Vacation rentals in Woodstock

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Top-rated vacation rentals in Woodstock

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Guest favorite

Loft in Woodstock

4.96 out of 5 average rating, 169 reviews

Curated Loft Retreat in The Heart Of Woodstock

Welcome to our spacious upper retreat with modern conveniences. We have great WiFi for you to stay in touch with and are well stocked with books for you to enjoy time unplugged. Close to the Historic Square (you may have seen it in the movie Groundhog Day) you can easily walk to unique shops, cafes, and restaurants. Our curated timeless decor is filled with storied items from our travels, and photos we've snapped locally. Come renew yourself here. We can't wait to share Woodstock IL with you.

Guest favorite

Loft in West Dundee

4.97 out of 5 average rating, 441 reviews

Hip Urban Loft - Small Town Charm - 124 LOFTS #2

Luxury one-bedroom loft in the heart of downtown Dundee. Newly renovated 125-year-old building with timber ceilings, exposed brick walls and beautifully restored hardwood floors. Tastefully decorated and features a king-size Beautyrest mattress, luxury bed linen, private bathroom, kitchenette with under counter refrigerator, Kuerig coffee maker and lightning fast Wi-Fi for streaming your favorite shows on the 60” LED smart TV. 124 LOFTS offers 4 separate luxury lofts. Loft 2 is our most spacious

Guest favorite

Guesthouse in Hampshire

4.95 out of 5 average rating, 39 reviews

Shiloh Place - Two Minutes Off The Highway

This stylish studio with all the amenities is two minutes off I-90 and just behind Dell Webb in Huntley. A 10 minute drive from the newly built Amazon facility Newly furnished and freshly painted, it features a full size kitchen, separate dining area with a private keyless entrance Sleeps up to four comfortably, featuring a king size memory gel foam mattress with luxurious bedding. Enjoy a 55” TV from the day bed that also opens to a double. The space is very suitable for short or long stays

Guest favorite

Home in Harvard

4.95 out of 5 average rating, 164 reviews

Sanctuary Woodland Guest House!

Our guest house is located on a picturesque 5 acres, next to a woodland forest. We also run a bird sanctuary on the property, Georgia's Place Bird Sanctuary, which makes this a paradise for an animal lover! We are happy to give guests a tour of our sanctuary. There is a large deck and fire pit for an enjoyable evening, and a walking trail for wildlife enthusiasts! We kindly ask guests not to bring meat onto the property as we are running a sanctuary that promotes compassion for all animals.

Guest favorite

Farm stay in Cherry Valley

4.97 out of 5 average rating, 273 reviews

Bed and Breakfast with Horse Hotel at VRR

Victory Reigns Ranch Horse Hotel and Bed and Breakfast boasts a beautiful ranch setting close to Deer Run Forest Preserve, Oak Ridge Forest Preserve and other equestrian trails. *Come with or without your horse. We also have an RV hookup if needed along with spacious trailer and RV parking. *If interested in horse boarding during your stay a 12 x 12 barn stall is $35 per night. Private pasture turn out available for $25 per horse per night. Trailer hook up is $35 per night per trailer.

Guest favorite

Apartment in Woodstock

5.0 out of 5 average rating, 47 reviews

Cute apartment near the Historic Woodstock Square

This cute, in-law apartment is a hidden gem nestled in a quiet neighborhood. It has all the comforts of home including your own private parking & key-pad self entry. It features a fully equipped kitchen, 1 bedroom, bathroom. The living room also has a trundle that can sleep 2, a smart TV w/streaming services (Netflix & more). There is also a desk set up if you need to work. We are close to the Metra train and Historic Woodstock Square that has shopping, restaurants & fun events year round.

Guest favorite

Guesthouse in McHenry

4.95 out of 5 average rating, 155 reviews

"The Apartment" in the heart of downtown McHenry

We welcome you to be our guest in this charming, historic home built in 1911 by a German mason. This upper unit Apartment is a spacious 1,100 square feet, lovingly restored with a vintage aesthetic in 2018. The private entrance to "The Apartment" will lead you to; 2 cozy bedrooms & 1 vintage inspired yet modern bath with walk in shower. A large living room, dining area and bright clean kitchen will make you feel right at home. 9 foot ceilings and tons of natural light through out.

Guest favorite

Condo in Lake Geneva

4.93 out of 5 average rating, 424 reviews

Charming, Cozy & Quaint Condo in Lake Geneva!

Quaint 1 BD 1 BA Condo by Lake Como. The association outdoor pool is newly remodeled. There is a boat launch and parking, paddle board rentals, and tennis court. The hotel next door has pools to use for a fee. Dine at the popular nearby Mars restaurant or check out the Ridge Hotel’s coffee shop, restaurant & huge outdoor fire pit! Condo offers towels, toiletries, games, WiFi, basic cable, Roku, electric grill, gas fireplace, drip & K-cup coffee, tea, & water!

Guest favorite

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 291 reviews

a SIMPLE place

Booking the entire house with 100% privacy. It has 2 driveway parking spaces and street parking. Garage may be available. CHECK-IN and OUT are flexible. I set checkout at 11am (text me if you need late checkout). The space is perfect for a family of 4. It is located about 20 minutes from O'Hare airport and 40 minutes from Chicago downtown. Infants and pets are welcome (please text me for over size pets or more than 2 pets) Play pan is available upon request.

Guest favorite

Apartment in Elkhorn

4.95 out of 5 average rating, 329 reviews

FarmWise Country Stay by Alpine Valley/Lake Geneva

Retreat to a quiet countryside experience at this all organic farm, where you can sit back, relax, and enjoy the country charm of your private space inside the main farm house. Optional for you are joining us for early morning chores in the barn. If you tell me the night before, you can try milking Carmel, the cow by hand, feeding the pig, collecting eggs from the chicken coop and more. Most loved of all are our friendly cats!

Guest favorite

Apartment in Woodstock

4.9 out of 5 average rating, 193 reviews

Historic Apartment on the Woodstock Square

Located on the Town Square, your private apartment is in the heart of Woodstock's downtown district. The apartment spans the full second story of what was once a 1900's saloon, 1920's confectionary shop, and a jewelers during the 1930's. Now a landmark, the neon glow of the Elgin Watches sign is the first thing travelers see when they turn onto Main Street en route to the Square!

Guest favorite

Condo in Crystal Lake

4.87 out of 5 average rating, 172 reviews

Crystal Lake newly updated, walk to beach

We are just minutes from historic downtown and just a few blocks away from Crystal Lake’s beautiful beach. We are block from Route 14 and within walking distance to several restaurants, library and some shopping. Perfect for a long relaxing weekend getaway.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Woodstock vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Woodstock's top sights

Woodstock Square Historic District11 locals recommend

Jewel-Osco4 locals recommend

Niko's Red Mill Tavern4 locals recommend

Woodstock Theatre9 locals recommend

D.C. Cobb's9 locals recommend

Culver's5 locals recommend

Other great vacation rentals in Woodstock

Guest favorite

Apartment in McHenry

5.0 out of 5 average rating, 69 reviews

Walkable to downtown McHenry near the Fox River

Superhost

Home in Woodstock

4.83 out of 5 average rating, 40 reviews

Grand 1800s Victorian Gem: Updated/by Downtown

Guest favorite

Cottage in Crystal Lake

4.93 out of 5 average rating, 27 reviews

Modern Cottage by the Beach

Guest favorite

Condo in Lake Geneva

4.96 out of 5 average rating, 55 reviews

LG Quaint Condo on Lakeshore Dr. W/boat parking

Guest favorite

Cottage in Fox River Grove

4.94 out of 5 average rating, 49 reviews

Little Fox Cottage - A Cozy Riverview Getaway

Guest favorite

Home in McHenry

5.0 out of 5 average rating, 10 reviews

Relaxin' on the River

Guest favorite

Apartment in Sycamore

4.97 out of 5 average rating, 38 reviews

Cozy 1BR Apt - heart of historic downtown Sycamore

Guest favorite

Cabin in Spring Grove

4.9 out of 5 average rating, 20 reviews

Enjoy a Getaway @ The Lake-Heim by Chain-O-Lakes

Show all

Quick stats about vacation rentals in Woodstock

Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
1.4K reviews
Nightly prices starting at
$30 before taxes and fees

Frequently Asked Questions

How much does it cost to stay in house rentals in Woodstock?
Experience the best of Woodstock with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Woodstock?
Yes! Work meets play with ease at over 10 vacation rentals in Woodstock featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Woodstock have free parking?
Absolutely! We offer over 10 house rentals with free parking in Woodstock. Enjoy a tailored experience with all the comforts you desire.
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.
Do house rentals in Woodstock have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Woodstock. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Woodstock

Top-rated vacation rentals in Woodstock

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Woodstock vacation rentals

Stay near Woodstock's top sights

Other great vacation rentals in Woodstock

Apartment in McHenry

Home in Woodstock

Cottage in Crystal Lake

Condo in Lake Geneva

Cottage in Fox River Grove

Home in McHenry

Apartment in Sycamore

Cabin in Spring Grove

Quick stats about vacation rentals in Woodstock

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

How much does it cost to stay in house rentals in Woodstock?

Are there vacation rentals with a dedicated workspace in Woodstock?

Do house rentals in Woodstock have free parking?

Are there pet-friendly vacation rentals in Woodstock?

Do house rentals in Woodstock have wifi?

Do house rentals in Woodstock have air conditioning?

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