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Winslow Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Winslow vacation rentals

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.

1. 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, (115 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
$231 nightly
The price is $253
Nov 8 - Nov 9
Total with taxes and fees
MJ's Penthouse ,a piece of paradise on Monroe's historic square
A red cabin with a porch, surrounded by trees.

2. 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, (45 reviews)
"Great place to stay"
United States
Mike G.
$148 nightly
The price is $157
Nov 15 - Nov 16
Total with taxes and fees
Peace & Simplicity in a Little Red Cabin on the Farm
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.
$206 nightly
The price is $225
Nov 9 - Nov 10
Total with taxes and fees
Lookout Loft over the Monroe Square
A family standing in front of a stone building with a wooden porch and a number '816' above the entrance.

4. 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, (54 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.
$215 nightly
The price is $235
Nov 9 - Nov 10
Total with taxes and fees
Hamilton Goebel House 816 E Louisa St Darlington Wi
A kitchen with a stove, a sign reading 'The Miner House,' and a bag of chips on the counter.

5. The Minor House - A Cozy Stay in Shullsburg WI

The Minor House - A Cozy Stay in Shullsburg WI
Shullsburg
10.0 out of 10, Exceptional, (6 reviews)
"Nicely set up and clean. The town has a great downtown with lots of local shopping and an even better coffee shop than the chains! Close to a park and local grocery store as well."
United States
Betty
$188 nightly
The price is $198
Nov 9 - Nov 10
Total with taxes and fees
The Minor House - A Cozy Stay in Shullsburg WI
A triangular-shaped cabin with a deck and a large window.

6. 🏠 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)
"The house was perfect for our little getaway."
United States
Teri S.
$233 nightly
The price is $259
Nov 18 - Nov 19
Total with taxes and fees
🏠 Mid-Century A-Frame Near Galena | Stargaze | Couples Retreat | 1 Bed/1 Bath
A wooden deck with outdoor furniture, a grill, and a railing.

7. 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, (15 reviews)
"Great Stay. Will book again!"
United States
Terry B.
$653 nightly
The price is $692
Nov 9 - Nov 10
Total with taxes and fees
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.

8. Lake Cabin | Sauna · River · Game Room

Lake Cabin | Sauna · River · Game Room
Brodhead
9.8 out of 10, Exceptional, (15 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.
$675 nightly
The price is $712
Nov 9 - Nov 10
Total with taxes and fees
Lake Cabin | Sauna · River · Game Room
A hot tub with a view of a snowy landscape through large windows.

9. 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, (88 reviews)
"Beautiful views. Enjoyed the stay."
United States
Andrew F.
$1,068 nightly
The price is $1,180
Nov 29 - Nov 30
Total with taxes and fees
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
A spacious kitchen with wooden cabinets and a stone fireplace.

10. 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
9.6 out of 10, Exceptional, (83 reviews)
"Great space to have large scale meetings and great food in nearby Galena"
United States
Jon-Paul R.
$2,625 nightly
The price is $2,900
Nov 10 - Nov 11
Total with taxes and fees
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
A two-story wooden house with a balcony adorned with string lights, a covered porch, and a chimney.

11. 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.
$5,486 nightly
The price is $6,079
Nov 16 - Nov 17
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

Eugene Hotel

Eugene Hotel

10/10 Excellent
"Very nice rooms, right by the town square. Definitely would stay again!"
James 1-night trip
Posted 15 hours ago
Eugene Hotel

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 $198 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?

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.