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Winslow Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Winslow holiday rentals

Exterior

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, (37 reviews)
"Great place to stay"
United States
Mike G.
The price is HK$1,098
HK$1,330 total
includes taxes & fees
10 Sept - 11 Sept
Peace & Simplicity in a Little Red Cabin on the Farm
Interior

2. Lookout Loft over the Monroe Square

Lookout Loft over the Monroe Square
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"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.
The price is HK$897
HK$1,850 total
includes taxes & fees
25 Aug - 26 Aug
Lookout Loft over the Monroe Square
Interior

3. 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, (110 reviews)
"Best location and fabulous hospitality!"
United States
Anne B.
The price is HK$1,529
HK$2,164 total
includes taxes & fees
23 Aug - 24 Aug
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Exterior

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$873
HK$2,127 total
includes taxes & fees
31 Aug - 1 Sept
🏠 Mid-Century A-Frame Near Galena | Stargaze | Couples Retreat | 1 Bed/1 Bath
Dining

5. 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, (5 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.
The price is HK$829
HK$2,533 total
includes taxes & fees
14 Sept - 15 Sept
The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
Exterior

6. 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, (51 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$699
HK$1,812 total
includes taxes & fees
2 Sept - 3 Sept
Hamilton Goebel House 816 E Louisa St Darlington Wi
Terrace/patio

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, (8 reviews)
"Wonderful house — very clean and cozy. We had a great stay and truly enjoyed our time here."
United States
Iryna S.
The price is HK$2,654
HK$5,306 total
includes taxes & fees
2 Sept - 3 Sept
Modern Lake Retreat with Hot Tub, Game Room & Two-Tier Deck
Exterior

8. Lake Cabin | Sauna · River · Game Room

Lake Cabin | Sauna · River · Game Room
Brodhead
9.8 out of 10, Exceptional, (11 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$2,762
HK$7,151 total
includes taxes & fees
1 Sept - 2 Sept
Lake Cabin | Sauna · River · Game Room
Dining

9. Golf Course Views & Family Fun – Large Apple Canyon Lake Vacation Home

Golf Course Views & Family Fun – Large Apple Canyon Lake Vacation Home
Apple River
10.0 out of 10, Exceptional, (4 reviews)
"Great house with many gathering spaces for our large family. We enjoyed the large outside deck, game room in basement, and appreciated the bed configuration in each bedroom to sleep all the young grands with their parents."
United States
Susan B.
The price is HK$3,136
HK$6,429 total
includes taxes & fees
25 Aug - 26 Aug
Golf Course Views & Family Fun – Large Apple Canyon Lake Vacation Home
Exterior

10. 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$27,442
HK$51,435 total
includes taxes & fees
1 Sept - 2 Sept
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

Super 8 by Wyndham Freeport

Super 8 by Wyndham Freeport

8/10 Good
"Breakfast was great! Air con worked and was tidy."
Charles 5-night trip
Posted 1 day ago
Super 8 by Wyndham Freeport

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?

Modern Lake Retreat with Hot Tub, Game Room & Two-Tier Deck: This holiday home rental outside of Winslow offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

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.