Holiday rentals in Woodstock

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Top-rated holiday rentals in Woodstock

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Guest favourite

Loft in Woodstock

4.96 out of 5 average rating, 170 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.

8–15 Oct

£120 per night

Guest favourite

Loft in West Dundee

4.97 out of 5 average rating, 442 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

28 Oct – 4 Nov

£129 per night

Guest favourite

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.

21–28 Feb

£110 per night

Guest favourite

Farm stay in Cherry Valley

4.97 out of 5 average rating, 277 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.

29 Sept – 6 Oct

£88 per night

Guest favourite

Flat 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.

24–31 Jul

£108 per night

Guest favourite

Guest house in McHenry

4.95 out of 5 average rating, 157 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.

10–17 May

£119 per night

Guest favourite

Apartment in Lake Geneva

4.93 out of 5 average rating, 427 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!

15–22 Oct

£121 per night

Guest favourite

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 292 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.

8–15 Apr

£88 per night

Guest favourite

Flat in Elkhorn

4.95 out of 5 average rating, 330 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!

28 Dec – 4 Jan

£87 per night

Guest favourite

Flat in Cary

5.0 out of 5 average rating, 155 reviews

A Peaceful Get-Away

Come and enjoy the quiet of nature. We are located off the beaten path, near the Fox River, but less than three miles from the Metra station (into Chicago); and less than five miles from the Norge Ski Club. Within driving distance, there are golf courses, hiking paths, and shopping. Our fully furnished apartment is attached to our main house and offers you a private entrance and driveway parking for one vehicle.

1–8 Nov

£114 per night

Guest favourite

Cabin in Kenosha

4.81 out of 5 average rating, 534 reviews

Lake Michigan Writer’s Cabin

Beautiful Lake Michigan retreat perfect for relaxing, boating, fishing, swimming and more! Fully remodeled. Perfect for ice fishing in the winter. A Sportsman’s paradise. Ideal for the adventurous. Relax, do some writing or work overlooking the breathtaking scenery. A stone's throw to the beach. Massive deck overlooking the tranquil landscape. A short walk to downtown shops, cafes and restaurants.

7–14 Dec

£108 per night

Guest favourite

Flat in Woodstock

4.9 out of 5 average rating, 194 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!

27 Feb – 6 Mar

£170 per night