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Darien Holiday Rentals

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Our top choices for Darien holiday rentals

1. Blue Beach Cottage - 5 Minute Walk to Private Beach!

Blue Beach Cottage - 5 Minute Walk to Private Beach!
Delavan
9.8 out of 10, Exceptional, (27 reviews)
"Great spot to go with family or friends. The house was comfortable and clean, and the location was quiet. Close to the private beach which you could walk or drive to. Also had a huge backyard that was perfect for outdoor activities and dogs!"
United States
Rachel T.
The price is NZ$829
includes taxes & fees
25 Oct - 26 Oct
Blue Beach Cottage - 5 Minute Walk to Private Beach!

2. Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark
3.5 star property
Lake Geneva
8.6 out of 10, Excellent, (3,495 reviews)
"Great place for families looking for a quaint stay. My kids absolutely loved it. We will return"
United States
Kimberly L
The price is NZ$294
includes taxes & fees
24 Nov - 25 Nov
Timber Ridge Lodge and Waterpark

3. The Basecamp 3-bedroom house with AC in charming Walworth

The Basecamp 3-bedroom house with AC in charming Walworth
Walworth
7.6 out of 10, Good, (9 reviews)
"Nice cozy place to stay. Bed was comfortable. Close by everything. Easy check in and out process."
United States
Andrea M.
The price is NZ$460
includes taxes & fees
4 Nov - 5 Nov
The Basecamp 3-bedroom house with AC in charming Walworth

4. Suite 3. Breakfast at Tiffany's Suite. Downtown Williams Bay. Steps to Beach.

Suite 3. Breakfast at Tiffany's Suite. Downtown Williams Bay. Steps to Beach.
Williams Bay
10.0 out of 10, Exceptional, (3 reviews)
"Very clean, fun and new decor, well-stocked kitchen, great location, comfortable bed"
United States
Kathy C.
The price is NZ$417
includes taxes & fees
25 Oct - 26 Oct
Suite 3. Breakfast at Tiffany's Suite. Downtown Williams Bay. Steps to Beach.

5. Private 3br, with SwimSpa, Gym, by Hwy 43, 67 & 50-Alpine Valley, Ice Age Trail-

Private 3br, with SwimSpa, Gym, by Hwy 43, 67 & 50-Alpine Valley, Ice Age Trail-
Elkhorn
9.6 out of 10, Exceptional, (31 reviews)
"The property was perfect for our girls getaway. The attention to detail was amazing. I hope to stay there again in the future."
United States
carol g.
The price is NZ$1,361
includes taxes & fees
25 Oct - 26 Oct
Private 3br, with SwimSpa, Gym, by Hwy 43, 67 & 50-Alpine Valley, Ice Age Trail-

6. Mill Creek Hotel

Mill Creek Hotel
2.5 star property
Lake Geneva
9.2 out of 10, Wonderful, (1,273 reviews)
"clean, comfortable and great location"
United States
Marshall
The price is NZ$370
includes taxes & fees
1 Nov - 2 Nov
Mill Creek Hotel

7. Abbey Villas Condo Steps to Pool Walk to Fontana Beach Dining and Marina

Abbey Villas Condo Steps to Pool Walk to Fontana Beach Dining and Marina
Fontana-on-Geneva Lake
9.8 out of 10, Exceptional, (7 reviews)
"Great place - attentive and welcoming host."
United States
Beth N.
The price is NZ$824
includes taxes & fees
1 Nov - 2 Nov
Abbey Villas Condo Steps to Pool Walk to Fontana Beach Dining and Marina

8. Unit 5. Parent Trap Suite The American Hotel. Dwtn Williams Bay. Steps to beach.

Unit 5. Parent Trap Suite The American Hotel. Dwtn Williams Bay. Steps to beach.
Williams Bay
10.0 out of 10, Exceptional, (3 reviews)
"The Parent Trap Suite at The American Hotel was perfect. It had everything one could need for your stay in Lake Geneva. The location is phenomenal, right in the middle of downtown Williams Bay. Terese was the consummate hostess. I will definitely stay here again when I return to Lake Geneva."
United States
Patti W.
The price is NZ$416
includes taxes & fees
24 Nov - 25 Nov
Unit 5. Parent Trap Suite The American Hotel. Dwtn Williams Bay. Steps to beach.

9. 2728 Harbor Court

2728 Harbor Court
4.0 star property
Delavan
The price is NZ$2,542
includes taxes & fees
4 Nov - 5 Nov
2728 Harbor Court

10. The American Hotel - Suite 6. Downtown Steps to beach, restaurants, coffee shop.

The American Hotel - Suite 6. Downtown Steps to beach, restaurants, coffee shop.
Williams Bay
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful place to stay that is very clean!! Will absolutely be back!"
United States
Kevin
The price is NZ$417
includes taxes & fees
25 Oct - 26 Oct
The American Hotel - Suite 6. Downtown Steps to beach, restaurants, coffee shop.

11. Lake Como View Condo at Geneva National, Balcony, Seasonal Pool

Lake Como View Condo at Geneva National, Balcony, Seasonal Pool
Lake Geneva
8.8 out of 10, Excellent, (13 reviews)
"Location was perfect…walk to restaurants and kayak rental on Lake Como. Condo was very clean and met all our needs. Enjoyed the pool very much. Great stay!"
United States
Mary L.
The price is NZ$1,357
includes taxes & fees
31 Oct - 1 Nov
Lake Como View Condo at Geneva National, Balcony, Seasonal Pool

12. The Ridge Retreat Renovated in 2024 - Steps from Lake Como & The Ridge

The Ridge Retreat Renovated in 2024 - Steps from Lake Como & The Ridge
Lake Geneva
9.6 out of 10, Exceptional, (17 reviews)
"Great stay!"
United States
Katie O.
The price is NZ$1,103
includes taxes & fees
31 Oct - 1 Nov
The Ridge Retreat Renovated in 2024 - Steps from Lake Como & The Ridge

13. New Renovated! The American Hotel. Suite 1. A Summer Place. 1.5 Block from Lake

New Renovated! The American Hotel. Suite 1. A Summer Place. 1.5 Block from Lake
Williams Bay
10.0 out of 10, Exceptional, (2 reviews)
"This cute little property has a great location and was perfect for our weekend getaway."
United States
Jennifer R.
The price is NZ$416
includes taxes & fees
24 Nov - 25 Nov
New Renovated! The American Hotel. Suite 1. A Summer Place. 1.5 Block from Lake

14. The Little Farm Fontana 5 min from Geneva Lake!

The Little Farm Fontana 5 min from Geneva Lake!
Fontana-on-Geneva Lake
10.0 out of 10, Exceptional, (1 review)
"Cute little place in a convenient location for a fair price."
United States
Linda C.
The price is NZ$414
includes taxes & fees
26 Oct - 27 Oct
The Little Farm Fontana 5 min from Geneva Lake!

15. Modern Lake Geneva Condo With Views

Modern Lake Geneva Condo With Views
3.5 star property
Lake Geneva
The price is NZ$1,394
includes taxes & fees
27 Oct - 28 Oct
Modern Lake Geneva Condo With Views

16. Quaint, quiet condo minutes from Lake Geneva

Quaint, quiet condo minutes from Lake Geneva
Lake Geneva
9.6 out of 10, Exceptional, (40 reviews)
"Nice reasonable price"
United States
Angela
The price is NZ$634
includes taxes & fees
29 Oct - 30 Oct
Quaint, quiet condo minutes from Lake Geneva

17. Romantic Escape for 2 - Yerkes Candlelight Walk. Blocks away.

Romantic Escape for 2 - Yerkes Candlelight Walk. Blocks away.
Williams Bay
9.4 out of 10, Exceptional, (15 reviews)
"The host was wonderful, the house was perfect for our work trip. "
United States
Matt W.
The price is NZ$788
includes taxes & fees
2 Nov - 3 Nov
Romantic Escape for 2 - Yerkes Candlelight Walk. Blocks away.

18. Dome House on Whitewater Lake

Dome House on Whitewater Lake
Whitewater
10.0 out of 10, Exceptional, (3 reviews)
"Very quiet, clean and lots of amenities! We had a hiccup with the water/shower, and our host not only communicated quickly but had a plumber over to fix it before the day was over!! She went above and beyond to make our stay comfortable!! A very enjoyable stay!"
United States
Rachel
The price is NZ$841
includes taxes & fees
1 Nov - 2 Nov
Dome House on Whitewater Lake

19. Newly Updated Modern, Spacious, and Cozy Condo- Right on the Lake!

Newly Updated Modern, Spacious, and Cozy Condo- Right on the Lake!
Lake Geneva
9.8 out of 10, Exceptional, (26 reviews)
"Relaxing condo with easy access to town. "
United States
John L.
The price is NZ$749
includes taxes & fees
8 Nov - 9 Nov
Newly Updated Modern, Spacious, and Cozy Condo- Right on the Lake!

20. Modern Lakefront Condo, Weekly Stays Welcome, Work & Relax by the Lake

Modern Lakefront Condo, Weekly Stays Welcome, Work & Relax by the Lake
Lake Geneva
8.8 out of 10, Excellent, (104 reviews)
"This is our second time staying in this condo and we had another amazing experience. This condo is just perfect for a relaxing lake trip!"
United States
Nicole K.
The price is NZ$711
includes taxes & fees
29 Oct - 30 Oct
Modern Lakefront Condo, Weekly Stays Welcome, Work & Relax by the Lake
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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Top Darien Hotel Reviews

Find out more about Darien

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Darien holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Darien. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Darien. Seeing all the best attractions is bound to make you fall in love with Darien. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Darien short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Darien?

Yes, there are holiday rentals close to the most popular sights in Darien, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Darien has to offer?

Luxury Lake Geneva cottage w/ sauna + hot tub + geodesic dome on 2-acres: This holiday home rental outside of Darien is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Darien?

Explore the area and family-friendly sights such as Yerkes Observatory, or get out into nature at a spot like Delavan Lake. In the wider area, you’ll find Lake Lawn Resort Marina and Fontana Beach.

What are holiday rentals like in Darien?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Darien. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family trips or small group gatherings.