Winslow Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Winslow vacation rentals

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, (4 reviews)
"Cozy cabin close to Galena. Host was very communicative and available if needed"
United States
Matthew S.
The price is ￥15,853
￥39,252 total
includes taxes & fees
Apr 19 - Apr 20
🏠 Charming A-Frame w/ Mid-Century Vibe 1 Bed/1 Bath near Elizabeth, Illinois🌲
Exterior

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, (18 reviews)
"Quiet, clean and absolutely lovely cabin! "
United States
Holley B.
The price is ￥22,210
￥26,901 total
includes taxes & fees
Apr 25 - Apr 26
Peace & Simplicity in a Little Red Cabin on the Farm
Exterior

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, (48 reviews)
"The property was beautiful and very tasteful decor. Kitchen was awsome and the rooms were comfortable and spacious. Definitely will stay here again."
United States
Shane S.
The price is ￥15,705
￥38,216 total
includes taxes & fees
May 18 - May 19
Hamilton Goebel House 816 E Louisa St Darlington Wi
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, (105 reviews)
"Lovely property, great location, quiet and comfortable. "
United States
T. K. D.
The price is ￥30,935
￥43,080 total
includes taxes & fees
Apr 30 - May 1
MJ's Penthouse ,a piece of paradise on Monroe's historic 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 ￥17,171
￥53,551 total
includes taxes & fees
Apr 21 - Apr 22
The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
Interior

Lookout Loft over the Monroe Square

Lookout Loft over the Monroe Square
Monroe
10.0 out of 10, Exceptional, (1 review)
"Couldn’t have asked for a better spot to stay. Monroe and the surrounding area have a lot to do. Stay at this place only heightened our experience. We will definitely be back. "
United States
Eric S.
The price is ￥15,772
￥34,346 total
includes taxes & fees
Apr 20 - Apr 21
Lookout Loft over the Monroe Square
Living area

The Minor House - A Cozy Stay in Shullsburg

The Minor House - A Cozy Stay in Shullsburg
Shullsburg
The price is ￥18,244
￥31,467 total
includes taxes & fees
Apr 21 - Apr 22
The Minor House - A Cozy Stay in Shullsburg
Exterior

Avail this weekend! Lake Cabin w/King, Sauna

Avail this weekend! Lake Cabin w/King, Sauna
Brodhead
10.0 out of 10, Exceptional, (6 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 ￥37,107
￥122,287 total
includes taxes & fees
Apr 21 - Apr 22
Avail this weekend! Lake Cabin w/King, Sauna
Terrace/patio

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

Modern Lake Retreat with Hot Tub, Game Room & Two-Tier Deck
Apple River
9.4 out of 10, Exceptional, (3 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 ￥36,580
￥82,380 total
includes taxes & fees
Apr 21 - Apr 22
Modern Lake Retreat with Hot Tub, Game Room & Two-Tier Deck
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)
"The house was great for our size family. We had 14 people and plenty of room. Joe the farm hand was great he met us on arrival and explained everything we needed to know.We would stay here again."
United States
Scott L.
The price is ￥67,626
￥162,602 total
includes taxes & fees
Apr 21 - Apr 22
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
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 ￥555,240
￥1,038,023 total
includes taxes & fees
May 4 - May 5
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

Super 8 by Wyndham Monroe WI

Super 8 by Wyndham Monroe WI

8/10 Good
"Nice staff, breakfast was a plus!"
Ken 2-night trip
Posted 2 days ago
Super 8 by Wyndham Monroe WI

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 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.