Winston Vacation Rentals

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Vacation Rentals in Winston

Modern Home in Gallatin

9.6 out of 10, Exceptional, (22)
"This home was perfect for our needs. It is in a quiet peaceful neighborhood. We enjoyed sitting on the back porch with our morning coffee watching the squirrels play in the branches overhead. A well-stocked grocery store was nearby and we bought delicious vegetables from the produce stand next door. "
The price is CA $155
CA $263 total
includes taxes & fees
Aug 10 - Aug 11
Modern Home in Gallatin

Hamilton Getaway -Entire House in DT Hamilton

10.0 out of 10, Exceptional, (45)
"This house is the cutest! The inside is so nicely updated, it was honestly the perfect house for some of our wedding party! "
The price is CA $218
CA $324 total
includes taxes & fees
Aug 6 - Aug 7
Hamilton Getaway -Entire House in DT Hamilton

Quilter's retreat! 3 quilting spaces and 2 full bathrooms!

9.8 out of 10, Exceptional, (27)
"A great place to stay it was clean. It was easy to get to had a great time. "
Quilter's retreat! 3 quilting spaces and 2 full bathrooms!

The Irene - Entire 2 Bedroom Apt in Quilt Town, USA

9.8 out of 10, Exceptional, (30)
"The property was so nice and close to downtown. We will definitely stay there again when in town. "
The price is CA $136
CA $233 total
includes taxes & fees
Aug 5 - Aug 6
The Irene - Entire 2 Bedroom Apt in Quilt Town, USA

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

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay. Were impressed by the fact that even tho it was a small apartment, it had a roomy shower/bathroom, and all we needed!"
The price is CA $105
CA $133 total
includes taxes & fees
Aug 10 - Aug 11
Charming 1-bedroom Guest Home with WiFi, AC in delightful Gallatin

The Deannie - Entire 2 Bedroom Apt in Quilt Town, USA

9.8 out of 10, Exceptional, (50)
"Excellent and a perfect place for my husband to sit out the day while I shopped."
The price is CA $136
CA $233 total
includes taxes & fees
Aug 5 - Aug 6
The Deannie - Entire 2 Bedroom Apt in Quilt Town, USA

8th Street Haven - House in DT Hamilton

9.8 out of 10, Exceptional, (12)
"We loved being able to sew and cook and hang out in the open space. It was a nice little space."
8th Street Haven - House in DT Hamilton

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

10.0 out of 10, Exceptional, (2)
"This lovely venue was perfext for our Anniversary getaway! Our host thought of every detail from the plush towels, pretty bedding and chocoates on our pillows. We will beback!!! "
The price is CA $138
CA $200 total
includes taxes & fees
Aug 12 - Aug 13
Foxy's Den cozy grain bin cabin with WiFi & AC in serene Kidder. Quiet & serene.

The Carolyn - Entire 2 Bedroom Apt in Quilt Town, USA

10.0 out of 10, Exceptional, (14)
"The Carolyn was just as described. The apartment was clean and close to all of the wonderful stuff in Hamilton. There were a couple of issues with the WiFi and internet connection but a message to the Host, it was quickly resolved. We enjoyed our stay and would definitely stay again."
The price is CA $161
CA $259 total
includes taxes & fees
Aug 5 - Aug 6
The Carolyn - Entire 2 Bedroom Apt in Quilt Town, USA

The Mary Lou - Entire 2 Bedroom Apt in Quilt Town, USA

9.6 out of 10, Exceptional, (35)
"Close proximity to all Missouri Star Quilt shops! Friendly, helpful management! "
The price is CA $150
CA $247 total
includes taxes & fees
Aug 5 - Aug 6
The Mary Lou - Entire 2 Bedroom Apt in Quilt Town, USA

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

10.0 out of 10, Exceptional, (1)
"Very clean, lots of room, well furnished kitchen. It was like being in a new model home. Very close to the quilt shops, easy walk. Great communication with the owners! Check-in was a breeze! Would definitely stay there again. "
The price is CA $398
CA $652 total
includes taxes & fees
Aug 5 - Aug 6
1920s Restored Home-walk to MSQC shops, Quilt Town USA

Piper's Place - 2 Bedroom House in DT Hamilton

8.8 out of 10, Excellent, (8)
"House was nicely updated, conveniently located; perfect for a landing spot while we were visiting family."
The price is CA $192
CA $294 total
includes taxes & fees
Aug 5 - Aug 6
Piper's Place - 2 Bedroom House in DT Hamilton

The Bernice - Entire 2 Bedroom Apt in Quilt Town, USA

9.6 out of 10, Exceptional, (15)
"Great apartment to stay while visiting The Missouri Star Quilt Co. Close to shopping. Nice to have a well stocked kitchen because close restaurants are scarce. Very nice grocery store right downtown. Tidy with comfortable beds. Plenty of closet space and easy parking. Would stay here again."
The price is CA $178
CA $278 total
includes taxes & fees
Aug 5 - Aug 6
The Bernice - Entire 2 Bedroom Apt in Quilt Town, USA

The Bird's Nest - 2 bedroom House

10.0 out of 10, Exceptional, (14)
"Property location was perfect."
The Bird's Nest - 2 bedroom House

10 min from downtown Jamesport, MO

2.0 star property
10 min from downtown Jamesport, MO

Family/pet-friendly, quiet glamping getaway. Belle Tent/ Yurt out the Country.

8.0 out of 10, Very good, (4)
"We had a great time spending two days at this property. The area is beautiful and the setup is so well thought out. The bed is surprisingly comfortable. We had a wonderful homestead breakfast one of the mornings. We will definitely return!"
The price is CA $93
CA $124 total
includes taxes & fees
Aug 5 - Aug 6
Family/pet-friendly, quiet glamping getaway. Belle Tent/ Yurt out the Country.

Cameron Suites

4.0 star property
Cameron Suites

Pet-Friendly 1BR Suite, Walk to Quilt Co, Travel Nurse Ready, Wi-Fi + Kitchen

10.0 out of 10, Exceptional, (11)
"Great stay"
The price is CA $116
CA $188 total
includes taxes & fees
Aug 10 - Aug 11
Pet-Friendly 1BR Suite, Walk to Quilt Co, Travel Nurse Ready, Wi-Fi + Kitchen

Secluded cabin on farmland with fire pit, pond, a/c & treehouse

2.0 star property
9.8 out of 10, Exceptional, (9)
"Property was amazing and relaxing. Host was super helpful and quick communication when I needed help. Highly recommend, just as described and pictured. "
Secluded cabin on farmland with fire pit, pond, a/c & treehouse

Enjoy this spacious ranch-style house next to the quilting capital of the world.

10.0 out of 10, Exceptional, (6)
"We liked the layout and the huge back yard. We sat there in the mornings and the evenings after it was shady. Travis was very accommodating and helpful. "
Enjoy this spacious ranch-style house next to the quilting capital of the world.
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

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?

Modern Home in Gallatin : Visitors like this Winston vacation home rental. It is equipped with a selection of games, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Winston?

While you're exploring the area, Dockery Park and Lake Allaman are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Daviess County Courthouse and Cameron Veteran's Memorial Golf Glub.

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.