Home Vacation Home Rentals By Owner In Galena, IL

Showing 291 Of 291 Vacation Rentals
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Exceptional(1)

$1,185

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Private Vacation Home

Brand New Home! Hot Tub Massage Chair Game Room, Dog Friendly, Fun for all ages!

Galena, Illinois, United States

Escape to The Blissful Stay, a 5-bedroom, 4.5-bath retreat in the heart of the Galena Territory. Perfectly located just minutes from Lake Galena, Owners Club and Eagle Ridge Resort, this home offers the best of both worlds: stylish interiors, endless entertainment options, and serene outdoor living. Whether you’re planning a wedding, family reunion, golf weekend, wine getaway, or ski trip, this luxe retreat is designed for making memories.brbr Owners club is open regular hours during the holidaysbrbrAt Galena Bliss, the days unfold effortlessly. Start with coffee on the deck as the hills wake around you, then head out for shopping, golfing, hiking, or a stroll by Lake Galena. Back at the house, the lower-level multi-purpose room is a perfect gathering space for board games and a movie, while the garage game room brings out everyone’s competitive side and provides convenient storage for your golf clubs or ski gear.brbrWhen evening comes, choose your rhythm: a soak in the hot tub under the stars, a glass of wine by the electric fireplace in the living room, stories shared around the outdoor firepit, or quiet time in one of the cozy bedrooms. Guests also enjoy access to resort-style amenities at the Owners’ Club, including a seasonal outdoor pool, year-round indoor pool, fitness center, sports courts, and scenic trails.brbr⭐ Amenities You’ll Love ⭐br-Private hot tub on the patiobr-Massage chair br-Fire pit with Adirondack seating, we provide fire woodbr-Fully equipped kitchen for group mealsbr-Private Game & movie rooms for family funbr-Basketball hoop in the driveway br-Access to the Galena Territory Owners’ Club (indoor & seasonal outdoor pools, basketball, tennis, fitness center, game room, seasonal craft room & more)br• Scenic Lake Galena for boating & fishingbr• Shenandoah Riding Center for horseback adventuresbr• 30+ miles of trails through protected greenspacebrbr❤️ Click the Heart icon to save this home to your wishlist! brbr Spread across three levels, Galena Bliss is thoughtfully designed for both gathering and unwinding.br• Main Level – The heart of the home, with a cozy living room featuring an electric fireplace, a fully equipped kitchen, and a dining area that opens onto the deck — perfect for morning coffee or evening meals outdoors. This level also includes the garage, transformed into a private game room with convenient storage for golf clubs or ski gear.br• Lower Level – A multipurpose room for gathering, movies, listening to records, and board games, plus walkout access to the backyard where you’ll find the hot tub and firepit — the ideal spot for evenings under the stars.brbr✨ Bedrooms & Baths ️brbrFive cozy bedrooms provide versatile sleeping arrangements for families and groups.br✔️ Upper Level – Four bedrooms:br• Primary Bedroom – King bed with luxury Helix mattress & ensuite bathbr• Bedroom 2 – Queen bed with Helix mattressbr• Bedroom 3 – Queen bed with Helix mattressbr• Bedroom 4 – Queen daybed, Full daybed, and futon (ideal for kids or flexible sleeping)br✔️ Lower Level – One bedroom + multipurpose room:br• Bedroom 5 – King bed with Helix mattressbr• Multipurpose Room – Sleeper sofa (“short queen” size) for additional guestsbrbr Each bedroom is equipped with a Roku smart TV, mirror, luggage rack, alarm clock, and hangers for your convenience.br With four full bathrooms (2 ensuites) mornings run smoothly—even with a full house. brbr✨ Game Room:brYour own private game room located in the garage — temperature controlled with on-demand heating and air conditioning, so it’s comfortable year-round. Perfect for fun after hours or when you’d rather stay in:br• Massage chair for relaxation anytime you wishbr• Pool table that converts into a ping-pong tablebr• Shuffleboard that also doubles as a bowling gamebr• Foosball tablebr• Wall-mounted games like backgammon and tic-tac-toebr• Two-hole practice putting green for golfers to sharpen their skillsbr• Roku smart TV br• EV charger and storage for golf gear and morebr• A fun “Meet Me in Galena” neon sign for photo opsbrbr✨ Other ways to play: board games, ️Arcade with 12 classic games (Ms PAC-MAN, Galaga, Dig Dug & more), Plinko Game, Axe Throwing, volley ball & cornhole for the back yard, basketball in the driveway, and more!brbr✨ LocationbrOur home is just:br 7 minutes to the Owners’ Club (pools, fitness center, courts, game room)br 6 minutes to Eagle Ridge’s North Golf Coursebr 7 minutes to Lake Galena’s marina for boating and fishingbr 11 minutes to Shenandoah Riding Center for horseback adventuresbr 11 minutes to historic downtown Galena with its shops, dining, and historybr 24 minutes (15 miles) to Chestnut Mountain Ski Resort for winter fun and Mississippi River viewsbr 40 minutes (28 miles) to Mississippi Palisades State Parkbr 1 hour 4 min (46 miles) to Field of Dreams Movie Sitebrbr✨ Why You’ll Love It HerebrbrWhether you’re planning a wine-tasting weekend, a family holiday, or a relaxing getaway, our home puts you at the center of it all. From eagle watching at Lake Galena to browsing Galena’s 19th-century Main Street, every day offers something new to discover.brbr✨ Book your stay today and experience the perfect balance of relaxation, recreation, and Galena charm.
Bed 5

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Bath 4

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Sleep 12

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$754.08

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Private Vacation Home

Lakeside is a spacious, flowing home located on the north shores of Lake Galena

Galena, Illinois, United States

Almost Heaven Rentals Galena who has been in the business of managing vacation rental’s since 2002 is happy to offer you this vacation rental.brLocated in the North end of The Galena Territory on the North Cove you will treasure the gorgeous views of Lake Galena as you enjoy two walk out balconies each with breathtaking lake views. br brAs you enter this flowing tri- level, five bedroom, (6 bed), five and a half bath home you will see a firewood stack for your use at the outdoor fire pit and wood burning fireplace.brbrThe main floor has an open floor plan. There are two bedrooms on the main floor of this home, one king bed suite with a sitting area and en-suite bathroom and one with two queen beds and a full bathroom next door. The kitchen has a large island with an eating counter and four stools, it is open to the dining area, living room and gorgeous two story wood burning fireplace. The main floor has a powder room off the kitchen as well. Behind the kitchen you will find the three seasons room and walk out entrance to the large deck overlooking the lake as well as a laundry room making this house ideal for longer vacation stays. The deck has a gas grill complete with a back up propane tank and dining table and chairs. brbrThe lower level has a second suite complete with a gas fireplace, private bath with jacuzzi tub and shower stall. At the other end of the lower level is the fifth bedroom with an attached bathroom also offering a jacuzzi tub and a shower stall. Between the two lower level bathrooms is the family room with a card table, leather furnishings and a TV. The hot tub is located on the lower patio just outside of the family room. brOn the back end of the family room is a bar room with a drink refrigerator, bar to sit at and four bar stools. Walking out the door in the bar room you will find a limestone rock seat rimmed fire pit for marshmallow roasting, chatting and star gazing in to the wee hours. This home comes with six proximity cards. Guests of this home enjoy all of the homeowners amenities within The Galena Territory including the two pools, fitness center, indoor and outdoor basketball courts, pickle ball and tennis. Lake Galena is about ten minutes away and can be accessed by calling the marina to reserve a pontoon boat or kayak. Whether this is your first time to the Galena Territory or your fiftieth this home and area have plenty to explore. Almost Heaven Rentals Galena management team lives in the area and are personally hands on, should an issue arise.
Bed 5

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Bath 5

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Sleep 12

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$334.79

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Private Vacation Home

Perfect Getaway - Cozy Cottage in The Galena Territory

Galena, Illinois, United States

The moment you walk into this updated home, you'll begin to breath easier. With 3 bedrooms and great gathering spaces, your whole group will enjoy your time together. Great for families, couples or girl's getaways.brbrThe Master suite (lower/living level) has a king-sized bed and ensuite with huge walk-in shower and double vanity. The upper level (entrance level) features 2 additional bedrooms and a second bathroom with a large jetted tub. brbrThe open concept living/dining/kitchen area on the lower level allows for easy conversations and hanging out. Enjoy a meal on the screen porch in the summer or the warmth of a crackling fire in the winter.brbrYou'll likely see wild turkey and deer cross the lawn. If you're lucky, you might catch a glimpse of Glenn the Galena Groundhog who lives under the deck. On clear nights, you can see the entire Milky Way.brbrRelax with our easy check in and check out process - no long list of things to do before leaving.brbrWe are pet friendly with a $50 pet fee for additional cleaning often needed when furry friends come along. Please be sure to add pets to your reservation and the fee will be added.brbrAs guests of The Galena Territory, you have access to indoor and outdoor pools, world class golf, game room, basketball/pickleball courts, hiking trails, horse riding and of course Lake Galena for fishing and boating. brbrIt's an easy drive (15 min) to charming downtown Galena shops and restaurants and Chestnut Mountain ski area. brbrGalena offers a balance of quiet relaxation with plenty to do!
Bed 3

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Bath 2

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Sleep 6

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Exceptional(52)

$680.34

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Private Vacation Home

Cozy cul de sac location on the northern quarter of the Galena Territory

Galena, Illinois, United States

brAlmost Heaven Rentals Galena has been in the business of managing vacation rental’s since 2002 and is happy to offer you this vacation home. Harmony house is located on the north side of The Galena Territory. Walk right in via the stair free entrance to this home with its open floor plan. Harmony house has 5 bedrooms and 5 bathrooms including one bedroom and bathroom that is wheelchair accessible. brbrOn the main level, you are greeted by a warm well furnished family room with a vaulted ceiling and a gas fireplace that can be started with the flip of a switch. Attached to the living room and separated by an island counter with three stools is the fully equipped open kitchen with a dining table that will accommodate 12 people.brbrThrough sliding glass doors, just off the dining area, is a secluded deck equipped with a gas grill complete with a back up propane tank as well as a dining table and chairs. Attached to the deck is a repeat guest favorite, a screened-in porch, with refreshed wicker furnishings perfect for reading books, chatting with friends and watching the wildlife of The Galena Territory leaving the bugs outside.brbrWith 2 bedrooms on the main floor behind the kitchen and living room this home is wonderful for multigenerational gatherings. One guest bedroom has a king size bed with a bathroom next door in the hallway that can double as a guest bathroom for the living room. The other guest bedroom has a king size bed and an attached bathroom, that is wheel chair accessible. brbrThe upstairs has a quiet reading/sitting area that overlooks the downstairs living room and the back yard. There are 2 bedrooms upstairs both with attached bathrooms one has a queen size bed with a walk in shower, the other has a king size bed with a tub shower combo.brbrThe fifth bedroom and bathroom are located on the lower level. This bedroom has a king size bed, its bathroom is next door with a shower stall and it can double as a guest bathroom for the TV/recreation room. Also on the lower level is a recreation room with a ping-pong table, a table for games or snacks and a conversation seating area. This living space also includes the sleeper sofa and the entertainment center that features a large smart TV for movie nights. brBehind the recreation room is a laundry room with two washers and two driers, this house is well suited for longer stays. brbrOff the recreation room, through sliding glass doors, is the lower level patio deck with outdoor furniture and a lovely 8 person hot tub perfect for morning coffee or star gazing. For the sunrise watchers there are two comfortable chairs on the covered front porch for your coffee. brbrThis home is located about seven minutes from The Galena Territory homeowners club and ten minutes to downtown Galena. Six proximity cards are available for your use in accessing the homeowners club and will be at the home when you arrive. Guests of this home enjoy all of the homeowners amenities in The Galena Territory including the two pools, fitness center, indoor and outdoor basketball courts, pickle ball and tennis. Lake Galena is about ten minutes away and can be accessed by calling the marina to reserve a pontoon boat or kayak. Whether this is your first time to the Galena Territory or your fiftieth this home and area have plenty to explore. Almost Heaven Rentals Galena management team lives in the area and are personally hands on, should an issue arise.
Bed 5

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Bath 5

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Sleep 12

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$202.89

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Private Vacation Home

Creekwood Haven - Quiet 2 BR, Fireplace w/Access 2 Owner's Club/Pools

Galena, Illinois, United States

This golf villa is approximately 7 miles or 15 minutes to Downtown Galena. 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.brbrCreekwood Haven is designed with your comfort in mind. It’s a 2-bedroom, two full bath, split-level golf villa with updates throughout. The open concept kitchen (with all new kitchen appliances), dining area, and living room flow out to the deck, perfect for breakfast outdoors while enjoying the wooded views of the South Golf Course. Enjoy the complimentary coffee bar and relax by the wood-burning fireplace in the living room (we supply the wood). Just off the deck is a gas grill for your use (we supply the propane). The main level bedroom with a super comfortable Queen-size bed is just steps from a full bath and the laundry area. The cozy Master bedroom upstairs has vaulted ceilings and a Queen-size bed with access to a private bathroom. Overlooking the living room and kitchen is the loft, the perfect sitting area with a sofa that converts to a queen-size bed, comfortably accommodating 2 more guests. After a busy day in the Galena area, Creekwood Haven is a quiet, relaxing place to come home to!!brbrAs our guest, you will have access to the GTA Owners Club. The indoor pool is open year-round and the outdoor pool is open Memorial Day through Labor Day (sometimes longer). The club is an exclusive amenity that can be used only by Galena Territory property owners and their guests. The Owners' Club includes an indoor swimming pool, outdoor swimming pool w/slides, a kiddie pool, fitness room, game room, indoor/outdoor basketball courts, tennis courts, seasonal snack bar, free WiFi, and outdoor playground. Don’t forget to visit Lake Galena, The Shenandoah Riding Center and hiking trails throughout the 6,800-acre property. Disclaimer: 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 to their closure.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. 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 receipt to guarantee your reservation. You must be 25 or older at the time of booking and present during the entire stay. 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 the travel insurance offered at check out.brbr**Check-in details are sent 3 days before your arrival to the email on file. This includes the address, 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 check in details will cover this process.
Bed 2

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Bath 2

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Sleep 6

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Exceptional(9)

$479.55

/ Nightly
Private Vacation Home

Galena Territory, dog friendly, 4BR/3.5 bath resort home, 2 ensuites, firepit

Galena, Illinois, United States

After 2 years with a property manager (and 4.95 star average rating) we are managing a large, group-friendly home. Plenty of space for gathering together or separating into smaller groups. brbrPrivate, heavily wooded cul-de-sac lot. Dog friendly. Central location in the Galena Territory. Close to the Owner's club and Eagle Ridge golf course. 8 miles to downtown Galena.brbrOpen floor plan. 3117s.f. 4 bedrooms (2 ensuite bedrooms), 4-season room, loft.br3 full bathrooms, 1 powder room. Mud/laundry room (washer/dryer).brbrLots of outdoor space; 2 decks, screen porch, 2nd bedroom balcony, and patio off of lower level bedrooms. Firepit.brbrIn addition to the 4 bedrooms, there is a queen Murphy bed in the 4-season room and a fold-down twin sofa bed in the loft.brbr2 night minimum, except for 3 night minimum on some holidays.brbrWe are dog owners and love our dogs as much as you do yours. However, some rules apply to help maintain the property for all guests:br - $100 fee applies.br - House trained spayed/neutered dogs only. No weight limit. 2 maximum.br- No cats.br- Dogs are not allowed in the 2 upstairs bedrooms/loft/bridge (carpeted areas).br- Dogs must do their business outside only (no inside potty pads).br- All waste must be removed. Poop bags are not provided.br- Dogs must be crated when you are not there (crate provided).br- When outside, dogs must be on leash (except for the fenced area).br- Dogs are not allowed on the furniture.br- The back yard area has a 4' wire fence but you are responsible for your pet's behavior and safety.
Bed 4

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Bath 3

Bath

Sleep 10

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Exceptional(6)

$189.86

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Private Vacation Home

Escape to our Ruby Ridge Cottage!

Galena, Illinois, United States

Welcome to A&D Rise Getaways @ Ruby Ridge Cottage, a cozy and charming 2-bedroom, 2-bathroom two-story retreat tucked away in The Galena Territory. Thoughtfully designed with a bedroom and bathroom on each level, this home offers comfort, privacy, and peaceful surroundings—perfect for couples, friends, or small families.brbrCurl up by the wood-burning fireplace, sip your morning coffee on the outdoor patio, grill up dinner under the stars, or explore all that Galena has to offer just minutes away. Whether you`re unwinding at the Owner’s Club or heading out for skiing, shopping, or trail rides, your perfect getaway starts here.brbrBEDROOMS:br• Bedroom 1 (Upper Level): Queen bed, bathroom with shower, and a dedicated desk spacebr• Bedroom 2 (Main Level): Queen bed with shared bathroom accessbr• Additional Sleeping Arrangements: Sleeper sofa in the living roombrbrKITCHEN & DINING:brThe kitchen comes fully stocked with essential cookware, a stove, oven, microwave, refrigerator, and a dual drip and Keurig coffee maker. Enjoy your meals at the dining area or step outside for a peaceful patio breakfast.brbrOUTDOOR GRILL:brA propane grill is available on the patio with seating for four. Propane is provided, and guests are asked to clean the grill after use.brbrTHINGS TO DO:brGalena offers year-round fun! Whether you`re shopping in historic downtown, sipping local wine, skiing at Chestnut Mountain, or cruising the lake, there’s something for everyone. Visit VisitGalena.com for ideas and events.brbrFIREPLACE:brThe home features a wood-burning fireplace in the living room—perfect for cozy nights in. Guests must provide their own firewood.brbrOWNER`S CLUB AMENITIES:brGuests have access to the Galena Territory Owner’s Club, located at 2000 Territory Drive, Galena, IL. Amenities include:br • Indoor and outdoor pools (please bring your own pool towels; bath towels are provided but not for pool use)br • Fitness centerbr • Game room and video arcadebr • Basketball, tennis, and pickleball courtsbr • Greenspace trails for hiking and bikingbr • Shenandoah Riding Center, offering trail rides and lessonsbr • Lake Galena, offering fishing, boating, and kayakingbrbrVisit the Galena Territory website to explore all amenities available during your stay. Key cards are provided for Owner’s Club access.brbrA&D RISE GETAWAYS EXCLUSIVE ADD-ONS:brTake your stay to the next level with our exclusive A&D Rise Getaways add-ons, available once your reservation is confirmed:br • Grocery Pickup Service – Arrive to a fully stocked kitchen with your favorite essentials.br • Birthday & Anniversary Packages – Celebrate in style with decorations, sweet treats, and surprises.br • Family Game Night Package – Enjoy a cozy night in with board games, card games, snacks, and drinks.brbrThese add-ons are available in the guest portal after booking—just select your favorites!brbrWHAT TO EXPECT:br Check-in is at 12 PMbr Check-out is at 12 PMbrbrWe’ve streamlined check-in and check-out for flexibility! Our professional cleaning team ensures every stay starts fresh and comfortable. If you`d like a little extra time to ease in or out, we recommend booking the night before or after.brbr Grills & LP Tanks:brOur owners generously provide grills at no cost. However, full LP tanks aren’t guaranteed. We do our best to make sure there’s at least 1/3 of a tank ready for you. If you need more, refills or exchanges are up to you.brbr✨ Starter Kit:brTo help you settle in, we provide:br• One roll of toilet paper per bathroombr• One roll of paper towelsbr(If you’re staying longer or with a group, you might want to bring along a few extras just in case!)brbrThanks so much for understanding — we can’t wait to host you! brbrADDITIONAL FEATURES & INFORMATION:br• WiFi: Available throughout the homebr • Washer & Dryer: Yesbr • Pet-Friendly: Nobr • Parking: On-site parking availablebr • Check-in/Check-out: Check-in is at 12 PM, and check-out is at 12 PMbrbrFor any questions or special requests, feel free to reach out before your stay.brbrWe look forward to hosting you at A&D Rise Getaways @ Ruby Ridge Cottage!br** Exterior lights must be turned off by 1am. The Galena Territory charges $150 for lights left on overnight **brbr*An additional cleaning fee will be charged for any property left in an unusually dirty condition following a guest’s stay. *
Bed 2

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Bath 2

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Sleep 6

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