Holiday Rentals in Winslow

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Holiday Rentals in Winslow

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
9.8 out of 10, Exceptional, (210)
"Roomy and comfy cabin. Enjoyed our stay!"
Debra K.
Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location
9.6 out of 10, Exceptional, (105)
"What a peaceful respite! Set in a lovely area, walking distance to the Apple Canyon Lake with a beach and restaurant, this was the perfect getaway for a family wedding weekend. The cabin is stunning and comfortable. Beautifully furnished, it had all of the amenities one could hope for in a vacation home."
Amy
Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location
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."
Katie L.
The price is €5,562
includes taxes & fees
27 Oct - 28 Oct
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
9.8 out of 10, Exceptional, (69)
"This was the perfect location for our family of 21 to gather for Thanksgiving. The ranch had so many animals and places to roam and all the kids had fun playing on the baseball field. Enough ovens for all of the Thanksgiving Turkey and sides to be eaten hot, and enough room for all to enjoy our time together. Great location near Galena!"
Ingrid E.
The price is €2,382
includes taxes & fees
27 Oct - 28 Oct
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
10.0 out of 10, Exceptional, (155)
"A comfy home in a quiet location, perfect for our weekend getaway. We've stayed here once before and would definitely come back again if it's available next time we're in the area. "
Amy K.
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Peace & Simplicity in a Little Red Cabin on the Farm
10.0 out of 10, Exceptional, (8)
The price is €129
includes taxes & fees
17 Nov - 18 Nov
Peace & Simplicity in a Little Red Cabin on the Farm
The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.
9.4 out of 10, Exceptional, (6)
The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.
Unwind at High Ridge: Hot Tub Nights, Arcade Lights & Fire Pit Fun!
9.8 out of 10, Exceptional, (119)
"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"
Deb C.
Unwind at High Ridge: Hot Tub Nights, Arcade Lights & Fire Pit Fun!
Hamilton Goebel House 816 E Louisa St Darlington Wi
9.8 out of 10, Exceptional, (45)
"This was a wonderful property. The hosts were so accommodating and helpful. We had a great time."
Peggy S.
The price is €203
includes taxes & fees
20 Oct - 21 Oct
Hamilton Goebel House 816 E Louisa St Darlington Wi
Spacious Suite w/ 2 King Beds | Near Trails, Lake & Golf
9.6 out of 10, Exceptional, (4)
"The hosts are very responsive. The room is clean and decorated nicely. Overall, we would recommend."
Tina I.
The price is €150
includes taxes & fees
2 Nov - 3 Nov
Spacious Suite w/ 2 King Beds | Near Trails, Lake & Golf
Cozy King + Queen Suite | Near Golf, Lake & Marina
6.0 out of 10, (1)
"Room was very clean, nicely decorated, and spacious. The bathroom is very cramped with a tiny shower and it seems odd that the mini fridge and coffee m"
Kim H.
The price is €150
includes taxes & fees
17 Nov - 18 Nov
Cozy King + Queen Suite | Near Golf, Lake & Marina
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"
Marcia T.
Cozy home with beautiful LAKE VIEW!
White Oak Retreat SW WI easy access to ATV and Snowmobile Trails
10.0 out of 10, Exceptional, (24)
"It was a great space with plenty of room. We had no issues during our trip and the host was very generous and kind helping us with getting a bonfire started and providing what we needed. I would recommend this place and go here again."
James H.
White Oak Retreat SW WI easy access to ATV and Snowmobile Trails
Chic Apple River Escape w/ Fire Pit!
3.0 star property
Chic Apple River Escape w/ Fire Pit!
Destination Driftless- A Trailside Retreat
9.4 out of 10, Exceptional, (30)
"Great place to stay. We werent at the house much. Just to sleep and get ready. House decor is very cute."
Srstenger@gmail.com G.
Destination Driftless- A Trailside Retreat
Bungalow in the Burg - 1 block from downtown
10.0 out of 10, Exceptional, (29)
"Nice place, will stay again when in the area."
Kim
Bungalow in the Burg - 1 block from downtown
Discover Elizabeth charm, just a quick 27-min drive away from Mississippi River
10.0 out of 10, Exceptional, (100)
"We had a girls weekend stay at the Derinda House. This is the second time staying. I love Sandy's cooking. We thoroughly enjoyed local wineries and shopping."
Kassidy S.
Discover Elizabeth charm, just a quick 27-min drive away from Mississippi River
MJ's Penthouse ,a piece of paradise on Monroe's historic square
10.0 out of 10, Exceptional, (98)
"My husband and I stayed here and were so happy we did this home was beautiful and really something special. I highly recommend the stay here! "
Katie B.
The price is €233
includes taxes & fees
26 Oct - 27 Oct
MJ's Penthouse ,a piece of paradise on Monroe's historic square
3 Bedroom, 3.5 bath house in The Galena Territory.
9.8 out of 10, Exceptional, (187)
"Beautiful and comfortable home backing up to the woods. Close enough to all Galena has to offer in an extremely peaceful setting. Management is very responsive. Our family had a wonderful stay."
Wendy F.
3 Bedroom, 3.5 bath house in The Galena Territory.
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
9.6 out of 10, Exceptional, (76)
"We had a lovely stay! We loved fishing at the pond, and hiking around the beautiful property. The house was well maintained and was easy to call home for our stay. Our host, Mark, was super responsive to anything we needed! My kids are begging me to book again next year. Would definitely return! "
Caroline S.
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
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

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 €129 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?

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe: This holiday home rental outside of Winslow is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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.