Vacation Rentals By Owner In Galena, IL

Discover this brilliant 1-bedroom gem in Galena. This terrific apartment features a cozy living room with additional full bed and 1 twin bed options, perfect for a small group of guests. With heating, a washing machine, AC, and WiFi, your stay will be enchanting and comfortable. Enjoy your time in Galena at our apartment.

Charming 1-bedroom apartment in fabulous Downtown Galena with WiFi, AC

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 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

Condo

1 Bedroom, 1 bath Condo in The Galena Territory

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.brbrbrUnit 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

Hotel Resort

Love the outdoors

Galena, Illinois, United States

Bed

Bath

Sleeps

$155.12

King size bed, small deck, double whirlpool in bath, double sided fireplace, access to indoor pool, fitness room, game room, lounge area, internet access, hot tub, outdoor patio with gas grills, approx. 6 miles from downtown Galena, antique shopping, golfing, spa, restaurants, wine tours, trolley tours, and near riverboat casino in Dubuque, IA.. In winter time there is skiing/snowboarding @ Chestnut Mountain Resort.

Studio Unit at Longhollow Point Inn

Galena, Illinois, United States

Bed

Bath

Sleeps

$198.63

Come enjoy this peaceful and centrally located townhouse in The Galena Territory! Bright and airy main level offers lots of natural light that features a large living room with updated flooring, cathedral ceilings with skylights, smart tv and a comfortable eat at breakfast bar with quartz countertops. Also on the main floor is a large bedroom with a king size bed and full bathroom. Upstairs you’ll find the loft area with a futon and the second bedroom with a queen bed and another full bath. There is an outdoor security camera/doorbell at the front door.brbr-Access to the Territory owners club which includes indoor pool, fitness room, and game room year round. Outdoor pool and tennis courts seasonal. br-Close to downtown Galena, multiple hiking and walking trails, Horse riding center, and 4 different golf courses.

Valleywood Villa

Galena, Illinois, United States

Bed

Bath

Sleeps

$223.62

Welcome to The Ace — Your Perfect Galena GetawaybrbrNestled in the heart of The Galena Territory, this charming townhome offers stunning views of the 15th green on Eagle Ridge Resort’s North Golf Course. Whether you're visiting for a weekend of golf, a relaxing retreat, or an outdoor adventure, The Ace is the perfect home base.brbrDesigned for ultimate privacy and relaxation, each level of the townhome features its own:brbrPrivate BedroombrFull BathroombrExceptional Golf Course ViewsbrbrSleeping Arrangements:brbrLower Level: King bedbrUpper Level: Queen bed with en-suite bathbrLoft: Sleeper sofabrLiving Room: Sleeper sofa brbrCozy Living Space featuring:brbrSmart TV with high-speed internet for streamingbrPower recliner and sleeper sofabrWood fireplace for those cozy cooler nightsbrbrStep out to your private outdoor deck with:brbrGas grillbrOutdoor dining areabrScenic views of the golf coursebrbrFully Equipped Kitchen with:brbrStainless steel appliances & solid surface countertopsbrKeurig coffee maker (drip and single serve), toaster, microwave & blenderbrCookware, utensils, and table settings for 8brBreakfast bar & table seating for 4brbr(Don’t forget to stock up on groceries before you arrive!)brbrEnjoy full access to all resort-style amenities at the Owner's Club Complex, including:brbrOutdoor pool with waterslidebrIndoor poolbrBasketball court & game roombrFitness centerbrbrFrom outdoor adventure to wine tasting, Galena has something for everyone:brbrGolf at one of the four renowned Eagle Ridge Resort coursesbrHike with goats at Hoof It Goat TreksbrKayak or paddleboard on the Galena River (rentals at Nuts Outdoors)brUnique shopping & dining in historic downtown GalenabrWine tasting at Galena CellarsbrCraft beer at Galena Brewing CompanybrDistillery tour & tasting at Blaum Bros. DistillerybrbrWant a sneak peek brbrCheck us out on Instagram @acegalena or visit www.acegalena.combrbrWhether you're planning a weekend getaway or a family vacation, a stay at The Ace is always a good idea.brbrBook your 2026 stay today!

Stay at The Ace! A great weekend place that's somewhere between home and hotel.

Galena, Illinois, United States

Bed

Bath

Sleeps

$298.4

pThis fabulous, dog friendly, 2 bedroom, 2 bath townhome is just steps from the South Golf Course (1 of 4 golf courses) in the beautiful Galena Territory. As they say… location, location, location, and this location is perfectly positioned for an easy drive to the Owners’ Club, Highlands Restaurant, the Country Store, Eagle Ridge Resort and Spa, and to downtown Galena with all its history, shops, and entertainment opportunities. The lovely back deck of the home is a perfect spot to sit and let your mind meander through the joys of your day, make fun plans for tomorrow, and savor your morning coffee. The grassy area off the deck is a great place to play your lawn games, enjoy a walk or just exercise your pup! Also off the back deck is a gas grill so the chef in the group can show off their culinary skills!/pbrbrpAs you step into the front door, you’ll find yourself on the upper level of the home with a sweet and comfortable landing area. On this level you will find a large bedroom with a king size bed and a private full bath. As you make your way downstairs, you will find a completely equipped kitchen, large dining table, and family gathering area. The wood burning fireplace (wood provided) will keep those winter nights warm and cozy! This floor also houses the second bedroom with queen bed and additional full bath./pbrbrpAs a guest in The Galena Territory, this home provides 6 Territory passes allowing our guests to enjoy the amenities of the Owners’ Club including indoor and outdoor (seasonal) pools, workout facility, gym, tennis and basketball courts, pickleball, and large game room including electronic games and other family favorites. The same passes provide access to Lake Galena where you can rent pontoon boats, fishing boats as well as canoes and kayaks. The Shenandoah Riding Center also located within The Galena Territory offers trail rides and many fun filled activities throughout the year including an annual 4th of July rodeo./pbrbrpThe Galena Territory boasts 32 miles of walking and hiking trails all with incredible views in every season. Don’t miss this beautiful activity!/p

Dog Friendly, Steps to Golf, Access to Pools! Adorable Inside and Out!

Galena, Illinois, United States

Bed

Bath

Sleeps

$259.23

Come stay in this beautiful Historic Building from 1845 overlooking Downtown Galena. The apartment extends from Main Street to Bench Street. Extra Spacious 2 bedroom apartment with 2 queen beds, living room, dining room, and kitchen. WiFi Included. Please note that the entrance for this apartment is located at 230 S. Bench Street. Children under 16 not allowed. No Pets allowed. No Smoking or Vaping allowed. We also have 8 other apartments available in the same building to select from.brbrThere is street parking on Bench where the entrance to the property is located. brbrRates are based on Double Occupancy.

Overlooking Historic Downtown Galena Suite #3

Galena, Illinois, United States

Bed

Bath

Sleeps

$167.58

Escape to this cool studio apartment located in the picturesque Historic Downtown Galena. This apartment offers guests a kitchenette, bathroom with a shower and hair dryer, along with amenities like iron, WiFi, heating, and AC. We think our place will help you experience everything Galena has to offer. Please note that the entrance for this apartment is located at 230 S. Bench Street. Maximum of 2 guests allowed in this apartment Per Galena City Code. Children under 16 not allowed. No Pets Allowed. No Smoking or Vaping allowed. We also have 8 other apartments available in the same building to select from.brbrYou can park anywhere on Bench Street where the entrance to the property is located.brbr

Studio apartment in Historic Downtown Galena

Galena, Illinois, United States

Bed

Bath

Sleeps

$1158.28

Luxury Galena Hilltop Retreat | Panoramic Views, Hot Tub, Firepit & Resort AmenitiesbrbrExperience the elevated luxury hilltop retreat in The Galena Territory, where sweeping valley views, peaceful wooded surroundings and resort-style amenities create the perfect setting for an unforgettable getaway. Designed for families, couples and group retreats, this private Galena cabin blends upscale comfort with the beauty of nature—just minutes from historic downtown Galena, wineries, golf, hiking and Chestnut Mountain.brbrWake up to panoramic hillside views from the expansive deck, spend your day exploring Galena’s charming Main Street or nearby wineries, then return to unwind in the private 6-person hot tub, gather around the firepit under the stars or relax indoors in beautifully curated comfort.brbr★ Panoramic Views + Outdoor LivingbrFew Galena vacation rentals offer this rare combination of privacy, views, and premium outdoor amenities.br• Private 6-person hot tub with scenic valley viewsbr• Outdoor firepit for cozy evenings year-roundbr• Expansive deck surrounded by naturebr• Peaceful wooded hilltop settingbr• Ideal for morning coffee, sunset drinks, and stargazingbrbr★ Luxury Interior ExperiencebrInside, vaulted ceilings and oversized windows bring the outdoors in, filling the home with natural light and stunning views. Designer furnishings, inviting gathering spaces and thoughtful amenities create a warm yet elevated stay.brbrPerfect for:br• Family vacationsbr• Romantic getawaysbr• Girls tripsbr• Group retreatsbr• Relaxing nature escapesbrbrAfter a day of wineries, golf, hiking or boutique shopping, recharge with spa-inspired comforts, including a relaxing steam shower and cozy indoor spaces designed for connection.brbr★ Galena Territory Owners Club AccessbrGuests enjoy access to sought-after resort amenities, including:br• Indoor and outdoor poolsbr• Fitness centerbr• Tennis, pickleball, and basketball courtsbr• Private hiking and biking trailsbr• Beautiful Galena Territory surroundingsbrbr★ Prime Location Near Downtown GalenabrEnjoy secluded luxury with convenient access to Galena’s best attractions:br• Historic Main Street Galenabr• Chestnut Mountain Resortbr• Local wineries and tasting roomsbr• Scenic hiking trailsbr• Championship golf coursesbr• Boutique shops and restaurantsbrbrWhether you’re searching for a Galena cabin with hot tub and firepit, a scenic family retreat or a peaceful luxury escape near downtown Galena, this hilltop getaway delivers the perfect blend of comfort, privacy, resort amenities and unforgettable views.brbr★ NEARBY ATTRACTIONS:br- 1 mile to Shenandoah Horse Riding Centerbr- 3 miles to Galena Territory Owner's Clubhousebr- 3.6 miles to Hot Air Balloon Ridingbr- 3.6 miles to Eagle Ridge Resort & Spabr- 5 miles to Thunder Bay Fallsbr- 5.7 miles to Hoof It Goat Treksbr- 6.4 miles to Galena Cellars Vineyardbr- 6.4 miles to Blaum Bros. Distilling Co.br- 10 miles to Washburne House State Historic Sitebr- 10 miles to U.S. Grant Home State Historic Sitebr- 10.5 miles to Belvidere Mansionbr- 10.6 miles to Grant Parkbr- 10.7 miles to Galena River Wine and Cheesebr- 10.8 miles to Embe Eatery and Loungebr- 10.8 miles to DeSoto homebr- 10.8 miles to Galena Trolley Toursbr- 10.8 miles to Galena Garlic Companybr- 11 miles to Galena Brewing Companybr- 11 miles to River Bend Gallerybr- 11 miles to Dowling Housebr- 11 miles to Downtown Galena, Wineriesbr- 11 miles to Fried Green Tomatoesbr- 11 miles to Old Market House State Historic Sitebr- 11 miles to P.T. Murphy Magic Theatrebr- 11 miles to Vinny Vanucchi's Italian Restaurantbr- 11 miles to Galena Cellars Wine Tasting Roombr- 11 miles to Galena History Museumbr- 11 miles to Galena-Jo Daviess County Historical Society and Museumbr- 12.4 miles to Horseshoe Mound Preservebr- 12.8 miles to Rocky Waters Vineyard and Winerybr- 13 miles to Chestnut Mountain Ski Resortbr- 13.5 miles to Galena Golf Clubbr- 14.8 miles to Casper Bluffbr- 19.9 miles to Apple River Canyon State Parkbr- 26 miles to Dubuque Downtown IAbrbrPREMIUM HIGHLIGHTSbr★ Ultra-Private Luxury Retreat in The Galena Territory: Escape to a secluded, high-end hilltop retreat surrounded by nature, just minutes from downtown Galena, award-winning wineries, golf courses, scenic hiking trails, boutique shopping and year-round attractions.br★ 5 King Bedroom Suites | Private En-Suite Bathrooms: Unwind in five spacious king suites, each thoughtfully designed with premium linens, upscale finishes and private en-suite bathrooms—perfect for families, couples, retreats and luxury group getaways.br★ Grand Living Spaces with Cozy Fireplaces: Gather in beautifully designed open living areas featuring cozy fireplaces, Smart TVs, a pool table and a curated bar area—ideal for relaxing evenings, celebrations and quality time together.br★ Private Theater + Game Room Experience: Enjoy your own entertainment retreat with a private home theater, arcade games, shuffleboard, poker table and game room amenities designed to create unforgettable moments for guests of all ages.br★ Outdoor Oasis with Hot Tub, Fire Pit & Valley Views: Relax in the private hot tub, gather around the fire pit, grill dinner on the BBQ or enjoy morning coffee and sunset conversations from the expansive three-season deck overlooking peaceful valley surroundings.br★ Chef’s Gourmet Kitchen for Group Gatherings: Cook, dine and celebrate with ease in a fully stocked chef’s kitchen featuring high-end appliances, an oversized island and everything needed for family meals, holiday stays and special occasions.br★ Spa-Inspired Bathrooms with Steam Showers: Refresh and recharge in luxury bathrooms with refined finishes and relaxing steam showers—designed to deliver a true resort-style retreat experience.br★ Family-Friendly + Pet-Friendly Luxury Stay: Thoughtfully equipped for large groups, families and well-mannered pets, this home makes traveling together comfortable, convenient and memorable.br★ Premium Comforts for a Seamless Stay: Enjoy complimentary firewood, dual washer/dryer sets, high-speed Wi-Fi, modern conveniences and carefully curated amenities that make every stay effortless from arrival to departure.br★ Perfect for Galena Getaways & Special Celebrations: Whether you’re planning a winery weekend, golf trip, family reunion, holiday escape or peaceful luxury retreat, this Galena Territory home delivers privacy, comfort, entertainment and elevated relaxation in one unforgettable setting.brbr★ TOP 2026 UPCOMING EVENTSbrbr- Pride Picnic — Jun 13, 2026br- Chamber Golf — Jun 18, 2026br- Balloon Race — Jun 19–21, 2026br- Foundation Concert — Jun 20, 2026br- Corkless — Jun 20, 2026br- Freedom Festival (Elizabeth) — Jul 1, 2026br- Galena July 4 — Jul 4, 2026br- Stockton July 4 — Jul 4, 2026br- Pickleball Tourney — Jul 18, 2026br- Elizabeth Fair — Jul 2026 *(TBD)*br- Jo Daviess Fair — Late Jul–Early Aug *(TBD)*br- Brew Fest — Aug 1, 2026br- Sidewalk Sale (Summer) — Aug 7–9, 2026br- Arts Festival — Aug 2026 *(TBD)*br- Corn Boil — Aug 29, 2026br- Ladies Getaway — Sep 11–13, 2026br- Stair Challenge — Sep 12, 2026br- Romantic Reads — Sep 12, 2026br- Cemetery Walk — Sep 12–13, 2026br- Harvest Fest — Sep 26, 2026br- Warren Pumpkin Fest — Sep 2026 *(TBD)*br- Oktoberfest Crawl — Oct 2, 2026br- Oktoberfest — Oct 3, 2026br- Scarecrow + Craft Fair — Oct 10–11, 2026br- Country Fair — Oct 10–11, 2026br- Pottery Tour — Oct 16–18, 2026br- Living History Walk — Oct 17, 2026br- Anvil Event — Oct 17–18, 2026br- Haunted Dinner — Oct 23, 2026br- Fall Half — Oct 24, 2026br- Halloween Parade — Oct 31, 2026br- Christmas Ball — Nov 14, 2026br- Nouveau — Nov 20, 2026br- Holiday Kickoff — Nov 28, 2026br- Holidaze — Dec 5, 2026br- Fire in the Sky — Dec 5, 2026br- Luminaria — Dec 12, 2026br- Snowflake Stroll — Dec 19, 2026br- Galena 200th — Dec 27, 2026brbr★ LAYOUTbrMain Levelbr- Bedroom 1: King bed, Roku TV, en-suite bath (tub)br- Living + Kitchen: Roku TV, coffee bar, seating for 4, dining for 10, cozy nookbrbrOutdoor: Front deck w/ views + back deck w/ BBQ & privacybr- Bedroom 2: King bed, Roku TV, hall bath (tub)brbrLower Levelbr- Bedrooms 3 & 4: King beds, Roku TVs, patio access, private baths (walk-in shower + steam shower)br- Game/Family Room: Roku TV, seating, pool tablebr- Outside: Screened patio to fire pit, hot tub, and parkingbr- Extras: Pack-and-playbrbrUpper Levelbr- Bedroom 5: King bed, full bath (tub + walk-in shower)brbrWi-Fi: Fast, reliable high-speed internet throughout the cabin.brbrGTA Amenity Access: Includes 6 Proximity Cards for Galena Territory Association amenities. Extra day passes are $5 at the Owners Club. Enjoy indoor/outdoor pools, fitness center, basketball/tennis, plus game & craft rooms.brbrExplore: 24+ miles of trails, 4 golf courses, Lake Galena boating/fishing and Shenandoah Riding Center horseback riding.brbr** Note: Lost proximity card fee is $100 per card. **brbrNOTE:brbrMax 12 guests.br25+ to book. Rental agreement + $500 security hold required (placed 2 days before arrival, released post-stay if no damages).brGuidebook located in binder by upstairs fireplace.brNo unapproved visitors.brStarter firewood included (~2 hrs); additional wood available for purchase or bring your own.brOutdoor lights off by 1 AM (GTA) or $150 fine per occurrence.brWinter: Roads are plowed, but 4WD/chains recommended.brPet-friendly: Max 2 house-trained pets (50 lbs max each). Fees: $250 first pet, $200 second pet.brSecurity: Schlage smart locks + 1 exterior Ring camera facing driveway only. No indoor/backyard cameras.brEarly check-in/late check-out available when possible for an added fee.brNo weather-related refunds; travel insurance recommended.brEarly/late check fees: $100 (≤2 hrs), $250 (2–4 hrs), 4 hrs = 1 night.brNon-Airbnb cancellations incur a 3% Stripe processing fee deduction.brOptional concierge services available (grocery pre-stocking, private chef, etc.).brbrPLEASE REVIEW THE HOUSE RULES BEFORE BOOKING. THANKS!!

Cabin

5King Bed 5Bath w/ Upscale Views Fire Pit Hot Tub Pets Cinema Luxe Amenities

Galena, Illinois, United States

Bed

Bath

Sleeps

$239.72

Newly-remodeled 2BR 2 BA end unit in the heart of the Galena Resort. This two-story condo boasts a modern and inviting feel, open floor plan and 'tree house' views of peaceful Lake Galena. Guests will love the screened-in porch, wood burning fireplace and lakeside deck. brbrNew king-size beds in each bedroom. The loft area allows additional room to relax and enjoy the views. Additional queen sleeper sofa in the loft along with arcade game table. Free Netflix streaming access; additional TV above fireplace in main living room. brThe fully-stocked kitchen features a coffee bar with a Keurig and an auto-drip coffee; complimentary coffee and tea provided. Brand-new extra-large capacity washer and dryer.brGuests have access to the Long Bay Point Complex Owner's Club which includes indoor and outdoor pool access, sports courts, children's play area, game room and snack shop. The condo is adjacent to the Eagle Ridge North Golf Course; one of four nationally-recognized courses in the Territories. This area also boasts many beautiful hiking trails and great fishing spots.

Condo

Beautiful Sunset Point! Arcade game table!

Galena, Illinois, United States

Bed

Bath

Sleeps

$250.79

✓ Romantic king suite in a peaceful, wooded settingbr✓ 2 Full bathsbr✓ Private feel with 2 full baths for added comfortbr✓ Steps to outdoor semi-private poolbr✓ Gas grill on the back deckbr✓ 2 min to golf, driving range & spa br✓ Access to indoor pool & fitness center at Owner’s Clubbr✓ Lake access + scenic walking trails nearbybr✓ Just 12 min to Downtown Galena (shopping, dining & historic attractions)br✓ 15 miles to Chestnut Mountain Resort (skiing, zipline & river views)brbrEnjoy a freshly updated interior featuring new flooring, cozy furnishings, and a warm modern-rustic feel. The entire villa is yours to enjoy privately during your stay. brbrUPPER LEVELbr• King Bedroom Suite: Relax in a plush king bed with a Smart TV (Roku + YouTube TV) and an attached full bath.br• Loft Workspace: Perfect for remote work with a desk, USB lamp, and free Wi-Fi.br• Fresh Linens Provided: Sheets, pillows, comforters, towels, and washcloths for both levels.brbrLOWER LEVELbr• Fully Equipped Kitchen: Cook your favorites in an updated kitchen with dual coffee makers (drip + Keurig), plus complimentary coffee, tea, sugar, and creamer. Please supplement kitchen, paper, and laundry supplies for stays longer than 7 days.br• Living Area: Bright, open, & cheery - Cozy up by the fireplace while streaming shows on the Smart TV (Roku + YouTube TV). Firewood is provided. Living area can accommodate up to 2 small people on the newer full size sofa bed. A preschool cot and mini pack n play are also provided. br• Laundry Room & Full Bath: Conveniently located off the kitchen.br• Central air conditioning and heating throughout the home provides additional comfort in every season. br• Private Deck: Relax outdoors with grill and patio seating for four overlooking the wooded backdrop.brbrDOG-FRIENDLYbr• One well-behaved, 50 lb or less, dog welcome for a $90 pet fee per staybr• Includes dog bed, bowls, and couch cover for your pet’s comfortbr• PLEASE NOTE: Dogs must be kenneled whenever left unattended in the home. We are unable to make exceptions to this policy.brbrPOOLSbr• Semi-private outdoor pool just steps away (open Memorial Day–Labor Day)br• Year-round indoor pool at the Owner’s Clubbr• Seasonal access to additional outdoor pools at the Owner’s ClubbrbrGTA OWNER'S CLUB AMENITIESbrAs guests, you’ll enjoy complimentary access to the outstanding amenities at the Galena Territory Owner’s Club, including:br• Fitness centerbr• Year-round indoor poolbr• Outdoor pool & kiddie pool (seasonal)br• Café (seasonal)br• Game room br• Gymnasium (ping pong, fuse ball, pool table)br• Outdoor basketball, tennis, & pickleball courts (seasonal)br• Lake Galena Marina with kayak, canoe, fishing boat, and pontoon rentalsbr• Marina bait shopbr• Thunder Bay Falls Park – beautiful waterfalls & picnic areabr• Shenandoah Riding Center (trail rides for all experience levels; additional fee)br• Nordic Center for winter sports (weather permitting; equipment rentals available)brbrMAIN ATTRACTIONSbrLocated just 6 miles away is the historic downtown Galena, voted Illinois’ “Best Small Town”, featuring:br• Belvedere Mansion, U.S. Grant Home, and Galena History Museumbr• Festivals, performing arts, and scenic trolley or walking toursbr• Unique shopping — from antiques to modern boutiquesbr• Excellent local diningbr• Nearby hiking trails and state parksbr• Chestnut Mountain Resort (15 miles): winter skiing; zipline, alpine slide, and Mississippi River cruises in summerbrbrPLEASE NOTE: br1. Due to owners' allergies, cats are NOT allowed on the property at any time. Violation of this policy will result in a $200 fine. Damage caused by a pet or failure to follow GTA pet policies will also incur a fine. br2. No parties or large gatherings!br3. No smoking or vaping on the townhome premises!br4. This townhome sleeps four and uses keyless entry. br5. You must be 21 or older at the time of booking and present during the entire stay. We do not allow third party bookings.br6. We are unable to issue refunds for weather, sickness, or similar circumstances that are beyond our control. It is recommended that you purchase travel insurance if you desire a refund for these situations.br7. These townhomes have interior and exterior stairs. They are set nicely away from the parking lot, giving plenty of privacy, but YOU WILL NEED TO BE ABLE TO NAVIGATE STAIRS.

King Suite, Semi-private Pool, Near Golf & Spa

Galena, Illinois, United States

1

Bed

Bath

Sleeps

$359.76

Our beautiful High Ridge Hideaway is just 3 miles to the GTA Owners Club and 20 mins to Downtown Galena. This home does not allow pets. Also, no events are permitted to be hosted in our home. Maximum Occupancy is 8 guests at any time. brbrThis 3-bedroom 3.5 bath home has ample space for you to enjoy with your friends and family. This amazing home is in the Shenandoah section of the The Galena Territory & just minutes from the Shenandoah Riding Center w/access to nature trails literally outside our door. Our home's main living area has an open kitchen, dining room and living room w/gas fireplace, flat screen TV and huge windows that provides an airy feel with views to the outdoors. In addition to the open concept living on the main floor there is a full-size laundry room and a powder room off of the kitchen. The master bedroom is also on the main level and has an en suite bathroom with soaking tub and Smart TV for streaming. The main level keeps on giving with a screened in porch, propane gas grill and deck. Your group will love the upper-level lofted area which affords you extra space to relax and play featuring an arcade game (with 3,000 games), foosball table and board games. It will become a favorite spot during your stay! The remaining sleeping is in the lower level, there are two additional bedrooms opposite of each other both feature smart TVs for streaming. One bedroom features a king bed and twin, and the other has a queen bed and twin, both with their own bathrooms. There is a second family room with flat screen TV and sofa sleeper in the lower level as well. You will then have access to the great outdoor amenities from the sliding glass doors. The hot tub is just a few steps out and is open all year round so you can enjoy the private, wooded view from the tub or start a fire in the outdoor fire pit! **More great perks - your stay will benefit the use of our 2-car garage, a New Keurig coffee machine and new Primary bedroom furniture and linens. br brEnjoy Access to the GTA Owners Club while staying with us. The indoor pool is open year-round and the outdoor pool is open Memorial Day - Labor Day. The club is an exclusive amenity that can be used by only Galena Territory property owners and their guests. The Owner's Club includes an indoor swimming pool, outdoor swimming pool w/slides, a kiddie pool, fitness room, game room, indoor/outdoor basketball courts, tennis courts and seasonal snack bar. Don't forget to visit Lake Galena, the Shenandoah Riding Center and hiking trails throughout the 6,800-acre property. brbrDisclaimer: You may not have enough cards for your entire group. Guest passes can be purchased for just $5 a day at the GTA admin office or pool entrance. Staying with us grants you access, it may not be free. Please remember usage of the amenities is never guaranteed. We do not discount or refund due their closure. When you book a home with us we will require 30% down, this is a payment not a deposit. The full balance is due 14 days prior to check in. If you cancel prior to the 14 days, you will receive the first payment less a $35 cancellation fee. At the 14 day mark your stay will become non-refundable and dates cannot be adjusted. Your payments will automatically be processed to the card you place on file at the time of booking. Your rental agreement (sent after booking) will reflect the due dates and amounts. Please Note: You will be required to sign an electronic rental agreement at the time of booking, we ask this be signed and filed within 48 hours of receiving to guarantee your reservation. You must be 25 or older at the time of booking. Please Note - there are no exceptions to our cancellation policy-we highly recommend travel insurance. brbrCheck-in details are emailed to you 3 days before arrival. This includes the home's address, the access code and other home/area information. Early check-in is not available from June to October. When available, it cannot be considered until the night before or morning of your arrival and is NEVER guaranteed. The check in details will cover this process.

Unwind at High Ridge: Hot Tub Nights, Arcade Lights & Fire Pit Fun!

Galena, Illinois, United States

3

Bed

3

Bath

8

Sleeps

$266.85

Our Harrison Downtown Retreat is .5 miles from Main St. downtown Galena - just a quick walk to dining, shopping, etc. This home is Dog Friendly, Maximum of 2, pet fee is required. The yard is not fenced or accessible due to the terrain (hill with prairie grasses). The neighborhood is safe and great for exploring.brbr*Golf Benefits: Guests have access to our Eagle Ridge Golf Membership with preferred rates and tee times at The General, The North Course and the South Course! Contact us for details.brbrOur Harrison Home is a modern 2 bedroom, 2.5 bathroom dog friendly farmhouse located in the heart of Galena with the feeling of country living. The home is less than a 5 minute ride to downtown or a 10 min adventure aka steep walk. If you can peel yourself away from the front porch overlooking the NEW Outdoor FIRE PIT you'll step into a large two-story living room w/a wood-burning fireplace between the living room and dining room. The skylights bring nature in and the airy rooms make this home feel large and welcoming. Relax in the living room in front of the flat screen TV with Blu Ray and cable or play games at the dining room table. Step into the kitchen and be delighted by the galley layout with a NEW Frigidaire stove and everything you need or would want, coffee maker, toaster oven, microwave and ice maker. Step outside form the kitchen and use the gas grill and we provide the propane. NOTE: This home does have many interior steps, it may not be the best for someone with mobility issues. Upstairs, you will enjoy the large master bedroom featuring a memory foam King mattress with private bath, closet and flat screen tv, this room has maximum light and is open to the living room below. The lower level features another seating area and a new washer and dryer in the laundry room. The bedroom has a Queen bed, private bath, flat screen smart tv for you to watch Netflix, HULU, etc. on. This home can sleep 4 people in beds and then there is an air mattress for an extra 2. The home has occupancy for up to 8. Also the owner has installed an electric vehicle charging station for you to use, this is mounted on the outside of the garage. This home has a steep driveway; we recommend a 4WD vehicle in the winter and also please consider purchasing travel insurance. If you cannot access the area or the home due to weather, there are no refunds. Feel free to use one side of the garage during your stay. Pet friendly homes do require a $150 pet fee.brbrPlease note this home is not part of the Galena Territory and does not have access to the GTA amenities. brbrWhen you book a home with us we will require 30% down, this is a payment not a deposit. The full balance is due 14 days prior to check in. If you cancel prior to the 14 days you will receive the first payment less a $35 cancellation fee. At the 14 day mark your stay will become non-refundable and dates cannot be adjusted. Your payments will automatically be processed to the card you place on file at the time of booking. Your rental agreement (sent after booking) will reflect the due dates and amounts. Our cancellation policy is NOT flexible; we highly recommend travel insurance. Travel insurance is offered at the time of booking and up until 15 days before check-in. The provider is CSA.brbrPlease NOTE: You will be required to sign an electronic rental agreement at the time of booking. We ask that this be signed and filed within 48 hours of receiving it to guarantee your reservation. You must be 25 or older at the time of booking and present for the duration of the stay.brbrCheck-in details are sent 3 days before your arrival to the email on file. This includes the home's address, the access code and other pertinent home/area information. Early check-in is never guaranteed and cannot be considered until the night before or morning of your arrival. The emailed check-in details will cover this process.

Secret Path 2 Main St Downtown, Dog Friendly, Fire Pit, Daily Deer Sightings!

Galena, Illinois, United States

Bed

Bath

8

Sleeps

$453.05

Galena craftsman home built in 1925. Impressive crown molding and woodwork throughout. Four bedrooms: 1 king size bed, 3 queen size beds. Three bedrooms on second floor, one on the main floor.brFully-equipped kitchen, high speed wireless internet and Direct TV. Living room easily accommodates 8. Front porch and large deck on hillside in backyard. Two off-street parking spots. Easy walk to shopping and restaurants on Main St. Washer and dryer with detergent available.

New Listing! Charming home two blocks from Galena Main St with deck and parking

Galena, Illinois, United States

Bed

Bath

Sleeps

$561.68

Discover our whimsical treehouse-themed retreat in Galena, IL, accommodating 8 guests. Immerse yourself in nature on 2+ secluded acres. Enjoy the warmth of a smokeless fire pit, relax on the screened-in porch, and play games for all ages. The modern design, cozy furniture, brand new kitchen, and walls of windows offer a unique blend of comfort and nature. Each of the 3 en-suite bathrooms ensures privacy and convenience. Escape to this enchanting oasis where the beauty of abundant nature meets thoughtful design for an unforgettable stay!

Treehouse: Hot Tub! Firepit! Cozy, Secluded, + Spacious.

Galena, Illinois, United States

Bed

Bath

Sleeps

$698.56

This home is 12 minutes to Downtown Galena. Ask us for the short cut to town! This home is NOT pet friendly.brbr*Enjoy Golf Benefits* Guests of this home have access to our Golf Membership at Eagle Ridge, which provides preferred rates and tee times at The General, The North Course, and the South Course! Contact us for details.brbrExperience thise brand-new, fully furnished 5-bedroom, 5-bath home located in the Galena Territory. Thoughtfully designed and impeccably finished, this stunning property blends modern luxury with the serene beauty of its natural surroundings—perfect for families, groups, or upscale getaways. Step inside to discover high-end interior finishes, spacious open-concept living areas, and designer furnishings throughout. Each of the five generously sized bedrooms offers privacy and comfort, paired with its own full bathroom—ideal for large groups seeking both togetherness and personal space. The fully equipped kitchen flows seamlessly into the dining and living areas, making it perfect for entertaining or relaxing after a day exploring Galena. Large windows fill the home with natural light, creating a warm and inviting atmosphere year-round where every detail has been carefully considered for comfort and style. Every bedroom features its own en suite bathroom, so guests can enjoy the convenience of having a private space to refresh and unwind. On the main level, you’ll find two inviting bedrooms: a spacious King bedroom and a cozy Queen bedroom, perfect for those who prefer easy access without stairs. Head down to the lower level, where there are three additional bedrooms. Two of these rooms each feature a Queen bed, while the third is a larger room with two Queen beds—ideal for families or groups traveling together. Altogether, the home comfortably sleeps up to 12 guests in beds, making it a wonderful gathering place for family trips, group getaways, or special celebrations. With ample sleeping arrangements and the added comfort of private bathrooms for every bedroom, everyone can enjoy both together time and their own relaxing retreat. Our home is designed for comfort, privacy, and plenty of space to relax together. brbrYou will have access to the GTA Owners Club while staying with us. The indoor pool is open year-round, and the outdoor pool is open from Memorial Day - Labor Day. The club is an exclusive amenity that can only be used by Galena Territory property owners and their guests. The Club features an indoor swimming pool, an outdoor swimming pool w/slides, a kiddie pool, a fitness room, a game room, basketball courts, tennis courts, a seasonal snack bar, free WiFi, and an outdoor playground. Please remember that the usage of the amenities is never guaranteed. We do not offer discounts or refunds due to their closure. We may not have enough proximity cards for your group, but daily guest passes are available.brbrWhen you book a home with us, we will require 30% down; this is a payment, not a deposit. The full balance is due 14 days before check-in. At the 14-day mark, your stay will become non-refundable, and dates cannot be adjusted. NOTE: You must sign an electronic rental agreement when booking. You must be 25 or older when booking and present during the entire stay. Your payments will automatically be processed to the card you place on file when booking. Our cancellation policy is NOT flexible. We highly recommend travel insurance. Travel insurance is offered when booking and up until 15 days before check-in. **Check-in details are sent to the email on file three days before your arrival. These include the address, access code, and other pertinent home/area information. Early check-in is never guaranteed and can only be considered the night before or the morning of your arrival. The check-in details will cover this process. Check-in for this home is 4 p.m., and check-out is 10 a.m.brbrThis home is part of the Grand Galena Collection - Grand Galena Retreat, Grand Galena Hideaway & Grand Galena on Genessee

New Construction - All En Suites! Hot Tub, Fireplace, Screened Porch & MORE!

Galena, Illinois, United States

Bed

Bath

Sleeps

$774.7

This home is flawless! From the serene, private location to the abundant amenities, our trip was perfect. My kids especially loved the theater room and gaming console. – SadiebrbrGolden Meadows Escape offers the perfect blend of tranquility and entertainment, with easy access to everything Galena has to offer. This beautifully designed home rests on a spacious 2+ acre lot, ensuring endless peace and family fun.brbrA taste of luxury with all the charm of the countryside – MattbrbrThe spacebrKEY FEATURES:br* Sleeps 10; 4 bedrooms, 2 kings, 1 queen, 1 Twin XL/queen bunk with twin trundle, 1 queen-size br sleeper sofabr* 4.5 bathrooms (all ensuite); 3 showers, 1 shower/tub combo, one jacuzzi tub, + half bathroombr* Spacious well-equipped kitchen with seating for 14 guestsbr* Hot tub, massage chair, shuffleboard table, theater room, pool table, arcade game console, fire br pit, fire table, large sunroombrbrLIVING SPACES:brbrWelcome to Golden Meadows Escape, your private country oasis where every detail has been thoughtfully and professionally designed. From the breathtaking vaulted ceilings to the cozy, elegant sunroom, and the luxurious bedroom suites—each with its own en-suite bathroom—you'll feel the care put into every inch of this retreat.brbrThe open floor plan welcomes you with a warm and inviting living area, complete with a new gas fireplace and a smart flat-screen TV. Enjoy the ambiance from the formal dining room, which seats 10, or from the kitchen counter, which seats 4. On the second-level landing, there’s a perfect kid hangout spot featuring a comfy couch, a flat-screen TV, and a Nintendo Switch gaming console for hours of entertainment.brbrHead down to the basement and dive into pure entertainment! You'll discover a theater room, massage chair, pool table, large flat-screen TV, arcade game console, and shuffleboard table. Whatever your idea of fun, you’ll find it here.brbr“We were blown away by all the amenities—there was so much to do, we didn’t know where to start! Our stay was incredible.” – JimbrbrKITCHEN & DINING:brbrSuite of stainless steel appliancesbrFully stocked kitchenbrNespresso Coffee StationbrEspresso MachinebrWaffle BarbrbrIn the fully stocked kitchen, you'll have everything you need to prepare a fantastic meal. Thanks to the open-concept design, the chef can always stay part of the action while cooking!brbrBEDROOMS & BATHROOMS:brbrEach bedroom is a private sanctuary designed for ultimate comfort, complete with luxurious beds, plush bedding, and blackout blinds to ensure you can sleep in as long as you desire.brbrBedroom 1 (first floor): King bed with ensuite bathroombrBedroom 2 (second floor): Queen bed with ensuite bathroombrBedroom 3 (second floor): Twin XL/Queen bunk with twin trundle bed and ensuite bathroombrBedroom 4 (lower level): Queen bed with ensuite bathroombrbrAdditionally, a convenient first-floor laundry room ensures easy access during your stay.brbrOUTDOORS:brbrThe outdoor spaces are just as impressive as the interior amenities. Start your day with a coffee and a good book on the front porch. Fire up the brand-new Weber 4-burner propane grill for a delicious meal. On the lower patio, enjoy a game of Jenga or Connect Four, or simply relax on the swing chair and chat. End your evening by the fire pit or gather around the fire table on the second-level deck, and don’t forget to indulge in a soothing soak in the hot tub.brbrLOCAL AREA:brbrBeyond the amenities offered by the house, both The Galena Territory and downtown Galena provide a wealth of activities. The Galena Territory boasts over 24 miles of hiking and horseback riding trails, with access just behind the house! At the Owner’s Club, you’ll find multiple pools, tennis, basketball, pickleball courts, a game room, meeting rooms, and a kids' play area. Plus, the home is conveniently located near many local attractions:brbrShenandoah Riding Center – 2 minutesbrThe General Golf Course – 7 minutesbrOwner’s Club – 6 minutesbrThe Marina – 8 minutesbrDowntown Galena – 15 minutesbrLong Hollow Canopy Tours – 5 minutesbrThe Country Store – 7 minutesbrGuest accessbrGuests have access to the entire home and outdoor area. An electronic lock code will be provided in your welcome email.brOther things to notebrThe house includes 6 proximity cards for access to the owner's club. Additional day passes can be purchased for $5 per day.

Golden Meadows Escape: A Luxurious Country Retreat

Galena, Illinois, United States

Bed

Bath

10

Sleeps

$188.39

Cozy 1 bedroom, 2 bath golf villa in the heart of The Galena Territory on the East Golf Course. Offers many updates; freshly painted: new window treatments; all new appliances; new furniture including a full pull-out bed in the living area; new gas grill; high speed internet; updated cable with new 50 inch plasma tv! This home offers a queen size bed and a double whirlpool tub on the upper level. Cozy up in front of the fireplace to take the chill off a cold fall/winter evening or have a cookout on the gas grill anytime. This home also provides Amenity Passes that allow you access to the Owners' Club where you can enjoy the indoor/outdoor swimming pools, Fitness Center, Game Room, indoor/outdoor basketball courts, tennis courts, free WIFI ,and more. Sleeps 4. Maximum Occupancy 4.

Nicely updated 1 bed-2 bath townhouse in a great location and a beautiful view!

Galena, Illinois, United States

1

Bed

Bath