Dating back to the 1830's, the lovingly restored Winn House belonged to Round Top's first settler, James Winn. Guests will find a carefully updated interior that balances the home's past while adding modern appeal. Wide plank walls and refinished hardwood floors blend with chic pendant lights and art collected from around the world. Located in downtown Round Top and walking distance to some of our favorite spots.
The Space:
1 King Bed | 1 Pull Out Sofa | 1 Bathroom with Shower | Kitchenette | WiFi | Sleeps 4
BEDROOM
- Primary: King bed, en-suite bathroom
- Lounge area with pull-out sofa
- There are no Blackout curtains or room darkening blinds in the rooms
- Smart TV in bedroom
BATHROOMS
- Primary Bath: walk-in shower + single vanity
- Shampoo, conditioner, body/hand soap, fluffy towels, and hair dryer provided in bathroom
KITCHEN
- Kitchen includes sink and full-size refrigerator/freezer with great counter space
- Use your login to access a variety of streaming apps
-Cable TV provided by Dish
- WiFi: please note, it can be spotty at times!
YARD AREA + FIRE PIT
- Gas Fire pit- may be shared with other guests
- Walking distance to shopping, wine, antiques & more!
Guest Access:
You will have access to the entire cottage and yard spaces. Yard area is shared. When other units are rented, we ask that you give each other privacy and respect.
The Neighborhood:
Just steps away from the center of town.
Getting Around:
Round Top Motel is in the heart of Round Top, walking distance from local shops and restaurants. Parking is available at local establishments if you choose to drive.
Other Things to Note:
-Pre-arrival form & rental agreement: we do ask for a copy of your ID as part of our guest screening process after the reservation is confirmed. You will also be asked to sign a rental agreement.
- For liability and security purposes, there are external cameras at the front of the house. There are NO inside cameras. Hosts may monitor external cameras at any time via a smartphone app, and cameras are not to be tampered with or covered.
- When you stay with HOSTIE Vacation Rentals, you are covered for any accidents that might happen up to $3000 with the added fee of $39 in your total. Coverage details are spelled out in your rental agreement. This is applied to all bookings.
- CANCELLATION POLICY : The initial deposit is fully refundable up to 30 days prior to your stay, less a 6% processing fee. No refunds for cancellations made within 30 days of check-in. For spring, fall, and winter antique show dates, no refunds for cancellations made within 60 days of check-in. The cancellation policy will be upheld with no exceptions. All guests are encouraged to purchase trip insurance.
- It is possible for the other houses on the property to be booked during your stay. If you would like to book the entire property, please send us a message or find the additional listing!
-OPTIONAL FEES - We offer additional services that may be available for an additional fee (must be pre-approved by the host, non-refundable):
* Early Check-In - $35/hour
* Late Check-Out - $35/hour
EARLY CHECK-IN/LATE CHECK-OUT NOT AVAILABLE DURING ANTIQUE SHOW DATES
-Please note that sightings of common insects or wildlife (such as skunks, snakes, scorpions, spiders, flies, wasps, mice, ants, etc.) do not qualify for refunds, as occasional encounters are possible in any rural environment.
-Concierge service available! Charcuterie Boards, dinner reservations, in-home massages and more!
Interaction with Guests:
This property is professionally managed by HOSTIE Vacation Rentals. They will be available during your entire stay!
*This is not an actual "motel" with a front desk. This is a stand alone vacation rental with contactless check-in. HOSTIE staff will be available to assist, if you have any questions.
Our prices include all fees. No hidden fees.
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Please review our house rules:
No smoking inside or out.
DO NOT rearrange furniture.
No loud music or parties.
No confetti or glitter allowed o...
Important information
You need to know
Property # 3861039vb
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Round Top
Round Top is home to this holiday home. Henkel Square Market and Winedale Historical Complex are local landmarks, and the area's natural beauty can be seen at Oak Thicket Park and Lake Fayette. Looking to enjoy an event or a game while in town? See what's going on at Spencer Field, or consider a night out at Big Red Barn Event Center.
The Round Top Historical Society - 8 min walk - 0.7 km
Festival Hill Concert Hall - 2 min drive - 1.9 km
Winedale Historical Complex - 6 min drive - 6.7 km
Blue Bell Creameries - 29 min drive - 48.2 km
Getting around
Eagle Lake, TX (ELA) - 84 min drive
Restaurants
J W's Steakhouse - 12 min drive
Busted Oak Cellars - 20 min drive
Boon & Company - 3 min walk
Royer's Round Top Cafe - 5 min walk
Merrit Meat Co - 6 min walk
Frequently asked questions
Is In Town | 1830s Roots, Modern Style | The Winn pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at In Town | 1830s Roots, Modern Style | The Winn?
As of 1 Jun 2026, prices found for a 1-night stay for 2 adults at In Town | 1830s Roots, Modern Style | The Winn on 12 Jul 2026 start from £356, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
What time is check-in at In Town | 1830s Roots, Modern Style | The Winn?
Check-in begins at 4:00 PM.
What time is check-out at In Town | 1830s Roots, Modern Style | The Winn?
Checkout is at 10:00 AM.
Where is In Town | 1830s Roots, Modern Style | The Winn located?
Situated in Round Top, this holiday home is within a 10-minute walk of Henkel Square Market and The Round Top Historical Society. Festival Hill Concert Hall is 1.1 mi (1.8 km) away.
Reviews
9.4
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
This one-bedroom cottage is part of a compound of similar properties, charmingly decorated, with a simple kitchen and comfortable sitting area. King bed, bizarre bathroom door we wished had actually closed, and the bathroom itself is tight, but these were minor concerns. Loved our stay!
great place- comfy bed. not a fan of the bathroom not having a true door, not enough privacy in such a small space. other than this- it was a great option and would stay again, except for the bathroom sliding shutter doors
The property is nice. Understandably looks a little weary as it is very old and totally fitting with the vintage of the neighborhood. We had very little time to spend at the house as this was a working trip. My only complaint is that the lighting is so poor it was next to impossible to read and work effectively. I appreciate that management check in on us regularly by text.
We stayed 3 nights in this darling cottage! It is beautifully updated with every amenity and the most comfortable bed! It is located directly across the street from shopping and dining. We can’t wait to return!
Stephanie G.
Stayed 3 nights in Jan 2024
About the host
Your host
Premier Host
They consistently provide great experiences for their guests