
House holiday rentals in Woodstock
Find and book unique houses on Airbnb
Top-rated house rentals in Woodstock
Guests agree: these houses are highly rated for location, cleanliness and more.

LakeHome Cozy Retreat! HotTub •FirePit•Bar•Fishing
Come enjoy our beautiful home it's the perfect place to relax, unwind & enjoy peaceful lake views. Whether you’re fishing, soaking in the hot tub or sipping coffee on the deck, it’s a quiet home away from home on a serene cul-de-sac. Enjoy stunning views of the lake while grilling or relaxing by the firepit on the beautifully landscaped patio & in the hot tub 🥂 🐶 Up to 2 furry babies are welcome & they’ll love the almost 1-acre fenced yard! 🌅 See weekly & monthly discounts for longer stays

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.

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.

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

Adults Only "Red Room" Home with Hot Tub
Unique adult themed home with a BDSM / "Red Room" experience. It's a great way for couples to turn their fantasies into reality and explore with each other. Includes St Andrews Cross, Swing, and Sybian! Relax on the patio or in the hot tub with a scenic view of the Rock River. Once you arrive you will not want to leave so we try to provide you with everything you may need for your stay! Frozen pizzas, Bottled Water, Coffee, Robes, Firewood and a special gift with each reservation.

Fully Renovated 2BR 1BA Gorgeous Exec Home #8ma-R
Enjoy your stay in Janesville, WI in this fully renovated two-bedroom cozy executive home Professionally Managed by Kevin Bush! The location is central to dining, shopping, and popular Janesville spots like the Rotary Botanical Gardens. This home will truly feel like your home away from home. Located just minutes from I39 giving you easy access for day trips to Madison, Milwaukee, Chicago, and surrounding. Please check out our listing on St. George Lane for more dates. Kevin, Host

Red Lodge-Game Room, Hot Tub, Near Lakes!
Conveniently located amidst Southeast Wisconsin's best attractions, The Red Lodge is a contemporary-styled retreat that offers the space and family-friendly amenities to keep everyone entertained for hours. Enjoy an 👾 room, a secondary game room, a hot tub, a fire 🔥 pit, and a BBQ pit. Rent a boat right in the neighborhood at Lauderdale Lakes. Bike and hike Kettle Moraine State Forest. Visit Lake Geneva for golfing and shopping—a quick 20-25 min drive. Alpine Valley is minutes away!

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 !

Buoys UP! Lake Life & Sunsets
Looking to unwind & enjoy Lake Life-where weekends begin any day of the week-any season you choose? Here at Buoys UP! you will be able to do just that. Enjoy private access to our newly remodeled 2 bedroom lake house at Lake Koshkonong, WI. Overlook the private road this little gem is located on and enjoy the wonderful lake views and the beautiful sunsets. Stroll down the road for apx. a 2 minute walk to take advantage of your personal lake access Buoys UP! offers just for you.

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!

Cozy Country Cottage near Lake Geneva, WI
Our Cozy Cottage features 3 comfortable bedrooms and nightly magnificent sunsets. Nestled on a country road, the house offers plenty of space to rest after visiting Lake Geneva, Lauderdale lakes, biking at Kettle Moraine or site seeing in the area. It’s close to Walworth County fair grounds where the flea market, Das Fest and Rib Fest are held. This is country living with plenty of opportunity to enjoy the beautiful outdoors or the peace and quiet of the countryside.

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 house rentals in Woodstock
House rentals with a pool

Spacious Home Near Lake Geneva - Heated Pool

Cozy cabin getaway near Lake Como and Lake Geneva

#EnglishPrairieBnB | 4 Bedrooms | 2.5 Baths

Grand 1800s Victorian Gem: Updated/by Downtown

Family Getaway near Lake Geneva Winterfest

Paradise with Pool & Games

Hot tub. Heated Pool. In town location.

HD Jameson House at River’s Edge
Weekly house rentals

Doc Holiday | 3BR Lake Geneva House – Pet-Friendly

Lakefront 2BR w/ Kayaks + Paddle Boards | Dogs OK

Lakefront Retreat with Dock, BBQ and Lake Access

Long Lake Retreat - Cottage in Burlington, WI

Romantic Escape ~ Adult Playhouse w Exotic Dungeon

Relaxing Lakefront Stay w/ Deck and great views

Serene Lakefront House on Fox Lake W/ Private Dock

Charming Pet-Friendly Rockford Escape
Private house rentals

Modern 4BD Home in Lake Hills Pet friendly

Moss Point House-Navy Families Welcomed!

Luxury & Comfort in a Large Home

Onyx Oasis Waterfront Hideout!

Blue Moon Lake House

Pelican LakeHouse w/boat slip & sauna (sleeps 4)

Little Rock Woods Retreat

Summer fun at Sunset Cottage!
Quick stats about house rentals in Woodstock

Total holiday rentals
Explore 10 holiday rentals in Woodstock

Verified guest reviews
Over 590 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Woodstock holiday rentals include wifi 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!
Destinations to explore
- Chicago Holiday rentals
- Upper Peninsula Holiday rentals
- Platteville Holiday rentals
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Detroit Holiday rentals
- St. Louis Holiday rentals
- Wisconsin River Holiday rentals
- Milwaukee Holiday rentals
- Windsor Holiday rentals
- Ann Arbor Holiday rentals
- Traverse City Holiday rentals
- Wrigley Field
- United Center
- Six Flags Great America
- Humboldt Park
- Alpine Valley Resort
- Lincoln Park Zoo
- Wilmot Mountain Ski Resort
- Brookfield Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Illinois Beach State Park
- Loyola University Chicago
- Naval Station Great Lakes
- The 606
- Union Park
- Riviera Theatre
- Donald E Stephens Convention Center
- Allstate Arena
- DePaul University
- Byline Bank Aragon Ballroom
- Northwestern University
- Lincoln Park Conservatory
- Gurnee Mills
- Lake Geneva Public Library




