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Holiday Rentals near Galena Trolley Tours

314 S Main St, Galena, Illinois 61036-2229
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    All 110 Rentals in Galena
    Family Friendly; Pet friendly Settlement Home1 / 17
    (14)Very good
    4.2 miles from Galena Trolley Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Stunning Home Away From Home.1 / 23
    (4)Excellent
    4.3 miles from Galena Trolley Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 8 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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    NEWLY RENOVATED!!  Beautiful Golf Villa Waiting Just For You!1 / 30
    (3)Excellent
    4.8 miles from Galena Trolley Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Indoor Pool
    • Air Conditioning
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 October 2019
    the unit was very clean and neat, with everything needed for our stay. The area was beautiful, set among 4 golf courses among winding roads and hilly countryside, and was...
    Reviewed 17 August 2019
    Accommodations impeccable. Amenities provide were wonderful. Everything you may need was provided in the Villa. Quiet and peaceful. Will visit again.
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    About this property
    NEWLY RENOVATED!! This beautiful golf villa is only a 7 iron away from the South Course, part of the award-winning Eagle Ridge Resort and Spa! Whether it’s golfing at any of the championship golf courses, hiking any of the 24 miles of walking trails, horseback riding, boating, fishing, relaxing at...
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    Location Information
    Galena, Illinois
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    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 Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 October 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 16 September 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
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    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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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2018
    Not a bad thing to say about this beautiful home! Clean, comfortable, view of the city is amazing, friendly owners!
    Reviewed 2 January 2018
    Wonderful location with excellent views. The house is super clean, well laid out, beautifully decorated with lovely antiques, and screams of history. A great back patio and...
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    About this property
    Built in 1856 by Asa Haile, a licensed riverboat captain and successful mason, this classic Federal-style brick home is located up on Quality Hill, where mansions overlook the entire historic district of Galena. A quick 5-minute walk puts you directly on Galena's Main Street, named “One of...
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    Galena, Illinois
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    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
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    • Shared Indoor Pool
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 October 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 22 June 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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    Location Information
    Galena, Illinois
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    4.4 miles from Galena Trolley Tours
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • 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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    Location Information
    Galena, Illinois
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    0.2 miles from Galena Trolley Tours
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    About this property
     Located on Main Street in the heart of Galena's Historic District! Clean, quiet and newly remodeled, this spacious apartment has all you need for a relaxing stay!  Walk to shops and restaurants.  Private Parking included. Offers a King and Queen size bed. Perfect for couples or small groups. Make...
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    Location Information
    Galena, Illinois
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    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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    Suitability
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.5 miles from Galena Trolley Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
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    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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    Location Information
    Galena, Illinois
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.1 miles from Galena Trolley Tours
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Wi-Fi
    • Patio
    • Air Conditioning
    • 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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    Location Information
    Galena, Illinois
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    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
    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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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
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    Location Information
    Galena, Illinois
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Striking 4 Bd/3.5 Ba, Incredible Wooded Views, Fireplace, Pool Table, Fire Pit1 / 24
    (45)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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    Galena, Illinois
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    *NEW*   Modern Hilltop House of Galena1 / 19
    (2)Excellent
    3.4 miles from Galena Trolley Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Galena, Illinois
    Holiday Rental House - 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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    Galena, Illinois
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    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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    Location Information
    Galena, Illinois
    Holiday Rental House - 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
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    Comfortable, Relaxing Vacation Getaway - 5 BR/5 BA1 / 24
    (39)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)
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    Galena, Illinois
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedroom 5 ⭐️ Home 37 Acres With Mississippi River Views Near Chestnut Mountain1 / 41
    (33)Excellent
    5.4 miles from Galena Trolley Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Galena, Illinois
    Holiday Rental House - 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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    Location Information
    Galena, Illinois
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Welcome to your Galena Get Away!!!1 / 16
    (83)Excellent
    5.0 miles from Galena Trolley Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Galena, Illinois
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Enjoy 3 floor, 5BR/5BA new house w/Views of Lake, Outside Jacuzzi, Game Room etc1 / 46
    (12)Very good
    5.1 miles from Galena Trolley Tours
    6 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Galena, Illinois
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 10
    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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    • Washer
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    Location Information
    Galena, Illinois
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Ironwood Vacation Home, Galena Territory1 / 21
    (64)Excellent
    5.9 miles from Galena Trolley Tours
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Galena, Illinois
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    ★★Sweet Retreat with Hot Tub, Ping Pong & Fire Pit★★1 / 30
    (6)Excellent
    6.2 miles from Galena Trolley Tours
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Galena, Illinois
    Holiday Rental House - 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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    PET FRIENDLY! 4 BR/4.5 BA, Tranquil Home Away From Home - Free Night!1 / 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
    Holiday Rental House - 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    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
    Holiday Rental House - 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
    Holiday Rental House - 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
    Holiday Rental House - 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
    Holiday Rental House - 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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    Location Information
    Galena, Illinois
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Cozy cul de sac location on the northern quarter of the Galena Territory1 / 47
    (10)Excellent
    4.6 miles from Galena Trolley Tours
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Shared Indoor Pool
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    Pet friendly
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    Location Information
    Galena, Illinois
    Holiday Rental House - 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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    • Air Conditioning
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    Location Information
    Galena, Illinois
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    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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    Location Information
    Galena, Illinois
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Stunning Home Away from Home1 / 38
    (49)Very good
    4.3 miles from Galena Trolley Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Housekeeping Included
    • Sauna
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    Galena, Illinois
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    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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    • Internet Access
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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
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
    All the comforts of home!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
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    Location Information
    Galena, Illinois
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedroom, 2 bath townhouse in The Galena Territory.1 / 26
    (30)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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    Location Information
    Galena, Illinois
    Holiday Rental House - 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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    • Shared Outdoor Pool (Unheated)
    • DVD Player
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    Pet friendly
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    Location Information
    Galena, Illinois
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    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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    • Washer
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    Pet friendly
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    Location Information
    Galena, Illinois
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Wide Open Countryside, 3 level Log Home, Hot Tub, Game Room1 / 32
    (19)Excellent
    4.2 miles from Galena Trolley Tours
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Patio
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    • Housekeeping Included
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    Pet friendly
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    Location Information
    Galena, Illinois
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    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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    Pet friendly
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    Location Information
    Galena, Illinois
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    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
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    Location Information
    Galena, Illinois
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Galena Territory 1 Bedroom House. Resort Core. Small Dogs OK.  Book Fall/Winter1 / 16
    (71)Very good
    4.1 miles from Galena Trolley Tours
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Galena, Illinois
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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