Photo by Erik Rowley

Holiday Homes in Woodstock

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Featured Holiday Homes in Woodstock

The Main Event Game House on the Huntley Square!

9.6 out of 10, Exceptional, (10)
"We had an amazing time during our stay! The house had a lot of character with antique details, like an old record player, tv and radio. There were many modern updates as well. The kitchen seemed pretty new and all of the appliances worked great! The house was clean and there was a lot of attention to detail. The hot and cold water are flipped in the shower, so beware! It is an older house, so be prepared for occasional creaking and settling noises. The game room is detached from the house and in...
The price is AU$466
includes taxes & fees
25 Nov - 26 Nov
The Main Event Game House on the Huntley Square!

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

9.8 out of 10, Exceptional, (80)
"This place was amazing. Located right in the center of it all. Communication was easy and everything was in order. The accommodations were clean, neat and beautifully decorated. The deck outside is amazing. It was a little chilly (November) however during the sunny daytime hours we enjoyed sitting out on the deck. This location is so close to everything. We enjoyed our stay."
The price is AU$635
includes taxes & fees
26 Nov - 27 Nov
Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking

Private Country House near Lake Geneva, Como and Williams Bay

10.0 out of 10, Exceptional, (73)
"This was the fourth year in a row that we have stayed at house in the woods. Each year I take my children and grandchildren and this year my first great grandchild a way to Wisconsin for a few days to really bond. This is a perfect place for a large group. We are a group of 20 adults and one infant and there is plenty of room for everyone to sleep comfortably and to be able to get privacy if they want it or otherwise to bond together with game playing and just playing conversations. I can’t...
Private Country House near Lake Geneva, Como and Williams Bay

Fox Lake "Funcation" ★ 3 King Beds ★ Chain O Lakes

9.6 out of 10, Exceptional, (61)
"Needed a place for our family and this worked great. It was a little smaller than we thought but it worked for our trip. Was very easy towork with management and they were very responsive to my requests and questions. Woul highly recommend. "
Fox Lake "Funcation" ★ 3 King Beds ★ Chain O Lakes

Spacious 4 BDR Home in Desirable Abbey Springs! Pool, Beach, Golf, & More

10.0 out of 10, Exceptional, (6)
"We booked a last minute stay here, for a group of 10. The house was absolutely exceptional! Full of amenities, was spotless clean, this house has it all. The pool/hot tub/game room was more than we expected and the kids loved it. The beds were very comfortable. I definitely recommend this place!"
Spacious 4 BDR Home in Desirable Abbey Springs! Pool, Beach, Golf, & More

Enchanting Lake Woods Retreat |Near Water Access |Fire Pit |Deck |Screened-in Gazebo |Tranquil Stay

8.0 out of 10, Very good, (1)
"The home was very cozy nice environment and area . Beds were very comfortable couch was very comfortable. I have little complaints. The washer machine didn’t work it didn’t spin all the way out. The property manager being on site is good and weird at the same time, but he didn’t bother us it was just a little odd. I would recommend this canin stay "
Enchanting Lake Woods Retreat |Near Water Access |Fire Pit |Deck |Screened-in Gazebo |Tranquil Stay

Cozy and Private Home Located within Minutes of Downtown and the Water

9.6 out of 10, Exceptional, (60)
"We had a wedding in the area and this property was perfectly located to downtown lake Geneva and many resorts. The property had two bedrooms upstairs for the kids, one was a loft with two twin beds but worked well to put a pack and play. Property was clean and decorated cutely. Definitely would stay again!"
Cozy and Private Home Located within Minutes of Downtown and the Water

Tulip Hill – Peaceful 4 BDR on Lake Como, 10 Min to Lake Geneva!

9.0 out of 10, Wonderful, (4)
"Property was nice. Clean and the beds were comfy.Only beef about the neighborhood was one inconsiderate that kept revving his engine and that would get his dog barking. I would stay here again,absolutely! Any questions I had were answered promptly."
Tulip Hill – Peaceful 4 BDR on Lake Como, 10 Min to Lake Geneva!

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (56)
"Got to stay in this wonderful home while visiting my son and his family. I loved it!"
The price is AU$487
includes taxes & fees
3 Dec - 4 Dec
Quaint Bungalow, near Great Lakes Naval Base

Downtown Hideaway - Entire Building |Fun, Convienent & Comfortable |Sleeps 14 |1000+ 5 Star Reviews

9.8 out of 10, Exceptional, (15)
"This place is in a perfect location to everything. We didn’t have to drive anywhere. Very clean and immediate response from owners about questions we had. Would definitely stay there again!"
The price is AU$1,078
includes taxes & fees
26 Nov - 27 Nov
Downtown Hideaway - Entire Building |Fun, Convienent & Comfortable |Sleeps 14 |1000+ 5 Star Reviews

Modern Home, Fire Pit, Golf Cart Included, Dog Friendly, Sleeps 6

10.0 out of 10, Exceptional, (15)
"The house was great. Lots of areas inside and out to eat and relax. Took walks along Lake Como, everyone is very friendly in the area. Only 10 minutes to Lake Geneva. Would stay again."
Modern Home, Fire Pit, Golf Cart Included, Dog Friendly, Sleeps 6

Lake/Beach Getaway (Remodeled)

9.8 out of 10, Exceptional, (26)
"Great location. Great view. Nice to be close to the park."
The price is AU$511
includes taxes & fees
24 Nov - 25 Nov
Lake/Beach Getaway (Remodeled)

Dog-friendly lakefront home with water toys, firepit, 2 kitchens, & 2 W/Ds

9.2 out of 10, Wonderful, (7)
"Perfect location and weather. "
Dog-friendly lakefront home with water toys, firepit, 2 kitchens, & 2 W/Ds

The Tailor House

10.0 out of 10, Exceptional, (38)
"A relaxing well appointed home with easy walking distance to downtown Woodstock!"
The price is AU$443
includes taxes & fees
26 Nov - 27 Nov
The Tailor House

New Construction! Community beach access on beautiful Lake Elizabeth!

10.0 out of 10, Exceptional, (22)
"The house was perfect with plenty of room and bathrooms! The family room and screened in porch with fireplaces were awesome! A great place to stay near Lake Geneva"
The price is AU$718
includes taxes & fees
25 Nov - 26 Nov
New Construction! Community beach access on beautiful Lake Elizabeth!

Historic Retreat - steps from the Lake and Downtown

10.0 out of 10, Exceptional, (24)
"We had a very nice weekend staying at the Maxwell House! The renovations in the home are beautiful, there is a lot of space, and the location is perfect! We were blessed with good weather, so we walked all over town. We hope to come back again. "
Historic Retreat - steps from the Lake and Downtown

Cottage walking distance to Lake Geneva!

10.0 out of 10, Exceptional, (31)
"Everything was great! Perfect size for my friend and I. Not too far from downtown. Zero problems while we were there and honestly no complaints. They got back to me fast if I had a question. We had a great time! "
Cottage walking distance to Lake Geneva!

Quaint Sleep 8 In Downtown Walk to Lake Pets OK

9.6 out of 10, Exceptional, (48)
"we really enjoyed ourselves, house is right next to in town in quiet area (only slight negative is gas station next door but that wasn't a problem as it turned out). Spacious, clean, all good. would stay again."
Quaint Sleep 8 In Downtown Walk to Lake Pets OK

#1 - Magnolia · LARGE 5 Bed Lake Geneva Home 4 Blocks from Lake!

9.8 out of 10, Exceptional, (19)
"Large space for 4 guys on golf weekend. Very well organized and communication with the host was great."
The price is AU$756
includes taxes & fees
25 Nov - 26 Nov
#1 - Magnolia · LARGE 5 Bed Lake Geneva Home 4 Blocks from Lake!

Spacious 3 BDR 15 Min Walk to Beach & Downtown Dining!

10.0 out of 10, Exceptional, (12)
"The house was spacious, clean and well stocked. It was a 10-minute walk to main street and the water. The patio on the house was amazing for hanging out and relaxing. The host was in constant contact. We would rent here again."
Spacious 3 BDR 15 Min Walk to Beach & Downtown Dining!
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.
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Other property types in Woodstock

Timber Ridge Lodge and Waterpark

3.5 star property
8.6 out of 10, Excellent, (2562)
"Clean and accessible for everyone old and young"
The price is AU$297
includes taxes & fees
9 Dec - 10 Dec
Timber Ridge Lodge and Waterpark

Mill Creek Hotel

2.5 star property
9.2 out of 10, Wonderful, (1135)
"Beautiful boutique hotel. "
The price is AU$216
includes taxes & fees
24 Nov - 25 Nov
Mill Creek Hotel

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

9.8 out of 10, Exceptional, (80)
"This place was amazing. Located right in the center of it all. Communication was easy and everything was in order. The accommodations were clean, neat and beautifully decorated. The deck outside is amazing. It was a little chilly (November) however during the sunny daytime hours we enjoyed sitting out on the deck. This location is so close to everything. We enjoyed our stay."
The price is AU$635
includes taxes & fees
26 Nov - 27 Nov
Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking
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.
Beautiful view of the beach with palm trees

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