Winslow Holiday Rentals

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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Holiday Rentals in Winslow

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
Fridge, microwave, oven, stovetop

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake

9.8 out of 10, Exceptional, (205)
"Roomy and comfy cabin. Enjoyed our stay!"
Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.
Exterior

The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.

8.8 out of 10, Excellent, (3)
"Quiet and peaceful. Close to Apple River Canyon and Yellowstone State Park. My wife and I had a wonderful time. Our dog had a blast too. We are planning on returning."
The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.
Peace & Simplicity in a Little Red Cabin on the Farm
Interior

Peace & Simplicity in a Little Red Cabin on the Farm

10.0 out of 10, Exceptional, (5)
The price is AU$224
includes taxes & fees
17 Sept - 18 Sept
Peace & Simplicity in a Little Red Cabin on the Farm
Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location
Dining

Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location

9.6 out of 10, Exceptional, (99)
"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."
Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location
Apple Canyon Lake Home, Life At The Lake
Pool

Apple Canyon Lake Home, Life At The Lake

10.0 out of 10, Exceptional, (85)
"Great location and property. It rained during our visit, but there were plenty of games to keep us entertained."
Apple Canyon Lake Home, Life At The Lake
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
Outdoor spa tub

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."
The price is AU$9,848
includes taxes & fees
17 Sept - 18 Sept
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
Destination Driftless- A Trailside Retreat
Interior

Destination Driftless- A Trailside Retreat

9.4 out of 10, Exceptional, (29)
"Great place to stay. We werent at the house much. Just to sleep and get ready. House decor is very cute."
Destination Driftless- A Trailside Retreat
3 Bedroom, 3.5 bath house in The Galena Territory.
Pool

3 Bedroom, 3.5 bath house in The Galena Territory.

9.8 out of 10, Exceptional, (182)
"Place was very nice and clean, I didn’t want for anything that was not there accept olive oil… which led me to the Galena garlic company where I found all sorts of olive oils and other goodies. My mom loved hearing the birds chirping while enjoying the hot tub. Fried green tomatoes was a family hit!"
3 Bedroom, 3.5 bath house in The Galena Territory.
Hamilton Goebel House 816 E Louisa St Darlington Wi
Fridge, microwave, oven, stovetop

Hamilton Goebel House 816 E Louisa St Darlington Wi

9.8 out of 10, Exceptional, (42)
"Will definitely stay again!"
The price is AU$349
includes taxes & fees
11 Sept - 12 Sept
Hamilton Goebel House 816 E Louisa St Darlington Wi
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Exterior

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

10.0 out of 10, Exceptional, (151)
"Fantastic area to explore"
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Cedar Cove Cabin, Private Beach near Galena
Exterior

Cedar Cove Cabin, Private Beach near Galena

2.0 star property
10.0 out of 10, Exceptional, (8)
"Our family loved this house and all the thoughtful details throughout it. The kids had a blast swimming and kayaking in the pond. The local town has great restaurants and the house has everything you could possibly need to cook at home too! We can’t wait to come back! "
Cedar Cove Cabin, Private Beach near Galena
Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table
Exterior

Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table

10.0 out of 10, Exceptional, (320)
"We had an amazing stay. The only downside was that we had so many plans we didn't get to enjoy the property more!"
Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table
Discover Elizabeth charm, just a quick 27-min drive away from Mississippi River
Fridge, microwave, oven, stovetop

Discover Elizabeth charm, just a quick 27-min drive away from Mississippi River

10.0 out of 10, Exceptional, (97)
"Our hostess thought of all our needs. The delicious breakfast that she made each morning was like clockwork at our requested time. The home was cozy, comfortable, and fulfilled our needs."
Discover Elizabeth charm, just a quick 27-min drive away from Mississippi River
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
Outdoor spa tub

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!"
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
New 5-bedroom house at Apple Canyon Lake. 30 minutes from downtown Galena!
Fridge, microwave, oven, stovetop

New 5-bedroom house at Apple Canyon Lake. 30 minutes from downtown Galena!

10.0 out of 10, Exceptional, (9)
"This is a beautiful brand new house with tons of room! We were able to walk down to the lake from the back yard to Ice fish."
New 5-bedroom house at Apple Canyon Lake. 30 minutes from downtown Galena!
White Oak Retreat SW WI easy access to ATV and Snowmobile Trails
Fridge, microwave, oven, stovetop

White Oak Retreat SW WI easy access to ATV and Snowmobile Trails

10.0 out of 10, Exceptional, (21)
"awesome property and stay"
White Oak Retreat SW WI easy access to ATV and Snowmobile Trails
Historic Country Farmhouse for ANY Season!
Property grounds

Historic Country Farmhouse for ANY Season!

10.0 out of 10, Exceptional, (45)
"Great weekend with girls. Host was very attentive. Location was great, close to shopping and wineries."
Historic Country Farmhouse for ANY Season!
Bungalow in the Burg - 1 block from downtown
Interior

Bungalow in the Burg - 1 block from downtown

10.0 out of 10, Exceptional, (29)
"Nice place, will stay again when in the area."
Bungalow in the Burg - 1 block from downtown
Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL
Terrace/patio

Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL

10.0 out of 10, Exceptional, (23)
"Lovely, comfortable and spacious, this house was close to so many places we wanted to go."
Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Interior

MJ's Penthouse ,a piece of paradise on Monroe's historic square

10.0 out of 10, Exceptional, (96)
"Had a great stay for St Pats Parade!"
The price is AU$415
includes taxes & fees
10 Sept - 11 Sept
MJ's Penthouse ,a piece of paradise on Monroe's historic square
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

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 favourite 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 depend 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 AU$224 per night. Entering your travel dates in the search wizard might find you 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?

The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.: This holiday home rental outside of Winslow is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities such as a stovetop and a microwave can make your holiday run smoothly.

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.