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Holiday Rentals near Shenandoah Riding Center

Galena, Illinois 61036-8726
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    Travellers to Galena are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    All 99 Rentals in Galena
    Serenity Cabins - Rustic, modern cabin w/fireplace, pool table & wifi1 / 20
    (3)Excellent
    1.9 kilometres from Shenandoah Riding Center
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    LUXURY HOME WITH A VIEW! DISCOUNTS FOR ONE WEEK!1 / 46
    (3)Excellent
    1.5 kilometres from Shenandoah Riding Center
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Family Friendly; Pet friendly Settlement Home1 / 17
    (16)Very good
    4.4 kilometres from Shenandoah Riding Center
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2.1 kilometres from Shenandoah Riding Center
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Sauna
    • Washer
    • Terrace
    • Balcony
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WorldMark Galena is situated near Eagle Ridge Resort's General, the most challenging of the four world-class Galena territory golf courses. Each unit includes a fireplace, cable TV, dining area and a deck. The resort features a glassed-in indoor pool, hot tub and game room. Stretch out and relax in...
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    Galena, Illinois
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Inviting, Serene Golf Villa in Galena Territory1 / 24
    (9)Excellent
    2.6 kilometres from Shenandoah Riding Center
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Parking
    • Shared Indoor Pool
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2020
    We stayed here for our anniversary. It was quite lovely. Nice and quiet. It looks just like the pictures. The bed is very comfortable.
    Reviewed 27 September 2019
    Easy and confident that we have selected a nice place to stay. It was comfortable with a wooded backyard. We enjoyed our visit.
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    About this property
    Set in one of Northern Illinois’ most beautiful and secluded locales, the 6,800-acre Galena Territory, this townhome is located on the 10th hole of the South Course. Golf right outside your door, and when you're finished...walk home. The home has one bedroom and one attached bathroom on each floor,...
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    Galena, Illinois
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Galena, IL: Studio w/Fireplace, Jetted Tub, Resort Pool & Outdoor Activities1 / 31
    (2)Average
    2.1 kilometres from Shenandoah Riding Center
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Grill
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    Pet friendly
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    Smoking allowed
    Reviewed 3 June 2019
    We’ve been here 3 times but this was the first time at the Wyndmark resort. I would definitely recommend staying there. But if you ever have a chance, I would stay at the Desoto...
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    About this property
    WorldMark Galena is situated near Eagle Ridge Resort's General, the most challenging of the four world-class Galena territory golf courses. The resort features a glassed-in indoor pool, hot tub and game room. Ideal for one or two people, this spacious studio condo features a Queen Size Murphy bed...
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    Galena, Illinois
    Condo/Apartment - 1 Bathroom, Sleeps 2
    GORGEOUS HOME WITH A VIEW! DISCOUNTS FOR ONE WEEK!1 / 47
    (1)Excellent
    1.5 kilometres from Shenandoah Riding Center
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Shared Indoor Pool
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 August 2020
    This home is in the heart of Galena Territory. The surroundings are so beautiful and serene. The home is very clean and I felt like I was at home. Ruby response rate is 100%. I...
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    About this property
    Beautiful, spacious home nestled in the tree tops. Impress long views of Elizabeth. Custom kitchen with commercial grade appliances. Two fireplaces, fantastic sound system. Foosball table, poker table, lots of games! Plenty of room to dine and enjoy time with family and friends! Master suite with...
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    Galena, Illinois
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    Comfort House1 / 15
    (5)Excellent
    4.8 kilometres from Shenandoah Riding Center
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Shared Indoor Pool
    • Patio
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 March 2020
    I have rented 24 vacation homes in the past, and Comfort House was one of the cleanest and best appointed homes where we have stayed. There were special touches all around...
    Reviewed 9 October 2019
    The house is set up with great personal touches by the owner that makes it feel warm, cozy and inviting, more like a 'Home' or visiting a relative then staying in a vacation...
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    About this property
    Located in the Galena Territory, the “Comfort House” offers a luxurious, peaceful, yet affordable convenient vacation rental. This distinctive 1700 sq. ft. interior has designer touches throughout and provides sleeping for eight with just the right amount of space and privacy. The master bedroom...
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    Location Information
    Galena, Illinois
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    2.9 kilometres from Shenandoah Riding Center
    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Balcony
    • Housekeeping Included
    • Central Heating
    • Grill
    • Patio
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful custom built 6 bedroom/7 bath home located on Eagle Ridge's South Course. Great place to entertain a crowd, seated dining for 24. Fully stocked main kitchen, additional outdoor kitchen with a wet bar, full sized fridge and a grill. Private hot tub on premise and passes to the Owner's...
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    Galena, Illinois
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 14
    Nice Galena Home w/Huge Patio, Hot Tub & Fire Pit1 / 24
    (2)Excellent
    1.7 kilometres from Shenandoah Riding Center
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2017
    Great house to stay in! All the amenities were provided and plenty of room for everyone to stay. Really enjoyed spending time in the hot tub and at the bonfire pit. Definitely...
    Reviewed 1 February 2017
    Very nice and clean. Plenty of room to spare for 7 adults and 2 kids. Only a minute away from the clubhouse with indoor basketball court, game room, fitness center and huge...
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    About this property
    Tranquility awaits you at this picturesque 4-bedroom, 3-bath Galena vacation rental house, nestled in a private, wooded area far from the hustle and bustle of the big city! Shred the slopes at Chestnut Mountain Resort or glide through the trees on a zipline at Long Hollow Canopy Tours. If you’re a...
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    Location Information
    Galena, Illinois
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Galena Territory / Family and Friend Get Aways / Wifi1 / 10
    (8)Excellent
    3.7 kilometres from Shenandoah Riding Center
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Balcony
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Shared Indoor Pool
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 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 23 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 patio, also a Bedroom with two Queen size beds. The first level has a great room with a stonewall fireplace, full kitchen, harvest...
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    Galena, Illinois
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    2.1 kilometres from Shenandoah Riding Center
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wyndham Galena, located just 7 miles from downtown Galena, puts you at the heart of one of our nation’s historic treasures. This resort is a modern vacation mecca with award-winning golf, shopping and park adventure. The resort offers an indoor pool and hot tub as well as a fitness center and game...
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    Location Information
    Galena, Illinois
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    5 Bedroom Suites, Private Bath, Large Fire Pit, Walking Distance to Owners Club1 / 45
    (35)Very good
    2.9 kilometres from Shenandoah Riding Center
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Shared Indoor Pool
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    • Hot Tub
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Galena, Illinois
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    Hot Tub, Jacuzzi, Pool, Pool Table, Fireplace & Double Oven1 / 17
    (5)Very good
    2.5 kilometres from Shenandoah Riding Center
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Galena, Illinois
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Adorable Settlement home with seasonal lake and waterfall views1 / 28
    (7)Excellent
    4.6 kilometres from Shenandoah Riding Center
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Galena, Illinois
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Boulder Creek, Galena IL1 / 29
    (56)Excellent
    4.1 kilometres from Shenandoah Riding Center
    4 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Galena, Illinois
    Holiday Rental House - 4 Bedrooms, 7 Bathrooms, Sleeps 10
    OFF SEASON SPECIAL: STAY 2 NIGHTS, GET A 3RD NIGHT FREE (excludes: 12/22-1/4)1 / 20
    (44)Very good
    4.0 kilometres from Shenandoah Riding Center
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Galena, Illinois
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    2 Bedroom, 2 bath Settlement Home in The Galena Territory.1 / 23
    (16)Excellent
    4.6 kilometres from Shenandoah Riding Center
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Galena, Illinois
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Beautiful Upscale 6Br/4.5Ba Vacation Home And Private Carriage House On 2.5 Acre1 / 44
    (68)Excellent
    3.1 kilometres from Shenandoah Riding Center
    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 / 33
    (76)Excellent
    1.5 kilometres from Shenandoah Riding Center
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Galena, Illinois
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Dressed for the Holidays!1 / 31
    (34)Excellent
    3.9 kilometres from Shenandoah Riding Center
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Galena, Illinois
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedroom, 2 bath house in The Galena Territory.1 / 25
    (27)Very good
    4.1 kilometres from Shenandoah Riding Center
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Galena, Illinois
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Welcome to your Galena Get Away!!!1 / 16
    (143)Excellent
    3.7 kilometres from Shenandoah Riding Center
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Galena, Illinois
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Beautiful 3 level Log Home in the Galena Territory1 / 19
    (28)Very good
    5.0 kilometres from Shenandoah Riding Center
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Housekeeping Included
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    Galena, Illinois
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Sweet Retreat With Hot Tub, Ping Pong & Fire Pit1 / 31
    (19)Excellent
    1.0 kilometres from Shenandoah Riding Center
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Galena, Illinois
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    The Galena Log Home, Galena IL1 / 26
    (20)Excellent
    2.1 kilometres from Shenandoah Riding Center
    5 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    Galena, Illinois
    Holiday Rental House - 5 Bedrooms, 8 Bathrooms, Sleeps 12
    PET FRIENDLY! Tranquil Home Away From Home, W/ Fire pit1 / 50
    (16)Excellent
    1.7 kilometres from Shenandoah Riding Center
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Galena, Illinois
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    OFF SEASON SPECIAL: STAY 2 NIGHTS, GET A 3RD NIGHT FREE (excludes: 12/22-1/4)1 / 27
    (81)Very good
    3.7 kilometres from Shenandoah Riding Center
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Galena, Illinois
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    The Cedar Townhouse in the center of the Galena Territory1 / 18
    (17)Very good
    3.9 kilometres from Shenandoah Riding Center
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Galena, Illinois
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    OFF SEASON SPECIAL: STAY 2 NIGHTS, GET A 3RD NIGHT FREE (excludes: 12/22-1/4)1 / 14
    (51)Very good
    2.8 kilometres from Shenandoah Riding Center
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Galena, Illinois
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
    2 Bedroom, 2 bath townhouse in The Galena Territory1 / 22
    (53)Excellent
    2.6 kilometres from Shenandoah Riding Center
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Galena, Illinois
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Cozy cul de sac location on the northern quarter of the Galena Territory1 / 44
    (15)Excellent
    5.3 kilometres from Shenandoah Riding Center
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Galena, Illinois
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    OFF SEASON SPECIAL: STAY 2 NIGHTS, GET A 3RD NIGHT FREE (excludes: 12/22-1/4)1 / 21
    (21)Very good
    3.0 kilometres from Shenandoah Riding Center
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Galena, Illinois
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Beautifully Furnished One Bedroom In The Heart Of Historical Downtown Galena1 / 21
    (47)Excellent
    11.3 kilometres from Shenandoah Riding Center
    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
    (31)Very good
    3.6 kilometres from Shenandoah Riding Center
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Galena, Illinois
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
    Luxurious Galena Territory 5 Bedroom home, Hot Tub, Wi-Fi1 / 25
    (57)Excellent
    1.8 kilometres from Shenandoah Riding Center
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
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    Galena, Illinois
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Bird Cottage * Sorriso Vineyard Galena Illinois1 / 20
    (40)Excellent
    3.9 kilometres from Shenandoah Riding Center
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed 3 weeks ago
    Spent the weekend here for a girls trip. 5 people stayed comfortably. I even slept on the hide-a-way bed and it was comfortable enough (queen-size). Ample kitchen size, nice...
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    Galena, Illinois
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    OFF SEASON SPECIAL: STAY 2 NIGHTS, GET A 3RD NIGHT FREE (excludes: 12/22-1/4)1 / 24
    (45)Very good
    3.9 kilometres from Shenandoah Riding Center
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Galena, Illinois
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Newly remodeled, Located in Galena Territories. Small Pets OK under 25 LBS1 / 50
    (66)Excellent
    3.5 kilometres from Shenandoah Riding Center
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Galena, Illinois
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Great Location/Great Reviews/Great Rates stay 2 nights 3rd night FREE1 / 25
    (148)Excellent
    3.5 kilometres from Shenandoah Riding Center
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Galena, Illinois
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Family/Friends Cozy Retreat-Enjoyment Guaranteed1 / 46
    (27)Excellent
    1.9 kilometres from Shenandoah Riding Center
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Galena, Illinois
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Enjoy the wooded privacy of  ~FOXTROT RETREAT~ Stylish updated interior1 / 43
    (34)Excellent
    1.9 kilometres from Shenandoah Riding Center
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Galena, Illinois
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Seclusion on 120 acres and yet one mile to town.1 / 47
    (29)Excellent
    11.9 kilometres from Shenandoah Riding Center
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Galena, Illinois
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Perfect Relaxing Getaway1 / 14
    (28)Excellent
    3.4 kilometres from Shenandoah Riding Center
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Galena, Illinois
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
    OFF SEASON SPECIAL: STAY 2 NIGHTS, GET A 3RD NIGHT FREE (excludes: 12/22-1/4)1 / 28
    (16)Excellent
    4.0 kilometres from Shenandoah Riding Center
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Galena, Illinois
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Beautiful 2 bedroom, 2 bath townhouse w/ access to Owner's Club pool/fitness rm1 / 50
    (66)Excellent
    3.4 kilometres from Shenandoah Riding Center
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Galena, Illinois
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Lakeside is a spacious, flowing home located on the north shores of Lake Galena1 / 40
    (36)Excellent
    4.8 kilometres from Shenandoah Riding Center
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Galena, Illinois
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    Territory View - A Dog Friendly Townhouse in the Resort Core - 3BR/2Bath1 / 39
    (51)Excellent
    3.1 kilometres from Shenandoah Riding Center
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Galena, Illinois
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    1 Bedroom, 2 bath townhouse in The Galena Territory.1 / 22
    (43)Very good
    3.4 kilometres from Shenandoah Riding Center
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Galena, Illinois
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Beautiful, High-end, Luxury Home Nestled On 4 Acres Close To All Amenities1 / 24
    (112)Excellent
    2.5 kilometres from Shenandoah Riding Center
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Galena, Illinois
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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