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The Tailor House

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Cozy single-story house with a front porch and grassy yard.
Relax in this classic living room with a large sofa, armchair, and wooden coffee table, perfect for leisure and intellectual pursuits.
Enjoy cooking in this well-equipped kitchen with a central island, sink, and ample storage.
Enjoy cooking in this kitchen with a central island, sink, and dishwasher, surrounded by cabinetry and a large window with an outdoor view.
Traditional hotel room with a wooden bed, matching bench, and ornate mirror.

Entire home

2 bedrooms1 bathroomSleeps 5

Popular amenities

  • Dryer
  • Fireplace
  • Washer
  • Kitchen
  • Barbecue grill
The current price is AU$441
includes taxes & fees
10 Aug - 11 Aug

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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:
-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!

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

Add dates for prices

Property amenities

Pool/Spa

  • Hot tub

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Electric car charging station on site
  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Separate dining area

Entertainment

  • Games
  • Smart TV

Outdoor areas

  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair
  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre

Things to do

  • Fishing nearby
  • Motor boating nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Electric car charging station
  • Garden

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 21

Check-out

Check-out before 11:00 AM
Contactless check-out

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets not allowed

Children and extra beds

Children are welcome

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

Woodstock's Newest and Oldest Vrbo on the Square Woodstock

About the area

Map
Woodstock, IL

What's nearby

  • Woodstock Square - 3 min walk - 0.3 km
  • Woodstock Opera House - 3 min walk - 0.3 km
  • Naturally McHenry County Visitor Center - 3 min walk - 0.3 km
  • McHenry County Fairgrounds - 20 min walk - 1.7 km
  • Bull Valley Golf Club - 6 min drive - 4.0 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.

How much does it cost to stay at The Tailor House?

As of 30 July 2025, prices found for a 1-night stay for 2 adults at The Tailor House on 10 Aug 2025 start from AU$441.30, 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 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.

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The Tailor House Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 39 out of 42 reviews
Rating 8 - Good. 2 out of 42 reviews
Rating 6 - Okay. 1 out of 42 reviews
Rating 4 - Poor. 0 out of 42 reviews
Rating 2 - Terrible. 0 out of 42 reviews

9.8/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

10/10 Excellent

shelley b., Seattle, WA

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location for a weekend visit!

This was a great little place for us- came home for my reunion, and this was just perfect. It’s a cozy space, but was clean and well kept. You cannot beat the location if you’re hanging out in Woodstock! Loved that we could walk to the Square, and owners were great communicators, providing great recommendations for local businesses. If you’re staying the weekend, make sure you get to the Saturday market in the square for local goods! Would definitely come back for this spot when coming home!
Stayed 3 nights in Sep 2022