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Places to stay in Woodstock

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Top-rated places to stay in Woodstock

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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A serene pathway lined with lush greenery features tall trees and blooming flowers. An inviting red chair is positioned in the background. A friendly sign indicating 'KEEP RIGHT' guides guests along the landscaped route toward the cottages.

Bungalow in Lake Geneva

4.97 out of 5 average rating, 143 reviews

Private Cozy Cottage Lake Geneva, WI

StefanyRating, 5 stars5 days ago

We love staying at Seven Oaks and have many times. I particularly enjoy the soaker tub and we appreciate the cheese tray, drinks, and breakfast foods. It makes it so much more enjoyable to get away and not have to think about running out to get food. We stay as often as we can get away. Such a great place!

4.85 out of 5 average rating, 68 reviews

A Comfortable Stay While You are Away in Oak Park

KarenRating, 5 stars2 weeks ago

The house looked just like the beautiful photos & Jay was incredibly responsive throughout the visit. This home is located close to 290 to go downtown or further out to the 'burbs quickly. We needed a home to stay last minute, and Jay was accommodating to that as well - we were happy to find this spot with all the space we needed inside and out. As a bonus, we met neighbors who were very friendly.

A cozy outdoor deck features a round table with two folding chairs and a lounge chair. Overhead, stained glass windows allow filtered light to illuminate the space. Potted plants and decorative cushions add a touch of greenery and comfort, inviting relaxation.

Apartment in Logan Square

4.95 out of 5 average rating, 693 reviews

Best in Chicago, private, amazing garden space

NatalieRating, 5 stars1 month ago

Meighan's apartment is cute and thoughtfully, stylishly laid out. From the living room, bedrooms, bathroom, kitchen/dining area, and lovely shared garden area, this was a really lovely space that was walkable, very homey, and refreshing. I commuted to downtown each day, and the walk to take the blue line was easy and close by. Meighan's bulletin board recommendations for nearby restaurants was great. I was able to find and use the 606 jogging path nearby thanks to a bulletin board brochure. Meighan was kind and welcoming to my dogs and me and it was so great to be able to bring them with me. Meighan responded quickly to my texts. Meighan provides a filtered water pitcher in the refrigerator which I recommend using for you and your pets. My dog got the runs a few days into our stay and he has a sensitive stomach when it comes to water and old pipes. As soon as I started giving my dog filtered water his issues cleared up immediately, which also alerted me to drink the filtered water.

Top guest favorite

A modern kitchen is presented with sleek white cabinetry and contrasting black hardware. The marble countertops are accentuated by under-cabinet lighting, highlighting a spacious layout. Stainless steel appliances integrate seamlessly, while a coffee maker and various kitchen utensils are arranged for convenience.

Townhouse in Elgin

4.96 out of 5 average rating, 25 reviews

Fully Renovated and Updated Home

NoelleRating, 5 stars2 weeks ago

We thoroughly enjoyed our stay at Kalim’s place. It was beautiful, clean, and very well kept. The beds were comfortable and it was nice to have a bathroom on each floor. Kalim was very responsive when we ran into an issue with the keypad. The neighborhood was also nice and quiet.

Apartment in Old Town

4.78 out of 5 average rating, 293 reviews

Superb 2BR Old Town APT, PRIME LOCATION!(+Parking)

LeeRating, 5 stars2 weeks ago

This is a great spot to stay in Chicago, the location really couldn’t be much better. Easy walk to red line which gets you everywhere you need to go, and it being a one way street keeps traffic low in comparison. That being said it’s not an alley or a sketchy area by any means. Walk right out 30 yards to your left to a good view of the Willis tower and lower skyline, or walk to your right for great shopping and restaurants in old town. It couldn’t be better. The place is nice, does get a bit chilly at night which is honestly ideal for sleeping, you will be sharing the one bathroom if you have multiple guests but with me and my family it worked fine. Thanks Nicole and Matt for a great stay on spring break with the kids!

Vacation rentals for every style

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Hotels

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Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Woodstock places to stay

Laptop-friendly workspace

Air conditioning

Stay near Woodstock's top sights

Ethereal Confections10 locals recommend

Woodstock Opera House10 locals recommend

D.C. Cobb's9 locals recommend

Woodstock Theatre9 locals recommend

ALDI7 locals recommend

Woodstock station6 locals recommend

Other great vacation rentals in Woodstock

A spacious outdoor deck is depicted, featuring a small seating area with two wicker chairs and a matching table. A grill is positioned to one side, with large glass doors leading into the house. Lush greenery is visible in the background.

Home in Fox Lake

4.87 out of 5 average rating, 124 reviews

Lakefront Paradise

Yi-TzuRating, 5 stars1 month ago

The place was quiet and comfortable, perfect for getting some rest. I would recommend it to anyone looking for a relaxing stay.

A bright and airy living area features a white-beamed ceiling and large windows that allow natural light to fill the space. Comfortable seating includes two soft couches, with a wooden coffee table at the center. A dining area with a large table and wicker chairs is visible in the background.

Home in Kenosha

4.92 out of 5 average rating, 271 reviews

Where Family & Friends Gather to Create & Remember

AliciaRating, 5 stars3 weeks ago

We had an amazing stay! The place is beautiful & looked exactly like the pictures. We would highly recommend staying here.

A modern dining area is highlighted by a wooden table surrounded by four chairs. The open-concept layout connects to a stylish kitchen featuring dark cabinetry and stainless steel appliances. Natural light fills the space, reflecting off the hard surface flooring and a cozy living room in the background.

Apartment in Jefferson Park

4.63 out of 5 average rating, 24 reviews

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars1 month ago

Peaceful, felt like home, very spacious and comfortable

The image showcases a sandy beach area beside a calm water channel. Colorful kayaks and a canoe are positioned along the shoreline. A spacious green lawn is framed by large trees, with blue lawn chairs and a hammock visible in the background.

Home in Antioch

4.92 out of 5 average rating, 116 reviews

Entertain on The Chain! water sports and sauna.

JoshuaRating, 5 stars2 weeks ago

Tucked along the quiet northern edge of Antioch, this house doesn’t just offer a place to stay - it gives you something to feel. Vaulted ceilings, custom barnwood beds, and raw concrete countertops set the tone: warm, solid, and built with intent. The private beach isn’t flashy - it’s better. Soft sand, still water, and no reason to rush. Grill outside, gather at the big family-style table, then sweat it all out in the sauna that feels like it was made to erase stress. The beds hit the sweet spot between firm and forgiving. Every corner of the place feels curated without being pretentious. Jewel is just up the road if you need supplies, but you’ll quickly forget the outside world exists. And Waylon? The kind of host you rarely get - quick to respond, genuinely helpful, and fully dialed in without hovering. This isn’t just a weekend rental - it’s the kind of place that makes you rethink how you spend your time off. You’ll leave better than you arrived.

Cabin in Trevor

4.92 out of 5 average rating, 346 reviews

Living the Lakehouse Dream

Andrea NicoleRating, 5 stars2 days ago

We really enjoyed our stay and all the amenities your place has to offer. Thank you!

A charming two-story house is set within a lush green lawn, featuring large trees that provide shade. The front porch is approachable and includes a railing, while an American flag gently waves. A fence encloses the backyard, creating a private outdoor space.

Home in Twin Lakes

4.86 out of 5 average rating, 65 reviews

beach access, pet friendly yard, hot tub, 5 bedrms

AaronRating, 5 stars1 month ago

Great place for our family to hang out and relax. The hot tub was great. Lots of space for everyone. The fenced in yard was great for our dog. The large gathering spaces were perfect for our kids to play games and for the adults to hang out.

Top guest favorite

Home in Lake Geneva

4.96 out of 5 average rating, 80 reviews

Huge! Sleeps 12, Perfect getaway for a large group

RachelRating, 5 stars2 days ago

This home was incredible for a weekend away with girlfriends. We loved the views of lake como m, the proximity to downtown lake Geneva, and how well stocked the house was with all the essentials and more (especially in the kitchen!). Only regret was not making our stay a full week long trip!

Top guest favorite

A serene landscape is visible, showcasing a calm body of water surrounded by lush greenery. Tall trees frame the scene, with a clear blue sky filled with soft clouds overhead, creating a peaceful natural setting.

4.92 out of 5 average rating, 26 reviews

Hideaway at the Ponderosa- 3bd 1Ba Country Cottage

KevinRating, 5 stars6 months ago

the host was amazing! very responsive and made check in a breeze. place was great and close to restaurants and shopping.

Quick stats about vacation rentals in Woodstock

Total rentals
30 properties
Total number of reviews
1.5K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Gym, BBQ grill, and Laptop-friendly workspace

Frequently Asked Questions

Are there house rentals with a dedicated workspace in Woodstock?
Yes! Work meets play with ease at over 10 house rentals in Woodstock featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Woodstock?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Woodstock?
Four-legged friends are welcome in Woodstock. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Woodstock have wifi?
Absolutely! We offer over 10 house rentals with wifi in Woodstock. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore