Woodstock Holiday Rentals from €224: Search Short-Term Rentals

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Holiday Rentals in Woodstock

Experience the thrill of Moose Mountain Falls at Timber Ridge Lodge, featuring water slides, a pool area with rope bridge, and seating areas.

"Had a great staycation here. "

includes taxes & fees

23 Jul - 24 Jul

Swimmers can enjoy a refreshing dip in the rectangular pool surrounded by a tiled deck and wooden beams.

"this mill creek inn has lower level reserved parking and excellent room decor-most enjoyable by us with guest laundry"

includes taxes & fees

3 Aug - 4 Aug

Cozy retreat with a wooden floor, round ottomans, and a staircase leading to an upper level.

"The property was decorated so nicely, we loved it! Great location with so much to do within walking distance."

includes taxes & fees

14 Jul - 15 Jul

Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

"Weekend trip to enjoy the outdoors. Lots of places for walking "

includes taxes & fees

21 Jul - 22 Jul

Enjoy water activities, sunbathing, and swimming in this scenic beach area.

"Great location for walking to shops & restaurants/bars. Comfortable & nicely decorated. Loved the veranda. "

includes taxes & fees

30 Jul - 31 Jul

Kitchen features a central island with a countertop, stainless steel appliances, and white cabinetry.

"Would stay again"

Enjoy cooking in this well-equipped kitchen with a microwave, oven, and refrigerator, and dine in the adjacent seating area.

"Had a great time "

Enjoy a serene lakeside retreat with a docked boat and picnic table on the sandy shore.

"We had a nice time visiting Antioch, IL. The property clean, quiet and well maintained. The camper was adorable and very comfortable. Thank you!"

Enjoy a serene garden view from the deck, featuring comfortable outdoor seating areas amidst lush greenery.

"We had a blast at Marks place. It’s just a short walk to a secluded beach and nearby all the fun stuff in town. The host was so accessible and welcoming. The cottage was well- appointed and very comfortable."

Enjoy the serene atmosphere from the cabin's spacious porch with large windows and a cozy seating area.

"Very convenient to William’s Bay."

Relax on the deck with a comfortable table and chairs, surrounded by lush plants and a stylish rug.

"We enjoyed our stay at the house. The open spaces and high ceilings made the space feel special. Would love to reserve the space again in the future."

includes taxes & fees

21 Jul - 22 Jul

Enjoy a serene lakeside picnic amidst lush greenery and a tranquil lake.

"Had a fantastic stay at this stunning new house near the lake. The house is spotless, thoughtfully designed and fully equipped with everything you need for a relaxing and fun-filled stay.The location was perfect, which is just a short walk to the lake and some local restaurants. The patio deck is a perfect spot for morning coffee or an evening cocktail. The neighborhood was quiet and felt very safe. The beds are comfortable, and the kitchen had all the essentials and then some. The host was very...

Enjoy cooking in this well-equipped kitchen with a central island, oven, and granite countertop.

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

Relax on the deck with a barbecue grill, surrounded by a well-maintained garden.

"We used this house as a landing spot for a wedding weekend and it was a great fit. Clean, plenty of space and beds, and communication with hosts was easy! We would stay here again!"

Guests can enjoy serene lake views from the dock, surrounded by lush greenery and a majestic tree.

"wonderful experience from beginning to end"

Overlooking the water, this hotel features a modern, flat-roofed building.

"Beautiful place, excellent hosts, fantastic neighborhood. Our only criticism was not being able to make a fire in the fireplace. One of the many reasons we chose this house was the fireplace feature. We also wanted a front porch, updated kitchen, and a spa tub. This place had all of that!"

Relax in this spacious living room with a large window, two armchairs, and a round coffee table.

"This beautiful home was just right for 9 high school friends celebrating 55+ years of friendship. The well-equipped kitchen was great for organizing and preparing snacks and meals. Lots of comfy gathering options and plenty of bedrooms and bathrooms! There’s even a great yoga space on the upper level! Highly recommended! "

Relax on the deck with a bench and hot tub, surrounded by lush greenery.

"The house felt like home, the yard was perfect. I imagined a summer baseball game. The neighborhood was close to plenty of activities, while being far enough away for peaceful quiet nights. Contact was easy, and accessible the whole stay. Would gladly stay again!"

Enjoy a serene forest view from this deck with a table and chairs.

"We had an amazing weekend at this house! Was spacious, clean, and well-equipped with everything we needed for a fun and relaxing stay. The location was convenient yet private, making it the perfect spot to unwind with friends. The host was responsive and accommodating, ensuring we had a seamless experience. Highly recommend for anyone looking for a great weekend escape!"

Relax in a serene outdoor space with a pergola, two wicker chairs, and a table for a peaceful retreat.

"The home is as lovely as described. Very spacious, clean, and great location. We enjoyed our stay very much."

includes taxes & fees

21 Jul - 22 Jul

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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 €224 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

5/5 Excellent

"I like it"

A verified traveller stayed at Hyatt Place Chicago/Hoffman Estates

Posted 23 hours ago

5/5 Excellent

"I like that there was an adult pool. It's always nice to have some adult time. There should be some music playing in the pool area. Plus, the bar should open earlier since people are vacationing and like an adult beverage poolside. The hotel was clean and I like that there are lots of activities for the kids."

A verified traveller stayed at Abbey Resort and Avani Spa

Posted 2 days ago

Holiday Inn Express & Suites Elkhorn - Lake Geneva Area by IHG

5/5 Excellent

"First time in Wisconsin and I was worried this hotel was in an industrial area but it wasn’t. It was the cleanest and friendliest hotel I’ve ever stayed at. I highly recommend this Holiday Inn Express location. When we visit again we will stay here again"

A verified traveller stayed at Holiday Inn Express & Suites Elkhorn - Lake Geneva Area by IHG

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?

Private Country House near Lake Geneva, Como and Williams Bay: This holiday home rental outside of Woodstock is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 12 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Woodstock?

Choose from 4 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

Mill Creek Hotel

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

Ground- Level Lake Geneva Villa!

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

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

Quiet 2bd 1ba ranch with off street parkingWalking distance to downtown/beach.

Cozy RV in our land with community private beach, fire pit, bring your boat.

Twin Lakes Rental One Block from Lake Elizabeth

Cozy Cabin in Williams Bay

Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.

LAKESIDE GEM ! ONE BLOCK FROM SHORELINE ! in fabulous Lake Geneva .

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

Relaxing Delavan home across street from lake sleeps 10, 4 bedrm.Dogs welcome!

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

Gorgeous Downtown Baker St Bungalow, Walk Everywhere!!!

Stunning Lakeside Retreat: Delavan Lake Home w/ Lake Views & Private Lake Access

🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲

Private Country House near Lake Geneva, Como and Williams Bay

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

Find out more about Woodstock

Recent reviews of Woodstock properties

Hyatt Place Chicago/Hoffman Estates

Abbey Resort and Avani Spa

Holiday Inn Express & Suites Elkhorn - Lake Geneva Area by IHG

Grand Geneva Resort & Spa

Lake Lawn Resort

Lodge Geneva National

Timber Ridge Lodge and Waterpark

DoubleTree by Hilton Libertyville - Mundelein

Comfort Suites Grayslake near Libertyville North

Frequently asked questions