Winslow Holiday Rentals

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Check prices for these dates

In two weeks
21 Nov - 23 Nov
In two months
2 Jan - 4 Jan
In three months
30 Jan - 1 Feb
In four months
27 Feb - 1 Mar

Holiday Rentals in Winslow

Fridge, microwave, oven, stovetop
Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
9.8 out of 10, Exceptional, (212)
"Roomy and comfy cabin. Enjoyed our stay!"
United States
Debra K.
Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
Dining
Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location
Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location
9.6 out of 10, Exceptional, (106)
"This was a beautiful cabin with all the amenities of home. Proximity to the community pool and restaurant was fantastic. We will definitely stay here again. "
United States
Brenton S.
Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location
Outdoor spa tub
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
10.0 out of 10, Exceptional, (4)
"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 NZ$10,961
includes taxes & fees
17 Nov - 18 Nov
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
Interior
MJ's Penthouse ,a piece of paradise on Monroe's historic square
MJ's Penthouse ,a piece of paradise on Monroe's historic square
10.0 out of 10, Exceptional, (100)
"Absolutely perfect! The best place in Monroe. Accommodating - from dinnerware to a pack-and-play - for every need! Five stars."
United States
Benjamin R.
The price is NZ$479
includes taxes & fees
10 Nov - 11 Nov
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Exterior
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
10.0 out of 10, Exceptional, (156)
"We came to volunteer out at a local race and this home couldn’t have been more convenient to the location. Everything was clean and comfortable, and the check in process couldn’t have been easier. "
United States
Elizabeth H.
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Interior
Peace & Simplicity in a Little Red Cabin on the Farm
Peace & Simplicity in a Little Red Cabin on the Farm
10.0 out of 10, Exceptional, (10)
"Wonderful hosts, a neat and clean little space, and surrounded by beautiful old, trees. This is a peaceful oasis (and it has a couple of breweries within a short drive)!"
United States
Todd H.
The price is NZ$299
includes taxes & fees
5 Dec - 6 Dec
Peace & Simplicity in a Little Red Cabin on the Farm
Outdoor spa tub
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
9.8 out of 10, Exceptional, (69)
"My family of 24 people (age ranges 1-70) stayed for one week at this wonderful rural property with pastoral views from an expansive deck. The evenings were serenely quiet and the days were filled with activities. We enjoyed petting Lucas the llama and the horses/donkey as well as viewing the peacocks. The equisitely historic town of Galena is a short drive away with plenty of shopping, eateries and tours. We biked along the Galena biking trail about 7 miles one way to Chestnut Mountain from...
United States
Thomas S.
The price is NZ$4,787
includes taxes & fees
10 Nov - 11 Nov
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
Indoor pool, outdoor pool
Unwind at High Ridge: Hot Tub Nights, Arcade Lights & Fire Pit Fun!
Unwind at High Ridge: Hot Tub Nights, Arcade Lights & Fire Pit Fun!
9.8 out of 10, Exceptional, (121)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: It was great"
United States
Deb C.
Unwind at High Ridge: Hot Tub Nights, Arcade Lights & Fire Pit Fun!
Pool
Cozy home with beautiful LAKE VIEW!
Cozy home with beautiful LAKE VIEW!
9.4 out of 10, Exceptional, (10)
"This house was Fantastic, we own a lot at the lake but it was great to beable to stay the whole weekend and have family come for a day to spend with us on the boat and at the pool to celebrate, a Birthday, Fathers Day, and an Anniversary"
United States
Marcia T.
Cozy home with beautiful LAKE VIEW!
Exterior
Apple Canyon Lake, Game Room, Hot Tub
Apple Canyon Lake, Game Room, Hot Tub
9.0 out of 10, Wonderful, (67)
"We stayed here for my families summer vacation and it was wonderful. We had lots of kids and adults, spacious house with convenient location to the lake. The back yard was a little smaller than we planned, but the atv trails are close for a quick walk down by the lake. Wonderful stay, beds and couches were so comfy! "
United States
Miranda H.
Apple Canyon Lake, Game Room, Hot Tub
Interior
Bungalow in the Burg - 1 block from downtown
Bungalow in the Burg - 1 block from downtown
10.0 out of 10, Exceptional, (29)
"The house is a block off Water Street, and everything was within walking distance. Will definitely stay here for the next family reunion."
United States
Jennifer F.
Bungalow in the Burg - 1 block from downtown
Dining
Destination Driftless- A Trailside Retreat
Destination Driftless- A Trailside Retreat
9.4 out of 10, Exceptional, (30)
"The hosts are very helpful and nice. The house has some nice features. The location is gorgeous However, we were not comfortable with the condition of the house--holes in the wall behind many outlets, old-fashioned wiring with electricity going from lightbulbs to power strips. I wouldn't bring toddlers again as there are too many decorative items within reach. If you do bring small children, bring your own plates, etc. for them as the beautiful dinnerware provided is not appropriate for kids....
United States
Anita D.
Destination Driftless- A Trailside Retreat
Fridge, microwave, oven, stovetop
Beautiful two story, downtown home, one block from the Square,
Beautiful two story, downtown home, one block from the Square,
10.0 out of 10, Exceptional, (35)
"We had a great time staying here and would definitely stay here again when returning to Monroe! The place was super clean and we loved all the decor :)"
United States
Breanna S.
The price is NZ$539
includes taxes & fees
3 Dec - 4 Dec
Beautiful two story, downtown home, one block from the Square,
Exterior
KC HOUSE Cozy Country Home. Enjoy the country life!
KC HOUSE Cozy Country Home. Enjoy the country life!
10.0 out of 10, Exceptional, (17)
"More than we expected! We were so comfortable and loved every minute being there. We will definitely be back! "
United States
Colleen R.
KC HOUSE Cozy Country Home. Enjoy the country life!
Exterior
The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.
The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.
9.4 out of 10, Exceptional, (8)
"Beautiful view, very clean and comfortable house. Pat responded very quickly. I am hoping to return next summer for a longer stay."
United States
Barbara D.
The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.
Indoor spa tub
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
9.6 out of 10, Exceptional, (77)
"We stayed here for a long weekend to ski nearby at Chestnut Mountain. The house was perfectly comfortable for three families with children. The surroundings are gorgeous. "
United States
Sarah S.
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
Fridge, microwave, oven, stovetop
White Oak Retreat SW WI easy access to ATV and Snowmobile Trails
White Oak Retreat SW WI easy access to ATV and Snowmobile Trails
10.0 out of 10, Exceptional, (24)
"Our stay was absolutely perfect! The place was beautiful inside and out! Absolutely no complaints whatsoever. Highly recommend and we will definitely stay here again! "
United States
Angie K.
White Oak Retreat SW WI easy access to ATV and Snowmobile Trails
Pool
3 Bedroom, 3.5 bath house in The Galena Territory.
3 Bedroom, 3.5 bath house in The Galena Territory.
9.8 out of 10, Exceptional, (188)
"We loved this place for a girls weekend, especially the en suite bathrooms in all the bedrooms. The drive to downtown was easy and scenic. Wasn’t there long enough to take advantage of the members club and pool. We enjoyed the house and the area. "
United States
Nancy M.
3 Bedroom, 3.5 bath house in The Galena Territory.
Terrace/patio
Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL
Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL
10.0 out of 10, Exceptional, (26)
"Lovely, comfortable and spacious, this house was close to so many places we wanted to go."
United States
Elizabeth M.
Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL
Exterior
🏠 Charming A-Frame w/ Mid-Century Vibe 1 Bed/1 Bath near Elizabeth, Illinois🌲
🏠 Charming A-Frame w/ Mid-Century Vibe 1 Bed/1 Bath near Elizabeth, Illinois🌲
10.0 out of 10, Exceptional, (2)
"This little A Frame house made for a wonderful, cozy stay for my husband and I on our second honeymoon! The online pictures didn't do this classy house justice! It was very clean, in a quiet neighborhood, good size lot, had everything we could need. Hope to stay here again!"
United States
Brian B.
The price is NZ$434
includes taxes & fees
12 Nov - 13 Nov
🏠 Charming A-Frame w/ Mid-Century Vibe 1 Bed/1 Bath near Elizabeth, Illinois🌲
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

Country Inn & Suites by Radisson, Freeport, IL

Country Inn & Suites by Radisson, Freeport, IL

10/10 Excellent
"Nice staff, clean rooms, good breakfast "
Latasha 1-night trip
Posted 4 days ago
Country Inn & Suites by Radisson, Freeport, IL

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, 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 NZ$299 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?

MJ's Penthouse ,a piece of paradise on Monroe's historic square: This holiday home rental outside of Winslow is located in the city centre, and has a balcony, a selection of games and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Cadiz Springs State Recreation Area 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.