The Tailor House

Photo gallery for The Tailor House

A white house with a porch and a chimney, surrounded by a grassy area and a brick path.
Interior
A cozy living room with a wooden ceiling, a dining area with a chandelier, and a staircase leading to another level.
A compact kitchen with a stone column, wooden countertop, and a trash bin.
A bedroom with a large bed, wooden dresser, and a chair.

Reviews

9.8 out of 10, Loved by Guests
Top 1% of guest reviews in this area

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Woodstock Square

Popular amenities

  • Spa pool on site
  • Patio
  • Dog-friendly
  • Barbecue
  • Air-conditioning
  • Electric vehicle charging point

Explore the area

View map
Woodstock, IL
  • Place, Woodstock City Hall
    ‪2 min walk‬
  • Place, Woodstock Square
    ‪3 min walk‬
  • Place, Woodstock Opera House
    ‪3 min walk‬
  • Airport, 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

1 bathroom, 1 half bathroom

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

Add dates for prices

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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.
View more Holiday homes in WoodstockOpens in a new window
Map
Woodstock, IL

What's nearby

  • Woodstock City Hall - 2 min walk - 0.2 km
  • 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 - 3 min drive - 1.5 km

Getting around

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

Restaurants

  • ‪Casey's General Store - ‬4 min drive
  • ‪Subway - ‬4 min drive
  • ‪Culver's - ‬5 min drive
  • ‪Niko's Red Mill Tavern - ‬3 min drive
  • ‪Taco Bell - ‬3 min drive

Frequently asked questions

Is The Tailor House pet-friendly?

Yes, this property allows dogs (limit 4 total).

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.
Learn moreOpens in a new window
Rating 10 - Excellent. 55 out of 59 reviews
Rating 8 - Good. 2 out of 59 reviews
Rating 6 - Okay. 2 out of 59 reviews
Rating 4 - Poor. 0 out of 59 reviews
Rating 2 - Terrible. 0 out of 59 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

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property is the perfect getaway! All of the thoughtfulness that has gone into its upkeep - and the amenities - is wonderful. And you can’t beat the location! In walking distance from the town square. We had a fantastic stay.
Stayed 1 night in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything we needed. Within walking distance to the lovely town square and Farmer market.
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing stay. So close to everything!
Stayed 1 night in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Thank you. Would definitely stay again.
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
I really enjoyed the place
Stayed 1 night in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Planning our next visit.
Stayed 7 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a wonderful property in an excellent location for visiting Woodstock. It’s comfortable, cozy, spotless, and had everything we needed for our stay. We especially appreciated the thoughtful preservation of this historic building while still offering all the modern amenities. The beds were exceptionally comfortable as well. Historic downtown Woodstock is a real gem, with its beautiful town square and plenty of great dining options nearby. We had a very positive experience with the host and would absolutely recommend this rental to others
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean and nice little place to stay. I loved that it was a restored 1960 house. I highly recommend this place.
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The area and location and great host. Plus this time used the hot tub! Felt so good in the cool of the night.
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Will come back
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 2 nights in Dec 2025
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great, as always! We've been coming here for years and we love the house and the neighborhood. Everything is great!
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
As advertized. Cozy and clean. Good food near by.
Stayed 1 night in Jun 2025
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The Tailor house was a great place to stay. My son and family stayed upstairs with plenty of room for them. My husband and I stayed in bedroom downstairs. Plenty of coffee, and a nice refrigerator and microwave. My grandchild was very happy to see arcade games in their bedroom upstairs. He didn't want to leave. The house was very clean, had board games in closet and easy access to everything we needed. We even walked to St. Mary's Catholic church. Beautiful house and church too. The host answered our questions very fast and was so easy to get into the house. We loved it.!!!!
Stayed 1 night in Jul 2026
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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

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
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