Winslow Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

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, (20 reviews)
"Quiet, clean and absolutely lovely cabin! "
United States
Holley B.
$160 nightly
The price is $170
May 15 - May 16
Total with taxes and fees
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, (49 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.
$209 nightly
The price is $229
May 11 - May 12
Total with taxes and fees
Hamilton Goebel House 816 E Louisa St Darlington Wi
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, (4 reviews)
"Cozy cabin close to Galena. Host was very communicative and available if needed"
United States
Matthew S.
$237 nightly
The price is $262
May 10 - May 11
Total with taxes and fees
🏠 Mid-Century A-Frame Near Galena | Stargaze | Couples Retreat | 1 Bed/1 Bath
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, (107 reviews)
"Lovely property, great location, quiet and comfortable. "
United States
T. K. D.
$248 nightly
The price is $272
May 10 - May 11
Total with taxes and fees
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.
$274 nightly
The price is $303
May 11 - May 12
Total with taxes and fees
The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
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
May 10 - May 11
Total with taxes and fees
The Minor House - A Cozy Stay in Shullsburg
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.
$263 nightly
The price is $288
Jun 9 - Jun 10
Total with taxes and fees
Lookout Loft over the Monroe Square
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.
$926 nightly
The price is $1,022
May 11 - May 12
Total with taxes and fees
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
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.
$697 nightly
The price is $702
May 10 - May 11
Total with taxes and fees
Modern Lake Retreat with Hot Tub, Game Room & Two-Tier Deck
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
May 22 - May 23
Total with taxes and fees
The Lake Place at Apple Canyon Lake
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.
$6,020 nightly
The price is $6,645
May 18 - May 19
Total with taxes and fees
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

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake

8/10 Good
"Really needs good cooking utensils. Had to wait over a half hour to get in because Cleaning crew was still there. Having a list of where things are located would have been very helpful, such as cushions for outside chairs place where we could get more firewood, etc. We loved the atmosphere."
Dianne D. 3-night trip
Posted 10 hours ago
Amazing Log Cabin with Beautiful Views at Apple Canyon Lake

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.

Explore a world of travel with Expedia

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, 3.5 bath house in The Galena Territory.: Visitors like this Winslow vacation home rental. It is located in a rural location and has a fireplace, a patio, 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. You and your friends and family can relax into your vacation with amenities like a hot tub.

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 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.