Holiday Rentals in Winslow

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Check prices for these dates

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

Our top choices for Winslow holiday 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
The price is €223
includes taxes & fees
15 Nov - 16 Nov
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.
The price is €146
includes taxes & fees
15 Nov - 16 Nov
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.
The price is €310
includes taxes & fees
4 Dec - 5 Dec
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.
The price is €205
includes taxes & fees
9 Nov - 10 Nov
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
The price is €181
includes taxes & fees
9 Nov - 10 Nov
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.
The price is €244
includes taxes & fees
23 Nov - 24 Nov
🏠 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.
The price is €636
includes taxes & fees
9 Nov - 10 Nov
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.
The price is €663
includes taxes & fees
9 Nov - 10 Nov
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.
The price is €1,137
includes taxes & fees
27 Nov - 28 Nov
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.
The price is €2,653
includes taxes & fees
10 Nov - 11 Nov
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.
The price is €5,494
includes taxes & fees
16 Nov - 17 Nov
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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Find out more about Winslow

Everything you need to know about Winslow holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winslow holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winslow holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winslow holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winslow holiday rentals we have selected for you start as low as €145 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winslow rentals

At Expedia, we put the best Winslow holiday 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 holiday.

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 holiday rentals in Winslow?

Yes, there are holiday rentals close to the most popular sights in Winslow, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winslow has to offer?

Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond: This holiday home rental outside of Winslow is located in a rural location, and has an outdoor pool, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 wider area.

What are holiday rentals like in Winslow?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winslow. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a family trip or a small group gathering.