Vacation rentals in Woodstock

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Top-rated vacation rentals in Woodstock

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Loft in Woodstock

4.96 out of 5 average rating, 168 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.

May 6 – 13

G$27,953 GYD per night
Guest favorite

Loft in West Dundee

4.97 out of 5 average rating, 437 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

Dec 30 – Jan 6

G$31,025 GYD per night
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.

Feb 21 – 28

G$26,486 GYD per night

Popular amenities for Woodstock vacation rentals

Stay near Woodstock's top sights

Woodstock Square Historic District11 locals recommend
Niko's Red Mill Tavern4 locals recommend
Woodstock Theatre9 locals recommend
D.C. Cobb's9 locals recommend
Culver's5 locals recommend
Jewel-Osco4 locals recommend

Other great vacation rentals in Woodstock

Guest favorite

Cabin in Kenosha

4.8 out of 5 average rating, 526 reviews

Lake Michigan Writer’s Cabin

Oct 10 – 17

G$26,736 GYD per night
Guest favorite

Home in Woodstock

4.92 out of 5 average rating, 98 reviews

The Tailor House | DT Square Woodstock

May 19 – 26

G$44,163 GYD per night
Guest favorite

Guesthouse in Hampshire

4.94 out of 5 average rating, 32 reviews

Shiloh Place - Two Minutes Off The Highway

Feb 26 – Mar 5

G$18,498 GYD per night
Guest favorite

Cottage in Crystal Lake

4.92 out of 5 average rating, 26 reviews

Modern Cottage by the Beach

Dec 28 – Jan 4

G$34,258 GYD per night
Superhost

Apartment in Algonquin

4.87 out of 5 average rating, 15 reviews

Waterfront 2 Room Studio w/Kitchenette, Downtown

Jun 14 – 21

G$17,411 GYD per night
Guest favorite

Apartment in McHenry

5.0 out of 5 average rating, 66 reviews

Downtown McHenry @ the Heart of the Fox River

Oct 5 – 12

G$32,166 GYD per night
Superhost

Home in Woodstock

4.82 out of 5 average rating, 39 reviews

Grand 1800s Victorian Gem: Updated/by Downtown

Apr 25 – May 2

G$166,190 GYD per night
Guest favorite

Apartment in Marengo

4.96 out of 5 average rating, 23 reviews

Spaciously Ideal Upper Apartment

Nov 11 – 18

G$26,962 GYD per night
Guest favorite

Farm stay in Marengo

5.0 out of 5 average rating, 16 reviews

Maria's La Petite Maison

Jan 2 – 9

G$59,737 GYD per night
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

May 1 – 8

G$24,447 GYD per night
Guest favorite

Home in McHenry

5.0 out of 5 average rating, 21 reviews

Huge Renovated Barn Estate/Perfect for Groups

Nov 4 – 11

G$176,931 GYD per night
Guest favorite

Farm stay in Harvard

5.0 out of 5 average rating, 52 reviews

Executives, Weddings, Families: Elite Farm Retreat

Nov 18 – 25

G$127,253 GYD per night

Quick stats about vacation rentals in Woodstock

Total rentals

30 properties

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

1.3K reviews

Nightly prices starting at

G$6,282 GYD before taxes and fees

Frequently Asked Questions

  • Do house rentals in Woodstock have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Woodstock. Enjoy a tailored experience with all the comforts you desire.

  • 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.

  • Are there family-friendly vacation rentals in Woodstock?

    Woodstock has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • 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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. McHenry County
  5. Woodstock