Vacation Rentals By Owner In Galena, IL

King bedroom, 2 queen Bedrooms, Bunks, twin bed, wood fireplace, large family room, deck with hot tub and gas grill, large yard, satellite tv, dvd player, single whirlpool, close to Owner Club which has the indoor/outdoor pool, game room, exercise room, basketball and tennis court, lounge area, free wifi at the Owner's Club, hiking trails, horseback riding, boat rentals at the Marina, and fishing!

Spacious Log Home with hot tub

Galena, Illinois, United States

Bed

Bath

Sleeps

$355.14

Spacious home with pool table, family room on main and lower levels, deck with gas grill, whirlpool in Master Bath, Gas Fireplace, Stereo, and Satellite TV/DVD/VCR, Pool Table, and large yard. Located near the Marina for boat rentals and fishing. Enjoy the Owner's Club for the indoor/outdoor pool, fitness center, game room, basketball court, tennis courts. There is horseback riding, walking trails, antique shopping, fine dining, wine tours, and much much more.

Charming home with pool table near the Marina

Galena, Illinois, United States

Bed

Bath

Sleeps

$565.22

This modern and newly remodeled house is designed for both relaxation and entertainment. With 4 private bedrooms, each with their own bathroom, you'll enjoy privacy and comfort during your stay. The house sleeps 10 guests comfortably in king & queen size beds, offering a perfect setting for families or groups of friends.brThis spacious home features relaxation areas both indoors & outdoors. It also has plenty of floor to ceiling windows that allow all the natural light to come in.brbrThe upper level is open concept with dining room, kitchen, and family room. The open kitchen is central to the deck, porch and great room for large family gatherings and entertaining. The kitchen is fully equipped with new appliances and everything you will need to prepare a meal. For the grilling chef, a barbecue grill awaits on one of the three patio areas. Dine alfresco or in the comfort of a screened porch. The master suite with a free standing tub and walk in shower is located on the first floor. An additional bedroom with a queen size bed and a fully private bathroom is located on the first floor.br brThe lower level features a large family room with poker/bumper pool table, and darts. The walkout lower level spacious family room has a fireplace and game area and leads out to a new concrete patio. Two bedrooms are located downstairs, both with queen size beds and full private bathrooms. Additional twin sleeper sofa located on lower level. Laundry is also located on lower level with provided iron and board.br brYour rental will include six proximity cards that allow you access to The Owners' Club that's only a short drive away. This is an exclusive amenity that can only be used by Galena Territory property owners and their guests. The Owners' Club includes an indoor swimming pool, outdoor swimming pool with slides, kiddie pool, fully equipped fitness room, game room, indoor/outdoor basketball courts, tennis courts, seasonal snack bar, WiFi and outdoor playground. You also get access to Lake Galena, The Shenandoah Riding Center and numerous hiking trails throughout the 6,800 acre property.brbrGuest accessbrThe whole inside of house (except a few closets) outside decks and huge backyard. Self-check-in with smart lock.brbrOther things to notebrJust a note to let guests know this home does have the Video Doorbell by the front door and a camera in the backyard that points to the back doors for security purposes. There are no cameras in the home itself.

Tranquil 4BD/4BA Galena Getaway - Sleeps 10

Galena, Illinois, United States

4

Bed

4

Bath

10

Sleeps

$395.08

Timbers Edge is a top-rated Galena vacation rental known for its cleanliness, peaceful wooded setting, and relaxing atmosphere.brbrLocated in The Galena Territory, this 3 bedroom, 3 bathroom home with ensuite bathrooms offers the privacy and comfort guests consistently highlight—making it ideal for couples, families, and golf groups.brbrWhy guests LOVE Timbers Edge!br✔ Spotlessly clean, peaceful wooded retreatbr✔ 3 ensuite bedrooms • Hot tub • Fire pit • Dog-friendlybr✔ Discounted golf available at Eagle Ridge + 3-week advanced tee times!br✔ 12 minutes to Downtown Galenabr✔ Access to Galena Territory Amenities • Indoor/Outdoor pool • Fitness Center • Pickleball Courts • Lake Galena & Marina • Shenandoah Riding Center & morebrbrFeatures & AmenitiesbrbrOutdoor Experiencebr• Private hot tub (year-round)br• Fire pit with wooded viewsbr• Spacious deck for relaxingbrbrIndoor Comfortbr• Floor-to-ceiling stone fireplacebr• Open-concept living and kitchenbr• Fully stocked kitchenbr• Smart TVs + high-speed WiFibrbrBonus Spacebr• 3-seasons room with foosball and gamesbr(Not fully climate controlled in extreme temperatures)brbrLayout & Bedroom ConfigurationbrYou will enter the home on the upper level and stairs are required to access the main level.brbrUpper Level:br• King bedroom with ensuitebr• Queen bedroom with ensuitebrbrMain Level:br• King bedroom with ensuite bathroom (also accessible from living room)br• Living room with wood burning fireplacebr• Fully stocked kitchenbr• Three-seasons room with foosball, games, and TVbr• Access the expansive deck off of the living room where the hot tub is located and the fire pit.brbrAdditional sleeping for guests 7–8 is available via an air mattress in the living area.brbrFor the best experience, the home is ideally suited for up to 6 guests.brbrPet-Friendly Galena Vacation RentalbrThis home is dog-friendly (fee applies), making it easy to bring your pet along.brbr• Quiet wooded setting ideal for walksbr• Great option for guests seeking pet-friendly vacation rentals in Galena Territorybr• Please review house rules for pet guidelinesbrbrLocationbr• Near Eagle Ridge Resort & golf coursesbr• 10–15 minutes to Downtown Galenabr• Close to dining, wineries, and outdoor activitiesbrbrAmenity AccessbrGuests enjoy access to the Galena Territory Owner’s Club, including:brbr✔ Indoor & outdoor pools*br✔ Fitness centerbr✔ Tennis & Pickelball courtsbr✔ Recreation areasbr✔ Endless walking and hiking pathsbr✔ Lake Galena & Marina br✔ Playground for the kids (located at Lake Galena)brbr* The outdoor pool is typically open Memorial Day weekend to Labor Day weekend, subject to change. The indoor pool is available year roundbrbrIdeal Forbr✔ Golf tripsbr✔ Couples traveling togetherbr✔ Families wanting privacybr✔ Weekend getaways from Chicagobrbr Book early—prime dates fill quickly, especially spring through fall.brbrOther things to note:brDog-policy: Maximum of 2 allowed + a $150 fee. Renters are liable for any damage caused by their dog and are responsible for picking up and properly disposing of all pet waste. Dogs only, no other pets -- no exceptions.brCancellation policy: Our cancellation policy is NOT flexible, therefore we highly encourage travel insurance to protect from the unexpected. Travel Insurance can be purchased directly through Vrbo or through us.brRental Agreement: a rental agreement is required to be signed within 48 hours of booking to secure your stay along providing a picture of your ID. The guest that books the stay is required to sign the agreement and provide the names of all guests staying, and must be present during the entirety of reservation. brMinimum age of Primary Renter: 25brAt the time of booking: Accurate guest count is required including number of dogs, if applicable. brbrCheck-in after: 4 PMbrCheckout before: 11 AMbr*note, early check-in or late checkout cannot be determined until the day before and is not guaranteed. brbrThree days before your arrival, you will receive a message via VRBO and email with house information, directions, what to bring, and how you will receive your unique door code for your stay.

Galena Retreat | 3 Ensuite BR | Hot Tub, Fire Pit, Dog Friendly | Amenity Access

Galena, Illinois, United States

Bed

Bath

Sleeps

$138.26

Come stay in this beautiful vintage building located in Downtown Galena, Cafe's, Restaurants and Shop's. Cozy studio apartment with 1 Double Bed NOT a Queen Bed. Wi-Fi Included. 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. 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

Apartment

Come stay in this Circa1845 Historical Building located in Downtown Galena.

Galena, Illinois, United States

1

Bath

Sleeps

Exceptional(33)

$899.59

Theater Room is complete! Large patio overlooking the golf course coming soon! No management fees! Enjoy all that Galena Territory and Jo Daviess County has to offer! Nearly 5k sq ft with 5 bdrm/5.5 baths and located on the number one handicap hole on The General golf course with views of holes 12, 13, 14, 15 and 16! A one-of-a-kind location on over 2 acres of land. About 20 min from Downtown and Chestnut Mtn! Minutes from golf, hiking, horseback riding, boat rentals, fishing, indoor/outdoor pool, fitness center and game room at the Owner's Club!brbrBuilt as an executive golfers dream home, this custom home features views of holes 14 & 15 plus distant views of 12, 13 & 16 on the General! The main level is open, yet separate with two living areas divided by a two-sided stone gas fireplace surrounded by windows with panoramic views. The defined dining room and gourmet kitchen with a gas stovetop island is perfect for entertaining. A master suite on the main level makes for easy living. The second master suite occupies the entire upper floor with his and her en-suites and an enormous walk in/through closet! The lower level is a great space for guests to unwind with another gas fireplace, wet bar, and a walk out paver patio to enjoy those great views. This level features a game room (with a pool/ping pong table, dart board, brand new TV and another wet bar and beverage fridge!), a bedroom with a private bathroom, and two more bedrooms that share a bathroom. The bedroom pictures in the lower level are not up to date but there are two queen beds in the tiled bedroom. We also swapped out the twin bed with a queen in the third bedroom in the lower level. brbrBrand new deck with gas fire table and grill right off the kitchen. Beautiful screened in porch connected to the deck! Brand new 7 person hot tub! There are so many outdoor games as well (pickleball court, basketball, bucket ball, two cornhole sets, bocce, disc golf, frisbee, and Kan Jam)! Go sledding in the front yard (we have sleds)! Hiking trails are within walking distance! Whether you want to take advantage of the beautiful home inside or all of the outdoor activities, there is plenty for everyone to enjoy! Come see all this great home has to offer and experience the peaceful setting!brbrWelcome to some of the most beautiful land in Illinois. The Galena Territory is a semi-private, 6,800-acre private recreational and residential lake community located six miles outside the historic city of Galena in Northwest Illinois. Nestled near the center of The Territory is Eagle Ridge Resort & Spa, known for its 63 holes of championship golf and open to the general public.brbrUsing a vehicle is the easiest way around the territory but there are plenty of trails and roads to walk on!brbrThe garage is not available for use but there is plenty of parking. The driveway can easily accommodate six vehicles!brbrWe have a Tesla wall charger installed in the garage. It is compatible with any EV as long as you have the appropriate adapter for non-Tesla vehicles. Please contact me if you would like to use the charger during your stay!

Stunning 5 bdm home on The General in Galena Territory!

Galena, Illinois, United States

Bed

Bath

Sleeps

$234.22

Experience Galena like a local in this charming 1-bedroom cottage. The cozy bedroom features a comfortable king bed, perfect for a good night's sleep. With 2 bathrooms, including a relaxing bathtub, guests can unwind after a day of exploring. The living room offers an additional space with a sofa bed for extra comfort. Enjoy all that Galena has to offer when you stay at our place.

Cottage

Charming 1-bedroom cottage in fabulous Galena with AC, WiFi Aiken 1083 LLC

Galena, Illinois, United States

Bed

Bath

Sleeps

$378.22

3 bedroom/ 3 bathroom rustic contemporary Galena territory retreat. Main level houses wood-clad cathedral ceiling great room. Gas fireplace and open dining area that feeds to large kitchen with granite countertops. Spacious master bedroom with more wood-clad cathedral ceilings and master bath with whirlpool tub/shower. Walkout lower level feature 2 bedrooms with 2 full bathrooms. Enjoy amazing views from the rear deck with gas grill and fire pit table or the airy 3 seasons room. Relax on the front porch or lower paver block patio. Close access to trail system that heads to the marina or the north cove of Lake Galena! Rental includes 6 keycards for access to the property owner's club with indoor & outdoor pools, fitness facility, pickleball, tennis, multisport gym and more. Located conveniently 10 minutes away from downtown Galena! Free highspeed WiFi internet- 1000Mbps. Four spaces are available for parking in the driveway. The fourth bed in the common area is a flip flop couch similar to a futon but built heavier duty. Sheets and pillows are available inside the flip flop when using it to sleep on. Please make sure to shut off outside porch lights and limit noise after 8 PM as the Territories is getting stricter about enforcing this.

Cozy 3 bedroom house

Galena, Illinois, United States

Bed

Bath

8

Sleeps

$657.83

5 Bedrooms • 5 Bathrooms • Hot Tub • Fireplace • Game Room • Owner’s Club AccessbrbrWelcome to The Gleneagle, a warm and inviting 5-bedroom home designed for unforgettable gatherings with family and friends. Located in the picturesque Galena Territory, this spacious retreat comfortably accommodates up to 12 guests, offering all the comforts and luxuries for a relaxing stay.brbrWhether you're enjoying a glass of wine on the front porch, relaxing in the hot tub after a long day exploring Galena, or cooking out on the large Weber grill, The Gleneagle delivers the this is exactly what we needed feeling.brbrWhat You'll Love:br- 5 Bedrooms, all with KING Beds and ensuite or adjacent bathroomsbr- New Premium Sealy Memory Foam Mattresses br- Sleeper Sofa for extra guests in the lower-level living roombr- Roku Smart TVs in every bedroom and both living areasbr- Wood-burning Fireplace for cozy nights inbr- Game Room with Foosball and Pac-Man arcade gamebr- Private Hot Tub on the deck with stunning viewsbrbrSpacious Living & Dining: Relax in the open living area with a wood-burning fireplace and Smart TV, perfect for gathering together. The large dining table seats 10, with additional seating at the breakfast bar. The fully equipped kitchen includes a French-door fridge, double oven, Keurig and drip coffee makers, dishwasher, microwave, and crockpot—everything you need for home-cooked meals.brbrFun for Everyone: Head to the lower level for some friendly competition in the game room, featuring a foosball table and classic Pac-Man arcade game. There's also a pub table that doubles as a great spot for remote work.brbrOutdoor Relaxation: Enjoy four outdoor decks, each with its own charm. Sip your morning coffee on the chair swing, fire up the gas grill for a cookout, sip wine in the evening on the screened porch, or unwind in the private hot tub while soaking in the beautiful surroundings.brbrExclusive Galena Territory Access: Your stay includes 6 access cards to the Galena Territory Owners Club, where you can enjoy pools, tennis, pickleball, hiking trails, and Lake Galena boat rentals. Additional day passes are available for purchase.brbrNearby Attractions:br- Eagle Ridge Resort: Golf courses, spa, dining, and winter activities like sledding and a golf simulator.br- Chestnut Mountain Resort: Skiing, summer zip-lining, and mountain biking.br- Downtown Galena: Historic charm, boutique shopping, dining, and river kayaking.brbrPlease Note: We recommend travel insurance, as we do not offer refunds for weather or COVID-19 restrictions. Access to some Owners Club amenities may require reservations.

Spacious 5BR Retreat with Hot Tub, Fireplace & Game Room | Galena Territory

Galena, Illinois, United States

Bed

Bath

12

Sleeps

$221.88

Valleywood Vibe is 10 minutes to downtown Galena and 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.brbrYou will love our cool, chic Vibe on Valleywood. Masterfully updated 2-bedroom 2-bath townhome in the resort core on Valleywood Lane. We are situated in a private wooded setting with golf fairways nearby. The townhome features a cozy, built-in dining area (seats 6 easily), a well-equipped kitchen with new Samsung appliances (including ice maker in the freezer), make your coffee (single and carafe maker) and relax! The lower level offers an open living room with a vaulted ceiling, multiple skylights, flat screen ROKU Smart TV and a wood-burning fireplace. Chill out and pair to our Klipsch Bluetooth radio while hanging in this bright and airy space. A large, beautifully appointed bedroom on this level features a queen bed, seating for reading, USB charging station, flat screen TV and an attached bathroom with granite tops and bath bathtub w/shower. You'll also have access to a stackable washer and dryer on the main level. Travel upstairs and you'll find a spacious loft area that overlooks the main floor with a trundle bed for your plus 2 to sleeping space. Additionally, on the upper level, you’ll find a spacious master suite featuring a King bed with a vaulted ceiling, flat screen TV, and a private updated bath w/walk in shower. The home features new TREX decks on the front and rear. Enjoy the umbrella and seating for 4 on the rear deck while your chef in the group grills on our gas grill, we provide the propane! Whether you're here for golf, hiking, skiing, spa weekends, or simply unplugging in style, Vibe on Valleywood delivers the perfect mix of modern comfort and laid-back luxury.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 Memorial Day through Labor Day. 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. Please remember that usage of the amenities is never guaranteed. We do not discount or refund due to their closure. brWhen 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. 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 receiving 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. We do not have a weather Cancellation Policy, we highly recommend the travel insurance offered at the time of booking. brThe entry code is available 3 days before your arrival. You will receive a web link to our guest guide at the time of booking. 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.brbrAsk us about our other 2 other Valleywood homes for your larger groups!

Valleywood Vibe - Modern 2BR - Fireplace, Patio & Pool Access!

Galena, Illinois, United States

Bed

Bath

Sleeps

$652.66

Perfect getaway pet friendly house with 4 bedroom,4 bath home with new hot tub, ping pong table and fire pit it is a great place to enjoy time with your family and your pet on this stay .The house sits on 1,5 acre lot in very quiet neighborhood .Great for running around with your pet or playing a fun yard games .Enjoy the sound of the creek or catch horseback rides through the trees on the trails behind the home. All the guests of the house gets passes to Galena Territory Associated to enjoy indoor ,outdoor pools ,tennis courts ,basketball , fitness center ,fishing ,boating ,over 24 miles of trails and a game room. The house is located 1 mile from the Shenandoah Riding Center ,11 miles from downtown Galena and 13 miles from Chestnut Mountain.

Sweet Retreat -hot tub,fire pit,pet friendly,access to pools ,outdoor games

Galena, Illinois, United States

Bed

Bath

Sleeps

$539.44

Family Friendly! 3BR, 2 Bath in the heart of The Galena Territory.!brClose to Shenandoah Riding Center!brWithin minutes to Owners Club, Pool, Galena Lake and many trails!brBeautiful deck around all house!

Lodge

Cozy Log Home-Your Perfect Escape! Enjoy Nature and Wildlife from the Deck!

Galena, Illinois, United States

Bed

Bath

6

Sleeps

$313.49

Nicely renovated house in the heart of the Galena Territory. This home offers 2 Bedrooms and 1.5 baths plus Air Hockey and a Hot Tub. This home is located only 3 minutes from the Owners' Club in the heart of The Galena Territory and comes with four amenity passes allowing you access to the Owners' Club where you will enjoy indoor, outdoor, and kiddie pools, a state of the art fitness center, indoor/outdoor basketball courts, tennis courts, Game Room, free WIFI, etc. The Galena Territory offers many activities to choose from, including horseback riding, hiking, and fishing and more.brbrThis home is perfect for a small family, two couples, or a romantic getaway. It sleeps 4 people comfortably. Both bedrooms offer a King bed and Smart Tv. Bright and spacious first floor family room with Smart Tv, gas fireplace, and dining area that seats 4 people. Large windows with a private view! Sliding door out from dining area to a deck with table seating and a gas grill. The kitchen is fully stocked with all the utensils and cookware you need for your stay. Full fridge, electric stove/cooktop, dishwasher, coffee maker, microwave, and toaster.brbrLake Galena is less than 5 minutes from this home and offers bait shop and boat rentals.brbrDowntown Galena is a short drive and is consistently ranked a top tourist town in the US! Enjoy history, shops, delicious restaurants, Grant Park and Grant's Home, the Galena River, and many other attractions! Chestnut Mountain is also a short drive and has downhill skiing in the winter and their famous alpine slide, new zip line and Segway tours in the spring, summer, and fall.brbrIf you are looking for a quiet comfortable retreat but with all the amenities of the Galena Territory this nicely updated home could be your perfect getaway.brbrSleeps 4, Maximum Occupancy 4.

2 Bedroom, 2 Bath Hot Tub home in the Galena Territory

Galena, Illinois, United States

Bed

Bath

Sleeps

$1106.35

WE'RE BACK! Summerdale Cottage - the Territory's favorite short term rental - has been offline for a little while. A simple insurance claim due to a burst pipe turned into a 28-month learning experience. brbrWe learned just how much people love this place. Some have vacationed at the cottage for over a decade while others simply left positive reviews saying they planned to return. brbrBut work was delayed. Then the work was shoddy. That work was promptly demolished, which caused more delays. Work was then done right, but slowly. We assumed being shut down for so long meant our loyal guests would move on and forget about us.brbrBut they didn't. brbrIn fact, we heard from so many of our favorite guests along the way it made us realize that the cottage was worthy of a more significant investment. So we did some upgrades. Then we did more. Once we realized we were getting a little carried away and knew it was time to stop--we kept going anyway. (And we're still going.) What started as an investment property has become a labor of love.brbrSo the cottage is looking pretty awesome now. It boasts several completely remodeled spa-like bathrooms, beautiful new hardwood floors, new and expanded decks, new furniture, fixtures, HVAC, hot tub and more. brbrThe cottage still has tons of common space in the middle with bedroom suites scattered in every direction. Each suite offers whatever degree of seclusion you want. If you feel like having drinks with other guests, common areas are just steps away. If other guests make you feel like drinking alone, your bedroom is an excellent sanctuary from the chaos. If you're sharing your bedroom with someone who might be a little much, you can slip away to your very own outdoor space. If they still manage to find you, other options remain.brbrThe house isn't formal or pretentious. Every piece of furniture is something we'd put in our own home, but nothing that we've passed down. The kitchen will feel like your own, but without a junk drawer. There are multiple gathering areas that feel intimate and comfortable--and not like a banquet hall. brbrThe mattresses are new and comfortable. The bedding and linens are high quality, and the bathrooms are well-appointed with glistening tile and solid fixtures. (Actually, the bathrooms are a little pretentious. They told us we needed Kohler toilets. We asked why. They said it's because they're better. Again-why Because they are. We couldn't argue with logic like that.)brbrThe house is often used for rehearsal dinners, large family reunions and anniversary parties. When guests are part of a larger group staying in multiple properties for such events, the cottage usually serves as the central meeting spot--not only due to its size and proximity to the Territory entrance, but also because the layout is conducive to large gatherings. Time after time, we're told it's perfect for these events. brbrThere's a lot happening inside:brbrLEVEL ONE: This level includes a generously-sized bedroom suite and a recreation room. The bedroom is completely remodeled. It includes a king size bed, 55 smart TV and dedicated screened-in porch. brbrBut the bathroom is where it's at. It's brand new and it's fantastic. It has a double vanity, double shower and a ton of shiny new tile. The vibe might make you blush--think Barry White inviting you in and telling you to slide your clothes off and lather up because you're gonna look FINE when you're done. But you might instead be lured in by the tasteful decor and abundance of bulk toiletries normally reserved for a property that rents for twice the price. So whether it's a sultry voice or fiscal responsiblity, just go with whatever turns you on.brbrThis level also includes a rec room with a pool table and lounge area. It includes a 65 smart TV, Sony PS4 and new furniture. It's an ideal place to escape--whether from adults, kids, your in-laws or law enforcement. We won't ask questions, and they won't be able to find you.brbrLEVEL TWO: There are two bedroom suites on this level. One includes a queen size bed and a smart TV. It has an adjacent screened-in porch with a door leading outside directly to the main deck, with quick and easy access to the hot tub.brbrThe bathroom in this suite has a walk-in shower that's over-the-top, with gorgeous tile that's rumored to have been stolen from the Vatican. (Fun fact: it was.) The fixtures are unique and fun, but they're legit. We have receipts to prove it.brbrThis suite is normally occupied by the first couple to arrive. Sure, they'll say something to stragglers like Oh, did you want this one We'll move. Seriously, it's no problem. You know us--we're fine staying anywhere. brbrBut they're lying.brbrBecause they played with the quirky vessel faucet. They let their minds wander as they followed the tile pattern that isn't really a pattern. They tried out the bed. Then they quickly unpacked. So if anyone actually tries to take them up on their offer to vacate, they're gonna throw hands. brbrThe second suite includes four bunk beds, a smart TV, and a screened-in deck with adjacent open-air private balcony. This bedroom is a party, plain and simple--at least until a fat guy takes a top bunk. Don't worry though--we have a futon for him that can be placed right next to the kitchen.brbrThe bathroom has yet to receive a big makeover, but it's decent. It has a single vanity, a jetted whirlpool tub and a separate shower. There's a new half bath immediately adjacent. Together, these bathrooms can clean a crowd of filthy boys as fast as a high school locker room, and the fancy Kohler toilets give fantastic swirlies.brbrThis level also includes a comfortable new TV room with a sofa, love seat, 65 smart TV and a bar table with stools. The main deck is accessible from here. It sports a large new Napoleon grill, eight-person hot tub, ample deck seating and even a fire pit area. It's good space.brbrLEVEL THREE: This level includes a new bedroom suite, plus the living room, dining room, kitchen and utility room.brbrThe suite layout is identical to the queen bedroom suite on Level Two. While the bathroom escaped the 2024 catastrophe, we tore it down to the studs anyway to keep things fair. The mood here is more subdued and elegant, rendering comparison with the suite below akin to choosing between Honey Crisp and Red Delicious. (That's apples to apples, btw.) The screened-in porch has access to a catwalk balcony leading to the living room. The llving room can also be reached by simply walking out the bedroom door. But come on--it's a catwalk! This suite is great for guests who want easy access to common areas without having to navigate stairs, and it affords a bird's-eye view of the deck and hot tub below. It's a useful perch from where the fun police can keep an eye out for any mischief down there and address the offenders accordingly--whether they need to be chastised or sprayed with a hose.brbrThe living room has a beautiful gas fireplace and new furniture, but no TV--because we thought nine TVs might keep people from actually talking with each other. Sure, this might eventually lead to you-know-who providing yet another unsolicited update about how her kid is so gifted that he doesn't feel challenged in class and his teacher is concerned that the other students are holding him back. But before she launches into her thoughts on the SAT versus the ACT, you can simply blurt out: Hey--is that a record player ! Because yeah, it is--complete with an enviable collection of vinyl ranging from Bach and Beethoven to Simon and Garfunkel, Fleetwood Mac to Elton John, and Kelly Clarkson to everyone except Nickelback. And If the LPs don't do the trick, the adjacent full-service bar is within arm's reach. brbrThe bar is stocked with over 200 glasses. (Call us superficial, but a proper toast requires matching champagne flutes.) There's a 12-seat dining table, and it's easy to configure the space to allow at least 25 people to comfortably dine together.brbrThe dining room serves as a pass-thru from the living room to the kitchen, where there's a six-person round table, an island with three bar stools, coffee station, six-burner gas stove, dishwasher, convection oven and microwave. The kitchen comes with ample cooking gear, a bunch of matching plates, flatware, servingware and everything else needed to entertain.brbrThe utility room includes a washer and dryer--feel free to use them.brbrLEVEL FOUR: This level includes a third loft-type living area overlooking the mezzanine entry, as well as a huge bedroom suite. The view from the loft is spectacular--affording views of several fairways of The General golf course through an entire wall of windows or from the large balcony. brbrThe bedroom includes a king size bed and futon, plus a stone gas fireplace and 55 smart TV. The bathroom has a double vanity, large whirlpool tub and separate shower. brbrThe cottage sits on an acre of property near the entrance to the Territory, and it's about as close to The General clubhouse as you can get. The driveway can accommodate 10-12 cars if parked creatively, and up to 20 when none of the vehicles have doors.brbrAMENITIESbrbrStay here and you'll have access to Eagle Ridge's restaurants, the Stonedrift Spa, and golf courses. The house is not affilliated with Eagle Ridge Resort & Spa, so it doesn't come with access to their amenities such as the Eagle Ridge swimming pool. Instead, we offer access to The Galena Territory amenities. They're way better, and include both an indoor and outdoor pool, a zero-entry kiddie pool with bubblers and a frog slide, as well as a basketball court and other stuff.brbrOur guests also have access to Lake Galena and the Marina, the Owners' Club fitness center, tennis and pickleball courts, and nearly 32 miles of trails and nationally recognized greenspace. Seriously, it's all incredible--you'll love it.brbrbrPlease reach out with any questions!

Summerdale Cottage - Huge Galena Territory Retreat

Galena, Illinois, United States

Bed

6

Bath

12

Sleeps

$260.56

Our Farmstead Townhome is approximately 10 miles, or a 15-minute drive, from Downtown Galena 1.5 miles from the GTA Owner's Club, which features pools, tennis courts, and a fitness center. We are dog-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.brbrWelcome to our 3-bed 3-bath Farmstead townhome. You will delight in this thoughtfully designed end unit. We can sleep up to 8 guests. Combine it with our other unit next door and sleep your larger group!brbrWe offer.....br*Room for Everyone – 3 bedrooms across 3 levels: 2 Twin Beds, 1 King Bed, + 2 Twin Bedsbr*Comfort Everywhere – 3 full bathrooms, one on each levelbr* Prime Location – In the resort core near the Inn & Spa; perfect for weddings, special events, or family getaways.br* Exclusive GTA Owners Club Access: Indoor pool (year-round) & outdoor pool w/slides (Memorial Day–Labor Day) Kiddie pool, fitness room, game room, basketball & tennis courts, playground, snack bar, free WiFibr* Explore the Territory - Lake Galena, Shenandoah Riding Center, and 6,800 acres of hiking trails.brPlease note that the number of access cards provided may not accommodate your entire group; additional guest passes can be purchased for $5 per day at the GTA administrative office or pool entrance. Access to the Owners Club is included with your stay, but some amenities may require a fee. Availability of all amenities is not guaranteed, and no refunds or discounts will be provided in the event of closures.brbrBooking & Stay Details:br30% down at booking (payment, not deposit); full balance due 14 days before check-inbrCancel before 14 days = refund minus $35; within 14 days = non-refundablebrElectronic rental agreement required (sign within 48 hours)brGuest must be 25+ and present during the entire staybrAmenities are exclusive but subject to availability; no refunds for closuresbrTravel insurance is strongly recommendedbrbrLocal Fun:brEagle Ridge Resort and Spa (5-6 minute drive)br• Stonedrift Spabr• Country Storebr• Peddlers BoutiquebrEagle Ridge Golf Courses:br• The General, 18-hole Championship)br• South course (18 holes)br• North Course (18 holes)br• East Course (9-hole Executivebr• Pro ShopbrGalena Territory Owner’s Club:br• Indoor/outdoor pools with water slidesbr• Indoor/outdoor basketball, tennis, and pickleball courtsbr• Outdoor playgroundbr• Fitness Centerbr• Game Roombr• Seasonal clubhouse/snack shopbr• Galena TerritorybrLake Galena and Marina:br• Boat/pontoon rentalsbr• Fishing rentalsbr• Pavilion rentalbr• 32 miles of walking and hiking trailsbr• Thunder Bay FallsbrShenandoah Riding Center:br• Trail ridesbr• Wagon ridesbr• Riding lesson

Farmstead Tee & Ski - Resort Core location, Fireplaces, Dog Friendly

Galena, Illinois, United States

Bed

Bath

Sleeps

$410.93

pstrongBluffwood Belle, Galena IL/strong/pbrbrpstrongEntire Home Vacation Rental, 3 Bed, 3 Bath, 8 Person Occupancybr/strongAs you walk into this bright and airy home you will be tickled with your home selection! On the main floor is a large great room with wood burning fireplace. The large master suite and bath is situated on the main level along with the kitchen and a half bath. The back deck of this home boasts beautiful wooded views and wildlife sightings, and the garden offers of a cozy fire pit. The screened porch is a favorite! The lower offers a second great room with wet bar. The second & third bedrooms, each with their own baths, are found on this level too. The special touches in this home will surprise and delight!brbrbr/pbrbrpstrongGuest Accessbr/strongYou will have access to the Galena Territory Owners' Club and all it's amenities such as indoor and outdoor pools, game room, fitness center, gym, tennis and basketball courts, and more. br/pbrbrpstrongThe Area/strongbrstrong/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/pbrbrpstrongGetting Aroundbr/strongA car is necessary to see all that Galena and the surrounding area has to offer! Taxi, Uber and Lyft services are available./p

3bd/3.5ba, Bright & Spacious, Fab Screened Porch, Fireplace

Galena, Illinois, United States

Bed

Bath

Sleeps

$311.06

Escape to this stunning 3-bedroom, 3-bath treetop retreat in The Galena Territory—perfect for relaxing, reconnecting, and enjoying everything Galena has to offer.brbr✨ HIGHLIGHTSbr• Game area (pool table + piano + board games)br• Wood-burning fireplacebr• Access to Owner’s Club (pool, fitness center & more)br• Smart TVs + fast WiFibr• Floor-to-ceiling windows + vaulted ceilingsbr• 12pm check-in & check-outbr• ~15 minutes to downtown Galenabr• Multiple decks with expansive wooded viewsbrbrWelcome to Lookout Trace Treehouse @ A&D Rise Getaways!brbrPerched high above the trees, this one-of-a-kind home offers three levels of living space filled with natural light and incredible views. Sip coffee on the decks, unwind by the fireplace, enjoy a game of pool, or gather around the piano—this is a space designed for both connection and quiet escape.brbr ️ SLEEPING ARRANGEMENTSbr• Main Level Bedroom: King bed with full bath nearbybr• Upper Level Bedroom: King bed with adjacent full bathbr• Lower Level Bedroom: Two twin-over-full bunk beds with full bath nearbybrbr KITCHEN & DININGbrFully equipped kitchen with everything you need:br• Stove, oven, microwave, refrigerator & dishwasherbr• Multiple dining areas for group mealsbr• Dual coffee maker (drip + Keurig, coffee provided ☕)brbr LIVING & OUTDOOR SPACESbr• Floor-to-ceiling windows with expansive viewsbr• Wood-burning fireplace (bring your own firewood)br• Pool table, piano + board gamesbr• Smart TVs with Wifibr• Three levels of indoor living spacebr• Multiple decks with seating + wooded viewsbr• Propane grillbrbr LOCATIONbrCentrally located in The Galena Territory:br• ~5–10 minutes to Owner’s Clubbr• ~15 minutes to historic downtown Galenabr• ~25 minutes to Chestnut Mountainbrbr OWNER`S CLUB ACCESSbrEnjoy access to:br• Indoor & outdoor poolsbr• Fitness centerbr• Game room & arcadebr• Pickleball, tennis & basketball courtsbr• Trails, marina, boating & golfbr• Horseback riding + spa servicesbrbrIncludes 6 proximity cards for access.brAdditional cards available for $5/day at the Owner’s Club (2000 Territory Drive).brbrPlease note: Amenity availability is managed by the Territory and is not guaranteed. No refunds are provided for closures.brbr✨ BEFORE YOU ARRIVEbrYou’ll receive a detailed digital guest guide with local recommendations, tips, and everything you need to plan your Galena getaway.brbr OPTIONAL ADD-ONSbrAvailable after booking in your Guest Portal:br• Grocery pickup servicebr• Birthday & anniversary packagesbr• Family game night packagebrbr GRILL INFObrGrill available for guest use. We do our best to provide at least 1/3 tank of propane, but additional refills are the guest’s responsibility. Please clean the grill after use.brbr STARTER SUPPLIESbr• 1 roll of toilet paper per bathroombr• 1 roll of paper towelsbr(We recommend bringing extras for longer stays.)brbr GOOD TO KNOWbr• Check-in: 12 PMbr• Check-out: 12 PMbr• Washer & dryer availablebr• On-site parkingbr• High-speed WiFibr• No petsbr• Home is accessed via outdoor stairs (adds privacy but may not be ideal for guests with mobility concerns)brbr Save this listing by clicking the ♥ to easily find it later!brbrWe can’t wait to host you at Lookout Trace Treehouse @ A&D Rise Getaways!br** Exterior lights must be turned off by 1am. The Galena Territory charges $150 for lights left on overnight **brbr*An additional cleaning fee will be charged for any property left in an unusually dirty condition following a guest’s stay. *

3 bedroom 3 bath, expansive views Treehouse feel

Galena, Illinois, United States

Bed

Bath

8

Sleeps

$313.34

✓ 2 King bedsbr✓ 2 full bathsbr✓ Steps to semi-private pool br✓ Modern, fully equipped kitchenbr✓ Private deck with grill & seating for 4br✓ Peaceful wooded end-unitbr✓ Full club amenities, including fitness centerbr✓ 3 Smart TVs br✓ Computer workspacebr✓ Paved walking trails nearbybr✓ Lake accessbr✓ 2 min to golf, driving range & spabr✓ 12 min to downtown Galenabr✓ 15 miles to Chestnut Mountain, zipline & skibrbrWelcome to a beautifully updated 2-bedroom, 2-bath end-unit villa in The Galena Territory — a tranquil wooded retreat perfect for a cozy getaway. This airy villa blends warmth, comfort, and tasteful modern updates just 12 minutes from downtown Galena, IL. Enjoy the privacy of the entire villa during your stay.brbrUnwind in Comfort ~ Gather by the wood-burning fireplace (Labor Day–Memorial Day) under a vaulted ceiling with skylights. Cook in a stylish kitchen with updated cabinetry, quartz breakfast bar, and dual drip/pod coffee machine (complimentary coffee, tea, sugar, creamer included; please supplement kitchen, paper, and laundry supplies for stays of more than 7 days). The dining area and living room, with an Amazon Fire TV, and Roku & YouTube TV on all three HD TVs, invite relaxation.brbrSleep Soundly ~ The main level bedroom features a king bed and full bath with quartz vanity and tub/shower. The 2nd level master bedroom, with a vaulted beamed ceiling, offers a private full bath with tile accents. A loft with a computer desk provides a cozy workspace. brbrExplore and Relax ~ Savor the outdoors on the rear deck or covered front porch. Take a dip in the semi-private pool (steps away, Memorial Day–Labor Day) or visit the North Course Driving Range (2 min drive). Enjoy 31 miles of paved trails or Owner’s Club amenities (fitness center, marina, more).brbrThoughtful Touches ~ Hotel style towels, a washer/dryer with laundry pods, and seasonal decor create a homey feel. Central air conditioning and heating adds additional comfort for every season. brbrDog-Friendly ~ for up to 2 dogs, 50 lbs. or less ($100 pet fee), with a doggy bed, bowls, and couch cover provided for your pup. ***PLEASE NOTE: Dogs must be kenneled whenever left unattended in the home. We are unable to make exceptions to this policy.brbrBook now for a warm, inviting Galena escape! brbrMAIN ATTRACTIONS (Just 6 Miles to Downtown Galena):br◆ Historic downtown Galena — voted Illinois’ “Best Small Town”br◆ Belvedere Mansion, U.S. Grant Home & the Galena History Museumbr◆ Festivals, performing arts, scenic trolley & guided walking toursbr◆ Unique shopping — antiques, artisan goods & modern boutiquesbr◆ Excellent local dining, cafes, breweries & wineriesbr◆ Nearby hiking trails & state parksbr◆ Chestnut Mountain Resort (15 miles): skiing, zipline, alpine slide & river cruises (seasonal)brbrGTA OWNER’S CLUB AMENITIES (Included with Your Stay):br◆ Fitness centerbr◆ Indoor swimming pool (open year-round)br◆ Outdoor swimming pool + kiddie pool (seasonal)br◆ Seasonal cafébr◆ Game room (ping pong, fuse ball, pool table)br◆ Gymnasiumbr◆ Outdoor basketball courts (seasonal)br◆ Outdoor tennis & pickleball courts (seasonal)br◆ Lake Galena Marina (kayaks, canoes, fishing boats & pontoons available for rent)br◆ Marina Bait Shopbr◆ Thunder Bay Falls Parkbr◆ Shenandoah Riding Center (riding fees apply)br◆ Nordic Center winter sports (weather permitting; equipment rentals available or bring your own)brbrPLEASE NOTE: br1. Due to owners' allergies, cats are NOT allowed on the property at any time. Two dogs are permitted. 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 six 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.

Spacious, King Beds, Pool steps away, Near Golf, Spa

Galena, Illinois, United States

Bed

Bath

Sleeps

$220.35

Take some time to relax and reconnect with nature at this peaceful and spacious wood-finished home in the heart of The Galena Territory! This 6,800-acre recreational and residential lake community offers numerous entertaining amenities for guests, including a state-of-the-art outdoor pool, a rec center, a fitness center, a marina, 31 miles of walking/hiking trails, Lake Galena for boating and fishing, an equestrian center, and a top-75 course, which awaits you in the backyard.brbr-- THE PROPERTY --brbrThis community also boasts impressive vistas, prairies, valleys, and woodlands. As you enter this two-story charmer, you will discover modern wood finishes that give the house a cafe-style atmosphere. Make yourself at home as you spread out comfortably in the welcoming and spacious living room, offering an inviting sofa, reading chairs, a Smart TV with streaming and cable services, and a gas fireplace to keep you nice and toasty during the winter months. Discover a coffee and wine bar next to the dining table, which is the perfect place to start and end your days memorably. You will find various coffees, teas, mugs, wine glasses, wine accessories, and a Keurig coffee maker. When mealtime comes, surprise your loved ones with exquisite homemade meals prepared in the well-appointed kitchen, complete with all stainless steel appliances, pots and pans, plates and silverware, and all the cooking essentials. Spend entertaining evenings on your private deck dining alfresco, hosting barbecues, or simply planning your next adventures. Additional perks include high-speed WiFi, board games, a washer/dryer, a high chair, and children's toys.brbrSleeping arrangements include one bedroom on the main level and one bedroom upstairs. The main-level bedroom has a Smart TV and a walk-in closet while the upper-level main suite features a Smart TV, a walk-in closet, and an en suite bathroom.brbr-- THE LOCATION --brbrEnjoy an unbeatable location within six miles of the historic city of Galena, Thunder Bay Falls, U.S. Grant Home State Historic Site, Grant Park, P.T. Murphy Magic Theatre, Horseshoe Mound Preserve, Chestnut Mountain Resort, Sundown Mountain Resort, and Bellevue State Park.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- Pet friendlybr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- Quiet hours are from 10:00 PM to 8:00 AMbrbrADDITIONAL INFORMATIONbr- Your safety matters. The property features an exterior security camera on the exterior of the house. The camera is outward facing and does not look into interior spaces, is on and not motion activated, and records video

Pool, Golf, Marina! Galena Territory Resort Home

Galena, Illinois, United States

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Bath