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The Tailor House

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Exterior
Living area
Outdoor spa tub
Room
Interior

Reviews

9.8 out of 10
Exceptional
2 bedrooms0+ bathroomsSleeps 5

Popular amenities

  • Dryer
  • Hot tub
  • Fireplace
  • Washer
  • Kitchen
  • Barbecue grill

Explore the area

Map
Woodstock, IL
  • Woodstock Opera House
    ‪3 min walk‬
  • Woodstock Square
    ‪5 min walk‬
  • McHenry County Fairgrounds
    ‪3 min drive‬
  • Chicago, IL (DPA-Dupage)
    ‪53 min drive‬

Rooms & beds

2 bedrooms (sleeps 5)

Front Room

1 Queen Bed

Master

1 Queen Bed and 1 Single Bed

2 half bathrooms

Bathroom 2

Soap · Toilet

Upper

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Office
Separate dining area
Garden
Dining Area

About this property

The Tailor House

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.)

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:
-Please note that the house features steep stairs, which may require extra caution.
-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!

We strive to ensure every guest has a memorable stay. Please note that the following limits may be imposed based on the host's discretion:

-Maximum 8 overnight guests
-Game room occupancy capped at 14 (where available)
-Parking limited to 3 cars in the driveway. (additional vehicle may park on any nearby public parking)

We kindly ask for your cooperation in observing all house rules and policies, as they contribute to the comfort of future guests and neighbors. Failure to comply may result in fines or, in severe cases, termination of the booking (This is the last thing we want to happen!)

Your understanding is greatly appreciated.

Thank You!

Property manager

Collin Reeser
Premier Host

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Amenities

Hot tub
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

Events allowed: family gatherings and weddings
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Pets

No pets allowed
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Smoking

Smoking is not permitted
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

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
Parties and events (including family gatherings and weddings) are allowed on site. Maximum attendees: 8
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 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 Donley's Wild West Town. 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.
Map
Woodstock, IL

What's nearby

  • Woodstock Opera House - 3 min walk - 0.3 km
  • Old Courthouse Arts Center - 4 min walk - 0.4 km
  • Woodstock Square - 5 min walk - 0.5 km
  • McHenry County Fairgrounds - 3 min drive - 1.7 km
  • Bull Valley Golf Club - 6 min drive - 3.9 km

Getting around

  • Woodstock Station - 7 min walk
  • Chicago, IL (DPA-Dupage) - 53 min drive

Restaurants

  • ‪McDonald's - ‬16 min walk
  • ‪Panera Bread - ‬16 min walk
  • ‪Culver's - ‬5 min drive
  • ‪Wendy's - ‬15 min walk
  • ‪Papa Murphys Take n Bake - ‬16 min walk

Frequently asked questions

Is The Tailor House pet-friendly?

No, pets are not allowed at this 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 within a 5-minute walk of Woodstock City Hall, Woodstock Opera House and Old Courthouse Arts Center. Woodstock Square and Emricson Park are also within 15 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 37 out of 40 reviews
Rating 8 - Good. 2 out of 40 reviews
Rating 6 - Okay. 1 out of 40 reviews
Rating 4 - Poor. 0 out of 40 reviews
Rating 2 - Terrible. 0 out of 40 reviews

9.8/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Dan R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Weekend getaway
We just wanted to enjoy some local food and small town life. Perfect!
Stayed 1 night in Mar 2025

10/10 Excellent

Joseph S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent amenities, superb location!
A relaxing well appointed home with easy walking distance to downtown Woodstock!
Stayed 3 nights in Oct 2024

10/10 Excellent

Scott R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family visit in Woodstock
Lovely little historic home in Woodstock, walking distance to the town square and the beautiful historic neighborhoods. Perfect for our stay!
Stayed 5 nights in Apr 2024

10/10 Excellent

John J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, well equipped, hot tub was awesome after long days of jiu jitsu training.
See title
Stayed 3 nights in Oct 2024

10/10 Excellent

Carrie L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay!
We were only there one night but property was clean, comfortable and great location! Definitely would recommend.
Stayed 1 night in Mar 2023

10/10 Excellent

Chelsea R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Vacay
Loved it and would definitely come back and stay again!
Stayed 1 night in May 2023

10/10 Excellent

Maureen C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cozy near the square
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!
Stayed 2 nights in Mar 2023

10/10 Excellent

Vivianne O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Stay
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!
Stayed 2 nights in May 2024

10/10 Excellent

Dana M L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean, great location and good management
We’ve stayed twice and loved it. The space is small but you have all you need and Colin is super responsive and helpful. We will stay again!
Stayed 3 nights in Jul 2023

10/10 Excellent

Judi S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Place
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 2 nights in Jan 2024

10/10 Excellent

Ruth T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Class reunion
The house was small and very clean. We would stay at the house again. It was easy walking distance to the square .
Stayed 2 nights in Jun 2024

10/10 Excellent

Paula B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect home in Woodstock
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.
Stayed 3 nights in Aug 2023

10/10 Excellent

Stacey M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Girls getaway
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!
Stayed 1 night in Jan 2024

10/10 Excellent

Katie F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cute & Cozy!
The house was clean, cute & cozy. It was perfect for our weekend trip to Woodstock. Very accommodating!
Stayed 2 nights in Feb 2023

10/10 Excellent

Judi S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Woodstock Fun
Sisters and I went for a few days to visit cousins. This house was perfect. So close to the square. Enjoyed the shops and the Farmers Marker and lunch on the square. One day just walked the neighborhood to see all the beautiful old homes. Already planning a return trip in the fall!
Stayed 2 nights in May 2024

10/10 Excellent

Judi S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Enjoy Woodstock
Just a short stay for family reasons. But got to visit the square all decked out for the holiday season. Beautiful lights, delicious dinner - all within walking distance from our house. A really cute, comfy home. Definitely plan to return time and again.
Stayed 2 nights in Dec 2023

10/10 Excellent

Jennifer D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect for a long weekend getaway!
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!
Stayed 4 nights in Jun 2022

10/10 Excellent

Judi S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Woodstock Gem
Taylor house was perfect for our visit to Woodstock and family. Cute historical house near the town square. Beautiful neighborhood. The property manager was great to work with. Very accommodating and answered any questions very quickly. We will definitely be back.
Stayed 2 nights in Oct 2023

10/10 Excellent

Lydia G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location. Really cute place!
We had an easy time renting this place, communicating with Collin and Carrie, and the place is really cool. It’s accurately described and shown on the website. Beds were comfortable. Kitchen clean and nice amenities. The place feels like a 2nd home / vacation home. The lights outside were a nice touch, as well. The location was wonderful, too.
Stayed 2 nights in Jan 2023

10/10 Excellent

Cha Ron S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Hemingway’s Hideaway in Woodstock
Fantastic little retreat for our family of four. Within walking distance of Metra and the heart of Woodstock. The upstairs sunny office is great to get focused work done while the family sleeps, and enjoy an old movie with your clan on the big TV, in the comfy couches. Great little spaces to read outside - and be sure to enjoy the morning drama with the squirrels on the rail fence and exquisite old oak out the front door.
Stayed 5 nights in Jun 2023

10/10 Excellent

Bernadette P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wedding Attendees
3 CA Family members joined the two of us from IL. We attended a June 15 family wedding at a nearby Woodstock Golf resort. The little home is charming and cozy and was perfect size for us to be comfortable. If there would be one thing I would suggest be added : Perhaps a couple of full length mirrors on the back of the bedroom doors so we ladies could have used those as we dressed for the wedding. Not earthshaking but I think it would be a nice addition. Thanks to the host owners for our enjoyable stay.
Stayed 2 nights in Jun 2024

6/10 Okay

David S.

Liked: Check-in, location, listing accuracy
Disliked: Cleanliness, communication
Stayed 2 nights in Nov 2024

10/10 Excellent

Kim M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Quaint and comfortable
Lovely little house not too far from the square with very comfortable beds. Only thing to note is that the full bath is up some extremely steep stairs.
Stayed 4 nights in Dec 2022

10/10 Excellent

Raluca B., Roselle, IL

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay, as usual!
Second time visiting and staying at this property. Highly recommended!
Stayed 2 nights in Dec 2022

10/10 Excellent

Connie P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Quint and Convenient
My husband and I were back for a class reunion and visit to our son’s family who lives in Crystal Lake. This was the perfect place! It’s so handy to walk to the Square, have the grandchildren over, and be accessible to all the nearby activities. Collin an excellent, attentive property manager, and we highly recommend others partake in this quaint, lovely little place!
Stayed 5 nights in Oct 2022

About the host

Hosted by Collin Reeser

Host profile image
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
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