyone.brbr First Floorbrbr King Bedroombr TVbr Jetted tubbr Walk-in showerbr Double vanitybrbr Second Floorbrbr King Bedroombr TVbr Shower over jetted tubbr Makeup vanitybr Double sinksbrbr Queen Bedroombr TVbr Shower over tubbr ‍ Deskbr Double sinksbrbr Twin Bedroom (2 Twins)br Shower over tubbr Double sinksbrbr ️ Den / Bonus Sleeping Areabr ️ Queen pull-out memory foam sleeper sofabrbr Basement Levelbrbr King Bedroombr Large 65” TVbr Semi-private bathroombr Double showerbrbr Twin Bedroom (2 Twins)br Shower over tubbr Double sinksbrbr Traveling with little ones brWe provide a Pack-n-Play for young infants for your convenience.brbr Pet Friendly (With Guidelines)brbr Quick screening via BetterPet Passport after bookingbr✔️ Dogs must be 2+ years old and fully house-trainedbr No cats or other petsbrbr Local Compliance & Guest PortalbrbrThis property has local compliance requirements (booking platform approved), which include:br✔️ Signed rental agreementbr✔️ ID verificationbr✔️ $1,500 security hold (pending transaction — not a traditional deposit)brbr Optional Damage Waiverbrbr$49 for stays up to 10 nightsbrbr+$2/day for stays longer than 10 nightsbrbrOptional, non-refundable, third-party coveragebrbrTo make this easy, we use Happy Guest — a secure, app-free guest portal where you’ll:br Complete required stepsbr Access house infobr ️ Find our favorite local recommendationsbrbr Current AvailabilitybrApril 10th - 12thbrMay 1st - 3rdbrMay 8th - 10thbrMay 15th - 17thbrMay 22nd - 24th

5000 sq. ft. Estate w/ Hot Tub · Theater · Valley Views

Galena, Illinois, United States

Bed

Bath

Sleeps

$674.5

Forget your worries in this spacious and serene space. Southridge Retreat is in a prime resort location - 3 miles to the Owners Club and 6 miles to Downtown Galena, and near many wedding & event venues such as Ashton Hill, Eagle Ridge, and more.brbrA modern chic retreat specially prepared with a lot of design and amenities, with 4 bedrooms and 4 bathrooms with 3 ensuite rooms, two large living spaces, a three seasons room, pool table, air hockey table, outdoor grill and seating area, private outdoor hot tub, outdoor seating, many parking spaces, Wi-Fi, Smart TV and much more. Every detail has been considered in this beautiful retreat which was designed for luxurious comfort and relaxation.brbrThis expansive home is great for families or small groups of 4-10 people with plenty of space for everyone.

Modern spacious 4 bedroom retreat with 3 en-suites and all year round hot tub

Galena, Illinois, United States

Bed

Bath

Sleeps

$294.11

Golf Packages: New for 2025 - inquire for more details!brbrEagle's Landing at Cedar Bluff! Your ideal vacation home to settle into for your Galena Territory vacation. brbrLocated in one of the best spots in the Galena Territory, this townhouse offers easy access to Eagle Ridge Resort, Stonedrift Spa (the newly expanded spa is receiving rave reviews!), Lake Galena, and walking/running trails. Golf enthusiasts will appreciate being able to walk to the North Course clubhouse in just 5 minutes and the East Course clubhouse in 10 minutes. The adjacent parking lot at Eagle Ridge Resort & Spa features an EV charger for your convenience.brbrStep into this spacious townhome and feel right at home. The well-appointed living room welcomes you with a cozy electric fireplace and great views from the rear patio. The fully-stocked kitchen is ready for your culinary adventures.brbrEagle's Landing features three bedrooms spread across three levels, each with an ensuite or adjacent bathroom. The primary and lower-level bedrooms feature comfortable King beds, while the upper bedroom offers a cozy Queen bed. Smart TVs or Amazon FireStick-enabled TVs are provided in each bedroom for your entertainment.brbrThe lower level also includes an additional family room with a Smart TV, perfect for movie nights or game sessions. In case you have more than six guests, the lower-level living room has a sleeper sofa. YouTubeTV is available as an alternative to traditional cable, accessible on all TVs with smart TV capabilities for your preferred streaming services.brbrAs guests of Eagle's Landing at Cedar Bluff, you'll have access to The Galena Territory Owner's Club amenities. Six access cards are provided for the use of indoor and outdoor swimming pools, basketball, pickleball, and tennis courts, Lake Galena, and the Marina. If needed, additional guest passes can be purchased at the Owner's Club. Please note, while this townhome is located next door to Eagle Ridge Resort, we are not affiliated with the resort.brbrConveniently located within walking distance to Eagle Ridge Resort and Spa, a 12-minute drive from Downtown Galena, and a short 15-minute drive to Piggly Wiggly and Walmart, Eagle's Landing offers both relaxation and convenience.brbrPlease note that we highly recommend purchasing travel insurance for your trip, as we do not have a COVID or Weather Cancellation Policy. All COVID-19 related restrictions have been lifted for the Owner's Club, with a few amenities still requiring reservations.brbrBook your unforgettable Galena retreat at Eagle's Landing at Cedar Bluff today!brbr**** END OF HOST DESCRIPTION - THE VERBIAGE BELOW THIS LINE IS A VRBO GENERATED (AI) DESCRIPTION AND MAY NOT BE ACCURATE ****

3BR Ensuites | Access to Pool, Pickleball, Lake & more | Walk to Golf & Spa

Galena, Illinois, United States

Bed

Bath

8

Sleeps

$305.22

Escape to this spacious 3-bedroom, 3-bath retreat in The Galena Territory—perfect for relaxing, reconnecting, and enjoying everything Galena has to offer.brbr✨ HIGHLIGHTSbr• Golf course views ⛳br• Screened-in porch overlooking the coursebr• Game area (foosball, ping pong + board games)br• Family-friendly layout with loft daybed + trundlebr• Remote-controlled fireplacebr• Access to Owner’s Club (pool, fitness center & more)br• Smart TVs + fast WiFibr• 12pm check-in & check-outbr• ~15 minutes to downtown GalenabrbrWelcome to Vista Verde @ A&D Rise Getaways!brbrStart your mornings on the screened-in porch overlooking the golf course, then unwind in the comfortable living space or gather downstairs for games and fun. With three levels of living space, this home offers plenty of room to spread out while still feeling warm, inviting, and connected.brbr ️ SLEEPING ARRANGEMENTSbr• Primary (Main Level): Queen bed with ensuite bathroombr• Upper Level Bedroom: Queen bedbr• Lower Level Bedroom: King bedbr• Loft Area: Twin daybed with trundle (great for kids or additional guests)br• 2 additional sofa sleepers - main level sofa and basement sofabrbr KITCHEN & DININGbrFully equipped kitchen with everything you need:br• Stove, oven, microwave & refrigeratorbr• Open layout for easy gatheringbr• Dual coffee maker (drip + Keurig, coffee provided ☕)brbr LIVING & OUTDOOR SPACESbr• Remote-controlled fireplacebr• Smart Tv and fast Wifibr• Screened-in porch with golf course viewsbr• Lower-level game area with foosball, ping pong + board gamesbr• Propane grillbr• Outdoor space perfect for relaxing or diningbrbr LOCATIONbrCentrally located in The Galena Territory:br• ~10 minutes to Owner’s Clubbr• ~15 minutes to historic downtown Galenabr• ~25 minutes to Chestnut Mountainbrbr OWNER`S CLUB ACCESSbrEnjoy access to:br• Indoor & outdoor poolsbr• Fitness centerbr• Game roombr• Pickleball, tennis & basketball courtsbr• Trails, marina, boating & golfbr• Horseback riding + spa servicesbrbrIncludes 6 proximity cards for access.brAdditional cards available for $5/day at the Owner’s Club (2000 Territory Drive).brbrPlease note: Amenity availability is managed by the Territory and is not guaranteed. No refunds are provided for closures.brbr✨ BEFORE YOU ARRIVEbrYou’ll receive a detailed digital guest guide 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 INFObrGrill 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• Family-friendly (games + kid-friendly spaces)br• No petsbrbr Save this listing by clicking the ♥ to easily find it later!brbrWe can’t wait to host you at Vista Verde @ A&D Rise Getaways!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. *

Family-Friendly Golf View Getaway

Galena, Illinois, United States

Bed

Bath

Sleeps

$106.33

Escape to this stylish 2-bedroom, 3-bath retreat just one block from Galena’s historic Main Street—perfect for extended stays, work assignments, or enjoying downtown living with comfort and convenience.brbr✨ HIGHLIGHTSbr• Walkable location — 1 block to Main Street ‍♀️br• Two king suites with ensuite bathroomsbr• Fully renovated modern interiorbr• Spacious layout ideal for longer staysbr• Smart TVs + fast WiFibr• 12pm check-in & check-outbr• 30+ day stay requiredbrbrWelcome to Downtown Haven @ A&D Rise Getaways!brbrEnjoy the ease of walkable downtown living with the comfort of a fully updated home. Whether you`re working remotely, settling in for an extended stay, or simply enjoying a slower pace, this space offers privacy, convenience, and a true home-away-from-home feel.brbr ️ SLEEPING ARRANGEMENTSbr• Primary Suite: King bed with ensuite full bathroombr• Second Suite: King bed with ensuite full bathroombr(Both bedrooms feature brand-new beds designed for comfort during extended stays)brbr KITCHEN & DININGbrFully equipped kitchen with everything you need:br• Stove, oven, microwave & refrigeratorbr• Quartz countertops + stainless steel appliancesbr• Cookware, tableware + essentials providedbr• Drip coffee maker (coffee provided ☕)br• Spacious dining areabrbr LIVING SPACESbr• Bright, updated interior with natural lightbr• Comfortable seating + Smart TVbr• Cozy spaces for relaxing or workingbrbr LOCATIONbrLocated just steps from downtown Galena:br• 1 block to Main Street shopping, dining + coffee shopsbr• Walk to boutiques, restaurants + local attractionsbr• ~16 minutes to Chestnut Mountain Resortbr• ~20 minutes to Dubuque, IAbrbr✨ BEFORE YOU ARRIVEbrYou’ll receive a detailed digital guest guide with local recommendations, tips, and everything you need to plan your stay.brbr OPTIONAL ADD-ONSbrAvailable after booking in your Guest Portal:br• Grocery pickup servicebr• Birthday & anniversary packagesbr• Family game night packagebrbr 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• On-site parkingbr• High-speed WiFibr• No petsbr• 30+ day stay requiredbrbr Save this listing by clicking the ♥ to easily find it later!brbrWe can’t wait to host you at Downtown Haven @ A&D Rise Getaways!brNo Cats Allowed.brbr*An additional cleaning fee will be charged for any property left in an unusually dirty condition following a guest’s stay. *

Charming Historic Gem in the Heart of Galena!

Galena, Illinois, United States

2

Bed

2

Bath

4

Sleeps

$471.58

Welcome to The Nook! This 3 bed, 2 bath locally listed cottage sits in the historic district of downtown Galena. Walk to town, enjoy the designer decor, grill in the yard, unwind by the fire pit, relax in the large hot tub & let your pets roam free in the large fenced yard. Indulge in luxury linens, towels, and bathrobes. Enjoy Roku smart TVs with streaming services. Your unforgettable Galena getaway awaits!

The Nook: Downtown Galena Cottage w/ hot tub & fire pit!

Galena, Illinois, United States

Bed

Bath

Sleeps

$810.12

Almost Heaven Rentals Galena who has been in the business of managing vacation rental’s since 2002 is happy to offer you this vacation rental. Located just off the south course in the southwest corner of The Galena Territory, this will be a rental home you will return to time and time again. Glen Creek is a beautiful and spacious 3 level home with spectacular views from both the upper and lower living rooms.brbrWalk right in and get settled in this home, the main level has a two step sunken living room with floor to ceiling windows, a wood burning fireplace and TV. This room connects to the kitchen and dining area where guests can prepare meals in the stunning open kitchen with its large island before sitting down at the dining table to enjoy those meals together brbrThe 3 seasons room located off the dining area is a favorite spot for enjoying the beautiful fresh air of the country without the bugs. On the other side of the three seasons room is an outside deck which holds the gas grill for which we always supply a back up tank. br brOn the other end of the main floor is a full bathroom with a shower stall, it is located in the hallway near the laundry area. Also located in this end of the main floor is the primary bedroom (king bed) with an attached full bath that has a soaking tub as well as a shower stall. There is a private deck in this room that also has a lovely view of the back yard and golf course.brbrUpstairs is a large bedroom with a king size bed and private full size bathroom with a walk in shower. This space has plenty of play room for the kids including a futon in the siting area for them to nap on when they wear themselves out. brbrThe lower level walk out has its own living room with a second wood burning fireplace, flat screen TV, beautiful shuffle board game table, wet bar and a full size sleeper sofa. brWalk out of the gathering room to the patio which holds the gorgeous outdoor hot tub for you to enjoy the daytime and night time views with a cool and refreshing beverage while relaxing and breathing in the fresh air. brbrOn the left end of the living room is a hall way full bath with a tub/shower combo. Along the outside of this end of the lower level is a king bedroom and a queen bedroom. brbrOn the right end of the gathering room is a king bedroom and a full bath with a walk in shower. brbrThis home is located about seven minutes from The Galena Territory homeowners club and the Inn. Six proximity cards are available for your use in accessing the homeowners club and will be at the home when you arrive. Guests of this home enjoy all of the homeowners amenities in The Galena Territory including the two pools, fitness center, indoor and outdoor basketball courts, pickle ball and tennis. Lake Galena is about ten minutes away and can be accessed by calling the marina to reserve a pontoon boat or kayak. Whether this is your first time to the Galena Territory or your fiftieth this home and area have plenty to explore. Almost Heaven Rentals Galena management team lives in the area and are personally hands on, should an issue arise.

Stunning 5 bedroom home great for groups of all kinds

Galena, Illinois, United States

Bed

Bath

Sleeps

$847.84