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Holiday Homes in Galena

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    Travellers to Galena are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    All 24 Rentals in Galena
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    Derinda House Bed and Breakfast1 / 27
    (17)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Enjoy 4 Bed/3Bath and true resort living1 / 16
    (15)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Serenity Cabins - Rustic, modern cabin w/fireplace, pool table & wifi1 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Family Friendly; Pet friendly Settlement Home1 / 26
    (12)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Shared Indoor Pool
    • Parking
    • DVD Player
    • Internet Access
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2018
    Thought the house was very clean, well decorated, and very comfortable. Richard O was great when there was an issue; he contacted us back that same afternoon.The only...
    Reviewed 8 May 2017
    Packed some amenities just in case but found everything available just as described. Got lucky with the weather (70's) except for one day when we limited a round to nine holes...
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    About this property
    2 bedrooms-each with a queen size bed; 2 full baths; gas grill on the back porch facing the woods with a seasonal view of Lake Galena Hiking trails immediately accessible. Minutes away from the marina - pontoon rentals available. Close to the owners club, featuring: indoor and outdoor swimming...
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    Location Information
    Galena, Illinois 60440
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Asa Haile House - overlooks historic Galena1 / 26
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Patio
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Parking
    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 3 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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    Location Information
    Galena, Illinois 61036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Enjoy a Cozy, Secluded, Affordable Galena Retreat!1 / 18
    (23)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Indoor Pool
    • DVD Player
    • Grill
    • Air Conditioning
    • Parking
    • Washer
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    The cottage is located in a beautiful and scenic part of Galena. It is a short drive to the city center, where there is plenty to see and do. My family enjoyed an entire day...
    Reviewed 4 July 2017
    My daughter and I drove to Galena, IL for a "get away". We stayed 3 nights at this wonderful, clean, and well accessorized cabin/condo. Wonderful relaxation and quiet...
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    About this property
    What’s your pleasure? Hiking … biking … golf … tennis … skiing … fishing … boating … swimming … bird watching … horseback riding … ballooning … antiques … shopping … old homes … Civil War history … or just Rest & Relaxation? Whether you are a Vacationing Family, a Romantic Couple or Friends on a...
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    Location Information
    Galena, Illinois 61036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • 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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    Location Information
    Galena, Illinois 61036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Walnut Hill House1 / 12
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Shared Indoor Pool
    • Air Conditioning
    • Porch
    • DVD Player
    • Parking
    • Washer
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 April 2017
    This house was very spacious, location to Galena great, and had everything we needed. Everything was very clean, in great shape and had a nice view. Loved the screened in porch!
    Reviewed 9 March 2017
    We were three couples that stayed at this really attractive, spacious home with an open floor plan. We'll be back in summer as it has a large party deck right on the golf...
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    About this property
    This beautifully furnished free standing 3 or 4 bedroom 3 or 4 bath home is centrally located within the Galena Resort core just across the street from the limited access Walnut Hill swimming pool. A large party deck overlooks the 15th fairway of the North golf course and you are just minutes...
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    Location Information
    Galena, Illinois 61036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Owl House1 / 25
    (2)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2018
    We will definitely be coming back.The location of the the Owl House is block "up" from the Main Street. Perfect location to go shopping, come drop items off and go...
    Reviewed 5 March 2018
    First let me start with explaining just how high our expectations tend to be...my husband has worked in hotels and hospitality for nearly 20 years...and my degree is in interior...
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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 61036
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Hot Tub
    • Sauna
    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. 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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    Location Information
    Galena, Illinois 61036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Inviting, Serene Golf Villa in Galena Territory1 / 24
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Parking
    • Shared Indoor Pool
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 April 2018
    Had a really nice time with the family in Galena for 5 days. The house was clean and well maintained as expected. Booking through TripAdvisor was very easy and the owner was...
    Reviewed 24 July 2017
    Cozy, cute, Clean! Loved the location. View from the pool is amazing! Fully equipped kitchen. Two bathrooms which was perfect! Washer/Dryer was convenient. Galena is a beautiful...
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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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    Location Information
    Galena, Illinois 61036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Cedar Rim Home1 / 28
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Shared Indoor Pool
    • Wi-Fi
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 2018
    The Cedar Rim home is amazing in every way. It. Is a spacious,clean, beautifully decorated home. The kitchen is fully stocked and every detail is paid attention to. The owner...
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    About this property
    Beautiful custom home on over 5 acres, located on the 5th hole of The General Golf Course. Game room with over 130 arcade games including 'Golden Tee', foosball & poker tables. 6 large flat screen tv's. Large custom kitchen, screened in room and deck. Two fireplaces and beautiful views! Way too...
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    Location Information
    Galena, Illinois 61036
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Galena Tree House - Resort Townhouse1 / 14
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
    • Washer
    • Wi-Fi
    • Grill
    • Shared Indoor Pool
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 October 2017
    This rental is fine...there's nothing particularly WRONG with it, but nothing great considering the price. That's about all we would say. The four of us who rented this...
    Reviewed 18 July 2017
    Galena is a quaint historic town the perfect distance from Minneapolis/St Paul. The Summerhouse has everything you need and lies in a quiet country setting just a few miles...
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    About this property
    ***Previously Listed as The Galena Treehouse. Under new ownership, but exact same (or upgraded) furnishings. Check out the reviews there.*** The Galena Treehouse 'Sommerhuset' is our family's getaway from the hustle and bustle of daily life. The moment we arrive in Galena and the Territory we just...
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    Location Information
    Galena, Illinois 61036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • DVD Player
    • Balcony
    • Patio
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful, newly remodeled 3 bed, 3.5 bath home in the heart of the galena territory. Sit on the deck and watch the hot air balloons float over, or enjoy a soak in the hot tub. Each bedroom features a private bath, and the master has a whirlpool tub. Each bedroom has its own television with...
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    Location Information
    Galena, Illinois 61036
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Perfect Getaway -Quiet Cul de Sac-Lg 3 bdrm 3 bath1 / 15
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Shared Indoor Pool
    • Air Conditioning
    • Balcony
    • DVD Player
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2018
    We stayed in this townhouse and we loved it! It was very cosy and cute! The finished basement with the sitting area, bedroom and bathroom was great for extra privacy for...
    Reviewed 22 November 2017
    We really enjoyed our stay! Your condo had everything we needed in a beautiful location. The living space in the lower level was an added bonus:) Thank you!
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    About this property
    This Townhouse is located on a quiet cul de sac overlooking the magnificent rolling landscape of The Galena Territory adjacent to Eagle Ridge Resort and the East Golf Course. There is a bedroom and bath on each level, along with two separate living areas which offers both privacy and room for group...
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    Location Information
    Galena, Illinois 61036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Stunning Home Away From Home.1 / 23
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Shared Indoor Pool
    • Grill
    • Housekeeping Included
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 October 2016
    Our family spent 4 days in earlier Sept 2016 at this home. It was well equipped, very clean, and comfortable. Lot of extras. Check in was 4 pm and check out was 10 am so...
    Reviewed 21 December 2015
    We had a terrific time during our stay! The house had a warm and welcoming appearance on the outside and inside. They thought of everything to make the stay enjoyable and...
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    About this property
    This home has a relaxing atmosphere, surrounded by woods and wildlife. Though, still easily accessible in the Galena Territory. You'll be sure to have a relaxing and wonderful time, in it's superbly decorated interior. Featuring mission and wine country styles all it's own. The rolling hills of the...
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    Location Information
    Galena, Illinois 60126
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Nice Galena Home w/Huge Patio, Hot Tub & Fire Pit!1 / 24
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Hot Tub
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • Wi-Fi
    • Washer
    • DVD Player
    • 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 setting far from the hustle and bustle of the big city. From soaking in the hot tub and roasting marshmallows around the fire pit in the yard, to relaxing on the screened porch or...
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    Location Information
    Galena, Illinois 61036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Parking
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just a close walk to downtown restaurants, shopping, golf, skiing, hiking and many other activities. Beautiful historic home just across the river from Grant Park with 4 bedrooms, 1 full bath, complete cook's kitchen and walking neighborhood. Plenty of off street parking and easy to find...
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    Location Information
    Galena, Illinois 61036
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Indoor Pool
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 the Spa, swimming,...
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    Location Information
    Galena, Illinois 61036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Comfort House1 / 15
    (2)Excellent
    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 23 October 2017
    This is a spacious home that gave everyone the space they wanted. We were able to cook our meals when we wanted or go out. The kitchen is fully stocked, so we didn't need to...
    Reviewed 18 August 2017
    We moved into the house and found that it has everything. We brought items from home in Arizona to be sure we had all the things we needed for a weeks stay. There were glasses...
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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 61036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Fall Rates /Stay 7 nights for the price of 5 /Wifi1 / 10
    (8)Excellent
    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 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 61036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    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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    Location Information
    Galena, Illinois 61036
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 14
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    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 61036
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Internet Access
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    • Shared Indoor Pool
    • Cable/satellite TV
    Suitability
    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 61036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Galena Holiday Rentals

    An enticing blend of rolling hills and scenic roads surrounding a Norman Rockwell-like downtown area peppered with historic buildings and storefronts, Galena is a unique place to experience a classic, traditional American holiday that’s fun for the entire family. It’s list of things-to-do is seemingly endless with ten golf courses, several wineries, antique shops, and art galleries, historic sites, and lots of options for hiking, biking, fishing, boating, and camping.

    Galena has an excellent inventory of value-oriented, amenity-rich holiday rentals so why stay in small hotel room? The Galena holiday rental menu includes spacious, multi-bedroom home rentals with hot baths and Jacuzzis, luxury townhomes on or near golf courses, secluded cabins, and condominiums with recreation amenities like swimming pools and tennis courts.

    Galena attractions and activities

    While Galena isn’t exactly Mayberry, it evokes the same kind of All-American ambiance. Walk Galena’s streets and historic buildings like the Dowling House, which was built in 1826, the Old Stockade on the Cobblestone Street, and the Old Market House State Historic Site will enamor you. Don’t miss the Ulysses S. Grant Home State Historic Site on Bouthillier Street.

    For outdoor recreation enthusiasts, prime spots include the Apple River Canyon State Park, Casper Bluff Land & Water Reserve, Hanover Bluff Nature Preserve. Bicyclists love the 3.5-mile Galena River Trail, which affords views of the towering bluffs and the Galena River.

    Golfers, bring your clubs. There are 10 courses within a 20-mile radius of Galena including high-profile layouts like the 63 holes at the Eagle Ridge Resort & Spa, Galena Golf Club, and Apple Canyon Lake Golf Course.

    Holiday rentals for families

    There are many superb settings for family holidays in the Galena area. Your options encompass holiday rentals in or near downtown, golf courses or pristine natural areas. One thing is for sure, your holiday rental will have more space than a typical hotel room and the fully equipped kitchen will allow you to forego pricey, budget busting restaurants to prepare all types of money-saving meals, from gourmet dinners to picnic fare for your family.

    Deals on Galena holiday rentals

    We can help you find the ideal holiday rental for your family in every price range. Special deals and discounts are available on a wide variety of properties in the Galena area. Better still, you can book with knowledge and confidence after examining our unbiased user reviews.

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