
Holiday rentals in Winston
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Top-rated holiday rentals in Winston
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Other great holiday rentals in Winston

Home in Gallatin
5 out of 5 average rating, 4 reviewsRudy's Place: Near Hamilton Quilt Town & Jamesport
Tonya.Rating, 5 stars3 weeks ago
Came to the area to visit family and Missouri Star Quilt Company shops. The house was tastefully decorated with copies of local historical pictures. Great combination of modern and farm-style decor. Great water pressure and plenty of hot water. Enjoyed the BBQ grill and firepit. She even had a supply of dry wood. Loved, loved, loved this place. Megan, if you ever want to sell I would like first dibs. Would definitely stay again. Don't hesitate to rent this unit.

Cabin in Maysville
4.57 out of 5 average rating, 7 reviews1BR cabin on farm with firepit, pond & treehouse
AnaRating, 5 stars2 months ago
What a beautiful place. My boyfriend and I went out for the weekend and loved it. It was super secluded as there was no sound of cars or traffic, also no neighbors. The dock and the pond were gorgeous and the fairly lights around the treehouse. There was a Greta market 3 minutes away too for food and anything we needed. One thing is that it doesn't have an oven and the stovetop smelt when heated.
Guest favourite

Cabin in Gilman City
4.89 out of 5 average rating, 9 reviewsWhispering Waters
ChristyRating, 5 stars3 days ago
We are a family of 6. Four kids ages 11-22 and 3 small dogs. Everyone had fun! Definitely would come back. Kept them off their electronics!! :)

Cabin in Gallatin
5 out of 5 average rating, 6 reviewsStandard 2 Bed Cabin with Solitude and amenities.
AlbinRating, 5 stars8 months ago
The cabin is a part of a resort of sorts with several other cabins, a really nice guest lodge and other facilities including open fishing ponds. There is comfortable space between the cabins and the resort is very private. Off you want to avoid a lot of dirt roads, approach it from the West (highway DD).

Cabin in Maysville
5 out of 5 average rating, 3 reviewsPony Express Cabin
AlejandrinaRating, 5 stars3 weeks ago
I don't have words to describe how beautiful and peaceful the place is..
Guest favourite

Guest house in Jamesport
5 out of 5 average rating, 11 reviewsHidden Paradise
MeganRating, 5 stars9 months ago
We enjoyed our stay very much. We had such a nice and relaxing time spent with family and this place was perfect for us. We loved seeing the deer outside. The beds were comfortable, shower was nice, and the kitchen and living room were perfect. We even enjoyed sitting outside on the patio.
Top guest favourite

Campervan/Motorhome in Jamesport
4.95 out of 5 average rating, 39 reviewsJamesport's Little Camper @ The Porch Sherwood
SusanRating, 5 stars1 week ago
This was a weekend getaway for my husband and I. Lori was so gracious and kind. The camper was well appointed and super clean. So many extra details including locally made cinnamon rolls upon check in. The bed and pillows were so comfortable. She provided a fire pit and wood for a lovely fire. It was so enjoyable sitting by the fire watching and listening to nature. Occasionally, we would see an Amish buggy travel down the road. I had a blissful soak in the hot tub as well. The camper is close to shops and restaurants in town. By the time I left, I felt like I had been reset and ready to take on the normal routine of life. I look forward to a return visit.
Top guest favourite

Home in Trenton
4.88 out of 5 average rating, 16 reviewsCountry Good Time
LindaRating, 5 stars6 days ago
My husband and I came into town for a few days (with our dog) for work, and this was an excellent choice! The house was clean and comfortable. It had so many extras that it was like being at home!! From the fully stocked kitchen for cooking, water in the fridge, amenities in the bathroom, and all the extra towels, we could not have been more spoiled. Plus being dog friendly, our pup loved the privacy and the space!!
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