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Winston Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Winston holiday rentals

Private kitchen

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, (8 reviews)
"Hoping to stay again next year."
United States
Theresa
The price is HK$705
HK$1,176 total
includes taxes & fees
24 Jul - 25 Jul
Charming 1-bedroom Guest Home with WiFi, AC in delightful Gallatin
Interior

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$1,168
HK$2,469 total
includes taxes & fees
20 Jul - 21 Jul
Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-free
Exterior detail

Cozy 1-bedroom cabin in peaceful Jameson with AC

Cozy 1-bedroom cabin in peaceful Jameson with AC
Jameson
The price is HK$384
HK$648 total
includes taxes & fees
4 Aug - 5 Aug
Cozy 1-bedroom cabin in peaceful Jameson with AC
Interior

Comfortable Two-Story Family Home in Picturesque Small Town USA

Comfortable Two-Story Family Home in Picturesque Small Town USA
Hamilton
9.8 out of 10, Exceptional, (122 reviews)
"Charming comfortable home that was clean. "
United States
Ruth M.
The price is HK$1,481
HK$2,413 total
includes taxes & fees
17 Jul - 18 Jul
Comfortable Two-Story Family Home in Picturesque Small Town USA
Coffee/tea maker, fridge, microwave, oven

Charming 2BR Cottage - Short walk to Missouri Star & Downtown Hamilton

Charming 2BR Cottage - Short walk to Missouri Star & Downtown Hamilton
Hamilton
10.0 out of 10, Exceptional, (4 reviews)
"Had a great stay"
United States
R F.
The price is HK$815
HK$1,706 total
includes taxes & fees
17 Jul - 18 Jul
Charming 2BR Cottage - Short walk to Missouri Star & Downtown Hamilton
Interior

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, (14 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$2,108
HK$3,734 total
includes taxes & fees
9 Aug - 10 Aug
1920s Restored Home-walk to MSQC shops, Quilt Town USA
Fridge, microwave, oven, stovetop

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, (1 review)
"It was very clean and had plenty of room"
United States
Sally D.
The price is HK$881
HK$1,641 total
includes taxes & fees
17 Jul - 18 Jul
Patchwork Paradise A - New 2BR Home - 5 Minute walk to Missouri Star
Exterior

Hamilton Getaway -Entire House in DT Hamilton

Hamilton Getaway -Entire House in DT Hamilton
Hamilton
9.8 out of 10, Exceptional, (60 reviews)
"Great stay-"
United States
IRENE H.
The price is HK$1,238
HK$1,842 total
includes taxes & fees
20 Jul - 21 Jul
Hamilton Getaway -Entire House in DT Hamilton
Private kitchen

Piper's Place - 2 Bedroom House in DT Hamilton

Piper's Place - 2 Bedroom House in DT Hamilton
Hamilton
9.2 out of 10, Wonderful, (15 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$1,089
HK$1,669 total
includes taxes & fees
24 Jul - 25 Jul
Piper's Place - 2 Bedroom House in DT Hamilton
Coffee/tea maker, fridge, microwave, oven

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
The price is HK$1,037
HK$1,835 total
includes taxes & fees
24 Jul - 25 Jul
Sewing Serenity A - New 2BR Home in Hamilton, 3 Blocks to Missouri Star
Coffee/tea maker, fridge, microwave, stovetop

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

Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-Free
Hamilton
The price is HK$846
HK$2,417 total
includes taxes & fees
17 Jul - 18 Jul
Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-Free
Exterior detail

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$848
HK$1,512 total
includes taxes & fees
20 Jul - 21 Jul
Spacious 1 BR Carriage House - 2 min walk to Missouri Star
Fridge, microwave, oven, stovetop

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$823
HK$1,571 total
includes taxes & fees
17 Jul - 18 Jul
Sewing Serenity B- New 2 BR Home in Hamilton, MO - 3 blocks to Missouri Star
Exterior

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, (44 reviews)
"2nd stay - great place and location "
United States
Garry M.
The price is HK$784
HK$1,197 total
includes taxes & fees
10 Aug - 11 Aug
Foxy's Den cozy grain bin cabin with WiFi & AC in serene Kidder. Quiet & serene.
Fridge, microwave, oven, stovetop

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

Patchwork Paradise B - New 2BR Home 3 Blocks from Missouri Star
Hamilton
The price is HK$905
HK$1,676 total
includes taxes & fees
21 Jul - 22 Jul
Patchwork Paradise B - New 2BR Home 3 Blocks from Missouri Star
Front of property

Firefly Lofts

Firefly Lofts
2.0 star property
Cameron
The price is HK$1,042
HK$2,598 total
includes taxes & fees
29 Jul - 30 Jul
Firefly Lofts
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 Winston Hotel Reviews

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

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

10/10 Excellent
"It felt like home! Just perfect for our overnight wedding stay"
Carman D. 1-night trip
Posted 13 hours ago
1920s Restored Home-walk to MSQC shops, Quilt Town USA

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?

1920s Restored Home-walk to MSQC shops, Quilt Town USA: 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 include a dishwasher, a stovetop and a microwave.

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 Cameron Veteran's Memorial Golf Glub and Adam-ondi-Ahman.

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.