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House vacation rentals in Woodstock

Find and book unique houses on Airbnb

Quick stats about house rentals in Woodstock

  • Total vacation rentals

    Explore 10 vacation rentals in Woodstock

  • Verified guest reviews

    Over 620 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!

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 backyard features a well-maintained lawn surrounded by gray gravel. A patio area includes a dining table and umbrella. The house is painted in a soft blue, while a grill is positioned near the side of the house. A condo building is visible in the background.
Home in Wauconda

The Adorable "Blue Breeze"!

Enjoy time at our centrally-located, family-friendly home. Close by, you'll find a public fishing dock and the popular Phil's Beach. A peaceful space with an outside patio and grill, perfect for relaxing at end of day. We also have a large driveway that can accommodate your boat making it easy to enjoy a day on Bangs Lake or a short 15 min trip to Fox Lake. Nearby attractions include the Volo Museum, Jurassic Gardens, and Lake County Discovery Museum. Please note the backyard is not fenced in.

LocationFamilyNearby

4.97 out of 5 average rating, 102 reviews
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

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.

LocationFamilyAccess

4.94 out of 5 average rating, 218 reviews
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

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.

LocationValueLong stay

4.94 out of 5 average rating, 131 reviews
Top guest favorite
Home in Woodstock

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. 🏡

FamilyValueNearby

4.9 out of 5 average rating, 153 reviews
Top guest favorite
A spacious living area features comfortable gray sectional sofas adorned with turquoise cushions. A light wooden coffee table is centered on a soft area rug. Soft lighting is provided by table lamps, and large sliding doors lead to an outdoor space with a view of greenery.
Home in Lake Geneva

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD

✔ 1000 Sq. Ft. Ground Level Condo ✔ Patio overlooking expansive lawn ✔ Resort-like community ✔ New community pool ✔ Tennis,v-ball Courts ✔K-cup & drip coffee, Big Screen TV, Cable, FAST wifi ✔Steps to the Ridge Hotel w/ restaurant, coffee/wine shop ✔ Direct lake access w/boat launch, kayak, SUP board rental ✔ 5 min drive to Shops and dining in DT Lake Geneva ✔ Fully equipped kitchen ✔ Close to summer fun: Lake, golf, zipline, hiking ✔Close to Winter fun: Ice Castle, skiing, snowshoeing

LocationFamilyBeach

4.95 out of 5 average rating, 119 reviews
Guest favorite
A spacious outdoor deck is covered with a bright shade sail, providing relief from the sun. Comfortable wicker chairs with soft cushions create a cozy seating area, overlooking the peaceful river and surrounding greenery.
Home in Algonquin

The River House Sauna/Kayaks/Hot Tub/Fire Pit

The newly remodeled water front 4 bd 2 bath home is within walking distance of Algonquin’s fabulous "Old Town District", restaurants, pubs and entertainment. Likewise, the gorgeously landscaped River Park is a short stroll away, giving one much to see and do. The residence feature a beautiful kitchen; large dining area adjoins the kitchen as does a brightly sun shined living room complete with big glass doors overlooking the water. A picturesque living for both work and play awaits!

FamilyValueWifi

4.87 out of 5 average rating, 133 reviews
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

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 !

FamilyLocationNearby

4.96 out of 5 average rating, 241 reviews
Guest favorite
Home in Fox Lake

Spacious Lakefront Retreat | Sunset VIEW | Firepit

Welcome to Howard House by Evereste Experiences. A hidden gem on the Fox Chain o' Lakes. Situated centrally on the lakefront of beautiful Nippersink Lake just an hour outside of Chicago, this spacious and stylish retreat is located on a hill with ultimate views of the lake and stunning sunsets over the water. Located near downtown Fox Lake and the Metra train stop. With a large back deck, over 60ft of lake frontage, a dock, firepit and swimming area, you'll never want to leave!

FamilyValueParks

4.9 out of 5 average rating, 167 reviews
Top guest favorite
A grassy area features multiple wooden lounge chairs facing the lake. A small fire pit is positioned in the center. Behind, a light-colored shed and a dock can be seen, with boats and kayaks stored nearby. A vibrant sky with colorful clouds adds to the scene.
Home in Fox Lake

Wonderful Mineola Bay Lakefront Cottage 4adu+4kids

Book a romantic weekend or bring the whole family to this cozy, clean and well-appointed lake house that has plenty of room for fun. Embrace lake-life at its finest when you call this Fox Lake cottage on Mineola Bay your home away from home! We have a dock to park your boat, so bring it. Access to restaurants, bars, convenience and grocery stores, boat launches and more. Or hang out and soak in the sunshine while paddle boarding, boating, kayaking, swimming and nature hikes.

LocationFamilyOutdoor spaces

5.0 out of 5 average rating, 122 reviews
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

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.

LocationFamilyWifi

4.98 out of 5 average rating, 140 reviews
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

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.

LocationValueIndoor spaces

4.93 out of 5 average rating, 253 reviews
Guest favorite
Home in Woodstock

Finally… A Home Big Enough for Everyone 8 Beds

Woodstock, IL | Perfect for Families & Extended Stays Welcome to this beautifully renovated, fully furnished 5-bedroom home in Woodstock—designed for families, traveling professionals, medical stays, work crews, and longer visits. With multiple living areas, modern amenities, and ample parking, this home makes group stays comfortable and stress-free. 8 beds

LocationComfortHospitality

5.0 out of 5 average rating, 10 reviews

Popular amenities for Woodstock house rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favorite
Home in Rockton

HD Jameson House at River’s Edge

FamilyLocationHospitality

4.97 out of 5 average rating, 116 reviews
Guest favorite
An outdoor pool area is surrounded by a well-maintained patio and wooden fencing. The clear blue water of the pool contrasts with the beige pavers, while a shaded gazebo provides seating nearby for relaxation. Lush greenery enhances the tranquil atmosphere.
Home in Rockford

Pool, Arcade, Hot Tub and more @16th and Aldeen

FamilyValueDecor

4.95 out of 5 average rating, 103 reviews
Top guest favorite
A decorative wall sign displays the word 'WELCOME' prominently. Beneath it, a white vase filled with yellow flowers adds a touch of color, set against a soft green wall, creating a friendly and inviting ambiance.
Home in Lake Geneva

Home away from Home

FamilyLocationCondition

4.93 out of 5 average rating, 172 reviews
Top guest favorite
The outdoor area features a spacious patio surrounded by decorative stone architecture. Comfortable seating arrangements are placed near the pool, which is bordered by lush greenery. A large umbrella and several lounge chairs add to the inviting atmosphere. The house showcases large windows and multiple levels.
Home in McHenry

Paradiso Vacation

ValueFamilyBeach

5.0 out of 5 average rating, 59 reviews
Guest favorite
A well-maintained in-ground pool is shown surrounded by a concrete deck and lush greenery. A wooden fence encloses the yard, offering privacy. Tall trees and shrubs provide a natural backdrop, while the bright blue sky adds to the inviting atmosphere.
Home in Crystal Lake

Hot tub. Heated Pool. In town location.

ValueLocationAccess

4.98 out of 5 average rating, 45 reviews
Guest favorite
Home in Crystal Lake

Private Heated Indoor Pool + Sauna, Family Retreat

LocationFamilyWalkability

4.9 out of 5 average rating, 40 reviews
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

Grand 1800s Victorian Gem: Updated/by Downtown

LocationFamilyCheck-in

4.9 out of 5 average rating, 99 reviews
Guest favorite
A refreshing pool surrounded by a wooden deck is visible, complemented by several loungers for relaxation. Lush greenery frames the area, providing a serene backdrop. Colorful flowers in the foreground add a touch of vibrancy to the peaceful outdoor setting.
Home in Lake Geneva

Cozy cabin getaway near Lake Como and Lake Geneva

FamilyLocationQuiet

4.98 out of 5 average rating, 49 reviews

Weekly house rentals

Guest favorite
Home in Crystal Lake

Charming Vintage Cottage Near the Lake

LocationFamilyCleanliness

5.0 out of 5 average rating, 8 reviews
Guest favorite
A spacious exterior view of the house showcases a light-colored exterior with a modern metal roof. A large deck with multiple seating arrangements is visible, surrounded by well-manicured grass and trees. The scene is complemented by a clear blue sky and scattered clouds.
Home in McHenry

Riverfront Entertainment Haven

FamilyLocationOutdoor spaces

5.0 out of 5 average rating, 16 reviews
Top guest favorite
The exterior of Blue Magnolia Cottage is showcased, featuring a charming blend of dark blue siding and a brick chimney. Lush greenery surrounds the property, with neatly manicured shrubs lining the pathway, creating an inviting entrance to the home.
Home in Crystal Lake

-NEW- Blue Magnolia Cottage -3 King Beds- Luxury

FamilyLocationAir conditioning

4.96 out of 5 average rating, 26 reviews
Guest favorite
Home in McHenry

Large & Convenient McHenry Home

LocationFamilyAccuracy

5.0 out of 5 average rating, 6 reviews
Guest favorite
An expansive deck is illuminated by string lights, creating a warm ambiance in the evening. A dining set with red chairs is placed on the wooden flooring, with a fire pit nearby. The surrounding wooded area adds a natural backdrop to the outdoor space.
Home in McHenry

Private 1 Bed w/Loft on 5 Wooded Acres + Rock Wall

FamilyLocationQuiet

4.83 out of 5 average rating, 60 reviews
Guest favorite
Home in McHenry

3/2 Riverwalk Retreat Luxury Home in Downtown

LocationFamilyBathroom

5.0 out of 5 average rating, 13 reviews
Superhost
An open-plan living and dining area is highlighted by a large dining table and comfortable seating arrangements. Natural light floods the space through expansive windows, with a fireplace adding warmth. Wooden beams adorn the ceiling, enhancing the inviting atmosphere.
Home in Wonder Lake

Luxury Lakefront Escape - 25 mins from Lake Geneva

LocationValueView

4.85 out of 5 average rating, 75 reviews
Superhost
Home in McHenry

Sunnyside Rental

ValueCleanlinessParking

4.71 out of 5 average rating, 7 reviews

Private house rentals

Superhost
Home in Crystal Lake

Chez Mundyo—Where Staying Feels Like a Celebration

LocationFamilyCleanliness

4.83 out of 5 average rating, 6 reviews
Guest favorite
A vibrant, multicolored blanket is draped over a swing, surrounded by lush green grass. The waterfront view features a wooden dock with outdoor seating, framed by trees and a clear blue sky, creating a serene outdoor space.
Home in McHenry

Heart of the Fox Riverhouse

FamilyValueQuiet

4.91 out of 5 average rating, 87 reviews
Top guest favorite
A modern two-story home is showcased from an aerial perspective, featuring a neatly trimmed yard and a fenced area. The property is positioned near a marina, with views of parked boats on the lake. An attached garage is visible, along with a spacious driveway.
Home in Wauconda

Modern 4BR Lake Retreat • Walk to Beach & Main St

LocationFamilyGrill

4.99 out of 5 average rating, 81 reviews
Superhost
Home in Wonder Lake

Charming 3 Bed Lakefront Home steps to the water!

LocationHospitalityAmenities

5.0 out of 5 average rating, 3 reviews
Top guest favorite
Home in Wonder Lake

Comfort, just off the lake

FamilyLocationCleanliness

4.95 out of 5 average rating, 22 reviews
Top guest favorite
A spacious living area features modern furniture, including a plush blue sofa and two accent chairs. Unique pendant lights provide ambient illumination, while an open kitchen with a sleek design offers an inviting atmosphere. Large windows allow natural light to fill the space.
Home in St. Charles

Luxury Meets Cozy

ValueLocationQuiet

4.98 out of 5 average rating, 60 reviews
Guest favorite
A spacious home is framed by green lawns and vibrant flower beds. A large wooden deck extends from the house, equipped with an umbrellaed table for outdoor seating. Scenic pathways meander through the well-maintained gardens, inviting relaxation within the tranquil surroundings.
Home in McHenry

The Emerald Retreat

ValueLocationTV

4.85 out of 5 average rating, 34 reviews
Top guest favorite
A spacious deck features a sectional sofa facing the sun setting over the Fox River. The area is surrounded by trees, providing a serene atmosphere. The deck's railing outlines the space while allowing unobstructed views of the water and landscape.
Home in Barrington

Barrington River Estate | Perfect for Groups

FamilyValueComfort

4.99 out of 5 average rating, 83 reviews

Destinations to explore