The Gleneagle ❄️ Holiday & ⛷️Winter Escape | Fresh 5BR /5 Bath King Beds | Hot Tub & Fireplace

  • Spacious main level living room
    Spacious main level living room
  • Private covered hot tub
    Private covered hot tub
  • Dining room table seats up to 10 with 4 additional stools at breakfast bar
    Dining room table seats up to 10 with 4 additional stools at breakfast bar
  • Primary bedroom -- King Bed
    Primary bedroom -- King Bed
  • Foosball table - perfect for kids and adults alike
    Foosball table - perfect for kids and adults alike
  • Ski Chestnut Mountain -- a 20 minute drive from The Galena Territory
    Ski Chestnut Mountain -- a 20 minute drive from The Galena Territory
  • Screened porch for afternoon happy hours
    Screened porch for afternoon happy hours
  • Main level living room
    Main level living room
  • Cozy wood burning fireplace
    Cozy wood burning fireplace
  • Fully stocked kitchen
    Fully stocked kitchen
  • Fully stocked kitchen
    Fully stocked kitchen
  • Fully stocked kitchen with large dining room adjacent
    Fully stocked kitchen with large dining room adjacent
  • Dining room - accommodates 10 + 4 at breakfast bar
    Dining room - accommodates 10 + 4 at breakfast bar
  • Microwave and coffee (Keurig and standard coffee makers available)
    Microwave and coffee (Keurig and standard coffee makers available)
  • Fully stocked kitchen
    Fully stocked kitchen
  • Weber Summit series 4-burner grill and outdoor dining
    Weber Summit series 4-burner grill and outdoor dining
  • Primary bedroom -- King Bed - with desk for those needing to tuck away to get some work done while on vacation.
    Primary bedroom -- King Bed - with desk for those needing to tuck away to get some work done while on vacation.
  • Primary bedroom -- King Bed - with desk for those needing to tuck away to get some work done while on vacation.
    Primary bedroom -- King Bed - with desk for those needing to tuck away to get some work done while on vacation.
  • Primary Bathroom - with double vanity, shower, soaking tub
    Primary Bathroom - with double vanity, shower, soaking tub
  • Primary Bathroom - with double vanity, shower, soaking tub
    Primary Bathroom - with double vanity, shower, soaking tub
  • Primary Bathroom - with double vanity, shower, soaking tub
    Primary Bathroom - with double vanity, shower, soaking tub
  • Primary Bathroom - with double vanity, shower, soaking tub
    Primary Bathroom - with double vanity, shower, soaking tub
  • King bed with bathroom directly adjacent
    King bed with bathroom directly adjacent
  • King bed with bathroom directly adjacent
    King bed with bathroom directly adjacent
  • King bed with bathroom directly adjacent
    King bed with bathroom directly adjacent
  • Bathroom on main level -- shared with queen bedroom
    Bathroom on main level -- shared with queen bedroom
  • Bathroom on main level -- shared with King bedroom directly adjacent
    Bathroom on main level -- shared with King bedroom directly adjacent
  • King size bed with ensuite bath
    King size bed with ensuite bath
  • King size bed with ensuite bath
    King size bed with ensuite bath
  • King bed with ensuite bathroom
    King bed with ensuite bathroom
  • Ensuite for Bedroom #3
    Ensuite for Bedroom #3
  • Ensuite for Bedroom #3
    Ensuite for Bedroom #3
  • King bed with ensuite bathroom and Roku Smart TV
    King bed with ensuite bathroom and Roku Smart TV
  • King bed with ensuite bathroom and Roku Smart TV
    King bed with ensuite bathroom and Roku Smart TV
  • King bed with ensuite bathroom and Roku Smart TV
    King bed with ensuite bathroom and Roku Smart TV
  • Ensuite bathroom for Bedroom 4
    Ensuite bathroom for Bedroom 4
  • King bed with ensuite bathroom and Roku Smart TV
    King bed with ensuite bathroom and Roku Smart TV
  • King bed with ensuite bathroom and Roku Smart TV
    King bed with ensuite bathroom and Roku Smart TV
  • King bed with ensuite bathroom and Roku Smart TV
    King bed with ensuite bathroom and Roku Smart TV
  • Ensuite for Bedroom #5
    Ensuite for Bedroom #5
  • Ensuite for Bedroom #5
    Ensuite for Bedroom #5
  • Laptop-friendly workspace or Pub Table - your choice! And foosball table
    Laptop-friendly workspace or Pub Table - your choice! And foosball table
  • Lowev level living room with Smart TV and foosball table
    Lowev level living room with Smart TV and foosball table
  • A throw back -- challenge your friends and family to a high-score on Pac Man!
    A throw back -- challenge your friends and family to a high-score on Pac Man!
  • Gather on the front porch with your morning coffee
    Gather on the front porch with your morning coffee
  • Laundry available during your stay
    Laundry available during your stay
  • Covered hot tub - available year round - cleaned and treated before each reservation
    Covered hot tub - available year round - cleaned and treated before each reservation
  • The Galena Territory Owners Club - Amenities
    The Galena Territory Owners Club - Amenities
  • Front of The Gleneagle
    Front of The Gleneagle
  • 6 access cards for use at The Galena Territory Owners club
    6 access cards for use at The Galena Territory Owners club
  • The Galena Territory Owners club amenities available to all of our guests
    The Galena Territory Owners club amenities available to all of our guests
  • The GTA Owners Club is available to guests which includes an outdoor pool (available Summer), indoor pool (year round), fitness center, game room, and gym
    The GTA Owners Club is available to guests which includes an outdoor pool (available Summer), indoor pool (year round), fitness center, game room, and gym
  • Fitness center available at The Galena Territory Owners club.
    Fitness center available at The Galena Territory Owners club.
  • Outdoor pool at the Owners club
    Outdoor pool at the Owners club
  • Indoor pool at The Galena Territory Owners Club - available year round for lap swimming or open swimming
    Indoor pool at The Galena Territory Owners Club - available year round for lap swimming or open swimming
  • The Galena Territory amenities -- guests will have access during their stat
    The Galena Territory amenities -- guests will have access during their stat
  • The Galena Territory is a boundless bouquet of vibrant colors in the Fall
    The Galena Territory is a boundless bouquet of vibrant colors in the Fall
  • Head on over to Lake Galena in the warmer months and take a sunset cruise on a pontoon boat or rent a fishing boat for a few hours
    Head on over to Lake Galena in the warmer months and take a sunset cruise on a pontoon boat or rent a fishing boat for a few hours
  • Tennis Courts and Pickleball Courts are available to guests
    Tennis Courts and Pickleball Courts are available to guests
  • Indoor basketball court at the Owners Club
    Indoor basketball court at the Owners Club
  • Shenandoah Riding Center is open to the public
    Shenandoah Riding Center is open to the public
  • Galena on the Fly offers Hot Air Balloon rides (generally May - October)
    Galena on the Fly offers Hot Air Balloon rides (generally May - October)
  • Thunder Bay Falls showcasing some late summer color
    Thunder Bay Falls showcasing some late summer color
  • Frozen over Thunderbay Falls - located in the Galena Territory
    Frozen over Thunderbay Falls - located in the Galena Territory
  • Within the Galena Territory - Eagle Ridge operates 4 golf courses, 2 restaurants (Woodlands open year round and Highlands open warmer months)
    Within the Galena Territory - Eagle Ridge operates 4 golf courses, 2 restaurants (Woodlands open year round and Highlands open warmer months)
  • The General Golf Course (and three others) are open to the public
    The General Golf Course (and three others) are open to the public
  • Golf The General on your next visit to Galena.
    Golf The General on your next visit to Galena.
  • Always something going on in Historic Downtown Galena
    Always something going on in Historic Downtown Galena
  • Stroll the Streets of Downtown Galena.
    Stroll the Streets of Downtown Galena.
  • Historic Downtown Galena
    Historic Downtown Galena
$399-1,000/night
5 Bedrooms • 5 Baths • Sleeps 1-12
Internet Fireplace Lake Hot Tub (more...)
Looking for the perfect space for your family get-together or a getaway with friends? Look no further than The Gleneagle! With the capacity to comfortably sleep up to 10 guests (12 with the use of the sleeper sofa), this space boasts five cozy bedrooms, each with its own ensuite bathroom (or directly adjacent bathroom), as well as a sleeper sofa in the lower level.
 
Inside the home, you will find: Smart TV’s in each bedroom and both living rooms, a wood-burning fireplace, a jacuzzi tub (master bath), ceiling fans in each bedroom, a large dining table for up to 10 people, and additional seating at the breakfast bar. Downstairs you will find a pub table which is perfectly suitable for remote work/laptop-friendly workspace, a foosball table, and an arcade Pac-Man game!
The kitchen is fully equipped with all the cooking basics, as well as a French door refrigerator with a water dispenser and ice maker, Keurig and regular coffee makers, dishwasher, double oven, microwave, and crockpot.
 
New updates include all new KING size beds in all bedrooms -- Three (3) with Sealy Cocoon 12" Memory Foam mattresses and Two (2) with 12" Sealy Memory Foam mattresses with cooling technology!  Rest easily at night on these super comfortable new beds.
 
Bedroom 1: King Bed with ensuite bathroom & jacuzzi tub | Bedroom 2: King Bed (bathroom located just outside bedroom door) | Bedroom 3: King Bed with ensuite bathroom | Bedroom 4: King Bed with ensuite bathroom | Bedroom 5: King Bed with ensuite bathroom | Additional sleeping area: Sleeper sofa in lower-level living room
 
Outside, you'll find four decks perfect for enjoying the beautiful Galena Territory. The front deck features a chair swing and rocking chairs, while the dining area deck offers a gas grill, dining table, chairs, and umbrella. The screened porch off of the kitchen is perfect for relaxing with a good book, and the lower deck boasts a pub table and hot tub. The driveway can accommodate up to 6 cars max.
 
During your stay, you'll be provided six access cards to the Galena Territory Owners Club; these provide access to Shenandoah Riding Center, hiking trails, an indoor pool open year-round (lap swimming and open swimming), a splash pool, and an outdoor pool with slides (available seasonally), tennis courts, fitness center, and pickleball courts (outdoor available seasonally and indoor have scheduled times), and Lake Galena where you may rent a pontoon boat and troll around. If you need additional access cards, they are available for purchase for $5 per person/day (required only for those 5 years and up).
 
Nearby, Eagle Ridge Resort offers four golf courses, a spa, Highlands Restaurant, Woodlands Restaurant & Lounge, a golf simulator at The General Golf Course in the winter months, and a Nordic Center (sledding & ice skating) with a daily bonfire to warm up. Chestnut Mountain is also nearby and offers excellent Midwest skiing during the winter and warmer weather activities such as Alpine Slide, Screaming Eagle zipline ride, Frisbee Golf, and Mountain Biking. And don't forget to check out historic Downtown Galena, where you'll find plenty of great restaurants, unique shopping experiences, and kayaking down the Galena River.
We do not have a COVID or weather cancellation policy, so we highly recommend purchasing Travel Insurance, which is available to purchase after booking. 
 
Please note that all COVID-19 related restrictions have been lifted for the Owners Club, except for a few amenities that still require reservations (lap swimming at the indoor pool, tennis courts, pickleball courts, and outdoor basketball courts, available seasonally). However, this is subject to change if the State of Illinois re-institutes restrictions related to the pandemic, and reservations cannot be guaranteed. There are no discounts or refunds if the Owner's Club amenities are not available.
I have been coming to Galena for the past five years and have fallen in love with the area and all it has to offer. From the historic downtown to skiing at Chestnut in the winter, there is truly something for everyone in this town. I live in Chicago with my partner and love our escapes to Galena when time permits. We own two other rentals -- one in the Territory and another in Delaware. We have 5+ years of experience in managing short-term/vacation rentals.

Galena, Illinois

Property Type House
Accommodation Entire Home
Check-In Smart lock
House Rules
  • Maximum occupancy: 12
  • Children welcome
  • Infants welcome
  • Smoking not allowed
  • Wheelchair inaccessible
  • Minimum age of primary renter: 25
  • Pets not allowed
Setting & View
  • Lake
  • River
  • Golf Course View
  • Resort
  • Rural
  • Resort View
  • Lake Access
  • Resort Access
General
  • Internet
  • Telephone
  • Fireplace
  • Air Conditioning
  • Central Heating
  • Linens Provided
  • Towels Provided
  • Washing Machine
  • Clothes Dryer
  • Hot Water
  • Private Living Room
  • Fitness Room/Equipment
  • Hair Dryer
  • Iron & Board
  • Firewood Provided
  • Wifi
  • Ceiling Fans
  • Laptop Friendly Workspace
  • Basic Soaps
  • Paper Towels
  • Shampoo
  • Toilet Paper
  • Hangers
  • Private Entrance
  • Lock On Bedroom Door
  • Extra Pillows & Blankets
  • Free Internet
  • Body Soap
  • Hair Conditioner
  • Shower Gel
  • Clothing Storage (closet or wardrobe)
  • Portable Fans
Kitchen
  • Kitchen
  • Refrigerator
  • Stove
  • Oven
  • Microwave
  • Dishwasher
  • Dishes & Utensils
  • Spices/Pantry Items
  • Coffee Maker
  • Toaster
  • Ice Maker
  • Freezer
  • Blender
  • Kettle
  • Pots & Pans
  • Kitchen Island
  • Dining Table
  • Baking Sheet
  • Barbeque/Grill Utensils
  • Coffee
  • Wine Glasses
Dining
  • Child's Highchair
  • Seating for 14 people
Bathrooms 5 Baths
  • Primary Bathroom – Jetted Tub, Shower, Toilet
  • Main level bathroom 2 – Combination Tub/Shower, Toilet
  • Lower level bathroom 1 – Combination Tub/Shower, Toilet
  • Lower level bathroom 2 – Combination Tub/Shower, Toilet
  • Lower level bathroom 3 – Combination Tub/Shower, Toilet
Sleeping Arrangements 5 Bedrooms, sleeps 1-12
  • Primary Bedroom – 1 King bed
  • Bedroom 2 – 1 King bed
  • Bedroom 3 – 1 King bed
  • Bedroom 4 – 1 King bed
  • Bedroom 5 – 1 King bed
  • Family room with sectional sleeper sofa queen) – 1 Sleeper Sofa/Futon
Each bedroom has its own bathroom.
Entertainment
  • Television
  • Satellite/Cable
  • Games/Board Games
  • Game Room
  • Pool Table
  • Foosball
  • Gym
  • Smart TV
  • Exercise Equipment
  • Arcade Machine
Family
  • Baby Gate
Outdoor
  • Outdoor Grill
  • Deck/Patio (uncovered)
  • Lanai/Gazebo (covered)
  • Balcony/Terrace
  • Lawn/Garden
  • Tennis
  • Walkable to Golf
  • Boat Available
  • Kayak/Canoe
  • Veranda
  • Private Yard
  • Outdoor Dining
  • Outdoor Seating
Pool/Spa
  • Communal Pool
  • Hot Tub
  • Indoor Pool
  • Heated Pool
  • Children's Pool
Vehicles
  • Parking
  • Free Parking
  • Free Parking On Premises
Theme
  • Adventure
  • Family
  • Historic
  • Romantic
  • Tourist Attractions
Attractions
  • Health/Beauty Spa
  • Marina
  • Museums
  • Winery Tours
Leisure
  • Antiquing
  • Bird Watching
  • Gambling/Casinos
  • Horseback Riding
  • Sledding
  • Boating
  • Shopping
  • Wildlife Viewing
  • Water Sports
Sports & Adventure
  • Basketball Court
  • Cycling
  • Cross Country Skiing
  • Fishing
  • Freshwater Fishing
  • Golf
  • Golf Privileges Optional
  • Hiking
  • Hunting
  • Ice Skating
  • Kayaking
  • Mountain Biking
  • Ski Lift Privileges Optional
  • Skiing
  • Water Skiing
  • Snowboarding
  • Snowmobiling
  • Swimming
  • Water Tubing
  • Bowling Alley
  • Mini Golf
  • Skate Ramp
Safety
  • Carbon Monoxide Detector
  • Deadbolt Lock
  • Emergency Exit Route
  • Fire Emergency Contact
  • Fire Extinguisher
  • First Aid Kit
  • Medical Emergency Contact
  • Exterior Lighting
  • Police Emergency Contact
  • Smoke Detector
  • Enhanced Cleaning Practices
  • Cleaning Disinfection
  • Common Surface Disinfectant Cleaned
  • Linens High Temp Wash
  • Cleaning Products
Expectations
  • Requires Stairs
  • Limited Parking
  • Cameras/Surveillance
  • Near Lake, River, or Water Body
Registration Number
23-150
Registration Expiration Date
Dec 31, 2023
Season Rate
Holidays
Dec 23, 2024 - Jan 5, 2025
Night
$367 - $775
Weekly
$3,474 to $4,194
MLK
Jan 16, 2025 - Jan 20, 2025
Night
$440 - $599
Presidents Day
Feb 13, 2025 - Feb 17, 2025
Night
$440 - $675
Summer Updated
6/1 - 10/31
Night
$449 - $799
Weekly
$3,189 to $4,359
Monthly
$12,079 to $14,727

Cancellation Policy: One hundred percent (100.00%) of the total booking charges (less $100.00 cancellation fee) will be refunded if the cancellation is made more than 45 days prior to the arrival date of the reservation. Fifty percent (50.00%) of the total booking charges (less $100.00 cancellation fee) will be refunded if the cancellation is made more than 30 days prior to the arrival date of the reservation. For cancellations made within 30 days prior to the arrival date, no refund will be issued.

Rates are subject to change. Cancellation Policy: One hundred percent (100.00%) of the total booking charges (less $100.00 cancellation fee) will be refunded if the cancellation is made more than 45 days prior to the arrival date of the reservation. Fifty percent (50.00%) of the total booking charges (less $100.00 cancellation fee) will be refunded if the cancellation is made more than 30 days prior to the arrival date of the reservation. For cancellations made within 30 days prior to the arrival date, no refund will be issued.