The Tailor House | House in Woodstock

9.8 (51 Reviews) |   Pet Friendly   2 Bedrooms  1 Bathroom  5 Guests
Woodstock House | The Tailor House

2 Bedroom House in Woodstock

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.)
TV: Enjoy free streaming on our Roku TV with apps like The Roku Channel, Tubi, Pluto TV, Crackle, and NewsON. While local antenna channels aren’t available, there’s plenty to watch! Please note that specific shows, movies, or events can’t be guaranteed, as content changes throughout the year.
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. We’re happy to host dogs at our place! There’s just a small pet fee that’s automatically included in your booking total when you add your pets to the guest list. The fee covers up to two dogs, and if you’re bringing more than two, there’s an additional $50/dog fee.
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!

The Tailor House is located in Woodstock. The Tailor House provides accommodation, featuring Balcony/Terrace, Fireplace/Heating, Kitchen, among other amenities. This House features Balcony/Terrace, Fireplace/Heating, Kitchen, to make your stay a comfortable one.

The Tailor House has 2 Bedrooms , 1 Bathroom, and max occupancy of 5 persons. The minimum rental for this property is 1 night, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Woodstock has interesting places to visit. If you want to learn more about the House in Woodstock, such as places to visit and things to do nearby, you can check below to learn more.

Show more
OneKey Logos

This Property is OneKey Eligible

Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.

JOIN TODAY

Unique Amenities

  • Air Conditioner
  • Parking
  • Pet Friendly
  • TV
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
  • Guest Services
  • Entertainment
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Hot Tub
  • Internet
  • Kitchen
  • Laundry
 
Read MoreRead Less

Policies

Event Policy
Event Policy No events allowed
Check-in
Check-in Check-in time starts at 4:00 pm contactless check-in available minimum check-in age: 21
Check-out
Check-out Check-out before 11:00 am contactless check-out available
Child Policy
Child Policy Children are welcome.
Pet Policy
Pet Policy 4 total pets note from host: pet fee included covers the first two pets only. pets allowed service animals are welcome, and are exempt from fees welcoming dogs only
Smoking Policy
Smoking Policy Smoking is not permitted
Other Policy
Other Policy 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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property long-term renters welcome onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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
 
Woodstock, 60098, USA

What Our Guests say 500 + Reviews

Dec 15, 2025 04:00:40 AM
Summary: 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!
David S. David S.
Oct 31, 2025 02:45:38 AM
Summary: The stone Chess set should be removed; there are too many broken pieces. The downstairs powder room is just too small for any tall or plus sized adult, and the upstairs bath is only accessible by very narrow stairs with high steps. The house is not accessible for aged or disabled guests and the website should be upfront about that. Two of the four stove burners don't function, but we lovedthe kitchen sink.
john f. john f.
Oct 29, 2025 06:07:14 AM
Summary: The area and location and great host. Plus this time used the hot tub! Felt so good in the cool of the night.
Judi S. Judi S.
Sep 29, 2025 01:52:22 AM
Summary: Great, as always! We've been coming here for years and we love the house and the neighborhood. Everything is great!
Raluca B. Raluca B.
Sep 26, 2025 03:30:49 AM
Summary: Planning our next visit.
Quentin B. Quentin B.
Sep 1, 2025 06:07:13 AM
Summary: Very clean and nice little place to stay. I loved that it was a restored 1960 house. I highly recommend this place.
Anthony M. Anthony M.
Aug 17, 2025 10:06:35 AM
Summary: I really enjoyed the place
Ahmed A. Ahmed A.
Jun 13, 2025 05:36:25 AM
Summary: As advertized. Cozy and clean. Good food near by.
Weston B. Weston B.
Jun 8, 2025 04:23:04 AM
Summary: 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. Joyce S.
Mar 9, 2025 09:04:38 PM
Summary: We just wanted to enjoy some local food and small town life. Perfect!
Dan R. Dan R.

FAQ's

Is this The Tailor House pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the The Tailor House have a swimming pool?

No, this The Tailor House does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in The Tailor House?

Best-rates for the The Tailor House starts from $260 per night with includes Internet, Air Conditioner, Pet Friendly, Security/Safety, Sports/Activities, Bedding/Linens, Wellness Facilities, Barbecue/Outdoor Cooking, Parking, Guest Services, Child Friendly, Balcony/Terrace, Fireplace/Heating, Kitchen, Laundry, TV, Entertainment, Hot Tub StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is The Tailor House a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the The Tailor House wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the The Tailor House has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the The Tailor House?

Based on the information reported by the owner or manager, the The Tailor House indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for The Tailor House?

Based on the information reported by the owner or manager, details for the cancellation policy for the The Tailor House are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

People Also Ask

Check House Availability
Nightly rates from:
US $260
You will be redirected to  
Hot Deal - It has been viewed 108 times today
Not the right fit? Check out our other properties in Woodstock
Golf Course
House
Map-icon
like-icon10.0
Exceptional
(9 Reviews)
1 Bedroom 2 Baths 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
US $344/Night 7 Nights - US $2,411
Golf Course
star-icons-4
Bed & Breakfast
Map-icon
like-icon9.7
Exceptional
(104 Reviews)
7 Bedrooms 7 Baths 19 Guests 566.18 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $163/Night 7 Nights - US $1,140
Golf Course
Hotel
Map-icon
like-icon8.8
Fabulous
(1009 Reviews)
1 Bath
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $108/Night 7 Nights - US $759
Golf Course
House
Map-icon
like-icon9.6
Exceptional
(24 Reviews)
2 Bedrooms 2 Baths 7 Guests 2200 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $323/Night 7 Nights - US $2,263
Golf Course
star-icons-3
Hotel
Map-icon
like-icon8.5
Fabulous
(221 Reviews)
9 Baths 340.86 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
US $136/Night 7 Nights - US $949
Golf Course
House
Map-icon
like-icon10.0
Exceptional
(42 Reviews)
7 Bedrooms 3 Baths 20 Guests 3500 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $1,024/Night 7 Nights - US $7,171
Golf Course
Hotel
Map-icon
like-icon7.3
Very Good
(138 Reviews)
2 Baths 208.55 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
US $128/Night 7 Nights - US $893
Golf Course
House
Map-icon
like-icon10.0
Exceptional
(20 Reviews)
6 Bedrooms 5 Baths 19 Guests 6700 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $1,484/Night 7 Nights - US $10,386
star-icons-3
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 3 Guests 796.53 ft²
  • Parking
    Parking
  • Internet
    Internet
More amenities
US $231/Night 7 Nights - US $1,617
Golf Course
House
Map-icon
like-icon10.0
Exceptional
(11 Reviews)
3 Bedrooms 2 Baths 7 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $374/Night 7 Nights - US $2,619
star-icons-4
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 3 Baths 8 Guests 2400.35 ft²
  • Private Beach
    Private Beach
  • Oceanfront
    Oceanfront
More amenities
US $948/Night 7 Nights - US $6,638
Golf Course
House
Map-icon
like-icon10.0
Exceptional
(11 Reviews)
3 Bedrooms 1 Bath 4 Guests 1600 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $265/Night 7 Nights - US $1,853
star-icons-4
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bedroom 2 Baths 7 Guests 2002.09 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • View
    View
More amenities
US $400/Night 7 Nights - US $2,798
Golf Course
House
Map-icon
like-icon10.0
Exceptional
(6 Reviews)
3 Bedrooms 2 Baths 9 Guests 1350 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $499/Night 7 Nights - US $3,490
Golf Course
House
Map-icon
like-icon9.8
Exceptional
(19 Reviews)
3 Bedrooms 2 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
US $628/Night 7 Nights - US $4,395
Golf Course
House
Map-icon
like-icon9.6
Exceptional
(14 Reviews)
4 Bedrooms 2 Baths 8 Guests 2500 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
US $491/Night 7 Nights - US $3,435
Golf Course
House
Map-icon
like-icon8.0
Excellent
(2 Reviews)
3 Bedrooms 1 Bath 11 Guests 1600 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $316/Night 7 Nights - US $2,213
Golf Course
Other
Map-icon
like-icon10.0
Exceptional
(31 Reviews)
5 Bedrooms 4 Baths 16 Guests 5000 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $1,076/Night 7 Nights - US $7,530
Golf Course
New
House
Map-icon
8 Bedrooms 4 Baths 20 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $1,900/Night 7 Nights - US $13,301
House
Map-icon
like-icon10.0
Exceptional
(24 Reviews)
2 Bedrooms 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $144/Night 7 Nights - US $1,009
House
Map-icon
like-icon10.0
Exceptional
(15 Reviews)
2 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
US $480/Night 7 Nights - US $3,357
Cottage
Map-icon
like-icon10.0
Exceptional
(15 Reviews)
1 Bedroom 1 Bath 3 Guests 800 ft²
  • Kitchen
    Kitchen
  • Parking
    Parking
More amenities
US $183/Night 7 Nights - US $1,279
House
Map-icon
like-icon10.0
Exceptional
(13 Reviews)
2 Bedrooms 1 Bath 5 Guests
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $240/Night 7 Nights - US $1,677
House
Map-icon
like-icon10.0
Exceptional
(9 Reviews)
2 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $274/Night 7 Nights - US $1,917