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The Tailor House

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Cozy single-story house with a front porch and grassy yard.
Enjoy cooking in this well-equipped kitchen with a central island, sink, and ample storage.
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 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.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms1 bathroomSleeps 5

Popular amenities

  • Dryer
  • Fireplace
  • Washer
  • Kitchen
  • Barbecue grill

Explore the area

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

Room options

About the neighborhood

Woodstock

Heart of Woodstock.At this vacation home, you'll be steps from Woodstock City Hall and Naturally McHenry County Visitor Center. Woodstock Opera House and Woodstock Square are also within half a mile (1 km).
View more Vacation Homes in WoodstockOpens in a new window

What's nearby

  • Woodstock City Hall - 2 min walk - 0.1 miles
  • Woodstock Square - 3 min walk - 0.2 miles
  • Woodstock Opera House - 3 min walk - 0.2 miles
  • McHenry County Fairgrounds - 20 min walk - 1.1 miles
  • Bull Valley Golf Club - 6 min drive - 2.5 miles

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

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

Property amenities

Pool/Spa

  • Hot tub

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Electric car charging station on site
  • Parking on site

Kitchen

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

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center

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

Policies

Check-in

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

Check-out

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

Special check-in instructions

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

Pets

  • No pets 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 there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Parties and events (including family gatherings and weddings) are allowed on site. Maximum attendees: 8. Long-term renters welcome. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.

Property is also known as

Woodstock's Newest and Oldest Vrbo on the Square Woodstock

Frequently asked questions

How close is The Tailor House to the airport?

This vacation home is 36.1 mi (53-min drive) away from the Chicago, IL (DPA-Dupage) airport, the closest popular airport to the property.

Does The Tailor House have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is The Tailor House to the beach?

This vacation home is 8.5 mi (18-min drive) from West Beach and 8.7 mi (15-min drive) from Main Beach. Don't forget your sunscreen!

Does The Tailor House offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at The Tailor House?

No, there is no casino at this vacation home.

What time is check-in at The Tailor House?

Check-in begins at 4:00 PM.

Is there free parking at The Tailor House?

Free parking is not available at this vacation home.

Does The Tailor House have a pool?

This vacation home does not have a pool.

Does The Tailor House have a spa?

There are no spa services available at this vacation home.

How close is The Tailor House to downtown Woodstock?

This vacation home is 0.1 mi away from Woodstock.

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

Weston B.

Liked: Cleanliness
As advertized. Cozy and clean. Good food near by.
Stayed 1 night in Jun 2025

10/10 Excellent

Joyce S.

Liked: Cleanliness

Family Visit

Darling home! Perfect for walking back and forth from Square! Clean and comfortable! Great communication from hosts! Can’t wait to come back!
Stayed 4 nights in Jun 2025

10/10 Excellent

Dan R.

Liked: Cleanliness

Weekend getaway

We just wanted to enjoy some local food and small town life. Perfect!
Stayed 1 night in Mar 2025

6/10 Okay

David S., Chicago

Disliked: Cleanliness
Stayed 2 nights in Nov 2024

10/10 Excellent

Joseph S.

Liked: Cleanliness

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

John J.

Liked: Cleanliness

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

Bernadette P.

Liked: Cleanliness

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

10/10 Excellent

Ruth T.

Liked: Cleanliness

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

Vivianne O., Dallas, US

Liked: Cleanliness

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

Judi S.

Liked: Cleanliness

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

Scott R., Buena Vista, CO

Liked: Cleanliness

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

Judi S.

Liked: Cleanliness

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

Stacey M.

Liked: Cleanliness

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

Judi S.

Liked: Cleanliness

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

Judi S.

Liked: Cleanliness

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

Paula B.

Liked: Cleanliness

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

Dana M L.

Liked: Cleanliness

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

Cha Ron S.

Liked: Cleanliness

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

Chelsea R.

Liked: Cleanliness

Vacay

Loved it and would definitely come back and stay again!
Stayed 1 night in May 2023

10/10 Excellent

Carrie L.

Liked: Cleanliness

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

Maureen C.

Liked: Cleanliness

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

Katie F.

Liked: Cleanliness

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

Lydia G.

Liked: Cleanliness

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

Kim M.

Liked: Cleanliness

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

Great stay, as usual!

Second time visiting and staying at this property. Highly recommended!
Stayed 2 nights in Dec 2022