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Winslow Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winslow vacation 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, (40 reviews)
"Great place to stay"
United States
Mike G.
The price is AED 514
AED 623 total
includes taxes & fees
18 Oct - 19 Oct
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.

2. 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 AED 546
AED 1,016 total
includes taxes & fees
27 Oct - 28 Oct
Lookout Loft over the Monroe Square
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.

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, (111 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 AED 716
AED 997 total
includes taxes & fees
4 Oct - 5 Oct
MJ's Penthouse ,a piece of paradise on Monroe's historic 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 AED 389
AED 958 total
includes taxes & fees
5 Oct - 6 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 AED 419
AED 985 total
includes taxes & fees
28 Oct - 29 Oct
Hamilton Goebel House 816 E Louisa St Darlington 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.

6. Lake Cabin | Sauna · River · Game Room

Lake Cabin | Sauna · River · Game Room
Brodhead
9.8 out of 10, Exceptional, (13 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.
Lake Cabin | Sauna · River · Game Room
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, (10 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 AED 1,090
AED 2,767 total
includes taxes & fees
5 Oct - 6 Oct
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.

8. 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 AED 12,856
AED 24,403 total
includes taxes & fees
12 Oct - 13 Oct
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
A spacious kitchen with wooden cabinets and a stone fireplace.

9. 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 AED 5,858
AED 10,932 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

Eugene Hotel

Eugene Hotel

10/10 Excellent
"The hotel has been nicely remodeled. Very friendly and quaint. The bed and pillows were soft,but comfortable."
Buffey 2-night trip
Posted 2 days ago
Eugene Hotel

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.