Winslow Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 17 - Oct 19
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28
In four months
Jan 23 - Jan 25

Vacation 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, (103)
"What a peaceful respite! Set in a lovely area, walking distance to the Apple Canyon Lake with a beach and restaurant, this was the perfect getaway for a family wedding weekend. The cabin is stunning and comfortable. Beautifully furnished, it had all of the amenities one could hope for in a vacation home."
Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location
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, (208)
"Roomy and comfy cabin. Enjoyed our stay!"
Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
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 ￥516,145
￥940,077 total
includes taxes & fees
Oct 13 - Oct 14
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
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, (100)
"We had a girls weekend stay at the Derinda House. This is the second time staying. I love Sandy's cooking. We thoroughly enjoyed local wineries and shopping."
Discover Elizabeth charm, just a quick 27-min drive away from Mississippi River
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, (43)
"This was a wonderful property. The hosts were so accommodating and helpful. We had a great time."
The price is ￥13,140
￥33,444 total
includes taxes & fees
Oct 6 - Oct 7
Hamilton Goebel House 816 E Louisa St Darlington Wi
Peace & Simplicity in a Little Red Cabin on the Farm
Interior

Peace & Simplicity in a Little Red Cabin on the Farm

10.0 out of 10, Exceptional, (8)
The price is ￥17,401
￥21,569 total
includes taxes & fees
Oct 13 - Oct 14
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, (69)
"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!"
The price is ￥232,265
￥398,692 total
includes taxes & fees
Oct 27 - Oct 28
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
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, (22)
"awesome property and stay"
White Oak Retreat SW WI easy access to ATV and Snowmobile Trails
Bungalow in the Burg - 1 block from downtown
Interior

Bungalow in the Burg - 1 block from downtown

10.0 out of 10, Exceptional, (29)
"Nice place, will stay again when in the area."
Bungalow in the Burg - 1 block from downtown
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, (155)
"A comfy home in a quiet location, perfect for our weekend getaway. We've stayed here once before and would definitely come back again if it's available next time we're in the area. "
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
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, (34)
"Everything was very clean and welcoming. The decor was cute and cozy. Overall great stay."
The price is ￥23,492
￥42,679 total
includes taxes & fees
Oct 8 - Oct 9
Beautiful two story, downtown home, one block from the Square,
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, (322)
"We had an amazing stay. The only downside was that we had so many plans we didn't get to enjoy the property more!"
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 ￥12,538
￥25,228 total
includes taxes & fees
Nov 2 - Nov 3
Cozy King + Queen Suite | Near Golf, Lake & Marina
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Interior

MJ's Penthouse ,a piece of paradise on Monroe's historic square

10.0 out of 10, Exceptional, (97)
"In town for girls getaway. This was our second stay at this location. Everything about the stay was perfect will definitely be back! Myron and Jane are great hosts. 10/10!!"
The price is ￥28,757
￥40,047 total
includes taxes & fees
Oct 8 - Oct 9
MJ's Penthouse ,a piece of paradise on Monroe's historic square
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, (13)
"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
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.

9.2 out of 10, Wonderful, (5)
The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.
Chic Apple River Escape w/ Fire Pit!
House (4 Bedrooms) | Interior

Chic Apple River Escape w/ Fire Pit!

3.0 star property
Chic Apple River Escape w/ Fire Pit!
Cozy home with beautiful LAKE VIEW!
Pool

Cozy home with beautiful LAKE VIEW!

9.4 out of 10, Exceptional, (10)
"This house was Fantastic, we own a lot at the lake but it was great to beable to stay the whole weekend and have family come for a day to spend with us on the boat and at the pool to celebrate, a Birthday, Fathers Day, and an Anniversary"
Cozy home with beautiful LAKE VIEW!
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, (186)
"Beautiful and comfortable home backing up to the woods. Close enough to all Galena has to offer in an extremely peaceful setting. Management is very responsive. Our family had a wonderful stay."
3 Bedroom, 3.5 bath house in The Galena Territory.
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, (75)
"We enjoyed how spacious the house was. W/ 11 of us, we felt like there was plenty of room for us to be comfortable. Having 5 bathrooms was a definite plus! The animals were a delight to visit. We made several trips down the path to visit them & named our favorites! Fishing was fun & kids even caught a large bass twice! Joe made sure to address any needs & concerns at check in & during our stay. He was friendly & informative. "
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winslow Hotel Reviews

Country Inn & Suites by Radisson, Freeport, IL

Country Inn & Suites by Radisson, Freeport, IL

10/10 Excellent
"Yes"
Colleen 2-night trip
Posted 4 days ago
Country Inn & Suites by Radisson, Freeport, IL

Find out more about Winslow

Find out more about Winslow

Search for holiday rentals in Winslow on Expedia! You can easily find your home rentals, villas, holiday apartments in Winslow using one of the methods below:

  • View our selection of featured holiday rentals in Winslow
  • Use the map to find apartments and other holiday homes in the Winslow neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winslow while they last

Look no further and take a look at our great range of rental properties in Winslow!

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?

Hamilton Goebel House 816 E Louisa St Darlington Wi : Visitors like this Winslow vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 Cadiz Springs State Recreation Area 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.