
House vacation rentals in Woodstock
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Top-rated house rentals in Woodstock
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Popular amenities for Woodstock house rentals
House rentals with a pool

2-Acre Highland Park Retreat with Heated Pool ~ 5*
We were in town for Thanksgiving visiting family with our dogs for 4 nights. Communication with host was great. The house was very clean, well furnished (we cooked the Thanksgiving meal there), recently renovated kitchen (huge kitchen island) with high end appliances, and yes there are 6 bedrooms (some small but nice). Rooms are split between three floors so everyone had room/privacy. Backyard with pool was great, lots of space for dogs, everything is fenced in but the front which was not a problem as the house is on a dead-end street with very little traffic. This is definitely a superhost home, all your condiments, lots of nice touches and snacks/gifts. We will definitely stay there again on our next visit to family in Chicago. House is locate between 41 and 94 making travel around Chicago easy.

Elssys Ranch 80 Acre Lake Geneva Retreat
We had an amazing time at this property! Nick was a fantastic host—super responsive and quick to answer any questions we had. The property itself is beautiful with plenty of space for kids to run around and play. The kitchen was well-equipped with lots of utensils and dishes, making it so convenient to cook and eat at the house. The fire pit and grill outside were a wonderful addition to our stay! The location is perfect too! It’s near a charming Boxed & Burlap coffee shop, and just a short 5-mile drive to downtown Lake Geneva. Downtown offers parks, a public library, great shopping, and stunning views of the lake with walking trails. We can’t wait to return and stay again! Highly recommend!

Whole House With Hot Tub And Spacious Bedrooms
Amazing stay! This place has everything you need for both short and long visits. The location is extremely safe and convenient with shops within walking distance. My family and I thoroughly enjoyed the entire property, especially the game room and TV room which were perfect for entertainment. Moiz, the host, was very kind and quick to respond to any needs we had. Thank you for everything! We would definitely stay here again

Grand 1800s Victorian Gem: Updated/by Downtown
Deidre is an amazing host. She goes above and beyond for each guest. We always appreciate her welcoming us into her home and her attentive and responsiveness to our requests. Highly recommend!

Oasis on Oak | Private In-Ground Pool | Hot Tub
It was a beautiful, restful setting for our family to celebrate my wife’s birthday. Thank you for providing a great place for us to meet!

Relaxing Four Season Getaway near Lake Geneva
We were genuinely surprised to find a place in this location so close to the relatives we were visiting. Genoa City is not exactly the hotspot on the border! The neighborhood was quiet and friendly, but no overly inquisitive citizens. Property was perfect for our requirements, with the fenced in back yard that allowed us to let our pet out whenever without having to use a leash. Nice personal welcoming touches were unexpected and truly appreciated, since we arrived late and weren't able to do any shopping before hand. Beds were comfortable and spaced throughout the second floor, with expansion in the lower basement if necessary for bigger families, especially those with older children. School immediately across the street is great for spontaneous recreation of all types if you have the equipment. Our dog has not had the opportunity to enjoy such a large open space for quite some time and it was great to wear him out for the evening prior to bedtime. Abundant TVs throughout the home!

N 2nd St Pool House
This property is just as described - cozy, relaxing and perfectly clean and stocked for a “home away from home” feel. The kitchen/living room area was lovely and served our family’s needs perfectly. Yuan made sure we had everything we might need and the home is close to Culver’s and grocery stores. There were also very nice touches, such as a gift bag with thoughtful welcome gifts as well as bubble bath and all the essentials in the bathrooms. The private pool was the showstopper — our family had such an amazing time swimming and playing and it was an absolute treat for us. Overall, a wonderful stay and we would love to go back some day.

Geneva Grove with Private Pool, 4bd/2ba Sleeps 8
I was super impressed with the quality and quantity of kitchen supplies. I have never been in an Airbnb that has so many kitchen supplies. The beds and pillows were comfortable. The house was spacious and offered my family the space we needed. Preferences: The pool was not as clear and clean as we prefer, and heat would have been a bonus. The garage was a wonderful space for us to spend time with energetic little ones, especially when it rained, but it could use a facelift. Overall, I recommend this spacious Lake Geneva, WI house for a family get-a-way. I realize Lake Geneva is an upscale community, but I thought the house was overpriced. I realized after I booked it that it was, in total, actually $822.62 per night.
Weekly house rentals

Modern 3 bedroom house, quiet residential street.
Very clean and comfortable, nice neighborhood and not too far from our venue. Bikash was super responsive and even recommended a great place to try out Chicago deep dish pizza.

Duplex Home RoscoeVillage/Wrigley Free St Parking
We enjoyed preparing pizzas from scratch in the perfectly sized kitchen with our adult kids who live in Chicago and their friends. There was plenty of space to sit around the spacious kitchen island and talk while cooking. The whole experience was made even better by using the Wolf stove top and Bosch wall-mount oven, which produced perfectly crisp crust and tasty toppings. The neighborhood felt safe and peaceful while providing everything we needed within walking distance. Parking was also easy. We had no trouble finding a space in front of the house all 4 days we were there. As a special bonus, a new chocolate cafe opened a few days ago (Hotel Chocolat Velvetiser Cafe) and is just a short walk away! We had a great time in this lovely home.

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA
Lovely place in a good location.

Modern home. Near naval base, Six flags and Casino
Great home in a great location. I would recommend this home for anyone with a large family

Private Lake House, with boat option- 14 beds
We stayed her over New Years and had a great time. The house is very open with lots of room for everyone. Beautiful views overlooking the wetlands and lake. There was plenty of beds and could easily accommodate a large group. Hot tub was in a great location out back with a beautiful view. Would love to see how beautiful it is in the summer!

Hideaway at the Ponderosa- 3bd 1Ba Country Cottage
the host was amazing! very responsive and made check in a breeze. place was great and close to restaurants and shopping.

Home for flexible term rental
We felt right at home during our stay. The house was thoughtfully arranged, well stocked, and clean. One of the cleanest stays we have had! The kitchen was well appointed. Great quality pots/pans/utensils. We cooked several meals during our stay & had everything we needed to prepare our various meals! Plenty of linens/blankets/towels out & were well displayed. There was also additional linens available if needed. All were good quality & comfortable. There was a great selection of books/board games/toys. The desk area was perfect for getting a bit of work done during our stay. The location was great & the neighborhood was so quiet. We felt safe during our entire stay. The playground across the street was so nice & there were nice sidewalks for our post-dinner strolls. The drive to the naval base was easy & not too far. Overall, we really enjoyed our stay! We will stay again if we find ourselves back in this area!

Root River Home - Waterfront property - Sleeps 8+
Need to spend a night in the Racine/Kenosha area and stumbled upon this gem! There were four of us and our little dog and it was perfect. I think each of us said, “it’s too bad we’re not staying for another night!” The pictures don’t really do it justice but Mindy’s house is homey, comfortable, and spotless! The kitchen was well-equipped, beds were comfy, and the backyard/river view is wonderful. Thank you Mindy!
Private house rentals

Powers Lakehouse Loft
It was exactly what we were looking for. Very quiet with beautiful views. Being able to sit in the hot tub and take in the sunset was incredible. Any questions we had were answered quickly by this very kind host.

All seasons country house
Agnieszka's place was perfect for our visit with our son as he graduated boot camp. The home had everything we needed. The minimal decorations made it very easy to clean and easy to find all our stuff when we left. The home is beautifully remodeled on the inside. Much respect to the designer. We brought extra toiletries and paper products and dishwasher tabs because we were staying so many days. There was an adequate amount for a simple weekend stay. Plenty of sleeping space for several people. Just remember there is one bathroom. By the way, there is a great Jewel-Osco grocery store close by. We also visited an exceptional museum in Volo. It was perfect for a family, especially the boys! I really enjoyed the short drive to Kenosha, WI to gather stones by Lake Michigan.

California King Bed | Fast Wi-Fi | 75" Smart TV
It was a comfortable stay. Tons to do in the area. Can’t go wrong!

Safe perfect location near everything, 3+ bedrooms
The house is in a neighborhood of nice homes, peaceful and walkable. It was very clean and comfortable. The kitchen was so well organized with everything you need and the bathrooms were spotless. It’s in a perfect location to restaurants. Highly recommend and will reserve again.

The Country Life! Entire House.
Cathy was a great host, very responsive! House was great, it accommodated our family size perfect. The only thing in my opinion that was missing was washer and dryer access in the home. We were traveling with toddlers and couldn’t wash a load of clothes. But aside from that everything else was great.

Country charmer house near NIU
This is our second year staying at this beautiful and convenient Airbnb. Only 15 minutes from the NIU Convocation Center! Close to a great pizza place that will deliver to the Airbnb. Cynthia is very responsive and very flexible. We love this space!

White House on Wisconsin|Horticultural Hall |Sl 20
This is the perfect house for larger groups- we used it previously for my bachelorette and it was perfect for our wedding party! There’s enough space for everyone and we all very much appreciate the mix of king and queen beds!

4 bedroom home rental in quiet neighborhood
Quiet neighborhood, spacious and comfortable home. The yard is inviting and a great entertaining space! Very kind hosts.
Quick stats about house rentals in Woodstock
Total rentals
10 properties
Total number of reviews
800 reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Niko's Red Mill Tavern, Woodstock Theatre, and D.C. Cobb's
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- Wrigley Field
- United Center
- Racine North Beach
- Frank Lloyd Wright Home and Studio
- Wilmot Mountain Ski Resort
- Humboldt Park
- Six Flags Great America
- Lincoln Park Zoo
- Wicker Park
- Geneva National Resort & Club
- Grand Geneva Resort & Spa
- Skokie Country Club
- Garfield Park Conservatory
- Alpine Valley Resort
- Moraine Hills State Park
- Chicago Golf Club
- Brookfield Zoo
- The 606
- Illinois Beach State Park
- Rock Cut State Park
- Raging Waves Waterpark
- Black Sheep Golf Club
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Villa Olivia
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