Winston Vacation Rentals

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Check prices for these dates

Our top choices for Winston vacation 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 CA $140
CA $202 total
includes taxes & fees
Nov 19 - Nov 20
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 CA $140
CA $238 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $101
CA $139 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $143
CA $248 total
includes taxes & fees
Dec 1 - Dec 2
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 CA $194
CA $287 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $157
CA $281 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $221
CA $316 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $157
CA $305 total
includes taxes & fees
Dec 1 - Dec 2
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 CA $168
CA $297 total
includes taxes & fees
Nov 18 - Nov 19
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 CA $296
CA $648 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $231
CA $624 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $264
CA $432 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $157
CA $281 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $377
CA $617 total
includes taxes & fees
Nov 22 - Nov 23
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 vacation rentals that suit your style

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Find out more about Winston

Everything you need to know about Winston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winston vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winston vacation rentals we have selected for you start as low as CA $100 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 vacation 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 vacation.

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 vacation rentals in Winston?

Yes, you can find vacation rentals close to top points of interest in Winston, or you can go with a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Winston?

Charming 2BR Cottage - Short walk to Missouri Star & Downtown Hamilton: Visitors like this Winston vacation home rental. It 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 larger area, you’ll find Cameron Veteran's Memorial Golf Club and Adam-ondi-Ahman.

What are vacation rentals like in Winston?

Vacation rentals are private accommodations you can stay in for a short or long stay in Winston. Vacation rentals feature extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family trips or small group gatherings.