Holiday Homes in Darien

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Featured Holiday Homes in Darien

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

Beautiful Log Cabin Retreat on 6 Acres of Forest Only 10 Minutes to Lake Geneva.

10.0 out of 10, Exceptional, (67)
"We celebrated my daughter's 16th birthday with her friends at this quiet cabin in the woods. Perfect for them to sing using the karaoke machine without bothering anyone! They also enjoyed the hot tub. Close to Lake Geneva for shopping too. The owner was very responsive and helpful when we didn't have heat when we arrived. It was an easy fix and we had a great stay!"
Beautiful Log Cabin Retreat on 6 Acres of Forest Only 10 Minutes to Lake Geneva.

Historic Lake Geneva 🏡. Walk 2 Everything! IN THE ❤️ OF DOWNTOWN!!

10.0 out of 10, Exceptional, (28)
"The location was excellent. Close to the lake, lakefront path and the downtown area. The back porch and communal areas were all wonderful to hang out in and catch up with old friends. More than enough towels available to use. I wish there were more showers, but we somehow managed as we didn't have tight schedules. I can't imagine 19 people staying there as with 12, we were pretty tight. But overall, we really enjoyed our stay."
Historic Lake Geneva 🏡. Walk 2 Everything! IN THE ❤️ OF DOWNTOWN!!

Log home Lake Koshkonong and Rock River !

10.0 out of 10, Exceptional, (25)
"Very relaxing and peaceful!! Home was very spacious!!"
Log home Lake Koshkonong and Rock River !

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

10.0 out of 10, Exceptional, (6)
Spacious 4 BDR Home in Desirable Abbey Springs! Pool, Beach, Golf, & More

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

9.8 out of 10, Exceptional, (180)
"Perfect for big groups. Everything is within walking distance. Coffee, shopping, drinks, food, and so much more! Owner is very responsive. Thanks for sharing your home with us!"
THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20

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$1,079
includes taxes & fees
2 Dec - 3 Dec
Downtown Hideaway - Entire Building |Fun, Convienent & Comfortable |Sleeps 14 |1000+ 5 Star Reviews

Welcome To Our Lake House!<br>

9.8 out of 10, Exceptional, (56)
"Adult annual girls trip! Perfect place to stay right on the lake! We enjoyed every minute of our stay! Thank you so much! We’ll definitely be back!"
Welcome To Our Lake House!<br>

Sleeps 17! DOWNTOWN LAKE GENEVA Fully Licensed for Weekend Rentals!

10.0 out of 10, Exceptional, (43)
"The property was as advertised, good communication from the host, comfortably able to sleep our 11. We will be coming back!"
Sleeps 17! DOWNTOWN LAKE GENEVA Fully Licensed for Weekend Rentals!

Pet-Friendly Home w/ Views of Lake Delavan!

8.8 out of 10, Excellent, (12)
"We had a wonderful stay. Our stay was a very busy weekend, doing the wedding cake and flowers. because one of our daughter's were getting married in a nearby town. the house was beautiful and spacious enough room for everybody. Will definitely stay again. "
Pet-Friendly Home w/ Views of Lake Delavan!

Charm& Chic in DT Lake Geneva Flexible Home Rental

10.0 out of 10, Exceptional, (23)
"Well, equipped, loved the kitchen because we cooked our meals, walking distance to everything we needed, overall great experience"
Charm& Chic in DT Lake Geneva Flexible Home Rental

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!

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

10.0 out of 10, Exceptional, (12)
Spacious 3 BDR 15 Min Walk to Beach & Downtown Dining!

Cozy Vacation Home Near Delavan Lake!

10.0 out of 10, Exceptional, (1)
"Our stay was wonderful! The place was clean, in a quiet neighborhood, and very comfortable. The house is only a couple blocks from the lake, so we walked our dog through the neighborhood daily. Roy was super responsive with anything we needed. Would definitely stay here again!"
Cozy Vacation Home Near Delavan Lake!

White House on Wisconsin-Main House |Renovated Colonial Revival |Steps to Horticultural Hall |Prking

10.0 out of 10, Exceptional, (6)
"Perfect location for us. Lovely home!"
The price is AU$1,454
includes taxes & fees
2 Dec - 3 Dec
White House on Wisconsin-Main House |Renovated Colonial Revival |Steps to Horticultural Hall |Prking

AMAZING LAKE GENEVA ABBEY SPRINGS HOME + HOT TUB + 2 GOLF CARTS!

9.8 out of 10, Exceptional, (12)
"We're 3 retired couples that annually get together for 3-4 days. This year we chose Lake Geneva as a new area to explore. This VRBO is in a gated community with beautiful homes and a golf course. It was early November so did not utilize the amenities of the community but did enjoy hikes, drives for tail end fall color, and dining in local haunts. The VRBO itself feels a bit dated. One couple noted the bathroom showed water damage from failed caulk, and the dishwasher likely had sat empty...
AMAZING LAKE GENEVA ABBEY SPRINGS HOME + HOT TUB + 2 GOLF CARTS!

Huge house for large groups! Basketball court, arcade, putting green.4 bathroom

2.0 star property
6.0 out of 10, (1)
"We enjoyed our stay, just had to clean a little first. We were not allowed to receive the address before the day of our arrival and we were driving 8 hours. By the time we got on our way, we couldn't access VRBO website. It kept saying they were having issues. So we had to find a number to call. Gentleman we reached sent us the address and access code. Other than some inconveniences, it was a great place for a lot of people. "
Huge house for large groups! Basketball court, arcade, putting green.4 bathroom

Beloit Home w/ Deck: 3 Mi to Health System Campus

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was a clean, comfortable and lovely home. It was located in a nice and quiet neighborhood. We especially enjoyed hanging out on the back deck. Definitely recommend!"
Beloit Home w/ Deck: 3 Mi to Health System Campus

HOT TUB + Large Groups + Fireplace + Game Room

10.0 out of 10, Exceptional, (3)
"We love this property. It's spacious, private, and full of amenities that suit our family: big kitchen, patio, hot tub, and tons of fun activities in the basement."
HOT TUB + Large Groups + Fireplace + Game Room

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$705
includes taxes & fees
3 Dec - 4 Dec
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.
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Other property types in Darien

Timber Ridge Lodge and Waterpark

3.5 star property
8.6 out of 10, Excellent, (2562)
"Not a poor experience at all! My daughter had a great time! Here is some feedback: Staff - All pleasant and helpful! Food choices on site - could have a quicker option for breakfast, maybe some healthier choices too. Everything is fried and packaged. Rooms - A bit outdated, hard to shower in the jacuzzi tub set up The last thing is not anything reflecting the lodge itself... our neighbor had kids that were beyond disrespectful and loud late at night and very earlier in the morning (4am)......
The price is AU$297
includes taxes & fees
16 Dec - 17 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
2 Dec - 3 Dec
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$705
includes taxes & fees
3 Dec - 4 Dec
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

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.