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Vacation Rentals near Galena Trolley Tours

314 S Main St, Galena, Illinois 61036-2229
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    Travelers to Galena are booking October dates now. Secure your vacation rental today, and have the perfect trip.
    All 117 Rentals in Galena
    Family Friendly; Pet friendly Settlement Home1 / 34
    (14)Very good
    4.2 miles from Galena Trolley Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Comfort House1 / 15
    (5)Excellent
    4.8 miles from Galena Trolley Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Asa Haile House - overlooks historic Galena1 / 26
    (2)Excellent
    0.1 miles from Galena Trolley Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Galena Territory / Family and Friend Get Aways / Wifi1 / 10
    (8)Excellent
    4.6 miles from Galena Trolley Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Balcony
    • Patio
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    • Shared Indoor Pool
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 26, 2016
    We stayed for the first time in this home to celebrate a special birthday. Everyone loved the home which is beautifully decorated and maintained. The fall colors and golf course...
    Reviewed June 22, 2015
    We just finished our 5th or 6th year staying at this wonderful house. We all went to college together as sorority sisters and this is a central place to gather together and...
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    About this property
    The home has been all updated. There are three level to the home. The lower level has Laundry facilities, Full bath, Family room area with sliding doors to outside deck, also a Bedroom with two full size beds. The first level has a great room with a stonewall fireplace, full kitchen, harvest...
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    Galena, Illinois
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Owl House1 / 25
    (4)Excellent
    0.1 miles from Galena Trolley Tours
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 17, 2019
    The Owl House is an absolute gem in downtown Galena! The location is perfect (one block off Main Street) and the home is immaculate. It's a very unique property that is...
    Reviewed September 15, 2018
    Cozy, safe, unique lodging within easy walking distance to all attractions. Would definitely stay here again.
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    About this property
    Originally built as a warehouse circa 1880, the Owl House has since been completely renovated into a modern and comfortable living space with industrial elements and charm. At approximately 1200 square feet on two floors, the Owl House sleeps up to 4 people. With original exposed ceilings,...
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    Location Information
    Galena, Illinois
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
    4.4 miles from Galena Trolley Tours
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Washer
    • Waterfront
    • Patio
    • Balcony
    • Sauna
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Galena Chalet is one of only five homes in the Galena Territory with a full lake view of Lake Galena. The home has 5 bedrooms and is tastefully furnished and organized for larger groups of 8-10 people. The beautiful Chalet is charming inside and out; nestled in the woods and located with the...
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    Galena, Illinois
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    4.9 miles from Galena Trolley Tours
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This romantic, secluded townhouse is located in the Galena Territory, a 3800-acre resort area with rolling hills, woodlands, championship golf courses, and 24 miles of walking trails and much more. Located in the heart of The Galena Territory, the townhouse is close to all the resort's amenities...
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    Location Information
    Galena, Illinois
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.1 miles from Galena Trolley Tours
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Wi-Fi
    • Patio
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    • Waterfront
    • Cable/satellite TV
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gorgeous home is located in the heart of beautiful Galena, and within walking distance to downtown shops, restaurants, bike path and boat launch. This is a great location, for you won't have to use your car, with everything being so close by. Our front porch looks out over the Galena River and...
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    Galena, Illinois
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    0.5 miles from Galena Trolley Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    History buffs, architecture fans and those looking to get away need look no further than this award-winning Galena home! The idyllic 3-bedroom, 2-bath vacation rental boasts an enclosed yard, fire pit, deck, and every amenity you need for maximum comfort! Just a stone's throw away, the historic...
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    Galena, Illinois
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2 bdrm, 2 bath Condo1 / 7
    (2)Very good
    4.6 miles from Galena Trolley Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Galena, Illinois
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Striking 4 Bd/3.5 Ba, Incredible Wooded Views, Fireplace, Pool Table, Fire Pit1 / 24
    (48)Excellent
    5.3 miles from Galena Trolley Tours
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
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    Galena, Illinois
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Cozy Hideaway with 3 Season Lake View1 / 8
    (4)Very good
    4.1 miles from Galena Trolley Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Galena, Illinois
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    *NEW*   Modern Hilltop House of Galena1 / 19
    (4)Excellent
    3.4 miles from Galena Trolley Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
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    Location Information
    Galena, Illinois
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Beautiful home near resort amenities, WIFI1 / 16
    (10)Excellent
    6.2 miles from Galena Trolley Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    • Hot Tub
    • Air Conditioning
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Galena, Illinois
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    OFF SEASON SPECIAL: STAY 2 NIGHTS, GET A 3RD NIGHT FREE (excludes: 12/22-1/4)1 / 19
    (20)Excellent
    4.4 miles from Galena Trolley Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Smoking allowed
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    Galena, Illinois
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Love the outdoors???1 / 20
    (1)Excellent
    6.1 miles from Galena Trolley Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Galena, Illinois
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful Upscale 6Br/4.5Ba Vacation Home And Private Carriage House On 2.5 Acre1 / 22
    (34)Excellent
    5.1 miles from Galena Trolley Tours
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Galena, Illinois
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    Comfortable, Relaxing Vacation Getaway - 5 BR/5 BA1 / 33
    (44)Excellent
    6.1 miles from Galena Trolley Tours
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
    • Patio
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    Smoking allowed
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    Galena, Illinois
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    3 Bedroom 5 ⭐️ Home 37 Acres With Mississippi River Views Near Chestnut Mountain1 / 42
    (33)Excellent
    5.4 miles from Galena Trolley Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
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    Smoking allowed
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    Galena, Illinois
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    Love the outdoors???1 / 20
    (4)Excellent
    6.1 miles from Galena Trolley Tours
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Galena, Illinois
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Welcome to your Galena Get Away!!!1 / 16
    (88)Excellent
    5.0 miles from Galena Trolley Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
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    Galena, Illinois
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3 BR 3BA   Want to REALLY Get Away!?  Galena Territory & Owners' Club Privileges1 / 22
    (50)Excellent
    5.1 miles from Galena Trolley Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Galena, Illinois
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Ironwood Vacation Home, Galena Territory1 / 21
    (70)Excellent
    5.9 miles from Galena Trolley Tours
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Galena, Illinois
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    ★★Sweet Retreat with Hot Tub, Ping Pong & Fire Pit★★1 / 30
    (7)Excellent
    6.2 miles from Galena Trolley Tours
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    Galena, Illinois
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Extraordinary Log Home w/Breathtaking Views, 2 Fireplaces, Pool Table, Fire Pit1 / 45
    (15)Excellent
    5.7 miles from Galena Trolley Tours
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Galena, Illinois
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    PET FRIENDLY! Tranquil Home Away From Home, W/ Fire pit1 / 50
    (5)Very good
    6.8 miles from Galena Trolley Tours
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Galena, Illinois
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    The Cedar Townhouse in the center of the Galena Territory1 / 18
    (15)Very good
    4.8 miles from Galena Trolley Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Galena, Illinois
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    OFF SEASON SPECIAL: STAY 2 NIGHTS, GET A 3RD NIGHT FREE (excludes: 12/22-1/4)1 / 14
    (23)Very good
    5.2 miles from Galena Trolley Tours
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Galena, Illinois
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
    Townhome located near amenities.1 / 7
    (8)Very good
    5.0 miles from Galena Trolley Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Galena, Illinois
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Beautiful Rustic Townhome - Lodge Theme1 / 12
    (11)Very good
    4.9 miles from Galena Trolley Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Galena, Illinois
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Condo with Lake View1 / 6
    (12)Excellent
    4.5 miles from Galena Trolley Tours
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Galena, Illinois
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Golf Villa in the heart of The Galena Territory1 / 19
    (127)Excellent
    5.3 miles from Galena Trolley Tours
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Galena, Illinois
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
    OFF SEASON SPECIAL: STAY 2 NIGHTS, GET A 3RD NIGHT FREE (excludes: 12/22-1/4)1 / 10
    (18)Very good
    5.7 miles from Galena Trolley Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Galena, Illinois
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Elle & Becks Loft Suite1 / 20
    (36)Excellent
    0.2 miles from Galena Trolley Tours
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Galena, Illinois
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Cozy cul de sac location on the northern quarter of the Galena Territory1 / 42
    (10)Excellent
    4.6 miles from Galena Trolley Tours
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Galena, Illinois
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Elle & Becks Second Floor Suite1 / 13
    (6)Excellent
    0.0 miles from Galena Trolley Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Galena, Illinois
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    OFF SEASON SPECIAL: STAY 2 NIGHTS, GET A 3RD NIGHT FREE (excludes: 12/22-1/4)1 / 21
    (7)Very good
    5.9 miles from Galena Trolley Tours
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Galena, Illinois
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Stunning Home Away from Home1 / 38
    (50)Very good
    4.3 miles from Galena Trolley Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Galena, Illinois
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    All the comforts of home!1 / 20
    (1)Excellent
    6.1 miles from Galena Trolley Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Galena, Illinois
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautifully Furnished One Bedroom In The Heart Of Historical Downtown Galena1 / 21
    (18)Very good
    0.0 miles from Galena Trolley Tours
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Galena, Illinois
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Elegant & Cozy 6 Bed 6 Bath Home Perfect for Gatherings of Family and Friends1 / 28
    (13)Excellent
    5.1 miles from Galena Trolley Tours
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Galena, Illinois
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
    2 Bedroom, 2 bath townhouse in The Galena Territory.1 / 26
    (31)Excellent
    5.1 miles from Galena Trolley Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Galena, Illinois
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Luxurious Galena Territory 5 Bedroom home, Hot Tub, Wi-Fi1 / 25
    (37)Excellent
    6.8 miles from Galena Trolley Tours
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Location Information
    Galena, Illinois
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    5.0 miles from Galena Trolley Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Location Information
    Galena, Illinois
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Newly remodeled, Located in Galena Territories. Small Pets OK under 25 LBS1 / 50
    (43)Excellent
    5.1 miles from Galena Trolley Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Location Information
    Galena, Illinois
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    OFF SEASON SPECIAL: STAY 2 NIGHTS, GET A 3RD NIGHT FREE (excludes: 12/22-1/4)1 / 24
    (26)Very good
    4.8 miles from Galena Trolley Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
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    Location Information
    Galena, Illinois
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Family/Friends Cozy Retreat-Enjoyment Guaranteed1 / 46
    (12)Excellent
    5.8 miles from Galena Trolley Tours
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Location Information
    Galena, Illinois
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    1 Bedroom, 2 bath townhouse in The Galena Territory.1 / 22
    (24)Very good
    5.3 miles from Galena Trolley Tours
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Shared Indoor Pool
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    Location Information
    Galena, Illinois
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
    Studio 1105 in Longhollow Point Inn1 / 12
    (1)Excellent
    6.1 miles from Galena Trolley Tours
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Shared Indoor Pool
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    Location Information
    Galena, Illinois
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Galena Territory 1 Bedroom House. Resort Core. Small Dogs OK.  Book Fall/Winter1 / 16
    (76)Very good
    4.1 miles from Galena Trolley Tours
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
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    Location Information
    Galena, Illinois
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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