Woodstock Holiday Rentals from €161: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Woodstock has to offer?

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub : This holiday home rental outside of Woodstock offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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Holiday Rentals in Woodstock

"Staff was helpful. Our overall experience was great! Will definitely come back! "

includes taxes & fees

11 Mar - 12 Mar

"The house is very spacious and had everything we needed. Easy 5 minute walk to coffee, restaurants and cute shops. We had a wonderful time!"

includes taxes & fees

2 Mar - 3 Mar

"Cute place. Upstairs could use some dusting."

"This was a beautiful stay in down town Lake Geneva. I surprised my family who didn’t know our accommodations meant glamping! Everyone loved it! Thank you for such a beautiful place"

includes taxes & fees

5 Mar - 6 Mar

"The house was very clean and spacious. A lot of activities to do "

includes taxes & fees

3 Mar - 4 Mar

"Second time here and will be back for sure. Hands up best place for a couple to stand in Downtown Lake Geneva. Excellent staff. Amazing rooms. Awesome breakfast! "

includes taxes & fees

2 Mar - 3 Mar

"There were so, so many activities for everyone, every age! Of course the “kidquarium” / pool and golf simulator (doubled as a big movie theater) were some faves. The shuffleboard, ping pong table and infinity digital game board were also pretty popular. Mike, our host, did not miss a detail! The house was filled with comfy, clean and fun furniture, including the bean bag chairs for kids and adults. Cords (yes, cords for Apple and Droid) and spaces to charge electronic devices available! Very...

includes taxes & fees

3 Mar - 4 Mar

Smart TV, fireplace, video games, table football

"This house was perfect for our quick weekend girls trip. The location was perfect, just ten minutes from downtown Lake Geneva but remote enough that we felt like we had some privacy. There was plenty of space for us in the large bedrooms and huge dining table for gathering. The basement was awesome though we admittedly didn't spend much time down there. The outside looks amazing, but our trip was in winter and we got about 6 inches of snow while we were there. The property looked so pretty in...

"This place was amazing. Located right in the center of it all. Communication was easy and everything was in order. The accommodations were clean, neat and beautifully decorated. The deck outside is amazing. It was a little chilly (November) however during the sunny daytime hours we enjoyed sitting out on the deck. This location is so close to everything. We enjoyed our stay."

includes taxes & fees

4 Mar - 5 Mar

"We stayed here while skiing in Wilmot. Easy drive there and back. Plenty of room upstairs and down stairs to hang out. "

"This was a very smooth experience from start to finish, and the home was very clean and comfortable. Communication was great! The property is a well maintained traditional lake house that is convenient to the lake and town. Would definitely rent again!"

"Overall, great experience. Myself and the group have come back to this location for 4 years straight because we know exactly what will be available. Overall, definitely a good place to book."

"GREAT LOCATION IN DOWNTOWN LAKE GENEVA A SHORT WALK TO ALL OF THE MAIN ATTRACTIONS !! ROOMS ARE SPACIOUS WE HAD A PRIVATE CHEF LOTS OF KITCHEN SPACE AND SEATING . TISH THE PROPERTY MANAGER IS VERY ATTENTIVE"

"Got to stay in this wonderful home while visiting my son and his family. I loved it!"

includes taxes & fees

3 Mar - 4 Mar

"Communication and check in was flawless.We had three generations for the holidays and this property was ideal for us.Property manager communication was easy and timely."

"Great place for 8 of us to gather! "

includes taxes & fees

2 Mar - 3 Mar

"We had an amazing stay with our family group of 30 people! The place is perfectly equipped for a large group, with plenty of kitchen utensils, beds, towels, sheets, and blankets—everything we needed for a comfortable stay. The view is absolutely breathtaking, and the area is so peaceful. We loved every moment and would highly recommend it to anyone looking for a great place for a big family gathering!"

"Adult annual girls trip! Perfect place to stay right on the lake! We enjoyed every minute of our stay! Thank you so much! We’ll definitely be back!"

"The property was beautiful, great location for walking. Love the decor. The bed was so comfy. Thank you for a great anniversary! "

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"This property is clean and in a quiet location. The room was comfortable as well as the bed. There was a nice variety of channels and the bathroom and shower was clean."

includes taxes & fees

27 Feb - 28 Feb

Couples treatment room(s), sauna, hot tub, steam room, body treatments

"Our stay was lovely! It was quiet and cozy. We enjoyed eating at the facility at 240, the cafe, and via room service! The spa amenities were great, too! We will for sure be back!"

includes taxes & fees

2 Mar - 3 Mar

"Staff was helpful. Our overall experience was great! Will definitely come back! "

includes taxes & fees

11 Mar - 12 Mar

Find out more about Woodstock

Everything you need to know about Woodstock holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Woodstock holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Woodstock holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woodstock holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woodstock. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodstock holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodstock holiday rentals we have selected for you start as low as €161 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Woodstock rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Woodstock holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woodstock. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Woodstock properties

Comfort Suites Grayslake near Libertyville North

5/5 Excellent

"It’s cozy "

A verified traveller stayed at Comfort Suites Grayslake near Libertyville North

Posted 2 days ago

Frequently asked questions

Can I find holiday rentals in Woodstock?

Yes, there are holiday rentals in Woodstock close to McHenry County Fairgrounds, or you can select a more secluded option if you're looking for a relaxing stay. Woodstock is known for its shopping and jazz scene. Make sure you have time to check out the golf courses while you're in the area.

What are some of the best holiday rentals that Woodstock has to offer?

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub: This holiday home rental outside of Woodstock offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Woodstock?

Choose from 6 Expedia holiday rentals in Woodstock for a memorable holiday.

What can I see and do in Woodstock?

Cultural attractions include Woodstock Opera House, whereas Emricson Park is a spot to enjoy nature. While here, Woodstock Square and McHenry County Fairgrounds are other places worth a visit.

What are holiday rentals like in Woodstock?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodstock. Holiday rentals offer extras such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a small group gathering.

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Holiday Rentals in Woodstock

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Holiday Rentals in Woodstock

Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

Walk to downtown/beach Huge historic house perfect for large groups or families

Walk to downtown/beach Huge historic house perfect for large groups or families

Lake Views, steps to Lake! Two story home, professionally decorated! Sleeps 6!

Lake Views, steps to Lake! Two story home, professionally decorated! Sleeps 6!

Experience Stay at the Glamping Loft Lake Geneva |Group Stays |12 Stylish Tent Suites |Kitchen & Bar

Experience Stay at the Glamping Loft Lake Geneva |Group Stays |12 Stylish Tent Suites |Kitchen & Bar

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

Mill Creek Hotel

Mill Creek Hotel

Indoor Kidquarium - Perfect for Large Groups - EnglishPrairieBnB

Indoor Kidquarium - Perfect for Large Groups - EnglishPrairieBnB

Vintage FUN 2-bedroom condo in the heart of Lake Geneva's downtown area!

Vintage FUN 2-bedroom condo in the heart of Lake Geneva's downtown area!

Luxury Lake Geneva cottage w/hot tub on 2-acres

Luxury Lake Geneva cottage w/hot tub on 2-acres

Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking

Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking

Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage

Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage

Private Country House near Lake Geneva, Como and Williams Bay

Private Country House near Lake Geneva, Como and Williams Bay

THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20

THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20

Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base

10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

Lincoln Log Cabin · Elkhorn 3 Bedroom 2 Bathroom Log Cabin Sleeps 8

Lincoln Log Cabin · Elkhorn 3 Bedroom 2 Bathroom Log Cabin Sleeps 8

White House, Amazing Cottage, Lake Front, That Sleeps 34!

White House, Amazing Cottage, Lake Front, That Sleeps 34!

Lake Delavan - Lake Front House

Lake Delavan - Lake Front House

NEWLY Updated! Cove of Lake Geneva, Private Luxury Resort Pool View

NEWLY Updated! Cove of Lake Geneva, Private Luxury Resort Pool View

Other types of properties in Woodstock you may be interested in

AmericInn by Wyndham Woodstock IL

AmericInn by Wyndham Woodstock IL

Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

Find out more about Woodstock

Find out more about Woodstock

Recent reviews of Woodstock properties

Recent reviews of Woodstock properties

Comfort Suites Grayslake near Libertyville North

Frequently asked questions