[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # The Tailor House Vacation home in Woodstock with kitchen and patio ![Exterior](https://images.trvl-media.com/lodging/68000000/67410000/67408000/67407979/d0500ebe.jpg?impolicy=resizecrop&rw=598&ra=fit) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/68000000/67410000/67408000/67407979/43f39203.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67410000/67408000/67407979/757dc995.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/68000000/67410000/67408000/67407979/610d86ef.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior](https://images.trvl-media.com/lodging/68000000/67410000/67408000/67407979/699efa63.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location Welcome to Woodstock's Timeless BNB, a blend of history and luxury. Experience the perfect harmony of old-world charm and modern comfort in this newly renovated historic home built in 1860, featuring a brand new kitchen with an original brick chimney, hot tub for relaxation and scenic backyard for outdoor gatherings. 10 Exceptional ### Entire home 2 bedrooms1 bathroomSleeps 5 ## Popular amenities - - Dryer - Kitchen - Fireplace - Washer - Parking available ## Add dates for prices Check-in Check-out Travellers ## 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! ~ 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 and the fee must be paid before check-in instructions will be sent. 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! ## 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) - First aid kit - Fire extinguisher - Deadbolt lock ### General - Electric car charging station - Garden ## Similar properties ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72610000/72601100/72601074/9b871c91.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 3 BR with Hot Tub & Arcade Games in DT Woodstock Square Woodstock - Hot tub - Kitchen - Washer - Dryer 9.6 Exceptional 25 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-18&endDate=2025-10-19&selected=72601074&PinnedHotelID=72601074&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74220000/74212700/74212613/1d1b546a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Sanctuary Woodland Guest House, located next to the conservation area! 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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) ### Pets Pets not allowed ### Children and extra beds Children are welcome ### Events Events allowed: family gatherings and weddings ### Smoking Smoking is not permitted ## 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, a first aid kit, 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 ### Property is also known as Woodstock's Newest and Oldest Vrbo on the Square Woodstock ## About the area Located in Woodstock, this vacation home is in the city center. 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? Motor boating, fishing and swimming adventures can be found near the property. [Visit our Woodstock travel guide](https://www.expedia.ca/Woodstock.dx7936) [View more Vacation homes in Woodstock](https://www.expedia.ca/Woodstock-Private-Vacation-Homes.d7936-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6¢er=42.31278,-88.44729&zoom=13&channel=expedia-HotelInformation&maptype=roadmap&scale=1&path=color:0xFFFFF|weight:2|fillcolor:0x005AEB7F|enc:%7DahaGpzyzO%3FU%3FU%3FS%40U%3FS%40U%40S%40U%40UBQ%40U%40UBSBSBSBUBSDSBSDSDSBSDQDSFSDQFSDSFQFQFQFQFQHQFQHOFQHQHMHQHOHOHMJQHMJMJOJMHMJMJKLMJKJMJKLMJILKLILKJILILILGLILINELILGLGNELGNELENELCNCNELCNCNCNALCN%3FNCNAN%3FN%3FLAN%3FN%3FN%40N%3FL%3FN%40NBN%3FNBL%40NBNBNBLDNBNBLDNDLDNFLDLFLFNHLDLHLHLFLHLHLHLJJHLJLHJLLJJLJJJLJJJLJLJLJNHLJNHNHLHNJNHPHLFPHPFNHPFPFPFPHPDPFPFRDRFPDRDRDPDRBRDRDRBRBRBTBRBRBRBT%40T%40P%40TBT%3FR%40T%40R%3FT%40R%3FT%3FT%3FR%3FTAT%3FTAPAT%3FTCRATARATCRCRCTCRCTCRCPERERCTEPERERERGPERGPGPEPIRGPGPGPINGPINGPININKPILININKLINKNKJKLKLKLKLKJKLMJKJMHMLKHMHMJMFMHMHMHMFMFOHMDMFMDOFMDODMDODOBMBOBODO%40MBO%40O%40OBO%3FM%40O%3FO%40O%3FO%3FMAO%3FOAO%3FOCOAMAOCOAOEMCOCOCMEOEMEOEMGOEMGMEMIOGMGMIMIMGMIKKMIMIMMKIMKKKKMKKMMKMKMIMKKKOKOIMKOIOIMIQIOIOIOGQIQGOIQGQGQGSGQGQEQGSEQGSESESCQESEUCSEQCSCUCSCUCSASAUCSAUASAUAU%3FQAU%3FU%3FU%3FS&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=r-ZveSPwMYfB8QKK40P5sv7Hohg=) 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 - ‪Dairy Queen - ‬6 min walk - ‪Holzlager Brewing Company - ‬14 min walk - ‪Wendy's - ‬15 min walk - ‪D.C. Cobb's - ‬5 min walk - ‪Napoli Pizza - ‬5 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 Oct 4, 2025, prices found for a 1-night stay for 2 adults at The Tailor House on Oct 14, 2025 start from CA $203.7, excluding 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](https://www.expedia.ca/Woodstock-Hotels-Woodstocks-Newest-And-Oldest-Vrbo-On-The-Square.h67407979.Hotel-Information?rfrr=HOT.HIS.question.link.click) 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? > Check-out is at 11:00 AM. ### Where is The Tailor House located? > Located in the heart of Woodstock, this vacation home is steps 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. ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## The Tailor House Reviews 10 ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.[More information](https://www.expedia.ca/lp/b/content-guidelines) ### 9.8 Cleanliness ### 10 Location ### 10 Property conditions & facilities 10 - Excellent 41 8 - Good 2 6 - Okay 1 4 - Poor 0 2 - Terrible 0 ### 10/10 Excellent #### Weston B. Jun 12, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy As advertized. Cozy and clean. Good food near by. ##### Weston B. Stayed 1 night in Jun 2025 ### 10/10 Excellent #### Joseph S. Nov 4, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Excellent amenities, superb location! A relaxing well appointed home with easy walking distance to downtown Woodstock! ##### Joseph S. Stayed 3 nights in Oct 2024 ### 10/10 Excellent #### Joyce S. Jun 7, 2025 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! ##### Joyce S. Stayed 4 nights in Jun 2025 ### 10/10 Excellent #### Dan R. Mar 9, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Weekend getaway We just wanted to enjoy some local food and small town life. Perfect! ##### Dan R. Stayed 1 night in Mar 2025 ### 10/10 Excellent #### Carrie L. Mar 10, 2023 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. ##### Carrie L. Stayed 1 night in Mar 2023 ### 10/10 Excellent #### Scott R. Apr 26, 2024 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! ##### Scott R. Stayed 5 nights in Apr 2024 ### 10/10 Excellent #### Chelsea R. May 29, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Vacay Loved it and would definitely come back and stay again! ##### Chelsea R. Stayed 1 night in May 2023 ### 10/10 Excellent #### Maureen C. Mar 8, 2023 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! ##### Maureen C. Stayed 2 nights in Mar 2023 ### 10/10 Excellent #### Dana M L. Aug 4, 2023 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! ##### Dana M L. Stayed 3 nights in Jul 2023 ### 10/10 Excellent #### John J. Oct 14, 2024 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 ##### John J. Stayed 3 nights in Oct 2024 ### 10/10 Excellent #### Paula B. Aug 8, 2023 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. ##### Paula B. Stayed 3 nights in Aug 2023 ### 10/10 Excellent #### Judi S. Feb 2, 2024 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. ##### Judi S. Stayed 2 nights in Jan 2024 ### 10/10 Excellent #### Ruth T. Jun 29, 2024 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 . ##### Ruth T. Stayed 2 nights in Jun 2024 ### 10/10 Excellent #### Judi S. May 16, 2024 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! ##### Judi S. Stayed 2 nights in May 2024 ### 10/10 Excellent #### Judi S. Dec 17, 2023 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. ##### Judi S. Stayed 2 nights in Dec 2023 ### 10/10 Excellent #### Lydia G. Jan 23, 2023 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. ##### Lydia G. Stayed 2 nights in Jan 2023 ### 10/10 Excellent #### Judi S. Oct 27, 2023 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. ##### Judi S. Stayed 2 nights in Oct 2023 ### 10/10 Excellent #### Cha Ron S. Jun 9, 2023 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. ##### Cha Ron S. Stayed 5 nights in Jun 2023 ### 10/10 Excellent #### Bernadette P. Jul 16, 2024 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. ##### Bernadette P. Stayed 2 nights in Jun 2024 ### 6/10 Okay #### David S. Dec 3, 2024 Liked: Check-in, location, listing accuracy Disliked: Cleanliness, communication ##### David S. Stayed 2 nights in Nov 2024 ### 10/10 Excellent #### Vivianne O. May 21, 2024 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! ##### Vivianne O. Stayed 2 nights in May 2024 ### 10/10 Excellent #### Stacey M. Jan 14, 2024 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! ##### Stacey M. Stayed 1 night in Jan 2024 ### 10/10 Excellent #### Katie F. Feb 5, 2023 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! ##### Katie F. Stayed 2 nights in Feb 2023 ### 10/10 Excellent #### Kim M. Dec 22, 2022 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. ##### Kim M. Stayed 4 nights in Dec 2022 ### 10/10 Excellent #### Raluca B., Roselle, IL Dec 4, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great stay, as usual! Second time visiting and staying at this property. Highly recommended! ##### Raluca B. 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