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House vacation rentals in Woodstock

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Top-rated house rentals in Woodstock

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

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Top guest favorite
The charming Victorian home features a welcoming front porch adorned with hanging flower baskets and a large American flag. A brick pathway leads through manicured hedges and colorful flower beds, enhancing the inviting outdoor space surrounded by mature trees.
Home in Woodstock
4.89 out of 5 average rating, 91 reviews

Grand 1800s Victorian Gem: Updated/by Downtown

Step back in time with this Victorian, pet friendly, home featuring original pocket doors, gorgeous inlaid floors, & sparkling leaded glass windows. You will feel right at home with the comfort of the updated kitchen and baths with tons of space for all sized groups. This home is just three blocks from downtown Woodstock where you can dine, shop, & visit the famous opera house. Don't forget to visit the many scenes the movie Groundhog Day was filmed at throughout town and toast to world peace!

Top guest favorite
A small outdoor deck features a round red table accompanied by two matching chairs. Lush greenery and hanging plants adorn the area, providing a serene view of the wooded backyard. The soft illumination adds a cozy touch, inviting relaxation.
Home in Roscoe
4.99 out of 5 average rating, 323 reviews

* Travelers Sanctuary 2bed 2bath unit-sf home

Two bedroom, two bath entire first-floor of a single family home. 1350 sq ft. Self check-in. Central Air. Parking in driveway. Host lives in lower unit, separate entrance. 1-acre, wooded backyard. 4 mi to I90/39-Exit Rockton Rd. 11 mi N of Rockford 7-8 minute drive to forest preserves, grocery. Ideal for biz class guests, couples. Safety issues for children under 8 years. Share a bit about yourself, why in the area, who you are traveling with & that you read & agree to "House Rules".

Guest favorite
Home in McHenry
5 out of 5 average rating, 19 reviews

Pet Friendly, Fenced In Yard, Lots to do Nearby!

Entire home included in your stay, big fenced in yard that is pet friendly! Updated, clean, 2 bedroom with 2 queen beds. 1 full bathroom. Laundry room with W/D. All hard surface flooring throughout (no carpet), kitchen has new appliances, dishwasher, coffee maker, toaster, microwave, fridge/freezer, quartz counters, all utensils stocked and available. There's a dining space with 4 chairs. Comfortable living room with couch and recliner, and wall mounted Smart TV. Patio, grill, outdoor space!

Guest favorite
An aerial view captures a sprawling five-acre property surrounded by a lush woodland forest. The landscape features a well-maintained green lawn with several trees and pathways, along with multiple buildings nestled together, offering a sense of tranquility in nature.
Home in Harvard
4.95 out of 5 average rating, 211 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.

Top guest favorite
A cozy seating area is presented with two sofas adorned with decorative pillows. A large lamp with a blue shade complements the space, while light filters through the large windows, enhancing the bright atmosphere. A piece of wall art and natural accents are also visible.
Home in Salem
4.94 out of 5 average rating, 122 reviews

Center Lake View Cottage, near Camp&Silver Lakes

Relax & enjoy your stay in this peaceful home in quiet, friendly neighborhood. Launch boat in Center Lake at end of street or several nearby lakes. Camp Lake is 2 mins away, close to Silver Lake and many others. This home has an awesome sled hill, fire pit with seating area, and a relaxing deck with lake views. Close to Lake Geneva, & Renaissance Faire. Ski at Alpine Valley or Wilmot Mountain. 25 mins to Six Flags or Lake Geneva, 1 hr to Chgo or Milwaukee. 35 mins to Great Lakes Naval Base.

Guest favorite
An inviting living area features a wooden dining table with four chairs, complemented by a cozy chair and a side table. A decorative sign is mounted on the wall, while an air conditioning unit is visible near the window. A faux stove adds aesthetic charm to the room.
Home in Lake Geneva
4.82 out of 5 average rating, 223 reviews

Cozy Cottage 1.5 Blocks From The Lake

Kick back and relax in this cozy, comfy and stylish 2 bedroom cottage located within walking distance to the shores of beautiful Lake Como and about a 10 minute drive to Lake Geneva. The home features a gourmet kitchen with everything you'll need to prepare and enjoy a great meal. The neighborhood of Lake Como is friendly and fun with plenty of options for dining and nightlife. We are always available to answer any questions prior to and during your stay and would be honored to host you.

Top guest favorite
Home in Woodstock
4.89 out of 5 average rating, 143 reviews

3 BR near DT Woodstock Square | Hot Tub & Arcades

Welcome to Woodstock's Victorian Square! Embark on a delightful escape to the serene embrace of Woodstock's Victorian Square. Nestled on a peaceful street, this inviting haven offers a perfect blend of tranquility and convenience. Enjoy a quiet night's sleep and a short stroll (2 blocks) to discover the delights of coffee, chocolate, art, and antiques. Historical Charm, Modern Comfort: Immerse yourself in the allure of a completely renovated (2021) historic home, built in the 1920s. 🏡

Top guest favorite
A spacious living area is highlighted by large windows offering views of the water. Colorful seating options, including bean bags and patterned chairs, complement a wooden coffee table. Sleek ceiling fixtures and a soft rug define the gathering space, enhancing the open layout.
Home in Richmond
4.96 out of 5 average rating, 229 reviews

TheGlassCabin @ HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

Top guest favorite
A serene living area features a large sliding glass door leading to a deck with unobstructed views of Round Lake. Natural wood accents adorn the wall, while a plush sofa and a small coffee table create a relaxing seating space.
Home in Round Lake Beach
5 out of 5 average rating, 200 reviews

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Top guest favorite
A modern house features an inviting front porch with landscaped gravel beds and well-maintained grass. A wooden garage door complements the green exterior walls. Surrounding trees and shrubs enhance the outdoor space, creating a welcoming entrance.
Home in Twin Lakes
4.98 out of 5 average rating, 130 reviews

4Bd 3.5ba Cozy New Construction! Close to lake!

Welcome to our cozy home! Twin Lakes is quintessential small town America situated surrounding lakes Elizabeth and Mary in Wisconsin. Less than 15 minutes from downtown Lake Geneva and less than 5 minutes from Richmond, Illinois. During your stay you can experience much of what the area has to offer including boating and fishing on Lakes Elizabeth and Mary, access to the community beach, local shopping, and peaceful country nights in this small family-oriented community.

Superhost
Home in Spring Grove
New place to stay

Waterfront Oasis w/ Hot Tub, Sauna, FirePit & Pier

Welcome to Whispering Willows Sanctuary, a rare and secluded wellness and waterfront escape nestled on Chain O' Lakes. Surrounded by water on two sides, this stunning 180° waterfront property offers a one-of-a-kind setting along a peaceful channel that flows directly out into the Fox River and Pistakee Lake. Anchored by a majestic weeping willow tree gently swaying over the shoreline, this property lives up to its name—offering a serene, private retreat.

Guest favorite
A small potted plant sits atop a wooden shelf, accompanied by blocks that spell out 'WELCOME.' The blocks are arranged in a neat line, showcasing a modern and friendly presentation.
Home in Fontana-on-Geneva Lake
4.93 out of 5 average rating, 243 reviews

The Little Farm Fontana 5 min from Geneva Lake!

Cozy cottage less than 2 miles from Fontana Beach and the sought after Geneva Lake! Minutes away from The Abbey Resort and just across the street from Abbey Springs Golf course, relax in this beautifully located home away from home out in the country with the luxury of quick and easy access to shopping and dining. We are within 15 minutes of downtown Lake Geneva if you are planning a day trip or a night on the town.

Popular amenities for Woodstock house rentals

Quick stats about house rentals in Woodstock

  • Total vacation rentals

    Explore 10 vacation rentals in Woodstock

  • Verified guest reviews

    Over 590 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Woodstock vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Woodstock rentals

  • 4.8 Average rating

    Woodstock stays are highly rated by guests—averaging 4.8 out of 5!

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