Holiday Rentals in Winston

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Check prices for these dates

Our top choices for Winston holiday rentals

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, (63 reviews)
"This is such an unusual but very comfortable place. The setting is gorgeous. We loved our stay here! It’s quiet and private but still very close to town. Highly recommend!"
United States
Tamara
The price is €132
includes taxes & fees
18 Nov - 19 Nov
Foxy's Den cozy grain bin cabin with WiFi & AC in serene Kidder. Quiet & serene.

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, (10 reviews)
"Great property."
United States
Annjlee S.
The price is €153
includes taxes & fees
16 Nov - 17 Nov
Charming 1-bedroom Guest Home with WiFi, AC in delightful Gallatin

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

Cozy 1-bedroom cabin in peaceful Jameson with AC
Jameson
The price is €91
includes taxes & fees
17 Nov - 18 Nov
Cozy 1-bedroom cabin in peaceful Jameson with AC

4. 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, (6 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 €160
includes taxes & fees
1 Dec - 2 Dec
Spacious 1 BR Carriage House - 2 min walk to Missouri Star

5. 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, (21 reviews)
"Very clean and close to Missouri Star."
United States
Lori D.
The price is €186
includes taxes & fees
7 Nov - 8 Nov
Piper's Place - 2 Bedroom House in DT Hamilton

6. 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
9.8 out of 10, Exceptional, (8 reviews)
"Great little place down the street from downtown."
United States
Tom K.
The price is €184
includes taxes & fees
7 Nov - 8 Nov
Patchwork Paradise A - New 2BR Home - 5 Minute walk to Missouri Star

7. Hamilton Getaway -Entire House in DT Hamilton

Hamilton Getaway -Entire House in DT Hamilton
Hamilton
9.8 out of 10, Exceptional, (63 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 €199
includes taxes & fees
6 Dec - 7 Dec
Hamilton Getaway -Entire House in DT Hamilton

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

Charming 2BR Cottage - Short walk to Missouri Star & Downtown Hamilton
Hamilton
9.8 out of 10, Exceptional, (9 reviews)
"Had a great stay"
United States
R F.
The price is €199
includes taxes & fees
1 Dec - 2 Dec
Charming 2BR Cottage - Short walk to Missouri Star & Downtown Hamilton

9. 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, (6 reviews)
"It was in a perfect location for us for exploring Hamilton and the surrounding towns."
United States
Anonymous traveller
The price is €192
includes taxes & fees
18 Nov - 19 Nov
Sewing Serenity A - New 2BR Home in Hamilton, 3 Blocks to Missouri Star

10. 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 €412
includes taxes & fees
13 Nov - 14 Nov
Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-free

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, (2 reviews)
"This was the perfect house to sit and relax with friends. And it was very convenient to the downtown area of Hamilton. I will be booking this house again if available for future visits."
United States
Sherril K.
The price is €396
includes taxes & fees
6 Dec - 7 Dec
Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-Free

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, (132 reviews)
"This house was super cute for the age. There were 7 ladies staying on our first trip to MSQC. Description of the property was accurate and we had no problems."
United States
monica S.
The price is €274
includes taxes & fees
9 Nov - 10 Nov
Comfortable Two-Story Family Home in Picturesque Small Town USA

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

Patchwork Paradise B - New 2BR Home 3 Blocks from Missouri Star
Hamilton
9.0 out of 10, Wonderful, (7 reviews)
The price is €183
includes taxes & fees
8 Nov - 9 Nov
Patchwork Paradise B - New 2BR Home 3 Blocks from Missouri Star

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, (23 reviews)
"Great house and the area is great."
United States
Debbi D.
The price is €409
includes taxes & fees
6 Dec - 7 Dec
1920s Restored Home-walk to MSQC shops, Quilt Town USA
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.

Find holiday rentals that suit your style

Find out more about Winston

Everything you need to know about Winston 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 Winston 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 Winston holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winston holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winston. 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 Winston 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 Winston holiday rentals we have selected for you start as low as €90 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winston rentals

At Expedia, we put the best Winston 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 Winston 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 Winston 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 Winston. 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 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?

Charming 2BR Cottage - Short walk to Missouri Star & Downtown Hamilton: This holiday home rental outside of Winston offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Club 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.