Winslow Vacation Rentals

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Check prices for these dates

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Jul 26 - Jul 27
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Jul 27 - Jul 28
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Aug 1 - Aug 3
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Aug 8 - Aug 10

Vacation Rentals in Winslow

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
Fridge, microwave, oven, stovetop

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake

9.8 out of 10, Exceptional, (200)
"We loved our stay! Great communication with Mia! We arrived early and she gave us the passes to the pool and beach so we could hangout there while the cabin was being cleaned. Great hosts! Loved the welcome basket with goodies because our kids were hungry. Such a great touch! Pictures are exactly what the home looks like. Thank You!"
Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
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, (146)
"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
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, (179)
"Everything was perfect. Thank you! "
3 Bedroom, 3.5 bath house in The Galena Territory.
Discover Elizabeth charm, just a quick 27-min drive away from Mississippi River
Fridge, microwave, oven, stovetop

Discover Elizabeth charm, just a quick 27-min drive away from Mississippi River

10.0 out of 10, Exceptional, (93)
"Great place to stay and great atmosphere. Close to Galena and plenty to do. "
Discover Elizabeth charm, just a quick 27-min drive away from Mississippi River
Spacious Suite w/ 2 King Beds | Near Trails, Lake & Golf
Exterior

Spacious Suite w/ 2 King Beds | Near Trails, Lake & Golf

9.0 out of 10, Wonderful, (2)
"The hosts are very responsive. The room is clean and decorated nicely. Overall, we would recommend."
The price is CA $112
CA $227 total
includes taxes & fees
Jul 27 - Jul 28
Spacious Suite w/ 2 King Beds | Near Trails, Lake & Golf
Apple Canyon Lake Home, Life At The Lake
Pool

Apple Canyon Lake Home, Life At The Lake

10.0 out of 10, Exceptional, (81)
"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
Peace & Simplicity in a Little Red Cabin on the Farm
Interior

Peace & Simplicity in a Little Red Cabin on the Farm

The price is CA $145
CA $182 total
includes taxes & fees
Jul 30 - Jul 31
Peace & Simplicity in a Little Red Cabin on the Farm
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, (66)
"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
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
The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.
Exterior

The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.

The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.
Relaxing Retreat with Hot Tub and Fire Pit
Exterior

Relaxing Retreat with Hot Tub and Fire Pit

10.0 out of 10, Exceptional, (27)
"Great location with nice vies"
Relaxing Retreat with Hot Tub and Fire Pit
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
Historic Country Farmhouse for ANY Season!
Property grounds

Historic Country Farmhouse for ANY Season!

10.0 out of 10, Exceptional, (42)
"Great weekend with girls. Host was very attentive. Location was great, close to shopping and wineries."
Historic Country Farmhouse for ANY Season!
Cabin on 35-Acre Farm in Blanchardville w/ Trails!
1 bedroom, desk, free internet, bed sheets

Cabin on 35-Acre Farm in Blanchardville w/ Trails!

10.0 out of 10, Exceptional, (28)
"Relaxing quiet and great host "
Cabin on 35-Acre Farm in Blanchardville w/ Trails!
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."
The price is CA $4,776
CA $8,670 total
includes taxes & fees
Aug 4 - Aug 5
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
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
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, (39)
"The owners were very helpful. The property on the inside was very clean. The yard was overgrown and needed attention."
The price is CA $122
CA $311 total
includes taxes & fees
Aug 4 - Aug 5
Hamilton Goebel House 816 E Louisa St Darlington Wi
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, (314)
"This was the perfect place for a relaxing girls weekend!!"
Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table
Cozy King + Queen Suite | Near Golf, Lake & Marina
Exterior

Cozy King + Queen Suite | Near Golf, Lake & Marina

6.0 out of 10, (1)
"Room was very clean, nicely decorated, and spacious. The bathroom is very cramped with a tiny shower and it seems odd that the mini fridge and coffee m"
The price is CA $112
CA $227 total
includes taxes & fees
Jul 27 - Jul 28
Cozy King + Queen Suite | Near Golf, Lake & Marina
New 5-bedroom house at Apple Canyon Lake. 30 minutes from downtown Galena!
Fridge, microwave, oven, stovetop

New 5-bedroom house at Apple Canyon Lake. 30 minutes from downtown Galena!

10.0 out of 10, Exceptional, (8)
"This is a beautiful brand new house with tons of room! We were able to walk down to the lake from the back yard to Ice fish."
New 5-bedroom house at Apple Canyon Lake. 30 minutes from downtown Galena!
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

Baymont by Wyndham Freeport

Baymont by Wyndham Freeport

10/10 Excellent
"Great"
Jack 2-night trip
Posted 2 days ago
Baymont by Wyndham Freeport

Frequently asked questions

Are there vacation rentals in Winslow?

Yes, we have vacation rentals near popular local attractions in Winslow, or you can select a more secluded option if you want a relaxing place to stay.

What's the top vacation rental that Winslow has to offer?

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe: Visitors like this Winslow vacation home rental. It is located in a rural location and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

What can I see and do in Winslow?

Explore the area and family-friendly sights such as SplashLand Family Water Park, or get out into nature at a spot like Apple River Canyon State Park. Lake Le Aqua Na State Park and Historic Cheesemaking Center are a couple of places you'll find in the larger area.

What are vacation rentals like in Winslow?

Vacation rentals are privately owned properties you can stay in for short or long periods in Winslow. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.