Winslow Vacation Rentals

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Our top choices for Winslow vacation rentals

Interior

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, (14 reviews)
"Quiet, clean and absolutely lovely cabin! "
United States
Holley B.
The price is ￥22,018
￥26,668 total
includes taxes & fees
Mar 8 - Mar 9
Peace & Simplicity in a Little Red Cabin on the Farm
Interior

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, (102 reviews)
"Lovely property, great location, quiet and comfortable. "
United States
T. K. D.
The price is ￥30,668
￥42,709 total
includes taxes & fees
Mar 5 - Mar 6
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Exterior

🏠 Charming A-Frame w/ Mid-Century Vibe 1 Bed/1 Bath near Elizabeth, Illinois🌲

🏠 Charming A-Frame w/ Mid-Century Vibe 1 Bed/1 Bath near Elizabeth, Illinois🌲
Elizabeth
10.0 out of 10, Exceptional, (3 reviews)
"Our stay was great! The cabin was exactly as expected like postures and clean. And the location was nice with a 5 minute drive to grocery stores and shops, as well as a 25 minute drive to Galena. "
United States
Lexi S.
The price is ￥14,766
￥38,778 total
includes taxes & fees
Mar 5 - Mar 6
🏠 Charming A-Frame w/ Mid-Century Vibe 1 Bed/1 Bath near Elizabeth, Illinois🌲
Living area

The Minor House - A Cozy Stay in Shullsburg

The Minor House - A Cozy Stay in Shullsburg
Shullsburg
The price is ￥14,469
￥26,879 total
includes taxes & fees
Mar 5 - Mar 6
The Minor House - A Cozy Stay in Shullsburg
Interior

Lookout Loft over the Monroe Square

Lookout Loft over the Monroe Square
Monroe
The price is ￥15,403
￥33,571 total
includes taxes & fees
Mar 5 - Mar 6
Lookout Loft over the Monroe Square
Dining

The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!

The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
Pearl City
10.0 out of 10, Exceptional, (3 reviews)
"Out of half a dozen or so cabin rentals, this one is the absolute best. It's clean, uncluttered, quiet, and huge! Water was hot, heater worked really well (it was a very cold week) and the kitchen worked well. Beds were comfy too. I can't say enough good things about this place!"
United States
Andrew R.
The price is ￥12,188
￥46,619 total
includes taxes & fees
Mar 5 - Mar 6
The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
Exterior

Avail this weekend! Lake Cabin w/King, Sauna

Avail this weekend! Lake Cabin w/King, Sauna
Brodhead
10.0 out of 10, Exceptional, (5 reviews)
"This is a beautiful home and area with a lot of fun activities. Love kayaking, playing pool, and sitting on the deck with the lake view."
United States
Jenelle K.
The price is ￥38,692
￥120,504 total
includes taxes & fees
Mar 11 - Mar 12
Avail this weekend! Lake Cabin w/King, Sauna
Exterior

Charming 4 BdRm Home

Charming 4 BdRm Home
Shullsburg
10.0 out of 10, Exceptional, (1 review)
"The property is a modernized old farm house. I reiterate its an old farm house and it fits the description perfectly.This property is in the country. That being said, that was the appeal for us in choosing this property. Probably 25 mintues to Galena and 40 to Dubuque. The views are spectacular. Its quiet, actually I expected some early farming activity, but other than cattle feeding which was not loud or disruptive there wasn't any on our visit. The cattle/cows are to the west and east of...
United States
Bruce G.
The price is ￥39,318
￥85,728 total
includes taxes & fees
Mar 5 - Mar 6
Charming 4 BdRm Home
Interior

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

Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
Elizabeth
9.6 out of 10, Exceptional, (80 reviews)
"We enjoyed our stay very much. Our whole group of friends enjoyed the stay. Joe was very quick to respond with any questions we had. He was great to work with. "
United States
Julie G.
The price is ￥66,840
￥160,711 total
includes taxes & fees
Mar 10 - Mar 11
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
Interior

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, (72 reviews)
"Great hosts and a ton to do. Could have spent 2 weeks here for our family reunion and could not have done everything!"
United States
Damian W.
The price is ￥235,119
￥451,950 total
includes taxes & fees
Mar 9 - Mar 10
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
Exterior

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 ￥550,445
￥1,035,392 total
includes taxes & fees
Apr 1 - Apr 2
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
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, Freeport, IL

Country Inn & Suites by Radisson, Freeport, IL

10/10 Excellent
"Clean rooms, comfortable bed, good breakfast on the morning. Great location with plenty of dining options close by."
Mark 1-night trip
Posted 1 day ago
Country Inn & Suites by Radisson, Freeport, IL

Find out more about Winslow

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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?

Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table: Visitors like this Winslow vacation home rental. It is located near skiing 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. 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 Little Cubs Field, or get out into nature at a spot like Apple River Canyon State Park. Lake Le Aqua Na State Park and Stagecoach Golf Course 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.