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Winslow Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Winslow vacation rentals

A red cabin with a porch, surrounded by trees.

1. Peace & Simplicity in a Little Red Cabin on the Farm

Peace & Simplicity in a Little Red Cabin on the Farm
Lena
10.0 out of 10, Exceptional, (39 reviews)
"Great place to stay"
United States
Mike G.
The price is ￥22,023
￥26,675 total
includes taxes & fees
Sep 27 - Sep 28
Peace & Simplicity in a Little Red Cabin on the Farm
A spacious living area with a wooden dining table, a sofa, and a hanging chair. There are large windows providing natural light and a view of the outside.

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

MJ's Penthouse ,a piece of paradise on Monroe's historic square
Monroe
10.0 out of 10, Exceptional, (111 reviews)
"The Penthouse is beautiful and the location is unbeatable! We had a wonderful stay and can't wait to come back."
United States
Andie
The price is ￥30,675
￥42,719 total
includes taxes & fees
Sep 27 - Sep 28
MJ's Penthouse ,a piece of paradise on Monroe's historic square
A spacious kitchen with wooden cabinets, a central island, and a dining area with a table and chairs.

3. Lookout Loft over the Monroe Square

Lookout Loft over the Monroe Square
Monroe
10.0 out of 10, Exceptional, (4 reviews)
"Great property and host! Would stay there again."
United States
Ann S.
The price is ￥21,347
￥40,946 total
includes taxes & fees
Oct 5 - Oct 6
Lookout Loft over the Monroe Square
A two-story wooden house with a balcony adorned with string lights, a covered porch, and a chimney.

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

Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
Elizabeth
10.0 out of 10, Exceptional, (4 reviews)
"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."
United States
Katie L.
The price is ￥550,585
￥1,042,157 total
includes taxes & fees
Oct 5 - Oct 6
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
A triangular-shaped cabin with a deck and a large window.

5. 🏠 Mid-Century A-Frame Near Galena | Stargaze | Couples Retreat | 1 Bed/1 Bath

🏠 Mid-Century A-Frame Near Galena | Stargaze | Couples Retreat | 1 Bed/1 Bath
Elizabeth
9.8 out of 10, Exceptional, (8 reviews)
"Cozy cabin close to Galena. Host was very communicative and available if needed"
United States
Matthew S.
The price is ￥16,820
￥41,244 total
includes taxes & fees
Sep 27 - Sep 28
🏠 Mid-Century A-Frame Near Galena | Stargaze | Couples Retreat | 1 Bed/1 Bath
A spacious kitchen with wooden cabinets and a stone fireplace.

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

LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
Elizabeth
9.8 out of 10, Exceptional, (79 reviews)
"Great space to have large scale meetings and great food in nearby Galena"
United States
Jon-Paul R.
The price is ￥251,133
￥472,276 total
includes taxes & fees
Oct 19 - Oct 20
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
A family standing in front of a stone building with a wooden porch and a number '816' above the entrance.

7. Hamilton Goebel House 816 E Louisa St Darlington Wi

Hamilton Goebel House 816 E Louisa St Darlington Wi
Darlington
9.8 out of 10, Exceptional, (52 reviews)
"Three couples stayed at this property. Very comfy beds. We all enjoyed our stay and already have plans to stay again in the fall. It is also close to the trails."
United States
Danette M.
The price is ￥16,140
￥39,894 total
includes taxes & fees
Oct 1 - Oct 2
Hamilton Goebel House 816 E Louisa St Darlington Wi
A wooden deck with outdoor furniture, a grill, and a railing.

8. Modern Lake Retreat with Hot Tub, Game Room & Two-Tier Deck

Modern Lake Retreat with Hot Tub, Game Room & Two-Tier Deck
Apple River
9.6 out of 10, Exceptional, (10 reviews)
"Wonderful house — very clean and cozy. We had a great stay and truly enjoyed our time here."
United States
Iryna S.
The price is ￥46,693
￥113,171 total
includes taxes & fees
Oct 1 - Oct 2
Modern Lake Retreat with Hot Tub, Game Room & Two-Tier Deck
A large, two-story log cabin with a stone chimney, a front porch with outdoor seating, and a snow-covered yard leading to a fire pit.

9. Lake Cabin | Sauna · River · Game Room

Lake Cabin | Sauna · River · Game Room
Brodhead
9.8 out of 10, Exceptional, (12 reviews)
"We love this property on the Sugar River. Very spacious, rustic but with all the modern amenities. Beautiful view of the water and lots of wildlife in area. "
United States
Lisa and Peter R.
The price is ￥33,116
￥116,705 total
includes taxes & fees
Oct 5 - Oct 6
Lake Cabin | Sauna · River · Game Room
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

Country Inn & Suites by Radisson, Stockton, IL

Country Inn & Suites by Radisson, Stockton, IL

8/10 Good
"Floors could have been cleaner"
Michelle 2-night trip
Posted 1 day ago
Country Inn & Suites by Radisson, Stockton, IL

Find out more about Winslow

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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?

Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond: Visitors like this Winslow vacation home rental. It is located in a rural location and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 National Historic Cheesemaking Center Museum 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.