Default HTG hotel image

Winston Holiday Rentals

  • 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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Winston holiday rentals

Exterior

1. Foxy's Den cozy grain bin cabin with WiFi & AC in serene Kidder. Quiet & serene.

Foxy's Den cozy grain bin cabin with WiFi & AC in serene Kidder. Quiet & serene.
Kidder
10.0 out of 10, Exceptional, (51 reviews)
"2nd stay - great place and location "
United States
Garry M.
The price is HK$784
HK$1,198 total
includes taxes & fees
31 Aug - 1 Sept
Foxy's Den cozy grain bin cabin with WiFi & AC in serene Kidder. Quiet & serene.
Private kitchen

2. Charming 1-bedroom Guest Home with WiFi, AC in delightful Gallatin

Charming 1-bedroom Guest Home with WiFi, AC in delightful Gallatin
Gallatin
10.0 out of 10, Exceptional, (9 reviews)
"Hoping to stay again next year."
United States
Theresa
The price is HK$706
HK$1,176 total
includes taxes & fees
31 Aug - 1 Sept
Charming 1-bedroom Guest Home with WiFi, AC in delightful Gallatin
Front of property

3. Firefly Lofts

Firefly Lofts
2.0 star property
Cameron
2.0 out of 10, (1 review)
"I travel for work so I have stayed in some pretty questionable places however this was by far the worst. I slept with a chair in front of the door and also went and bought shower shoes to wear in the shower. This is also the only time I have ever left a review for a place. This place needs a lot of work. It has potential however at this time I would never recommend this place for anyone."
United States
Jailayia
The price is HK$1,043
HK$2,599 total
includes taxes & fees
31 Aug - 1 Sept
Firefly Lofts
Private kitchen

4. Sewing Serenity A - New 2BR Home in Hamilton, 3 Blocks to Missouri Star

Sewing Serenity A - New 2BR Home in Hamilton, 3 Blocks to Missouri Star
Hamilton
10.0 out of 10, Exceptional, (2 reviews)
"It was in a perfect location for us for exploring Hamilton and the surrounding towns."
United States
Anonymous traveller
Sewing Serenity A - New 2BR Home in Hamilton, 3 Blocks to Missouri Star
Exterior

5. Hamilton Getaway -Entire House in DT Hamilton

Hamilton Getaway -Entire House in DT Hamilton
Hamilton
9.8 out of 10, Exceptional, (60 reviews)
"The location was perfect for our group! We had a nice stay and the town of Hamilton was everything we hoped for and more!"
United States
Cindy O.
The price is HK$1,239
HK$1,866 total
includes taxes & fees
31 Aug - 1 Sept
Hamilton Getaway -Entire House in DT Hamilton
Exterior detail

6. Spacious 1 BR Carriage House - 2 min walk to Missouri Star

Spacious 1 BR Carriage House - 2 min walk to Missouri Star
Hamilton
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful home within walking distance of Missouri Star Quilt Company. Spacious and comfortable with great parking. Extremely comfortable place for my husband to spend time while I shopped! I would definitely stay here again next time I visit"
United States
Joanne H.
The price is HK$757
HK$1,414 total
includes taxes & fees
31 Aug - 1 Sept
Spacious 1 BR Carriage House - 2 min walk to Missouri Star
Private kitchen

7. Piper's Place - 2 Bedroom House in DT Hamilton

Piper's Place - 2 Bedroom House in DT Hamilton
Hamilton
9.4 out of 10, Exceptional, (19 reviews)
"The shops of Hamilton, particularly Missouri Star Quilt Company is a very short drive into town. Easy to access from Pipers Place."
United States
Jeri L.
The price is HK$1,090
HK$1,693 total
includes taxes & fees
31 Aug - 1 Sept
Piper's Place - 2 Bedroom House in DT Hamilton
Private kitchen

8. Patchwork Paradise A - New 2BR Home - 5 Minute walk to Missouri Star

Patchwork Paradise A - New 2BR Home - 5 Minute walk to Missouri Star
Hamilton
10.0 out of 10, Exceptional, (3 reviews)
"Great little place down the street from downtown."
United States
Tom K.
The price is HK$815
HK$1,586 total
includes taxes & fees
31 Aug - 1 Sept
Patchwork Paradise A - New 2BR Home - 5 Minute walk to Missouri Star
Exterior detail

9. Cozy 1-bedroom cabin in peaceful Jameson with AC

Cozy 1-bedroom cabin in peaceful Jameson with AC
Jameson
The price is HK$325
HK$585 total
includes taxes & fees
8 Sept - 9 Sept
Cozy 1-bedroom cabin in peaceful Jameson with AC
Private kitchen

10. Sewing Serenity B- New 2 BR Home in Hamilton, MO - 3 blocks to Missouri Star

Sewing Serenity B- New 2 BR Home in Hamilton, MO - 3 blocks to Missouri Star
Hamilton
The price is HK$840
HK$1,613 total
includes taxes & fees
1 Sept - 2 Sept
Sewing Serenity B- New 2 BR Home in Hamilton, MO - 3 blocks to Missouri Star
Private kitchen

11. Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-Free

Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-Free
Hamilton
10.0 out of 10, Exceptional, (1 review)
"The home was well stocked with high quality items, everything you need, very quaintly decorated. I enjoyed coming to Hamilton to shop the quilt shops. The home had a quilters theme with beautiful quilts and crafts which was fun."
United States
John G.
The price is HK$1,294
HK$3,034 total
includes taxes & fees
31 Aug - 1 Sept
Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-Free
Interior

12. Comfortable Two-Story Family Home in Picturesque Small Town USA

Comfortable Two-Story Family Home in Picturesque Small Town USA
Hamilton
9.6 out of 10, Exceptional, (127 reviews)
"Check in and check out was very smooth. The home was beautifully decorated with antiques and quilts. Very, very clean and fully stocked with linens and the softest beds. A beautiful rest was had by all. We had breakfast and enjoyed our welcome treat on the front porch. Jennafer was amazing and gave us info to find a place to eat and a place to charge one of the cars. We all highly recommend staying here! It was a joyful wedding weekend and this beautiful home was the icing on the cake!"
United States
Jeanette
The price is HK$1,482
HK$2,445 total
includes taxes & fees
31 Aug - 1 Sept
Comfortable Two-Story Family Home in Picturesque Small Town USA
Interior

13. Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-free

Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-free
3.0 star property
Hamilton
The price is HK$1,662
HK$3,006 total
includes taxes & fees
31 Aug - 1 Sept
Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-free
Interior

14. 1920s Restored Home-walk to MSQC shops, Quilt Town USA

1920s Restored Home-walk to MSQC shops, Quilt Town USA
Hamilton
10.0 out of 10, Exceptional, (18 reviews)
"We loved our stay at this perfectly renovated home! Very clean, well organized and stocked with everything you need. We highly recommend staying at this property! "
United States
Heather T.
The price is HK$1,793
HK$3,401 total
includes taxes & fees
1 Sept - 2 Sept
1920s Restored Home-walk to MSQC shops, Quilt Town USA
Private kitchen

15. Patchwork Paradise B - New 2BR Home 3 Blocks from Missouri Star

Patchwork Paradise B - New 2BR Home 3 Blocks from Missouri Star
Hamilton
10.0 out of 10, Exceptional, (3 reviews)
"Very nice and clean space for a fun one night stay in Hamilton! Plan to make this trip again in the future for more crafting supplies and will absolutely plan to stay here again."
United States
Reed C.
The price is HK$856
HK$1,638 total
includes taxes & fees
31 Aug - 1 Sept
Patchwork Paradise B - New 2BR Home 3 Blocks from Missouri Star
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 Winston Hotel Reviews

SureStay Hotel by Best Western Cameron

SureStay Hotel by Best Western Cameron

10/10 Excellent
"This is the hotel I stay at with my dog when I am passing through this area. The staff are nice, easy checkin, and the rooms are comfortable and clean. Park right outside of your room. Decent breakfast. Nice area next to the hotel to run or walk your dog. Just an overall nice experience."
Nancy 1-night trip
Posted 2 days ago
SureStay Hotel by Best Western Cameron

Find out more about Winston

Search for holiday rentals in Winston on Expedia! You can easily find your home rentals, villas, holiday apartments in Winston using one of the methods below:

  • View our selection of featured holiday rentals in Winston
  • Use the map to find apartments and other holiday homes in the Winston neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winston while they last

Look no further and take a look at our great range of rental properties in Winston!

Frequently asked questions

Are there holiday rentals in Winston?

Yes, there are holiday rentals close to the most popular sights in Winston, 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 Winston has to offer?

The Bird's Nest - 2 bedroom House: This holiday home rental outside of Winston has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a dishwasher and kitchenware can make your holiday run smoothly.

What can I see and do in Winston?

While you're exploring the area, Dockery Park and Kelsey Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Adam-ondi-Ahman and Wallace State Park.

What are holiday rentals like in Winston?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winston. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for a family trip.