Holiday houses in Winslow Township

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Top-rated holiday rentals in Winslow Township

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Home in Galena

4.95 out of 5 average rating, 44 reviews

4bd/4ba Hot Tub/Fab Game Room/Wow Sunsets/Fire Pit!

NicoleRating, 5 stars3 weeks ago
Felt like we were at home! Very spacious with lots of amenities and items available to us as guests! Definitely would choose to stay there again!
Superhost

Townhouse in Galena

4.87 out of 5 average rating, 169 reviews

Galena Territories 3 level Townhome Sleeps nine

LaurieRating, 5 stars1 month ago
Everything was great. Our host Ryan and housekeeper Shannon were super flexible and kind. Galena is nice area for a getaway and this place is perfect for a big group.
Guest favourite

Townhouse in Dubuque

4.93 out of 5 average rating, 120 reviews

The Fenelon Place

SteveRating, 5 stars1 month ago
We have made a habit of staying at Jeremy’s place a couple of times a year when we come up for family events. We are always comfortable and happy with our choice.
Guest favourite

Cabin in Savanna

5 out of 5 average rating, 44 reviews

River Rail Retreats Blue Cabin at Palisades

MikaelRating, 5 stars1 month ago
Cozy cabin with all necessary utilities. Relaxing atmosphere with a great aesthetic interior design. Fast and flexible communication with host. Would recommend to friends. Host also provides sizable guide book for the area and local activities, national parks, and places to eat
Guest favourite

Home in Freeport

4.98 out of 5 average rating, 168 reviews

Willow Lake Getaway Cozy for 2 - or large families

DeniseRating, 5 stars2 weeks ago
We absolutely loved this Willow Lake oasis! Perfect for a few middle aged moms to have a weekend away. Bright, spacious, peaceful, well stocked amenities, things labeled and easy to find, comfy beds and chill spaces, literally everything we needed and a great collection of funny mugs and community pantry cabinet to top it off. We would love to return here for another weekend of R&R, or with our families. Any time of year, this place is a gem. Host Roger was always so responsive - answered questions before the trip, checked in via message to make sure all ok during. We will be back!
Superhost

Townhouse in Galena

5 out of 5 average rating, 20 reviews

Cozy Sunrise Villa!

MichelleRating, 5 stars1 month ago
Such a cute little getaway in the territory! So peaceful and quiet. The golf course has a couple restaurants close by and a small general store in case you forgot to pack something! About a 10-15 min drive to downtown with lots of shops and restaurants. We felt right at home staying here. Everything was very clean except for a few utensils in the drawer. Looks like the dishwasher didn’t completely clean them but no biggie! There are some games in the breakfast area to play, a bird watching book and binoculars. The TV has Netflix, but you’d have to connect your own account but has the free Samsung TV so whatever is on. We loved the coziness of all of the decor, especially the electric fireplace! We will definitely go back!
Guest favourite

Home in Rockford

4.92 out of 5 average rating, 39 reviews

Beautifully home with 5 bedrooms

SarahRating, 5 stars1 month ago
Great family home for 3 couples and 2 children. Beds were very comfortable and the house was well supplied. The bins of toys were a big hit with our toddlers. Would stay again when we come to visit family in Rockford.
Guest favourite

Townhouse in Galena

5 out of 5 average rating, 16 reviews

Perfect Getaway: Newly Renovated

CathyRating, 5 stars4 months ago
Julie's place was absolutely beautiful, surrounded by stunning natural scenery. The property was impeccably clean, and Julie was incredibly responsive throughout our stay. The house club pools were a fantastic bonus that added to the overall experience. We will definitely come again!
Guest favourite

Home in Galena

5 out of 5 average rating, 9 reviews

New listing for Fall - 4BR FP/Deck/Games/EV

NicolaRating, 5 stars6 days ago
We had an amazing stay at Aviad’s house! We had our parents visiting us from England and treated them to a trip before they went back home, I was recovering from knee surgery and the house was perfect for manoeuvring around on 2 crutches. The kids loved the basement playing cards and pool and the adults loved a cosy chat round the log fire! The house is beautifully equipped with everything and more that you will need and the decor of the house is perfect. The house feels really homely but lots of space and we loved all the separate areas I.e the enclosed sun room and the dining/reception room. Everyone enjoyed exploring the territories and Galena, and we had a lovely bar meal at the hotel, staff there were lovely. We would definitely look to rebook in the future, especially when we have family visiting, it’s a great house to get together in.
Superhost

Cabin in Galena

4.88 out of 5 average rating, 126 reviews

Serenity Cabins - A rustic, yet upscale cabin!

SunnyRating, 5 stars3 months ago
I felt super confident in my booking right from the moment I booked it as Dan guided me the entire way and is super amazing at responding and communicating. It was super accomodating when I needed help and it was so reassuring to have a host so kind and responsible.
Guest favourite

Home in Galena

4.98 out of 5 average rating, 56 reviews

Jackson Ready Properties

RocioRating, 5 stars1 month ago
Kelly's place was great. As soon as you walk in you are welcomed with a clean cozy home. We were looking forward to spending the holidays in a private area with things to do and this place delivered. Would highly recomend it.
Guest favourite

Home in Galena

4.92 out of 5 average rating, 154 reviews

DunPuttin Place

JulieRating, 5 stars1 week ago
Eleven adults we call Framily stayed for the weekend. We have been doing this for years. Usually we sit around a table and play games. Your game room was so much fun and a refreshing change. The living room was very comfortable, we could all sit and play games in there. The hot tub was a bonus. Bedrooms were comfortable. The outdoor areas looked inviting. Hope we can return in the fall.

Popular amenities for Winslow Township holiday rentals

Other great holiday rentals in Winslow Township

Apartment in Savanna

4.73 out of 5 average rating, 11 reviews

Missi-Vanna (B)

AlexisRating, 5 stars3 months ago
Charming home, lots of character. Kid friendly, and within walking distance of a park and grocery store. Host was very gracious and helpful when things broke, or needed maintenance. We would recommend this stay to anyone who does not require wheelchair access, and who is comfortable with proximity to trains. TLDR Beautiful, comfortable, clean, not wheelchair accessible and conveniently located!
Guest favourite

Home in Galena

5 out of 5 average rating, 24 reviews

Modern spacious 4 bedroom retreat with 3 en-suites

KamilRating, 5 stars1 week ago
Great location and place to stay.
Guest favourite

Farm stay in Dixon

5 out of 5 average rating, 7 reviews

Urban Escape: 20-Acre Farmhouse

MicheleRating, 5 stars4 months ago
Fantastic grounds and house! Beautiful all around and perfect place for a small group. Highly recommend!
Superhost

Villa in Dixon

4.82 out of 5 average rating, 55 reviews

Private Island

LaneRating, 5 stars1 month ago
Very nice place for my family Christmas. private and cozy with great views.

Home in Galena

5 out of 5 average rating, 3 reviews

Galena Treehouse

AnneRating, 5 stars5 months ago
We had a great stay here! The house is beautiful and private. We grilled, used the hot tub, played pool. We thoughts the beds and the linens were very comfortable!! Our whole group was impressed with the house.
Superhost

Home in Galena

4.71 out of 5 average rating, 14 reviews

Expansive 5 Bedroom Home - Hot Tub & Amazing Views

KevinRating, 5 stars1 month ago
Beautiful home and surrounding area, but it was also fairly pricey.
Guest favourite

Home in Darlington

5 out of 5 average rating, 33 reviews

Driftless Victorian Cottage, Pet Friendly

SigneRating, 5 stars3 weeks ago
Whoa, words cannot discribe how much of gem this place truly is... beautiful, scenic, serene, and welcoming with all the amenities (washer/dryer/ stocked kitchen, welcome basket, spice rack), we felt right at home; The walking trails and near by pond were a lovley outdoor experience as well and the stars were incredible!
Guest favourite

Home in Galena

4.95 out of 5 average rating, 43 reviews

Sweet Retreat- dog friendly,hot tub,access to pool

MarilynRating, 5 stars1 month ago
Lovely home that was perfect for our extended family!! We used the kitchen for our family meals. Wonderful setting in beautiful countryside!!!

Destinations to explore