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Winslow Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winslow holiday rentals

A red cabin with a porch, surrounded by trees.

1. 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, (43 reviews)
"Great place to stay"
United States
Mike G.
The price is HK$1,099
HK$1,331 total
includes taxes & fees
22 Oct - 23 Oct
Peace & Simplicity in a Little Red Cabin on the Farm
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.

2. 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, (114 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 HK$1,530
HK$2,157 total
includes taxes & fees
19 Oct - 20 Oct
MJ's Penthouse ,a piece of paradise on Monroe's historic square
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 HK$824
HK$1,745 total
includes taxes & fees
18 Nov - 19 Nov
Lookout Loft over the Monroe Square
A triangular-shaped cabin with a deck and a large window.

4. 🏠 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)
"Cozy cabin close to Galena. Host was very communicative and available if needed"
United States
Matthew S.
The price is HK$883
HK$2,131 total
includes taxes & fees
21 Oct - 22 Oct
🏠 Mid-Century A-Frame Near Galena | Stargaze | Couples Retreat | 1 Bed/1 Bath
A family standing in front of a stone building with a wooden porch and a number '816' above the entrance.

5. 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 HK$805
HK$1,990 total
includes taxes & fees
19 Oct - 20 Oct
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.

6. 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, (4 reviews)
"We had a great stay! This house had everything and anything you would need! Very cozy, would definitely stay here again!"
United States
Catherine A.
The price is HK$947
HK$1,678 total
includes taxes & fees
19 Oct - 20 Oct
The Minor House - A Cozy Stay in Shullsburg WI
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.

7. Lake Cabin | Sauna · River · Game Room

Lake Cabin | Sauna · River · Game Room
Brodhead
9.8 out of 10, Exceptional, (14 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 HK$1,488
HK$5,620 total
includes taxes & fees
19 Oct - 20 Oct
Lake Cabin | Sauna · River · Game Room
A wooden deck with outdoor furniture, a grill, and a railing.

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

Modern Lake Retreat with Hot Tub, Game Room & Two-Tier Deck
Apple River
9.8 out of 10, Exceptional, (12 reviews)
"Great Stay. Will book again!"
United States
Terry B.
The price is HK$2,299
HK$5,872 total
includes taxes & fees
1 Nov - 2 Nov
Modern Lake Retreat with Hot Tub, Game Room & Two-Tier Deck
A two-story wooden house with a balcony adorned with string lights, a covered porch, and a chimney.

9. 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 HK$27,468
HK$52,425 total
includes taxes & fees
26 Oct - 27 Oct
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
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
9.8 out of 10, Exceptional, (79 reviews)
"Great space to have large scale meetings and great food in nearby Galena"
United States
Jon-Paul R.
The price is HK$12,518
HK$23,541 total
includes taxes & fees
19 Oct - 20 Oct
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

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake

10/10 Excellent
"Loved staying here! It was the perfect get away :)"
Kaitlyn M. 2-night trip
Posted 1 day ago
Amazing Log Cabin with Beautiful Views at Apple Canyon Lake

Find out more about Winslow

Search for holiday rentals in Winslow on Expedia! You can easily find your home rentals, villas, holiday apartments in Winslow using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winslow!

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.