Winslow Vacation Rentals

Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Winslow vacation rentals

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, (25 reviews)
"Great location! It was perfect to celebrate our sons birthday - he loved the loft!! "
United States
Emily M.
$160 nightly
The price is $170
Jun 11 - Jun 12
Total with taxes and fees
Peace & Simplicity in a Little Red Cabin on the Farm
Exterior

🏠 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
10.0 out of 10, Exceptional, (5 reviews)
"Everything was very beautiful"
United States
Gissell
$233 nightly
The price is $257
Jun 8 - Jun 9
Total with taxes and fees
🏠 Mid-Century A-Frame Near Galena | Stargaze | Couples Retreat | 1 Bed/1 Bath
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, (50 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.
$211 nightly
The price is $231
Jun 8 - Jun 9
Total with taxes and fees
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, (108 reviews)
"Lovely property, great location, quiet and comfortable. "
United States
T. K. D.
$248 nightly
The price is $272
Jun 7 - Jun 8
Total with taxes and fees
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Living area

The Minor House - A Cozy Stay in Shullsburg

The Minor House - A Cozy Stay in Shullsburg
Shullsburg
$189 nightly
The price is $199
Jun 17 - Jun 18
Total with taxes and fees
The Minor House - A Cozy Stay in Shullsburg
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.
$297 nightly
The price is $328
Jun 7 - Jun 8
Total with taxes and fees
The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
Exterior

Lake Cabin | Sauna · River · Game Room

Lake Cabin | Sauna · River · Game Room
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.
$772 nightly
The price is $814
Jun 8 - Jun 9
Total with taxes and fees
Lake Cabin | Sauna · River · Game Room
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.
$235 nightly
The price is $258
Jun 22 - Jun 23
Total with taxes and fees
Lookout Loft over the Monroe Square
Pool

The Lake Place at Apple Canyon Lake

The Lake Place at Apple Canyon Lake
Apple River
10.0 out of 10, Exceptional, (7 reviews)
"Activities for all ages, host was very easy to get a hold of, just as advertised, would stay here again!"
United States
Harry D.
$1,398 nightly
The price is $1,615
Jun 14 - Jun 15
Total with taxes and fees
The Lake Place at Apple Canyon Lake
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, (73 reviews)
"Great space to have large scale meetings and great food in nearby Galena"
United States
Jon-Paul R.
$3,152 nightly
The price is $3,478
Jun 28 - Jun 29
Total with taxes and fees
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
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

A-Frame Cabin Retreat

A-Frame Cabin Retreat

10/10 Excellent
"Clean, lovely space. Appreciated being able to stay here. It was quiet and secluded. The posting never claimed to have wifi, but I didn't check for it either, so was mildly surprised when it didn't have any (just assumed). Made the trip more in the moment, but might surprise others as well."
Ben H. 2-night trip
Posted 4 days ago
A-Frame Cabin Retreat

Find out more about Winslow

Everything you need to know about Winslow vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winslow vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winslow vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winslow vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winslow. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winslow in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $170 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winslow rentals

At Expedia, we put the best Winslow vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winslow rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winslow vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winslow. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe: Visitors like this Winslow vacation home rental. It is located in a rural location and has a fireplace, 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. You can relax into your vacation with a garden and a selection of games.

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 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.