Vacation rentals in Woodstock

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Woodstock

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

Guest favorite
Loft in Woodstock
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.
Aug 31 – Sep 7
ﺩ.ﺇ446 per night
4.96 out of 5 average rating, 168 reviews
Guest favorite
Loft in West Dundee
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
May 29 – Jun 5
ﺩ.ﺇ475 per night
4.97 out of 5 average rating, 437 reviews
Guest favorite
Guesthouse in Hampshire
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
Dec 28 – Jan 4
ﺩ.ﺇ279 per night
4.93 out of 5 average rating, 28 reviews

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
Cottage in Crystal Lake
Modern Cottage by the Beach
Apr 26 – May 3
ﺩ.ﺇ408 per night
4.92 out of 5 average rating, 25 reviews
Superhost
Home in Woodstock
Grand 1800s Victorian Gem: Updated/by Downtown
Aug 8 – 15
ﺩ.ﺇ2,545 per night
4.82 out of 5 average rating, 39 reviews
Guest favorite
Apartment in McHenry
Downtown McHenry @ the Heart of the Fox River
Apr 6 – 13
ﺩ.ﺇ500 per night
5.0 out of 5 average rating, 64 reviews
Guest favorite
Apartment in Marengo
Spaciously Ideal Upper Apartment
Nov 1 – 8
ﺩ.ﺇ399 per night
4.96 out of 5 average rating, 23 reviews
Guest favorite
Farm stay in Union
Twin Brook Dairy Farm
Jan 24 – 31
ﺩ.ﺇ1,102 per night
5.0 out of 5 average rating, 15 reviews
Guest favorite
Home in McHenry
Highwood Haven
Jan 20 – 27
ﺩ.ﺇ3,410 per night
5.0 out of 5 average rating, 28 reviews
Guest favorite
Cabin in Spring Grove
Enjoy a Getaway @ The Lake-Heim by Chain-O-Lakes
May 1 – 8
ﺩ.ﺇ372 per night
4.89 out of 5 average rating, 19 reviews
Guest favorite
Farm stay in Marengo
Maria's La Petite Maison
Jul 21 – 28
ﺩ.ﺇ918 per night
5.0 out of 5 average rating, 16 reviews
Guest favorite
Cottage in Fox River Grove
Little Fox Cottage - A Cozy Riverview Getaway
Feb 17 – 24
ﺩ.ﺇ656 per night
4.93 out of 5 average rating, 46 reviews
Guest favorite
Home in McHenry
Huge Renovated Barn Estate/Perfect for Groups
Jun 17 – 24
ﺩ.ﺇ2,794 per night
5.0 out of 5 average rating, 21 reviews
Guest favorite
Farm stay in Harvard
Executives, Weddings, Families: Elite Farm Retreat
Dec 15 – 22
ﺩ.ﺇ2,102 per night
5.0 out of 5 average rating, 50 reviews
Guest favorite
Cabin in McHenry
Riverside Retreat : A Nature Lover’s Dream!
Aug 7 – 14
ﺩ.ﺇ1,019 per night
4.97 out of 5 average rating, 67 reviews

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

ﺩ.ﺇ110 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