Darien Holiday Rentals

    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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Darien

Timber Ridge Lodge and Waterpark

3.5 star property
8.6 out of 10, Excellent, (2903)
"The staff was amazing from check in to check out."
The price is NZ$394
includes taxes & fees
25 Aug - 26 Aug
Timber Ridge Lodge and Waterpark

Mill Creek Hotel

2.5 star property
9.2 out of 10, Wonderful, (1179)
"Love the Mill Creek! I had a wonderful stay over the fourth of July and really enjoyed the staff."
The price is NZ$447
includes taxes & fees
3 Aug - 4 Aug
Mill Creek Hotel

Experience Stay at the Glamping Loft Lake Geneva |Group Stays |12 Stylish Tent Suites |Kitchen & Bar

10.0 out of 10, Exceptional, (29)
"We came to Wisconsin for a bachelorette party! This place was described perfectly and was absolutely perfect for our girls! We are very very pleased and would recommend this highly!"
Experience Stay at the Glamping Loft Lake Geneva |Group Stays |12 Stylish Tent Suites |Kitchen & Bar

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

9.8 out of 10, Exceptional, (88)
"Overall a very nice stay (2 nights). Note that there are steep steps (indoors) up to the unit for anyone that may be challenged in stair-climbing and toting bags/luggage. The view is absolutely lovely. During high-season you might expect some noise as the location is right amidst the restaurants and tourist activities. It was wonderful to be able to walk to most everything we wanted to do. The kitchen was well-appointed and clean. Fun to sit out on the rooftop deck and listen to the...
The price is NZ$1,538
includes taxes & fees
30 July - 31 July
Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking

Ground- Level Lake Geneva Villa!

9.2 out of 10, Wonderful, (63)
"Weekend trip to enjoy the outdoors. Lots of places for walking "
The price is NZ$630
includes taxes & fees
6 Aug - 7 Aug
Ground- Level Lake Geneva Villa!

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

10.0 out of 10, Exceptional, (101)
"Great property for a big group and a terrific location!!"
Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage

Quiet 2bd 1ba ranch with off street parkingWalking distance to downtown/beach.

9.6 out of 10, Exceptional, (8)
Quiet 2bd 1ba ranch with off street parkingWalking distance to downtown/beach.

*LAKE GENEVA*⛵️ My Lake COMO WATERFRONT☀️ “My Place in the 🌞 Sun”❣️

10.0 out of 10, Exceptional, (62)
"Good location close to Lake Geneva beaches. Nice pool on property."
*LAKE GENEVA*⛵️ My Lake COMO WATERFRONT☀️ “My Place in the 🌞 Sun”❣️

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

9.8 out of 10, Exceptional, (185)
"We loved our time at the Downtowner. The rustic modern style was really fun, the rooms were cute and comfortable, and the kitchen was amazing! "
THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20

10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

9.4 out of 10, Exceptional, (8)
"Communication and check in was flawless.We had three generations for the holidays and this property was ideal for us.Property manager communication was easy and timely."
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

Private Country House near Lake Geneva, Como and Williams Bay

10.0 out of 10, Exceptional, (86)
"Good place to stay nice location "
Private Country House near Lake Geneva, Como and Williams Bay

Cozy Cabin in Williams Bay

9.0 out of 10, Wonderful, (60)
"Very convenient to William’s Bay."
Cozy Cabin in Williams Bay

LAKESIDE GEM ! ONE BLOCK FROM SHORELINE ! in fabulous Lake Geneva .

10.0 out of 10, Exceptional, (2)
"Had a fantastic stay at this stunning new house near the lake. The house is spotless, thoughtfully designed and fully equipped with everything you need for a relaxing and fun-filled stay.The location was perfect, which is just a short walk to the lake and some local restaurants. The patio deck is a perfect spot for morning coffee or an evening cocktail. The neighborhood was quiet and felt very safe. The beds are comfortable, and the kitchen had all the essentials and then some. The host was very...
LAKESIDE GEM ! ONE BLOCK FROM SHORELINE ! in fabulous Lake Geneva .

NEWLY Updated! Cove of Lake Geneva, Private Luxury Resort Pool View

9.0 out of 10, Wonderful, (99)
"Great location! "
NEWLY Updated! Cove of Lake Geneva, Private Luxury Resort Pool View

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

2.0 star property
9.4 out of 10, Exceptional, (8)
"Such a charming property in a great town. Close to so many things. Comfy, well appointed."
The price is NZ$549
includes taxes & fees
27 July - 28 July
Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva

THE ULTIMATE 6 BEDROOM LAKEHOUSE

9.8 out of 10, Exceptional, (33)
"Great house to entertain a larger group with views to the lake."
The price is NZ$2,799
includes taxes & fees
27 July - 28 July
THE ULTIMATE 6 BEDROOM LAKEHOUSE

#2 Tamarack aka Como Escape · Como Escape 4 bed 3 bath by LAKE

10.0 out of 10, Exceptional, (24)
"lovely 4 bedroom rental with things for all of us to do! Arcade, darts and a nice quiet patio to read a book!"
The price is NZ$982
includes taxes & fees
29 July - 30 July
#2 Tamarack aka Como Escape · Como Escape 4 bed 3 bath by LAKE

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

10.0 out of 10, Exceptional, (156)
"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!

Williams Bay beach cottage with hot tub on 2-acres

9.6 out of 10, Exceptional, (39)
"Had a fun weekend getaway with friends and this property was the perfect place to reconnect and hangout outside. Slept everyone comfortably and we had a blast. "
The price is NZ$2,022
includes taxes & fees
20 Aug - 21 Aug
Williams Bay beach cottage with hot tub on 2-acres

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

10.0 out of 10, Exceptional, (29)
"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
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Darien Hotel Reviews

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?

Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva: This holiday home rental outside of Darien is located near skiing, and offers a balcony, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 Williams Bay Beach. In the wider area, you’ll find Lake Lawn Resort Marina and Dancing Horse Theatre.

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.