Winslow Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Winslow

Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location
Dining
Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location
9.6 out of 10, Exceptional, (66)
"We were married in this little cabin and in was a delightful experience. We would stay again. We definitely appreciated the complimentary snacks upon arrival! 😄"
Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location
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, (294)
"The property was lovely- clean, cozy and comfortable. It had everything we needed and was located in a very quiet and peaceful area in the Galena Territory. It was convenient to many activities/attractions. The owner was very helpful and hospitable."
Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table
Apple Canyon Lake Home, Life At The Lake
Pool
Apple Canyon Lake Home, Life At The Lake
10.0 out of 10, Exceptional, (66)
"Lovely setting. Comfortable home. Great basement well-stocked with games and entertainment for whole family. We enjoyed a fun family weekend with everything we needed. Will return. "
Apple Canyon Lake Home, Life At The Lake
Beautiful Apple Canyon Lake Log Cabin in the Woods
Pool
Beautiful Apple Canyon Lake Log Cabin in the Woods
9.8 out of 10, Exceptional, (164)
"The log cabin has a lot of space and volume. Three bedrooms that can sleep at least 8 people. The large surround deck is great for quiet relaxing or a loud game of UNO . Tcampfire"
Beautiful Apple Canyon Lake Log Cabin in the Woods
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, (168)
"Very spacious cabin. Fully equipped kitchen, we had everything we needed. "
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, (130)
"Nice communication with host and very nice place!! Great location too! "
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Quiet Farmhouse-Style Cabin w/ Front Porch!
Terrace/patio
Quiet Farmhouse-Style Cabin w/ Front Porch!
10.0 out of 10, Exceptional, (45)
"I had meetings in Dodgeville, and tho it was a 25 min. drive each way, this cabin and location provided the scenery, wildlife, privacy and space to revive my soul. The hosts were super responsive, and I couldn't have asked for more! "
Quiet Farmhouse-Style Cabin w/ Front Porch!
Beautiful turn of the century home in Elizabeth,Il 10 minutes from Galena
Smart TV
Beautiful turn of the century home in Elizabeth,Il 10 minutes from Galena
9.8 out of 10, Exceptional, (18)
"A great place to stay! Just be fully aware that the full bathroom and larger beds are ip a long, but beautiful staircase. "
Beautiful turn of the century home in Elizabeth,Il 10 minutes from Galena
3 Bedroom, 3.5 bath house in The Galena Territory.
Outdoor spa tub
3 Bedroom, 3.5 bath house in The Galena Territory.
9.8 out of 10, Exceptional, (164)
"Loved the house and the location! "
3 Bedroom, 3.5 bath house in The Galena Territory.
KC HOUSE Cozy Country Home. Enjoy the country life!
Exterior
KC HOUSE Cozy Country Home. Enjoy the country life!
10.0 out of 10, Exceptional, (6)
"An amazing ranch. The house was perfect and so comfortable for all of us! The peace you get in this place is priceless! The breathtaking views are amazing and the property manager made our stay extra special with the horses. My family and I enjoyed it so much we will come back. "
KC HOUSE Cozy Country Home. Enjoy the country life!
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, (3)
"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 HK$27,227
HK$49,864 total
includes taxes & fees
8 Oct - 9 Oct
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
View from property
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
9.6 out of 10, Exceptional, (60)
"We loved our stay here - we surprised my mother in law for the weekend with the whole family & had a fantastic time! The property is gorgeous & Joe the property manger was extremely friendly & helpful. I highly recommend it & we will be back! "
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
Peaceful Blanchardville Cabin on 35-Acre Farm
1 bedroom, desk, WiFi, bed sheets
Peaceful Blanchardville Cabin on 35-Acre Farm
10.0 out of 10, Exceptional, (20)
"Everything about this stay is perfect. Beautiful location. Comfy setting. Our kids loved seeing the cows, kittens, and horses! And the host even gave us a ride when we got caught in the rain. Would absolutely recommend to anyone looking for a relaxing getaway."
Peaceful Blanchardville Cabin on 35-Acre Farm
Comfortable ,and beautifully furnished,with antiques,and comfy furniture .
Fridge, microwave, oven, stovetop
Comfortable ,and beautifully furnished,with antiques,and comfy furniture .
10.0 out of 10, Exceptional, (77)
"Great place to stay and great atmosphere. Close to Galena and plenty to do. "
Comfortable ,and beautifully furnished,with antiques,and comfy furniture .
Apple Canyon Lake, Game Room, Hot Tub
Exterior
Apple Canyon Lake, Game Room, Hot Tub
9.0 out of 10, Wonderful, (49)
"The house is gorgeous and has a lot of character. It was perfect for a weekend getaway with friends. Our favorite part was the enclosed porch on the upper floor. It went perfectly with the late August weather. "
Apple Canyon Lake, Game Room, Hot Tub
MJ's Penthouse ( a piece of paradise on Monroe's historic square)<br>
Smart TV
MJ's Penthouse ( a piece of paradise on Monroe's historic square)<br>
10.0 out of 10, Exceptional, (76)
"Beautiful place! We loved our short overnight stay!"
The price is HK$1,517
HK$2,036 total
includes taxes & fees
30 Sept - 1 Oct
MJ's Penthouse ( a piece of paradise on Monroe's historic square)<br>
Destination Driftless- A Trailside Retreat
TV
Destination Driftless- A Trailside Retreat
9.4 out of 10, Exceptional, (22)
"Great location. Clean, easy to access. Fun weekend had by my group."
Destination Driftless- A Trailside Retreat
Log Home w/hot tub in Apple Canyon Lake
Property grounds
Log Home w/hot tub in Apple Canyon Lake
9.0 out of 10, Wonderful, (28)
"Stayed before and was still very nice. The hot tub however was replaced since our last stay the new tub is much smaller and notas comfortable for four adults."
Log Home w/hot tub in Apple Canyon Lake
Peaceful Retreat in Galena Country Jo Daviess County
Outdoor dining
Peaceful Retreat in Galena Country Jo Daviess County
10.0 out of 10, Exceptional, (13)
"We enjoyed this cozy place. It was clean and accommodating to our needs!"
Peaceful Retreat in Galena Country Jo Daviess County
Relaxing Retreat with Hot Tub and Fire Pit
Exterior
Relaxing Retreat with Hot Tub and Fire Pit
10.0 out of 10, Exceptional, (17)
"We are four "mature" women who annually get together somewhere in the Midwest. We enjoyed our stay at Sara and Andrew's place. They were very responsive to our needs and followed up quickly. The location was fine and we certainly got to be with nature! The home has all the amenities in the bathrooms and kitchen areas that one needs for a brief stay. We enjoyed our time in Galena and the home we stayed in certainly made the experience there even better. "
Relaxing Retreat with Hot Tub and Fire Pit
Don't see what you're looking for?
See all available properties in Winslow
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Winslow you may be interested in

Country Inn & Suites by Radisson, Stockton, IL
Lobby
Country Inn & Suites by Radisson, Stockton, IL
2.5 star property
8.6 out of 10, Excellent, (526)
"Always happy to return to Country Inn in Stockton, IL, I made several trip to this area and never regret. "
The price is HK$460
HK$511 total
includes taxes & fees
16 Oct - 17 Oct
Country Inn & Suites by Radisson, Stockton, IL
Baymont by Wyndham Freeport
Premium bedding, desk, iron/ironing board, rollaway beds
Baymont by Wyndham Freeport
2.5 star property
8.0 out of 10, Very good, (585)
"Nice stay"
The price is HK$622
HK$690 total
includes taxes & fees
13 Oct - 14 Oct
Baymont by Wyndham Freeport
Country Inn & Suites by Radisson, Freeport, IL
Lobby
Country Inn & Suites by Radisson, Freeport, IL
2.5 star property
9.0 out of 10, Wonderful, (725)
"Extremely clean facility."
The price is HK$870
HK$966 total
includes taxes & fees
8 Oct - 9 Oct
Country Inn & Suites by Radisson, Freeport, IL
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.

Frequently asked questions

Are there holiday rentals in Winslow?

Yes, there are holiday rentals close to the most popular sights in Winslow, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winslow has to offer?

Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table: This holiday home rental outside of Winslow is located near skiing, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 Lake Le Aqua Na State Park. Minhas Craft Brewery and Apple River Canyon State Park are a couple of places you'll find in the wider area.

What are holiday rentals like in Winslow?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winslow. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a family trip or a small group gathering.