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Aug 22 - Aug 24
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Aug 29 - Aug 31
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Sep 12 - Sep 14
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Oct 10 - Oct 12

Vacation Homes in Winslow

3 Bedroom, 3.5 bath house in The Galena Territory.
Pool

3 Bedroom, 3.5 bath house in The Galena Territory.

9.8 out of 10, Exceptional, (180)
"Place was very nice and clean, I didn’t want for anything that was not there accept olive oil… which led me to the Galena garlic company where I found all sorts of olive oils and other goodies. My mom loved hearing the birds chirping while enjoying the hot tub. Fried green tomatoes was a family hit!"
3 Bedroom, 3.5 bath house in The Galena Territory.
Beautiful two story, downtown home, one block from the Square,
Fridge, microwave, oven, stovetop

Beautiful two story, downtown home, one block from the Square,

10.0 out of 10, Exceptional, (31)
"Everything was very clean and welcoming. The decor was cute and cozy. Overall great stay."
$309 nightly
The price is $338
Sep 9 - Sep 10
Total includes taxes and fees
Beautiful two story, downtown home, one block from the Square,
Destination Driftless- A Trailside Retreat
Interior

Destination Driftless- A Trailside Retreat

9.4 out of 10, Exceptional, (28)
"Perfect place to stay when visiting the Cheese trail, will definitely return to this property! "
Destination Driftless- A Trailside Retreat
Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table
Exterior

Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table

10.0 out of 10, Exceptional, (315)
"This was the perfect place for a relaxing girls weekend!!"
Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table
Historic Country Farmhouse for ANY Season!
Property grounds

Historic Country Farmhouse for ANY Season!

10.0 out of 10, Exceptional, (44)
"Great weekend with girls. Host was very attentive. Location was great, close to shopping and wineries."
Historic Country Farmhouse for ANY Season!
Cozy home with beautiful LAKE VIEW!
Pool

Cozy home with beautiful LAKE VIEW!

9.6 out of 10, Exceptional, (8)
"Amazing place!!!"
Cozy home with beautiful LAKE VIEW!
Beautiful turn of the century home in Elizabeth,Il 10 minutes from Galena
Exterior

Beautiful turn of the century home in Elizabeth,Il 10 minutes from Galena

10.0 out of 10, Exceptional, (21)
"It is a beautiful home with plenty of room. Our stay was great! "
Beautiful turn of the century home in Elizabeth,Il 10 minutes from Galena
Bungalow in the Burg - 1 block from downtown
Interior

Bungalow in the Burg - 1 block from downtown

10.0 out of 10, Exceptional, (28)
"Nice place, will stay again when in the area."
Bungalow in the Burg - 1 block from downtown
Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL
Terrace/patio

Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL

10.0 out of 10, Exceptional, (20)
"Lovely, comfortable and spacious, this house was close to so many places we wanted to go."
Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL
White Oak Retreat SW WI easy access to ATV and Snowmobile Trails
Fridge, microwave, oven, stovetop

White Oak Retreat SW WI easy access to ATV and Snowmobile Trails

10.0 out of 10, Exceptional, (20)
"awesome property and stay"
White Oak Retreat SW WI easy access to ATV and Snowmobile Trails
Hamilton Goebel House 816 E Louisa St Darlington Wi
Fridge, microwave, oven, stovetop

Hamilton Goebel House 816 E Louisa St Darlington Wi

9.8 out of 10, Exceptional, (42)
"The owners were very helpful. The property on the inside was very clean. The yard was overgrown and needed attention."
$208 nightly
The price is $228
Aug 13 - Aug 14
Total includes taxes and fees
Hamilton Goebel House 816 E Louisa St Darlington Wi
Relaxing Retreat with Hot Tub and Fire Pit
Exterior

Relaxing Retreat with Hot Tub and Fire Pit

10.0 out of 10, Exceptional, (29)
"Great location with nice vies"
Relaxing Retreat with Hot Tub and Fire Pit
Spacious Apple Canyon Lake home - just minutes from Galena, Illinois
Pool

Spacious Apple Canyon Lake home - just minutes from Galena, Illinois

10.0 out of 10, Exceptional, (12)
"House was perfect, updated and close to everything. Owner was responsive and great to work with. Would definitely stay again."
Spacious Apple Canyon Lake home - just minutes from Galena, Illinois
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
Outdoor spa tub

Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.

10.0 out of 10, Exceptional, (4)
"We had 14 people stay for a business retreat. Each had their own bedroom and bathroom. We gathered in the great room for our meeting, experienced cooking together and a ‘family dinner’ around the big table. We hiked as our activity and enjoyed a bonfire too. We went into galena one evening for dinner - just a quick 20 minute drive. We enjoyed our short stay and would consider returning."
$5,962 nightly
The price is $6,319
Aug 19 - Aug 20
Total includes taxes and fees
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
Outdoor spa tub

LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS

9.8 out of 10, Exceptional, (68)
"This was the perfect location for our family of 21 to gather for Thanksgiving. The ranch had so many animals and places to roam and all the kids had fun playing on the baseball field. Enough ovens for all of the Thanksgiving Turkey and sides to be eaten hot, and enough room for all to enjoy our time together. Great location near Galena!"
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Exterior

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

10.0 out of 10, Exceptional, (148)
"We enjoyed our stay, peaceful, clean and everything we needed. "
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Apple Canyon Lake Home, Life At The Lake
Pool

Apple Canyon Lake Home, Life At The Lake

10.0 out of 10, Exceptional, (84)
"Great location and property. It rained during our visit, but there were plenty of games to keep us entertained."
Apple Canyon Lake Home, Life At The Lake
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
Indoor spa tub

Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond

9.6 out of 10, Exceptional, (74)
"We stayed here for a long weekend to ski nearby at Chestnut Mountain. The house was perfectly comfortable for three families with children. The surroundings are gorgeous. "
$1,005 nightly
The price is $1,065
Aug 18 - Aug 19
Total includes taxes and fees
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
Beautiful Lakehouse with private dock on Apple Canyon Lake!
Interior

Beautiful Lakehouse with private dock on Apple Canyon Lake!

9.8 out of 10, Exceptional, (95)
"Great location and house. Perfect for us as a couple looking to getaway and relax alone."
Beautiful Lakehouse with private dock on Apple Canyon Lake!
Historic farmhouse with WiFi, dog-friendly, close to rec trails
Fridge, microwave, oven, stovetop

Historic farmhouse with WiFi, dog-friendly, close to rec trails

2.0 star property
9.8 out of 10, Exceptional, (11)
"its perfect place for spend good time from city "
Historic farmhouse with WiFi, dog-friendly, close to rec trails
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winslow Hotel Reviews

Apple Canyon Lake Home, Life At The Lake

Apple Canyon Lake Home, Life At The Lake

10/10 Excellent
"Had a fantastic girls weekend at the property! Plenty of space and extra amenities. We spent the afternoon at the private beach and went for walks on the trail. I highly recommend a stay here!"
Jessica H. 2-night trip
Posted 12 hours ago
Apple Canyon Lake Home, Life At The Lake