Welcome to Woodstock's Timeless BNB - A Blend of History and Luxury! Discover the perfect harmony of old-world charm and contemporary elegance at our newly renovated historic BNB, a timeless gem built in 1860. Situated just 2 blocks from the enchanting Woodstock Town Square, this abode promises an unforgettable stay.
Historical Beauty, Modern Comfort: Immerse yourself in the character of a 160-year-old home, meticulously renovated to preserve its unique design features while offering all the modern comforts you need for a delightful stay.
***Space Overview***
Bedrooms: ❖1st Bedroom: Unwind in a cozy room featuring a comfortable queen-sized bed, promising restful nights and a peaceful ambiance. ❖2nd Bedroom: Ideal for a small group or family, this room offers a queen-sized bed and an additional single bed, making it perfect for accommodating your needs.
Bathrooms: ❖ Full Bathroom ❖ Half Bathroom (compact, offering limited space only.)
TV: Enjoy free streaming on our Roku TV with apps like The Roku Channel, Tubi, Pluto TV, Crackle, and NewsON. While local antenna channels aren’t available, there’s plenty to watch! Please note that specific shows, movies, or events can’t be guaranteed, as content changes throughout the year.
Kitchen: Discover the joy of cooking in a brand new kitchen, tastefully designed with the original brick chimney, blending the old and the new seamlessly.
Relaxing Hot Tub: Rejuvenate in the inviting hot tub, a delightful addition for unwinding after a day of exploring the local attractions.
Scenic Backyard: Step outside to a charming backyard, a peaceful oasis providing the perfect backdrop for relaxation and outdoor gatherings.
Laundry Room: Enjoy the convenience of a dedicated laundry room, equipped to keep your clothes fresh and clean throughout your stay.
Additional Notes: -This 1860 home features stairs steeper than modern standards though customary for it's time. The primary bedroom and full bath are on the 2nd level. Please use caution when using the stairs. Please also note the half bath on the main level is quite small.
-The half bath is compact, offering limited space only.
Experience the charm of a bygone era while enjoying the comforts of the present in this unique historical space. Book your stay now and let the serenity of Woodstock envelop you!
***Guest Access*** Enjoy full access to the entire home, including all the amenities provided onsite, during your stay.
***Interaction with Guest*** We are just a message away. Let us know how we can earn your 5 star review. Feel free to send a message via the app, and we’ll respond promptly. Rest assured, we are dedicated to ensuring your stay is seamless and delightful!
~ THINGS TO NOTE ~
We want each guest to have an exceptional stay - Including your group! We put a lot into this house and into the exceptional experience we want for our guests. Please review the following and pass along to all guests.
✓ Check in/out: We love that you are enjoying our place! If you wish to stay longer please give us as much heads up as possible so we can accommodate a few extra minutes to another restful night! Unfortunately, if our cleaning team arrives and check-out has not occurred we may charge for the additional hours at our cleaning team's rates (minimum $50/hr). Thank you for your understanding!
✓ Guests: -For bookings of 2 guests or more, at least one staying guest must be 21 or older. -Please no unregistered guests without prior approval.
✓ Guests with fewer than 2 five-star reviews must submit IDs for all guests within 5 days of booking, or immediately if booked within 5 days of the stay.
✓ Noise: This is a residential area. Please treat our neighbors with respect and allow them to enjoy their homes in peace as you would like to enjoy yours.
✓ Local Bookings: Please contact us before making a booking from the local community.
✓ Parties: NO PARTIES. Please do not disturb the neighborhood
✓ Pets: Only pre-approved pets are allowed. We’re happy to host dogs at our place! There’s just a small pet fee that’s automatically included in your booking total when you add your pets to the guest list. The fee covers up to two dogs, and if you’re bringing more than two, there’s an additional $50/dog fee. Note: Unfortunately, we're unable to host cats due to the house owner's allergies.
ⓧ Smoking: No Smoking allowed on the property: $300 fine minimum (usually over $1000 to remediate)
✓ We kindly request our guests to refrain from ordering any additional media services, including but not limited to TV packages, during their stay. Any charges resulting from such orders will be appreciated to be settled by the respective guest
PET POLICY: ✓ Pets should not be left alone outside a kennel within the unit. ✓ Please make sure your pets are good neighbors, keeping noise levels in check to avoid any ruff-housing! ✓ Be a responsible pet parent and clean up after your pet, both inside and outside the property. ✓ Pets, as much as we love them, are not allowed on furniture or bedding. ✓ Any additional cleaning or damages caused by your pet will be responsibly handled and charges will be charged accordingly.
We kindly ask for your consideration of our great neighbors and future guests. In the rare case of disturbance to the neighborhood, you may be asked to leave
Please enjoy this wonderful space we worked so hard to create for you! We welcome any questions or comments you may have.
Thank You!
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We kindly ask guests not to order extra media services during their stay. Any resulting charges are to be settled by the guest.
Guests with fewer than 2 five-star reviews must submit IDs for all guests within 5 days of booking, or immediately if booked within 5 days of the stay
Please follow check-in/out times as specified, unless otherwise approved. Unapproved late checkouts could result in an additional charge (min $50/hr)
Important information
You need to know
Property # 2302837vb
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
Long-term renters welcome
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, a first aid kit and a deadlock
About the area
Woodstock
Located in Woodstock, this holiday home is in the city centre. Woodstock Opera House and Illinois Railway Museum are cultural highlights, and some of the area's attractions include McHenry County Fairgrounds and Corn Maze. Royal Oak Farm Orchard and Royal Oak Carousel are also worth visiting. Looking to get your feet wet? Power boating, fishing and swimming adventures can be found near the property.
Naturally McHenry County Visitor Center - 3 min walk - 0.3 km
McHenry County Fairgrounds - 3 min drive - 1.5 km
Getting around
Woodstock Station - 7 min walk
Chicago, IL (DPA-Dupage) - 53 min drive
Restaurants
McDonald's - 16 min walk
Casey's General Store - 4 min drive
Culver's - 5 min drive
Subway - 4 min drive
Starbucks - 5 min drive
Frequently asked questions
Is The Tailor House pet-friendly?
Yes, this property allows dogs (limit 4 total).
How much does it cost to stay at The Tailor House?
As of 11 May, 2026, prices found for a 1-night stay for 2 adults at The Tailor House on 3 Aug, 2026 start from S$295, 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.
How much is parking at The Tailor House?
On-site parking is available at the property.
What time is check-in at The Tailor House?
Check-in begins at 4:00 PM.
What time is check-out at The Tailor House?
Checkout is at 11:00 AM.
Where is The Tailor House located?
Located in the heart of Woodstock, this holiday home is steps away from Woodstock City Hall and Naturally McHenry County Visitor Center. Woodstock Opera House and Woodstock Square are also within 10 minutes. Woodstock Station is 7 minutes by foot.
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
wonderful home for a weekend vacation! house is within walking distance to the tow square that is filled with bars, shops, and restaurants! the entire house had a very comfortable, warm feel to it. everything was extremely clean and well equipped! My girlfriend and I loved it so much we’ve talked about making it a yearly trip!
What a delightful cozy home near the Woodstock square. Clean and well stocked, we found everything we needed for a weekend stay! Very enjoyable, we can’t wait to return!
We loved staying at this property. Easy walk to a cute town square surrounded by fun shops and restaurants. Home had everything we needed. Hosts were attentive when needed.
Once again, a great place to stay. Location to family and the local town square can’t be beat for us. Very good service and communication. We will keep coming back.
Stayed here with friends for a getaway. Hot tub was fantastic. The place was adorable. Comfy beds. A couple blocks from the square. We may stay here again!
We enjoyed our stay at your property. The neighborhood, the house, and its surroundings were so charming. We came to Woodstock to visit with family and when we return, we will return to your beautiful property! Thank you so much!
My husband and I were in town to visit with family that lives in Woodstock. The property is located a short walk from the square which is great! We explored the pop up market and shops on the square on Saturday morning and visited the local watering holes at night. We had everything we needed for our stay and the beds were comfortable. The little patio in the back was a nice place for coffee in the morning. We would love to stay here again!
Jennifer D.
Stayed 4 nights in Jun 2022
About the host
Hosted by Christina Morales
We absolutely love building/creating unique spaces for you to enjoy. One of our favorite things is to reveal the character of 100+ year-old houses.. to bring them into the modern era of amenities while maintaining the character and workmanship from generations past! We host our own places and we help others with their own. If you are interested in the space send us a message!
Why they chose this property
Take a walk through the oldest Victorian-era homes in Woodstock!
What makes this property unique
The Taylor home was a long and fascinating renovation pealing back 160 years of history. Originally it was the town tailor house/shop. The last 30 were occupied by a couple of dentists so it was super neat to take down all the big florescent lights and create the kitchen and living space
Premier Host
They consistently provide great experiences for their guests