Holiday Rentals in Winslow

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 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

Apple River
9.8 out of 10, Exceptional, (215)
"Wonderful and perfict family getaway "
United States
Hillel E.
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

Apple River
9.6 out of 10, Exceptional, (108)
"Beautiful cabin in a very scenic area. We really enjoyed our stay and the addition mail amenities that the host included, giving us access to the pool and beach. Really nice stay, we will definitely be back."
United States
David T.
Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location
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

Elizabeth
9.8 out of 10, Exceptional, (71)
"Great hosts and a ton to do. Could have spent 2 weeks here for our family reunion and could not have done everything!"
United States
Damian W.
The price is €2,427
includes taxes & fees
8 Dec - 9 Dec
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
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.

Elizabeth
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 €5,433
includes taxes & fees
17 Dec - 18 Dec
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
Exterior
Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table

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

The Galena Territory
10.0 out of 10, Exceptional, (327)
"We came here just to relax for a couple of days. We enjoyed the hot tub and the pool table and just sitting on the deck. We really enjoyed our time at this cabin. Thanks Ginger!"
United States
Marlys W.
Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table
Exterior
A-Frame Cabin Retreat

A-Frame Cabin Retreat

2.0 star property
Stockton
10.0 out of 10, Exceptional, (1)
"The house is very nice and comfortable"
United States
Yu C.
A-Frame Cabin Retreat
Pool
3 Bedroom, 3.5 bath house in The Galena Territory.

3 Bedroom, 3.5 bath house in The Galena Territory.

The Galena Territory
9.8 out of 10, Exceptional, (190)
"The house was spacious and clean and all bedrooms had an attached bathrooms, which was great for a getaway with other couples! "
United States
Ashley S.
3 Bedroom, 3.5 bath house in The Galena Territory.
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

Elizabeth
9.6 out of 10, Exceptional, (78)
"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! "
United States
Caroline S.
The price is €833
includes taxes & fees
9 Dec - 10 Dec
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
Interior
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, (12)
"Quiet, clean and absolutely lovely cabin! "
United States
Holley B.
The price is €149
includes taxes & fees
17 Dec - 18 Dec
Peace & Simplicity in a Little Red Cabin on the Farm
Interior
Bungalow in the Burg - 1 block from downtown

Bungalow in the Burg - 1 block from downtown

Shullsburg
10.0 out of 10, Exceptional, (29)
"Nice place, will stay again when in the area."
United States
Kim
Bungalow in the Burg - 1 block from downtown
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!

The Galena Territory
9.8 out of 10, Exceptional, (122)
"Third time here, very nice."
United States
George S.
Unwind at High Ridge: Hot Tub Nights, Arcade Lights & Fire Pit Fun!
Fridge, microwave, oven, stovetop
New 5-bedroom house at Apple Canyon Lake. 30 minutes from downtown Galena!

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

Apple River
10.0 out of 10, Exceptional, (12)
"Beautiful home!"
United States
Abbey E.
New 5-bedroom house at Apple Canyon Lake. 30 minutes from downtown Galena!
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

Elizabeth
10.0 out of 10, Exceptional, (26)
"An absolute GORGEOUS hillside view. The home had everything we needed for a comfortable stay. "
United States
Shantyana R.
Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL
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

Shullsburg
10.0 out of 10, Exceptional, (24)
"the property was absolutely beautiful! my friends and I will definitely be back!!"
United States
hailey k.
White Oak Retreat SW WI easy access to ATV and Snowmobile Trails
Fridge, microwave, oven, stovetop
Discover Elizabeth charm, just a quick 27-min drive away from Mississippi River

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

Elizabeth
10.0 out of 10, Exceptional, (104)
"Great place to stay and great atmosphere. Close to Galena and plenty to do. "
United States
Tammy K.
Discover Elizabeth charm, just a quick 27-min drive away from Mississippi River
Dining
Destination Driftless- A Trailside Retreat

Destination Driftless- A Trailside Retreat

Darlington
9.2 out of 10, Wonderful, (32)
"Nice location. Quiet and close to trails"
United States
Johanna D.
Destination Driftless- A Trailside Retreat
Terrace/patio
Modern Lake Retreat with Hot Tub, Game Room & Two-Tier Deck

Modern Lake Retreat with Hot Tub, Game Room & Two-Tier Deck

Apple River
10.0 out of 10, Exceptional, (1)
"We loved our stay at this lake house! Everything was clean, cozy, and exactly as described. The hot tub, views, and game room made the weekend perfect. Great host and a great place — we would definitely come back!"
United States
Nazar L.
Modern Lake Retreat with Hot Tub, Game Room & Two-Tier Deck
Exterior
Relaxing Retreat with Hot Tub and Fire Pit

Relaxing Retreat with Hot Tub and Fire Pit

The Galena Territory
10.0 out of 10, Exceptional, (37)
"Without a doubt, my favorite VRBO. The hosts are great. The house is amazing. It’s easy to find. Everything is just incredible. "
United Kingdom
Megan H.
Relaxing Retreat with Hot Tub and Fire Pit
Living area
Darlington River View House - Direct Trail Access

Darlington River View House - Direct Trail Access

Darlington
10.0 out of 10, Exceptional, (2)
"Very cute place to stay. "
United States
Srstenger@gmail.com G.
Darlington River View House - Direct Trail Access
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

Monticello
10.0 out of 10, Exceptional, (156)
"Fantastic area to explore"
United States
Bill N.
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winslow Hotel Reviews

Beautiful compound, 10 mile views, on 300 acre ranch, next to Galena Territory

Beautiful compound, 10 mile views, on 300 acre ranch, next to Galena Territory

10/10 Excellent
"Host was extremely welcoming and helpful. Great communication especially when there was internet glitch with the internet provider (so not issue of host). They went above and beyond to make sure we had a place for us to watch/stream the Packers game on Thanksgiving and issue was fixed by Friday morning. Great space in both homes and we loved the event barn. Did dinner in there one night as well as a Paint Your Partner Challenge and watched the Bears on the big screen tv. Beautiful views and the animals were a bonus for the grandkids. "
Kathy D. 3-night trip
Posted 6 days ago
Beautiful compound, 10 mile views, on 300 acre ranch, next to Galena Territory

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 €149 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, 3.5 bath house in The Galena Territory.: This holiday home rental outside of Winslow is located in a rural location, and has a fireplace, a patio 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 and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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 Historic Cheesemaking Center 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.