Photo by Erik Rowley

Holiday Homes in Woodstock

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
3 Oct - 5 Oct
In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov

Featured Holiday Homes in Woodstock and around

Our top choices for Woodstock holiday homes

Charming 3-bedroom house in Grayslake
Fridge, microwave, oven, stovetop

Charming 3-bedroom house in Grayslake

9.8 out of 10, Exceptional, (17)
"Fells like home very cozy calm area definitely a get away relaxing place "
The price is €448
includes taxes & fees
27 Sept - 28 Sept
Charming 3-bedroom house in Grayslake
Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (106)
"Out bachelor party stay was fantastic, everything about the trip was a breeze! "
Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage
Large Lakefront Home on Lake Como - Private Pier!
Fridge, microwave, oven, stovetop

Large Lakefront Home on Lake Como - Private Pier!

9.8 out of 10, Exceptional, (23)
"We had a wonderful time, enjoying the amenities of the house and the surrounding area. I would 100% recommend it to family and friends."
Large Lakefront Home on Lake Como - Private Pier!
Cottage walking distance to Lake Geneva!
Property grounds

Cottage walking distance to Lake Geneva!

10.0 out of 10, Exceptional, (38)
"Comfortable cottage with great kitchen and 2 porches. We used it as a home base while visiting Lake Geneva, Elkhorn and Madison. I would definitely recommend it for anyone visiting Lake Geneva. "
Cottage walking distance to Lake Geneva!
4Bed 3.5Ba Cozy New Construction! Close to Lake Geneva!
Outdoor dining

4Bed 3.5Ba Cozy New Construction! Close to Lake Geneva!

10.0 out of 10, Exceptional, (32)
"Beautiful home, tons of room for a family. Close easy drive to Lake Geneva. We enjoyed it so much we definitely will be back."
The price is €390
includes taxes & fees
25 Sept - 26 Sept
4Bed 3.5Ba Cozy New Construction! Close to Lake Geneva!
THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20
Fridge, microwave, oven, stovetop

THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20

9.8 out of 10, Exceptional, (190)
"I booked this property for a bachelorette party and everyone had a great time! It is in the perfect location for being able to walk to everything, which was perfect for a large group! The kitchen/living room space was perfect for all the girls to hang out together and play games. Parking is very limited, but there is a free lot nearby that we were able to utilize as well. "
THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20
Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva

2.0 star property
9.4 out of 10, Exceptional, (11)
"Had a great trip and the property was perfect for the 4 of us. Really appreciated the accessible shower."
Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva
Chic 3 bedroom Get-a-way in downtown Lake Geneva
Fridge, microwave, oven, stovetop

Chic 3 bedroom Get-a-way in downtown Lake Geneva

9.8 out of 10, Exceptional, (8)
The price is €280
includes taxes & fees
25 Sept - 26 Sept
Chic 3 bedroom Get-a-way in downtown Lake Geneva
Does your dog need a vacation? We are people and pet friendly!
Fridge, microwave, oven, stovetop

Does your dog need a vacation? We are people and pet friendly!

10.0 out of 10, Exceptional, (162)
"Had a great time. Location is perfect, grandaughter loved the play set. We had wonderful family time."
Does your dog need a vacation? We are people and pet friendly!
This is a VACATION spot with a million dollar view!
Exterior

This is a VACATION spot with a million dollar view!

9.8 out of 10, Exceptional, (16)
"The house was beautiful and very close to my sisters house"
The price is €532
includes taxes & fees
29 Sept - 30 Sept
This is a VACATION spot with a million dollar view!
Lake Front 2.20 acre estate Private boat launch with pier
Interior

Lake Front 2.20 acre estate Private boat launch with pier

9.8 out of 10, Exceptional, (19)
"Great stay. Everything that was listed was there and more. We utilized all of their courts/fields throughout the weekend and it was a really great time."
Lake Front 2.20 acre estate Private boat launch with pier
Fully renovated lake front home on Delavan’s North Shore
Games room

Fully renovated lake front home on Delavan’s North Shore

9.0 out of 10, Wonderful, (4)
"Great place to stay. Super clean, owner was great with communication. Very nice place to stay. Only small issue was the water in the shower was hot and cold. Then you are really close with the house behind you. Owner was awesome. "
Fully renovated lake front home on Delavan’s North Shore
3-bedroom House in Cozy Mundelein with Private Patio and Grill
Microwave, oven, stovetop, dishwasher

3-bedroom House in Cozy Mundelein with Private Patio and Grill

10.0 out of 10, Exceptional, (3)
"We had a great stay. Comfortable beds and plenty of space. "
3-bedroom House in Cozy Mundelein with Private Patio and Grill
Charming 4 Bedroom home in the heart of Elgin
Fridge, microwave, oven, stovetop

Charming 4 Bedroom home in the heart of Elgin

9.6 out of 10, Exceptional, (36)
"Cute older house with nice details. Will definitely stay again when visiting family. Lots of stairs."
Charming 4 Bedroom home in the heart of Elgin
Williams Bay Lake House-1 Block to Geneva Lake
Interior

Williams Bay Lake House-1 Block to Geneva Lake

9.6 out of 10, Exceptional, (39)
"Great place. "
Williams Bay Lake House-1 Block to Geneva Lake
Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking
Beach

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

9.8 out of 10, Exceptional, (92)
"Located right in town with a view of the lake and beach with a wonderful balcony."
The price is €486
includes taxes & fees
1 Oct - 2 Oct
Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Terrace/patio

Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!

9.8 out of 10, Exceptional, (90)
"We loved the beach the kids could have stayed there all day! Fishing was wonderful too! Such a fun house!"
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Stunning Lakeside Retreat: Delavan Lake Home w/ Lake Views & Private Lake Access
Exterior

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

10.0 out of 10, Exceptional, (31)
"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! "
Stunning Lakeside Retreat: Delavan Lake Home w/ Lake Views & Private Lake Access
All You Need Is Your Fur Baby And The Beach! (% of each stay donated to rescue)
Property grounds

All You Need Is Your Fur Baby And The Beach! (% of each stay donated to rescue)

10.0 out of 10, Exceptional, (48)
"Property was very nice, clean, and decorated well. Had a great time catching up around a camp fire on the backyard patio while our dogs played in the fenced yard."
The price is €455
includes taxes & fees
1 Oct - 2 Oct
All You Need Is Your Fur Baby And The Beach! (% of each stay donated to rescue)
Beautiful and spacious lakefront home! Close to everything!
Exterior detail

Beautiful and spacious lakefront home! Close to everything!

9.6 out of 10, Exceptional, (51)
"A three night stay We were comfortable and pleased with all the amenities. Fishing by the dock, kayaking and enjoying an adult beverage. A magical place to celebrate a new stage. Just one hour away but distant enough to relax the mind "
Beautiful and spacious lakefront home! Close to everything!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Woodstock Hotel Reviews

The Cove Of Lake Geneva

The Cove Of Lake Geneva

10/10 Excellent
"Beds were very comfortable."
Leanne 2-night trip
Posted 2 days ago
The Cove Of Lake Geneva

Find out more about Woodstock

Find out more about Woodstock

Woodstock Holiday Homes information

Number of reviews
972
Accommodation
559 Holiday Homes
Lowest Price
€280
Highest Price
€532

Explore a world of travel with Expedia

Explore a world of travel with Expedia