Apartment

Charming Woodstock Square Retreat

Photo gallery for Charming Woodstock Square Retreat

A bathroom with a toilet, sink, and shower curtain with floral patterns.
A living room with a blue sofa, a beige armchair, a small round table, and a blue patterned rug.
A room with two armchairs, a small table with a lamp, a framed painting, and a view through a window.
A kitchen with a refrigerator, microwave, stove, sink, and various plants.
A bedroom with a wooden headboard, floral bedding, a nightstand with a lamp, and a wall-mounted artwork.
1 bedroom1 bathroomSleeps 3

Popular amenities

  • Air-conditioning
  • Non-smoking

Explore the area

View map
Woodstock, IL
  • Place, Woodstock Square
    ‪2 min walk‬
  • Place, Naturally McHenry County Visitor Center
    ‪2 min walk‬
  • Place, Woodstock City Hall
    ‪3 min walk‬
  • Airport, Chicago, IL (DPA-Dupage)
    ‪53 min drive‬

Rooms & beds

1 bedroom (sleeps 3)

Bedroom 1

1 Queen Bed

1 bathroom

Bathroom 1

Soap · Towels provided · Bathtub or shower · Bidet · Toilet · Shampoo

About this property

Charming Woodstock Square Retreat

Welcome to your cozy hideaway on the Woodstock Square

Stay a while, kick off your shoes, and settle into your own little downtown retreat. This charming apartment blends historic character with cozy comfort — think tall arched windows, leafy plants soaking up the sunshine, comfy corners made for morning coffee, and a space that somehow whispers “just one more cup of tea…”

Whether you're here for a weekend adventure, a work trip, or simply a change of scenery, this space was designed to feel warm, inviting, and wonderfully easy to sink into.

The space

Living room made for lounging
Stretch out on the oversized sectional, curl up in one of the cozy lounge chairs with a blanket, or gather around for movie nights, long conversations, and peaceful moments with a view of downtown.

Plant-filled, light-filled charm
Large arched windows bring in beautiful natural light, while happy plants and cozy touches give the space a relaxed, lived-in feel.

Cloud-level sleeping situation
At the end of the day, your Queen Casper mattress is waiting for you. Soft, supportive, and ridiculously comfortable — the kind of bed that has guests saying, “Okay… what mattress is this and where do I buy one?” Sleep in is fully encouraged.

Slow mornings welcome
Wake up slowly, sip coffee, watch the town wake up outside your windows, and enjoy not having to rush anywhere.

Location, location, location
You're right in the heart of historic Woodstock — steps from the Square, local coffee shops, restaurants, boutiques, events, and all the small-town charm that makes people fall in love with this place.

Perfect for:

• Weekend getaways
• Couples retreats
• Work trips with extra coziness
• Square explorers
• Coffee lovers
• People who accidentally take three-hour naps because the bed was too comfortable

You'll have the entire apartment — all yours to enjoy!

No shared spaces, no awkward hallway encounters, and no wondering if you’re in someone else’s way. During your stay, the whole apartment is your private retreat.

Make it feel like home for a little while — stretch out on the sectional, settle into the reading chair with your morning coffee, and find your favorite cozy corner to unwind.

Whether you’re lounging, recharging, or just enjoying a slow moment between adventures, this is your space to relax and feel completely at ease in the heart of Woodstock.

Come stay, settle in, and make yourself at home — the plants love visitors, and the comfortable bed is ready for you.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: limit 1 total
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Smoking

Smoking is not permitted
Plants are cared for between stays, please do not touch nor water them.

Important information

You need to know

Property # 5313936vb
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
On-site parties or group events are strictly prohibited
Safety features at this property include a carbon monoxide detector and a smoke detector

About the area

Woodstock

Woodstock is home to this property. 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.
Map
Woodstock, IL

What's nearby

  • Woodstock Square - 2 min walk - 0.2 km
  • Naturally McHenry County Visitor Center - 2 min walk - 0.2 km
  • Woodstock Opera House - 2 min walk - 0.2 km
  • Woodstock City Hall - 3 min walk - 0.3 km
  • McHenry County Fairgrounds - 18 min walk - 1.5 km

Getting around

  • Woodstock Station - 2 min walk
  • Chicago, IL (DPA-Dupage) - 71 min drive

Restaurants

  • ‪McDonald's - ‬15 min walk
  • ‪Casey's General Store - ‬4 min drive
  • ‪Subway - ‬5 min drive
  • ‪Starbucks - ‬5 min drive
  • ‪Dunkin' - ‬18 min walk

Frequently asked questions

Is Charming Woodstock Square Retreat pet-friendly?

Yes, Charming Woodstock Square Retreat allows pets (limit 1 total).

What time is check-in at Charming Woodstock Square Retreat?

Check-in begins at 4:00 PM.

What time is check-out at Charming Woodstock Square Retreat?

Checkout is at 11:00 AM.

Where is Charming Woodstock Square Retreat located?

Situated in Woodstock, this property is steps away from Woodstock Square, Naturally McHenry County Visitor Center and Woodstock Opera House. Woodstock City Hall and Emricson Park are also within 1 mile (2 km). Woodstock Station is only a 2-minute walk.

About the host

Hosted by Jennifer

Host profile image
I mostly like to keep things easy and hands-off so you can enjoy your space in peace.

Think of me as your quiet local backup—close enough if something comes up, but otherwise happily staying out of your way so you can settle in, relax, and enjoy the apartment as if it’s your own little home base in Woodstock.

If you need recommendations, help with anything in the space, or just a quick question answered, I’m only a message away. Otherwise, I’ll let you enjoy your privacy and your time here uninterrupted.

Why they chose this property

Woodstock has a way of feeling both alive and grounded at the same time, which is exactly why I chose to live here and why I love sharing it with guests.

It’s a place where history and everyday life sit side by side — the historic Square filled with local cafés, shops, music, and community events, all wrapped around a town that still feels personal and connected. There’s always something happening, but it never loses its small-town warmth.

I love being able to step outside and feel part of it all — morning coffee walks, spontaneous live music on the Square, seasonal festivals, and evenings when the town lights up with energy and conversation. And then, just as easily, you can slip into a quieter moment, find a cozy corner, and slow everything down.

It’s that balance that makes Woodstock special: lively when you want it, calm when you need it, and always full of character.

What makes this property unique

What makes this place special is simple: you’re right on the Square, inside a charming historic building, and steps away from everything Woodstock has to offer.

Step outside and you’re in the middle of cafés, shops, live music, and that small-town buzz that makes the Square feel alive—especially in the evenings. Step back inside, and it’s your cozy little retreat to unwind and recharge.

It’s the best of both worlds: all the energy of downtown, with your own quiet space just upstairs to call home while you’re here.
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