Vacation Rentals By Owner In Galena, IL

Located within the Galena Territory - our charming cottage is located just a 6-minute drive to Downtown Galena. Surrounded by towering trees and rolling hills, this serene oasis offers the perfect getaway to experience tranquility, and the beauty of Galena. You won't believe the amazing night sky, perfect for stargazing!brbrSerenity Woods invites you to escape the hustle and bustle of everyday life and immerse yourself in a cozy retreat like no other. brbr✔️ 2 comfortable bedroomsbr✔️ Open Design Livingbr✔️ Fully Equipped Kitchenbr✔️ Smart TVsbr✔️ High-Speed Wi-Fibr✔️ Resort Amenitiesbrbr⭐️The Space⭐️brA blend of comfort, contemporary style, locally crafted details, and convenience greet you as soon as you enter this cozy living space. The comfortable seating, quaint dining area, and large windows flood the room with natural light, offering picturesque views of the surrounding countryside.brbr⭐️Tranquil Bedroom Retreats⭐️brTwo comfortable bedrooms are designed to offer all the rest you need after a long day of exploring Galena’s charming shops and historic landmarks.br br✔️ Main Level Bedroombr✔️ Master Bedroom- Upper LevelbrbrBoth bedrooms have similar amenities - a queen bed, premium pillows, blankets, and sheets. Closets with hangers and nightstands with a reading light. brbrEXPLORE GALENA- or not!!brbr⭐️ If you don’t feel like leaving the cottage, but want to catch a breath of fresh air and soak up the sun, step out onto the deck and relax with comfortable furniture. brbr⭐️ Just steps outside the back door is the start of the 24-mile walking trail that winds the greenspaces throughout the Territory. brbr⭐️ Check out the four championship golf courses that the Territory offers. brbr⭐️ Resort Amenities GALORE!br✔️ Indoor and Outdoor Pools br✔️ Fitness Centerbr✔️ Basketball Courtsbr✔️ Video Arcadebr✔️ Game Room with Ping Pong and Pool Tablesbr✔️ Outdoor Tennis and Pickleball br✔️ Business CenterbrAll included with your stay!brbrbr HERE’S THE FINE PRINT brbr✔️ NO SMOKING INSIDEbrPlease refrain from smoking inside the home. Any smoking evidence will result in a fee for odor removal and furniture cleaning.brbr✔️ PARTIES/EVENTSbrWe'd like to ask that you treat our home as your own to keep its pristine condition for future guests and your return visits. brbrTHANK YOU for understanding!brbrINTERACTION WITH GUESTSbrWe are accessible 24/7 for our guests via phone or text. You can expect a prompt response. brWe give our guests space but are available for emergencies. brbrYOUR PERFECT GETAWAY AWAITS!brWhether you’re seeking a romantic retreat for two or a peaceful getaway with friends, Serenity Woods offers the perfect blend of charm, comfort, and convenience. Book your stay with us and discover why Galena is known as one of the Midwest’s premier destinations for relaxation and rejuvenation. See you soon!

ESCAPE to Galena! Serenity Woods is your PREMIER, relaxing getaway!

Galena, Illinois, United States

Bed

Bath

Sleeps

$268.01

Complement your next getaway to Galena with a stay at this fully furnished and family-friendly townhome near the Eagle Ridge Resort! The 3-bedroom, 3-bath vacation rental delivers all the basics and includes a balcony, a gas grill, and multiple living areas with Smart TVs. Plus, with a prime location in the Plum Cove neighborhood of The Galena Territory community, seasonal Lake Galena views, 2 pools, an equestrian center, a game room, and a gym. High-quality and fun-filled family time awaits!brbr-- THE PROPERTY --brbrFree WiFi | Family Friendly | Gas Grill (Propane Provided)brbrBedroom 1: Queen Bed | Bedroom 2: Queen Bed, 2 Twin Beds | Bedroom 3: Queen Bed | Additional Sleeping: CribbrbrCOMMUNITY AMENITIES: Indoor & outdoor pools, marina on-site (Lake Galena views), hiking trail access on-site, business center, game room, community center, indoor gymnasium (pickleball & basketball), outdoor tennis/basketball courts, fitness center, equestrian center (fee required to ride), pontoons/kayaks/canoes available to rentbrTOWNHOUSE AMENITIES: Smart TVs, dining table, high chair, electric fireplace, work desk, board games & booksbrKITCHEN: Well-equipped w/ refrigerator, microwave, dishwasher, dishware/flatware, stove/oven, cooking basics & spices, slow cooker, drip & Keurig coffee makers (K-cups provided, coffee filters provided), blender, toasterbrGENERAL: Linens/towels, complimentary toiletries, central A/C, washer & dryer (starter detergent provided), hair dryer, hangers, iron/board, trash bags/paper towelsbrFAQ: 3 steps to enter, located in a dark-sky areabrPARKING: Open community lot (3 vehicles, no parking passes required), passes provided for amenity parkingbrbr-- THE LOCATION --brbrOPT OUTSIDE: Shenandoah Riding Center (3 miles), Tapley Woods State Natural Area (6 miles), Apple River Canyon State Park (13 miles), Apple Canyon Lake (16 miles)brLOCAL ATTRACTIONS: Ashton Hill Farm Galena (6 miles), Hoof It Goat Treks (6 miles), U.S. Grant Home State Historic Site (7 miles), Thunderbird Effigy Mound - Mississippi River (15 miles)brTEE OFF: Eagle Ridge East Golf Course (0.5 miles), Eagle Ridge North Golf Course (0.7 miles), Eagle Ridge South Golf Course (2 miles), Galena Golf Club (10 miles)brAIRPORTS: Dubuque Regional Airport (30 miles), Chicago Rockford International Airport (73 miles), Dane County Regional Airport (107 miles)brbr-- 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- NOTE: This property requires 3 steps to enterbr- NOTE: There will be 6 complimentary keycards for accessing the community amenities. Additional guests can access these amenities by purchasing daily passes for $5 each, paid for on-sitebr- NOTE: This home is located in The Galena Territory, which is a designated Dark Sky Friendly Development of Distinction. There are lights in the parking lot but no exterior lights on the home/porch. Fines may be imposed if lights are left on overnight

Tasteful Galena Townhome w/ Community Amenities

Galena, Illinois, United States

Bed

Bath

8

Sleeps

$533.27

Why Guests Love The Retreat at Shagbark!brbr• Quiet secluded wooded settingbr• Private hot tub for relaxing eveningsbr• Game room with pool table for entertainmentbr• Cozy wood-burning fireplacebr• Spacious layout ideal for families and groupsbr• Fully equipped kitchen for preparing meals togetherbrbrThe peaceful natural surroundings make this home a perfect escape from busy city life.brbrMain Levelbrbr• Open living room with wood-burning fireplacebr• Fully equipped kitchen and dining areabr• Deck overlooking peaceful wooded surroundingsbr• Bedroom 1: King Bed with Ensuite bathroombrbrUpper Levelbrbr• Bedroom 2: Primary Bedroom with a King bed with large ensuite bathroombrbrLower Levelbrbr• Game room with pool tablebr• Second living area perfect for movies or relaxing + sleeper sofabr• Bedroom 3: Queen bed + Ensuite bathroombr• Bedroom 4: Two Twin beds + Ensuite bathroombrbrThis layout allows groups to gather together while still enjoying space and privacy.brbrOutdoor SpacebrThe Retreat at Shagbark is surrounded by the natural beauty of the Galena Territory.brbrGuests enjoy:br• Private hot tubbr• Deck seating for morning coffee or evening drinksbr• Peaceful wooded surroundingsbr• Quiet setting perfect for relaxingbrbrThe outdoor space is ideal for enjoying the calm atmosphere of this beautiful area.brbrLocationbrThe home is located within the beautiful Galena Territory community near historic Galena.brbr**Planning a golf trip to Galena Guests of The Collection Vacation Homes receive exclusive discounted golf passes to the award-winning courses at Eagle Ridge Resort & Spa.**brbrNearby attractions include:brbr• Golf at Eagle Ridge Resortbr• Lake Galena and scenic trailsbr• Wineries, breweries, and restaurantsbr• Shopping and historic architecture in downtown GalenabrbrDriving times:br5 minutes → Eagle Ridge Golf Courses, The Galena Territory Owners Clubbr10 minutes → Lake Galenabr15 minutes → Downtown Galenabr20 minutes → Chestnut Mountain ResortbrbrGuests have access to the Galena Territory Owner’s Club, which includes:brbr• indoor pool available year-roundbr• seasonal outdoor poolbr• fitness centerbr• basketball courtbr• pickleball and tennis courtsbr• game roombrbrThe Retreat at Shagbark is especially popular for:brbr• Family vacationsbr• Friends’ getaway weekendsbr• Golf tripsbr• Fall foliage trips to Galenabr• Holiday gatheringsbrbrLooking for a relaxing Galena cabin with a hot tub, game room, and peaceful wooded setting The Retreat at Shagbark is the perfect place to unwindbrbrStairs required: To access this home, you will need to descend a full set of stairs from the driveway to the front porch. brbrPlease note that Travel Insurance is HIGHLY recommended as we do not have a COVID or Weather Cancellation policy; may purchase after booking.

Secluded Galena Retreat | Hot Tub | Game Room | Fireplace | Dog-friendly

Galena, Illinois, United States

Bed

Bath

Sleeps

$475.47

Step into a retro mid-century modern birdhouse-themed escape! With 3 bedrooms (3 King beds + 1 Twin Bunk Bed), a hot tub, fire pit, and game room, it's perfect for families, friends, or couples! Bright, playful spaces, modern comforts, and a short drive to historic Galena makes this a one-of-a-kind getaway.

BiRDHOUSE! Hot Tub, Fire Pit, & Game Room!

Galena, Illinois, United States

Bed

Bath

Sleeps

$351.82

After a long day taking in all the shopping, dining, and entertainment that Galena has to offer, wake up to the tranquility of the Galena Territories. This 3 bed 3.5 bathroom(3 enusuite baths) home has 2 living spaces over a split level design. Large windows offer a treehouse feel the moment you walk into the door. Sitting on over an acre of wooded property, you’re provided privacy and space for outdoor activities. Whether you're a family looking for a Midwest getaway or a corporate partner hosting clients, this is the space for you.

Cabin

HoneyComb Hideaway Galena Territories

Galena, Illinois, United States

Bed

Bath

Sleeps

$604.87

Immerse yourself in nature at your own private oasis. Features include:br• 3 bedrooms/3.5 bathrooms (up to 8 guests)br• 12 mins to downtown Galenabr• Outdoor hot tub on lower deck br• Grill & dining space on upper deckbr• Seasonal views of Lake Galena (glimpses while foliage is present in late spring/summer/early fall & full views during late fall/winter/early spring)br• Lounge space with pool table & smart TVbr• Full Kitchen w/fridge, oven, microwave, dishwasher, keurig coffee machine, air fryer, instant pot, & crockpotbr• Upstairs family room includes smart TV, fireplace, & board gamesbrbrNestled in the woods above Lake Galena, following a long tree-lined drive, sits a hidden retreat for you to enjoy with your family and friends. This house is within easy driving distance to all of the Galena sights, from the beautiful Main Street shops, to the historic landmarks, and the exciting outdoor adventures. After a day of exploring, come back to our well-appointed home and enjoy a relaxing soak in the hot tub, a game of pool, or grilling with your friends.brbrSave this listing by clicking the ♥ in the upper right corner.brbrSome of the amenities you'll enjoy are listed below. Plus, our house is conveniently located less than 15 minutes away all the best shops, restaurants, and attractions in downtown Galena. Come stay with us and see why the Hidden Forest Retreat is so special!brbr• Two Outdoor Decks: Upper deck featuring dining space and gas grill (propane tanks on site – may require refill prior to use). Lower deck featuring outdoor hot tub.br• Screened-in Sunroom with propane fire tablebr• Fully Stocked Kitchen: Keurig Coffee Machine featuring full coffee carafe or single cup brewing; Stainless Steel Appliances; Air Fryer and Crock Potbr• Linens, Towels, paper goods, and hand soap providedbr• Lower level living room featuring smart TV, electric fireplace, and Pool Tablebr• Washer & Dryer (Located on Lower Level)br• High Speed Fiber Wi-Fibr• Main level indoor fireplace (Available Seasonally)br• No Pets due to allergensbr• 2200 Sqft of space to relax and enjoybrbrLOCAL ATTRACTIONS:brbro Downtown Galena Main Street – shopping, dining, and more (12 mins)bro President Ulysses S. Grant Home (14 mins)bro Galena Trolley Tours (13 mins)bro Eagle Ridge Resort & Spa (10 mins)bro Galena Territories Owner’s Club (6 mins) includes access to seasonal outdoor pools, indoor pool, fitness center, business center, tennis courts, basketball court, and game roombro Galena Territories Marina (6 mins)bro Long Hollow Canopy Tours – Ziplines (13 mins)bro Hoof It Galena (15 mins)bro Blaum Bros Distilling Co (12 mins)bro Galena Cellars Vineyards and Winery (7 mins)bro Dowling House (13 mins)bro Galena River Trail (16 mins)bro Belvedere Mansion and Gardens (14 mins)bro P.T. Murphy’s Magic Theater (12 mins)bro Linmar Gardens (14 mins)brbrbrOur home is perfect for friends and families, open all year round and welcome to everyone from all over the world! brYou will get a personalized front door key code before check-in. No need to meet anyone for physical keys.brYou will have access to whole home (except owners closet).brbrPrior to your arrival, you will be sent a relatively comprehensive guidebook which includes house rules, things to do around town, check in-instructions, emergency contact information, and other general info such as what essential toiletries we provide.brbrYou will be able to self check-in upon arrival.brbrWe are always available to answer any questions, help prepare for your trip, assist with any special requests you may have, and provide local tips or suggest attractions, but our level of interaction is up to you.brbrWe have one security camera that views the front porch and driveway. brbrWe have three sensors (two inside and one outside) to detect noise levels (NO audio recording) and cigarette smoke.

Seasonal Lake Views/HotTub/Movie Room! Cozy! Forest Vibes! Sunroom, Decks, Grill

Galena, Illinois, United States

Bed

Bath

Sleeps

$201.62

Living Room/Dining Room, wood fireplace, kitchen, deck and gas grill, Queen Bedroom on upper floor, Full Bath on Upper Floor, and Twin Bedroom on Main Level, Bathroom with Toilet off of Kitchen Area, WIFI, and board games/card/poker chips. Wooded area, 3 Season Lake View, located in Galena Territory just miles away from some unique shopping and dining. Take a ride on the Trolley to view beautiful historic Galena. Enjoy the Owner's Club Facility which has a Game Room, Indoor/Outdoor Pool, Workout Room, basketball courts, tennis courts, enjoy horseback riding at the Shenandoah Riding Center.

Cottage

Cozy Hideaway with 3 Season Lake View

Galena, Illinois, United States

Bed

Bath

Sleeps

$224.68

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.brbrI can accept a 1-night stay for a weekend night if the date is within 2 days. Otherwise, Friday or Saturday nights are a mandatory 2-night minimum stay meaning: Thursday/Friday, Friday/Saturday, or Saturday/Sunday.brbrOne Bedroom: King in master, queen Murphy bed in living area. Maximum occupancy 4.brbr***Please review ALL details in each field***brbrThe Resort maintains a high standard through its maintenance, upgrade, and refurbishment program. As a result the unit characteristics may change from time to time and vary. brbrAt check-in, the resort Front Desk requires a $250 security deposit HOLD on a credit or debit card for potential damages. This HOLD will be released upon departure.brbrABSOLUTELY NO PETS ALLOWED! If you have a service animal, you must let us know in writing prior to booking.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

All the comforts of home!

Galena, Illinois, United States

Bed

Bath

Sleeps

$580.24

Relax, unwind, & explore in Galena Territory! Hawk's Hideaway is the perfect stylish escape to stay with family or friends. brbrYou will be staying in a charming modern rustic cabin near the heart of The Galena Territory with plenty of privacy in the woods. You will stay on almost 1 acre of land adjoining a large greenspace and the Old Horse Camp Loop nature trial. This is a can't miss Galena Territory escape!

Cabin

Modern Hideaway Hot tub Great for large groups!

Galena, Illinois, United States

Bed

Bath

Sleeps

$615.49

pstrongNorth Star, Galena IL/strong/p pstrongEntire Home Vacation Rental, 4 Bed, 4 Bath, 10 Person Occupancy br/strongThis rare find offers so much space you will forget you are not the only one in the house! The main floor of the home has a large gathering area, dining room, kitchen and all season room. Access the upper deck from the dining or all season room and find a dining table and fire table to enjoy the views by day and by night. Exit the opposite door and you will find a quaint garden and grill for preparing those 'stay at home' meals. The gathering area has a wood burning fireplace and the all season room enjoys a wood stove for additional warmth on those crisp winter days. Also on the main floor you will find a full bath plus two bedrooms, one with a queen bed and a set of full size bunk beds, and the second with a queen and a twin bed./p pThe upper level occupies a primary suite with a king bed, grand bathroom with jetted tub, and a large loft outfitted with toys and play furniture. You will also find a computer for your use while you are our guests./p pThe lower level will amaze you! Here you will find the fourth bedroom with a queen bed, two full baths, and a fantastic game/family room with air hockey, slot machines, bar, jukebox, large screen TV, second fireplace, and wait..., a second full kitchen! The sliding door will lead you straight to the covered hot tub, available year round. The fire pit is a perfect spot to end the evening with stories of the days adventures./p pstrongGuest Access br/strongYou will have access to the Galena Territory Owners' Club and all its amenities such as indoor and outdoor pools, game room, fitness center, gym, tennis and basketball courts, and more.br/p pstrongThe Area br/strongGalena IL has hundreds of unique gift and clothing shops, antique stores, art galleries and artist studios. It boasts a rich performing arts community, live music, gourmet delights, as well as a multitude of museums, wineries, historical sites and tours. There are opportunities to enjoy the outdoors golfing, skiing, playing tennis, boating, fishing, zip-lining, hiking, horseback riding, hot-air ballooning and much more.br/p pstrongGetting Aroundbr/strongA car is necessary to see all that Galena and the surrounding area has to offer! Taxi services are available./p

Wow Sunsets/Hot Tub/Fab Game Room/Fire Pit! Close to Owners' Club, Golf and Spa!

Galena, Illinois, United States

Bed

Bath

Sleeps

$868.06

Escape to this historic 7-bedroom inn in Galena—perfect for group getaways, family gatherings, and unforgettable stays just steps from downtown.brbr✨ HIGHLIGHTSbr• Full private access to entire 7-bedroom inn br• Walk to Main Street (1.5 blocks) ‍♀️br• Smart TVs, mini fridges + coffee in every room ☕br• Each bedroom has private ensuite bathroombr• Built in 1838 with historic charm ✨br• Outdoor patio with firepit + seatingbr• Free off-street parkingbr• Fast WiFibr• 12pm check-in & check-outbrbrWelcome to Briarstone Inn @ A&D Rise Getaways!brbrStep into one of Galena’s most historic homes—beautifully preserved and thoughtfully updated for modern comfort. With exclusive access to all seven private suites, this one-of-a-kind stay offers the perfect blend of boutique charm and group-friendly convenience.brbrWhether you’re gathering with family, celebrating a special occasion, or planning a group retreat, this space was designed to bring people together—while still giving everyone their own private space to unwind.brbr ️ SLEEPING ARRANGEMENTSbrEach of the 7 private suites includes:br• Queen bed with plush pillow-top mattressbr• Private ensuite bathroombr• Smart TV with streamingbr• Mini fridge + Keurig coffee station ☕br• Smart lock entry for privacybr• Vintage-inspired décor with historic charmbrbr ️ SHARED & OUTDOOR SPACESbr• Cozy shared living room with seating + board gamesbr• Outdoor patio with firepit br• Gathering spaces perfect for relaxing or socializingbrPlease note: Fireplaces are currently inoperablebrbr LOCATIONbrStay just steps from the heart of Galena:br• 1.5 blocks to Main Street (shops, restaurants, galleries)br• ~16 minutes to Chestnut Mountain Resortbr• ~22 minutes to Dubuquebr• Surrounded by wineries, golf courses, trails & outdoor adventuresbrbr⭐ WHAT SETS THIS PROPERTY APARTbr• One of Galena’s oldest historic inns (built in 1838)br• Walkable location (huge for Galena )br• Exclusive access to all 7 suites—perfect for private groupsbr• Boutique-style stay with hotel-style amenitiesbr• 5-star guest support from A&D Rise Getawaysbrbr✨ BEFORE YOU ARRIVEbrGuests receive a detailed digital guide with local recommendations, dining spots, and everything you need to plan your stay.brbr OPTIONAL ADD-ONSbrAvailable after booking:br• Grocery pickup servicebr• Birthday & celebration packagesbr• Family game night packagebrbr ️ EXCLUSIVE PERKbrEnjoy special guest discounts at a local favorite: Campeche Restaurant br(Details shared after booking)brbr GRILL INFObrCharcoal grill available—please bring your own charcoal and clean after use.brbr STARTER SUPPLIESbr• 1 roll of toilet paper per bathroombr• 1 roll of paper towelsbr(We recommend bringing extras for larger groups.)brbr GOOD TO KNOWbr• Check-in: 12 PMbr• Check-out: 12 PMbr• High-speed WiFi throughoutbr• Free off-street parkingbr• No petsbr• No washer/dryer (laundromat ~1 mile away)br• Accessibility Note: Bedrooms 1-5 are on the second floor, all bedrooms require at least a few stairs.br• The City of Galena requires Small Inns to have an Innkeeper live on site. There is an 8th room that will be occupied by the Innkeeper.brbr Save this listing by clicking the ♥ to easily find it later!brbrWe can’t wait to host you at Briarstone Inn @ A&D Rise Getaways!br*An additional cleaning fee will be charged for any property left in an unusually dirty condition following a guest’s stay. *

Briarstone Inn | Historic 7-Room Inn w/ Private Baths | Walk to Downtown Galena

Galena, Illinois, United States

Bed

Bath

Sleeps

$574.04

Unique, enormous 2,500+sqft 4 bedroom ( 3 king beds & one room with 2 queen beds)2 bathroom suite right in the center of Main Street! Experience Galena’s Main Street shopping and restaurants with the added assurance that your luxury loft is just steps away and yet as private as you could ask for! Sleeps up to 10 people!brAlso great for hosting party events as the main living area is absolutely enormous!

The Loft Suite Sleeps 10! Located overlooking Main Street in downtown Galena, IL

Galena, Illinois, United States

Bed

Bath

Sleeps

$252.19

Golf Packages New for 2025 - inquire for more details!brbrWelcome to The Bogey at Oak Glen, where you'll experience a beautiful and spacious townhouse that will take your breath away from the moment you step in. The upper level boasts a bedroom with a king bed and an ensuite bath, while downstairs features an open and modern living area with a wood-burning fireplace, smart TV, and sofa sleeper. The open kitchen allows all guests to spend time together in the living areas without separation. This floor also includes a second bedroom with a king bed and an ensuite bathroom. Linens for the two king beds and towels are provided, but please plan to bring linens (sheets/blanket/pillows) for the sleeper sofa if you need to use it to accommodate your group.brbrFor golf enthusiasts, head to the deck off of the living room for a view of the 1st hole and enjoy a glass of wine and a BBQ on the gas grill during your stay. brbrEnjoy the wonders of a Dark Sky Community -- The Galena Territory is a Dark Sky Community offering a place to star gaze free from light pollution. brbrThe Bogey is dog-friendly, but please note that only hypoallergenic dogs are allowed, with a maximum of two up to 30 lbs each. A $150 dog fee applies.brbrLocated just minutes away from Eagle Ridge Resort, the newly expanded and gorgeous Stonedrift Spa, Lake Galena, and walking/running trails, The Bogey at Oak Glen is the perfect getaway spot. Staying at The Bogey also offers access to The Galena Territory Owner's Club amenities, with six access cards provided for the use of the indoor and outdoor swimming pools, basketball, pickleball, and tennis courts, Lake Galena, and the Marina.brbrYou are just steps away from the South Course Club House, a four-minute drive to the Country Store, a five-minute drive to the Owners Club (indoor/outdoor pool, fitness center, tennis and basketball courts, and game room), a 12-minute drive from Downtown Galena, and a 15-minute drive to Piggly Wiggly and Walmart if you need to pick up any essentials or supplies for your trip. brbrWe strongly encourage purchasing travel insurance to protect your plans -- we do not have a weather or COVID-specific cancellation policy.

Fresh! 2BR Golf Villa w/ King Beds, Dog-Friendly, Amenity Access, Near Trails

Galena, Illinois, United States

Bed

Bath

Sleeps

$259.65

A rental space designed for families, couples or individuals looking to unwind & relax in the heart of the Galena Territory.brbrWhat this place offersbrScenic viewsbrGolf course viewbrBathroombrBathtubbrHair dryerbrCleaning productsbrShampoobrConditionerbrBody soapbrHot waterbrBedroom and laundrybrFree washer – In unitbrFree dryer – In unitbrEssentialsbrTowels, bed sheets, soap, and toilet paperbrHangersbrBed linensbrExtra pillows and blanketsbrRoom-darkening shadesbrIronbrClothing storage: closet and dresserbrEntertainmentbrHDTV with RokubrFamilybrFireplace guardsbrBoard gamesbrHeating and coolingbrCentral air conditioningbrIndoor fireplace: wood-burningbrCeiling fanbrCentral heatingbrHome safetybrSmoke alarmbrCarbon monoxide alarmbrFire extinguisherbrInternet and officebrWifi – 16 MbpsbrVerified by speed test. Stream HD videos.brKitchen and diningbrKitchenbrSpace where guests can cook their own mealsbrRefrigeratorbrMicrowavebrCooking basicsbrPots and pans, oil, salt and pepperbrDishes and silverwarebrBowls, chopsticks, plates, cups, etc.brFreezerbrDishwasherbrElectric stovebrSingle ovenbrCoffee maker: drip coffee maker, Keurig coffee machinebrWine glassesbrToasterbrBaking sheetbrBlenderbrCoffeebrLocation featuresbrPrivate entrancebrSeparate street or building entrancebrFree resort accessbrGuests can use nearby resort facilitiesbrOutdoorbrPrivate patio or balconybrShared backyard – Not fully fencedbrAn open space on the property usually covered in grassbrOutdoor furniturebrOutdoor dining areabrParking and facilitiesbrFree driveway parking on premises – 2 spacesbrServicesbrSelf check-inbrKeypadbrCheck yourself into the home with a door code

The Galena Getaway Townhouse in Galena Territory

Galena, Illinois, United States

Bed

Bath

Sleeps

$580.2

Galena Haven, a beautiful 3br/3bth custom decor home, and lots of fun things to do!br- Enjoy a private hot tub (open all year!) br- Axe throwing game (plastic)br- Relax by indoor wood fireplacebr- Surrounded by 2 acres for privacy, especially in the back of the home with woods. br- Outdoor firepit with wood providedbr- Year round community indoor pool and seasonal outdoor pool ‍♂️ ‍♀️ br- Popcorn machine br- snow cone maker br- cotton candy makerbr- air hockey/ping pong tablebr- hammockbr- Ms. Pac Man Arcade gamebr- Large Connect 4 gamebr- sleds and more for winterbrbr A wonderful place for a family getaway! Kid and dog friendly! Up to 2 dogs allowed.br brBedrooms-brPrimary suite - king bed. Smart TV. On main floor. Attached bathroom with shower and separate jacuzzi tubbrBedroom 2 - king bed. Smart TV, attached bathroom with showerbrBedroom 3 - Bunk room- great quality, sturdy full over full bunk beds with stairs. Smart TV , tons of games ♟️ . Attached bathroom with showerbrSleep and rest in pleasure! All bedrooms with memory foam, new mattresses.brbrMain floor living room/dining room-br-Smart TVbr-Comfortable seatingbr-gamesbr-screened in porch with gas firepitbr-Outdoor deck with grillbrbrDownstairs living room has big comfy couch.br-ping pong/air hockeybr-Ms Pacmanbr-Washer/DryerbrbrLocation:br10-15 Min to downtownbr10 Min to vineyardsbr5 Min to owners club/poolbrbrKitchen-brVery well stocked!br- Crock Potbr- Full set of dishesbr- Baking warebr- Snow cone, popcorn and cotton candy makersbr- Dishwasherbr- Coffee pot (drip and French press)brbrKid friendlybr- booster chairbr- pack and playbr- infant bathtubbr- booksbr- kids dinnerware (BPA free)br- lots of toysbr- laser tag gunsbrbrWe do not ask guests to do chores before leaving, so you can relax :)brbrThe backyard has a Backyard has fire pit and outdoor seating. Also a screened in porch to enjoy the sounds of nature, bird watch. Enjoy the Dark Sky neighborhoodbrEnjoy the many amenities of the Galena Territory- community indoor year round pool, gym, and seasonal outdoor pools. Lake Galena is a scenic lake, great for fishing and boating (not swimming). Kayaks and pontoons can be rented from the Galena Territory. Also a beautiful waterfall (10-15 min drive), riding stables and more! Downtown Galena is really special- amazing shops, restaurants, wine tasting, historic sites, Haunted Tours, Trolly Tours, and more. Chestnut Mountain is about 25 min drive away, for skiing, zip lining and more. brbrDogs are welcome if well behaved. Extra pet fee will apply.brbrFamily managed property :) We are so excited to host you!brbrParking is free, and on the property. brbrPlease note, the property is surrounded by woods, so there are insects outside and occasionally inside. brbrAmazing nearby attractions, including golfing, wineries, fishing, hiking, horse stables and more. Downtown Galena is approximately at 10 minute drive, and has trolley tours, haunted ghost tours, fabulous restaurants and shopping and more. brbrYou will have the entire house other than small locked owners closet. brbrWe are family owned home. We will share our cell phone upon booking in case issues arise. brbrThis home is in the Galena Territory- it's surrounded by wooded areas, trails, and community amenities. brbrThere isn't easy public transportation so you will need a car. Uber is only sometimes available. brThere is plenty of parking.brbrBlink doorbell with camera in front of house with view of front of house/driveway.brbrWe provide firewood. You may need to bring kindling wood/cardboard, although we try to provide when able. brbrWe do not give refunds due to weather. We strongly encourage everyone to buy travel insurance.

Cabin

Hot tub, Wood Fireplace, Firepit, Pool/Marina Access

Galena, Illinois, United States

Bed

Bath

8

Sleeps

$375.28

Welcome to Gazette Suites - On Main! You will love our two-bedroom two-bathroom w/loft luxury suite overlooking Main St. We include a dedicated parking spot. This home is NOT pet-friendly. 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.brbrThis charming, historic, 2-bedroom home with a loft is located in the heart of downtown Galena, offering a unique blend of character and modern comfort. With its prime location and distinctive style, this home is a perfect mix of old-world charm and contemporary living in one of Galena’s most sought-after areas. Nestled above Main Street, the home boasts stunning views of the bustling town below, with its quaint shops, cafes, and rich history steps away. The spacious interior features original architectural details, including exposed wood beams, hardwood floors, and large windows, inviting abundant natural light. The cozy bedrooms featuring King beds offer a restful retreat. One is located in the loft up a set of spiral stairs with it's own private bathroom and space to spread out in, the other King on the main level with a private bath. The King bedroom on the main level also has a trundle pullout bed for your +2. Our large kitchen will be an amazing place to entertain, We include a crock pot, blender, Keurig and regular coffee maker. *Please note there are approximately 20 steps to the home entrance on the second floor.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. If you cancel before the 14 days, you will receive the first payment with a cancellation fee of less than $35. 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 your 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 that this be signed and filed within 48 hours of receiving it to guarantee your reservation. You must be 25 or older when booking and be present during the entire stay.brbrOur cancellation policy is not flexible, so please review it carefully. We highly recommend travel insurance. Check-in details are sent 3 days prior to 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 the morning of your arrival. The check-in details will cover this process. Please note we do not provide toiletries at home. We will provide dish soap, dish detergent, hand soap, laundry detergent and paper products.brbrIf we are not available for your dates please check out our sister suite - Gazette Suites ON Commerce!

Apartment

Prime Main St Suite! Walk 2 Dining & Shopping! Spiral Stairs to Loft Bedroom!

Galena, Illinois, United States

Bed

Bath

Sleeps

$447.21

Beautiful 3 bedroom 3 bath Golf Course View home.brbrThis immaculate free standing 3 bedroom 3 bathroom home is centrally located within the Galena Resort core just across the street from the limited access Walnut Hill heated swimming pool.brbrThis beautiful Galena, Illinois vacation rental home has over 1800 sq. ft. of single level living space overlooking the 15th fairway of the North golf course in the Galena Territory, just minutes from downtown Galena Illinois.brbrIt boasts a large deck with Weber grill and screened porch, perfect for your private meals in relaxed setting. This tastefully decorated home offers lots of natural sunlight and fantastic views from large windows.brbrThe Master Suite Features: king bed, a private bath with separate tub and shower. 50 Smart TV.brbrThe Second Bedroom Features: king bed, a private bath with a shower/tub combination and Smart TV.brbrThe Third Bedroom Features: Set of rustic bunk beds with twin on top and queen on the bottom, a private bath with a shower/tub combination and Smart TV.brbrThe Great room has a bluetooth stereo system, 55 Smart TV provided for your enjoyment.brbrFor meals at home the complete kitchen with brand new stainless steel appliances and cookware is adjacent to the dining area. The dining area seats 6 people.brbrThe Galena Resort has 63 holes of scenic play for the golfing enthusiast and a short walk will bring you to the Galena Golf Practice Range as well as the entrance to a lovely nature trail.brbrIf fishing is on your to do list, the water in Lake Galena is stocked with fish from perch to tiger muskie. Boats and tackle are available for rental at the marina.brbrThe Galena Territory General Store is just a short drive up the road where you will find groceries, spirits, bakery goods and a great deli for freshly made sandwiches. The store also offers a self serve gas station.brbrYou can enjoy fine dining in an elegant setting at the Highlands Restaurant or if something lighter is in order, stop for a sandwich and drink at the friendly lounge inside Eagle Ridge Resort. brbrAlso, you'll find Chestnut Mountain, the premier Galena ski resort with Alpine Slides for summer fun only minutes from your door!brbrFor your protection the house is equipped with a Ring Security System that includes a camera on the front porch monitoring the stairs, walkway and driveway.

Pool just steps from home on the 15th fairway

Galena, Illinois, United States

Bed

Bath

8

Sleeps

$915.59

CELEBRATE, RELAX AND ESCAPE ANYTIME OF YEAR IN BEAUTIFUL GALENA LUXURY! brbrImagine those charming Currier & Ives paintings of hilly countrysides. That's the perfect beauty of The Galena Territory. And there is no more satisfying and exciting way to enjoy this comfort, beauty and timely refuge than staying at Coyote Cove.brbrLuxuriously relax, anytime, during a fun escape to our lovely vacation rental home near Galena, IL. Every season is a special delight. Refresh in the Spring breezes on the porches and decks, play in the Summer sun; marvel at the festival of Fall colors, or enjoy cozy Winter warmth by the huge hearth! brbrPopular dates book fast, and it's never too early to think about reservations. Reserve your dates soon to get your first choice. A truly luxurious escape is when you get away while others work! Steal away for weekdays, too, any time of year. So, indulge yourself and enjoy much lower midweek rates.brbrYou’ll be captivated by the breathtaking setting, casually sophisticated décor, convenience and amenities galore! Open-air hot tub, three large gathering rooms, big HD TVs, pool table, pub table, huge kitchen island (w/5 barstools), silky linens and superior mattresses – SPACE, COMFORT and DREAMY EASE are yours at Coyote Cove. There’s a big stone fireplace and hearth waiting to greet your family or dear friends! Multi-generational groups rave, “It’s like this house was made just for us!”brbrExcellent location! Coyote Cove is only 3 turns from US Hwy 20. And offers the closest access to Galena’s restaurants, shopping and historic charm. It couldn’t be better!brbrSeat 12 adults, comfortably, at the custom Harvest Table, plus seats for 5 more at kitchen island (note: maximum legal occupancy overnight is 14 persons). Thoroughly outfitted kitchen is a group-cooking delight, down to the cookie sheets and cooling racks. Aromas of hot cocoa, warm cookies, cider … endless memory-making possibilities for all. Plenty of large, beautiful baking dishes, a big slow cooker, even a large roaster, for brunch in pajamas, maybe chili & cornbread lunches, and decidedly relaxed dinners! Enjoy easy access to the gas grill, with unforgettable views! brbrThe large hot tub is a vacation all by itself – day or night! Giant, plush hot tub towels are here for you. Find action, friendly competition and laughter around the pool and pub tables. Catch favorite sports and movies, from the luscious leather furniture (adjoining media room), on the largest of Coyote Cove's three HD TVs. Marvel at the Vista Room’s spectacular views - Lake Galena, the glorious hills, woods and countryside. An ideal spot for reading, board games, playing cards, scrapbooking, earnest conversations and TV. The sofa bed creates a private 6th bedroom. The views, the views, the views! brbrSavor artfully inviting bedrooms (w/dedicated bathrooms), luxury high-count sheets and charming bedding (3 King, 2 Queen & comfy gel mattress on sleeper sofa). Excellent mattresses promise your delightful days end with nightly rewards!brbrPool players, golfers, shoppers, fishers, nature lovers and sports and movie watchers, this is your dream-come-true home! Brand new indoor/outdoor pool, weight room/rec center and more at the Owners Club, first-rate Riding Center - recreational options for absolutely everyone.br brCoyote Cove’s many decks, large screen porch and big yard are privately perfect! It is just 5 minutes (and three turns) to superb golf! Lake Galena offers fantastic fishing and small motor boating, one of three great play areas for the kids to burn off some energy, and tennis courts. The many hiking trails – gems of The Galena Territory - are professionally maintained, and are enjoyed by all ability/stamina levels. brbrReconnect with nature and surround yourself in relaxing luxury and comfort -- away from all your other cares. Come to Coyote Cove! brbrPlease review availability, rates and policies below. You'll always treasure your time at Coyote Cove! Thanks, and enjoy your stay!

Escape! Hot Tub, Fire Pit, 3 Decks, WiFi, Pool Table

Galena, Illinois, United States

6

Bed

5

Bath

14

Sleeps

$260.71