25 Best Galena Vacation rentals on Holiday Lettings - Cabins

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29 Vacation rentals

(16) Excellent 

Certificate of Excellence

15

Vacation apartment with shared pool in Galena

Illinois / Galena

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Whether you're seeking total seclusion and relaxation or an active retreat, you'll find everything you desire nearby! Hiking...4 championship golf courses..Tennis.. Skiing..Fishing..Swimming..Horseback riding.. Hot air balloon rides..Antiquing..Shopping..Historic Homes …see more

Certificate of Excellence

from $128 / night

$762 / week

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from $128 / night

(22) Excellent 

Certificate of Excellence

18

Vacation apartment rental

Illinois / Galena

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 Roma …see more

Certificate of Excellence

from $137 / night

$677 - $777 / week

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Responds fast!
avg. 2 hours 58 minutes

from $137 / night

30

Vacation home in Galena

Illinois / Galena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
We are the official and exclusive partner for Wyndham Worldwide for rentals at vacation resorts. Only rent from official listings in order to ensure your reservation gets delivered to the resort and you receive the best possible guest experience at our properties. Book …see more

from $75 / night

$523 - $1,170 / week

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from $75 / night

(1) Excellent 

15

Vacation townhouse with shared pool in Galena

Illinois / Galena

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 bo …see more

from $175 / night

$1,100 - $1,200 / week

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from $175 / night

(2) Excellent 

24

Vacation home rental

Illinois / Galena

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 rela …see more

from $315 / night

$2,205 - $2,590 / week

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Responds fast!
avg. 8 minutes

from $315 / night

(1) Excellent 

8

Galena Vacation home rental

Illinois / Galena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Air conditioning
  • Private garden
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 …see more

from $200 / night

$1,400 / week

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from $200 / night

10

Home rental in Galena

Illinois / Galena

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
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 st …see more

from $225 / night

$1,250 / week

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from $225 / night

(13) Excellent 

16

Vacation home with shared pool in Galena

Illinois / Galena

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our clean fully stocked home will offer you all the comforts of home. 1 King Bed, 2 Queen beds and 2 twin beds. All you will need to do is bring your walking shoes for a lovely stroll in the picturesque Galena Territory Resort area or downtown Galena. Where can you f …see more

from $175 / night

$1,300 / week

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Responds fast!
avg. 59 minutes

from $175 / night

28

Home rental in Galena with shared pool

Illinois / Galena

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 a …see more

from $749 / night

$4,500 / week

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Responds fast!
avg. 1 hour 49 minutes

from $749 / night

(3) Very Good 

14

Vacation townhouse with shared pool, golf nearby in Galena

Illinois / Galena

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
***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 Gal …see more

from $140 / night

$1,100 - $1,200 / week

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from $140 / night

(3) Very Good 

18

Galena Vacation b&b rental

Illinois / Galena

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
Escape to a romantic get-a-way in an 1880 ITALIANANTE Victorian Mansion. Experience the luxury of fireplaces and whirlpools for 2. Lounge in the soft robes provided while watching a complimentary DVD's from our extensive collection. Enjoy all of the amenities including …see more

from $165 / night

$1,155 / week

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Responds fast!
avg. 1 hour 44 minutes

from $165 / night

(1) Excellent 

20

Vacation log cabin with shared pool in Galena

Illinois / Galena

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to Serenity Cabins. Whether your stay here is for a vacation, anniversary, family get together, romantic get away, or spiritual retreat, you'll find your stay to be welcoming, relaxing, memorable, full of charm and you'll love the luxurious modern amenities whil …see more

from $259 / night

$1,813 / week

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Responds fast!
avg. 10 minutes

from $259 / night

(11) Very Good 

Certificate of Excellence

13

Vacation cottage rental

Illinois / Galena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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: …see more

Certificate of Excellence

from $148 / night

$880 / week

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from $148 / night

(1) Excellent 

25

Vacation home in Galena

Illinois / Galena

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
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 origin …see more

from $225 / night

$1,700 - $2,000 / week

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Responds fast!
avg. 28 minutes

from $225 / night

(4) Excellent 

12

Vacation home with shared pool, golf nearby in Galena

Illinois / Galena

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
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 …see more

from $295 / night

$2,065 / week

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Responds fast!
avg. 2 hours 49 minutes

from $295 / night

27

Vacation home in Galena

Illinois / Galena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
We are the official and exclusive partner for Wyndham Worldwide for rentals at vacation resorts. Only rent from official listings in order to ensure your reservation gets delivered to the resort and you receive the best possible guest experience at our properties. Book …see more

from $92 / night

$641 - $1,347 / week

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from $92 / night

(15) Excellent 

20

Galena Vacation home rental

Illinois / Galena

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Air conditioning
  • Private garden
Derinda House ,Private country retreat. An uncommon B&B - really a whole house rental,for 1 or 2 couples traveling together,or small family.With gourmet breakfast provided. Other meals available Area Attractions Antique Shopping, Art Galleries, Casino, Gourmet/Fine Di …see more

from $149 / night

$1,043 / week

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from $149 / night

(7) Excellent 

24

Vacation villa with shared pool in Galena

Illinois / Galena

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 att …see more

from $99 / night

$599 / week

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Responds fast!
avg. 37 minutes

from $99 / night

(4) Excellent 

23

Vacation home with shared pool, golf nearby in Galena

Illinois / Galena

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 …see more

from $300 / night

$1,700 / week

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from $300 / night

(2) Excellent 

15

Vacation home with shared pool in Galena

Illinois / Galena

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 …see more

from $320 / night

$2,240 / week

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Responds fast!
avg. 2 hours 58 minutes

from $320 / night

17

Vacation home rental

Illinois / Galena

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
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 …see more

from $549 / night

$3,500 / week

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Responds fast!
avg. 1 hour 49 minutes

from $549 / night

17

Galena Vacation home rental

Illinois / Galena

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a stunning luxury home that offers both luxury and style in a warm and inviting setting. The most frequent comment we get from our guests is “This is perfect! It’s even better than we imagined!” With 5 bedrooms, 3.5 baths, 2 separate living areas, a hot tub, a f …see more

from $599 / night

$4,193 / week

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Responds fast!
avg. 2 hours 17 minutes

from $599 / night

12

Vacation home in Galena

Illinois / Galena

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
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 premis …see more

from $900 / night

$6,300 / week

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from $900 / night

6

Vacation hotel apartment with shared pool in Galena

Illinois / Galena

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 …see more

from $200 / night

$1,400 / week

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from $200 / night

(8) Excellent 

10

Vacation home rental

Illinois / Galena

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 …see more

from $425 / night

$2,600 - $2,775 / week

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Responds fast!
avg. 2 hours 30 minutes

from $425 / night