Southeast Wisconsin Holiday Rentals

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Holiday Rentals in Southeast Wisconsin

Timber Ridge Lodge and Waterpark

3.5 star property
8.6 out of 10, Excellent, (2605)
"Amazing place "
The price is AU$278
includes taxes & fees
9 Jan - 10 Jan 2025
Timber Ridge Lodge and Waterpark

The Plaza Hotel

3.0 star property
8.6 out of 10, Excellent, (1053)
"Great for kitchenettes and proximity to Milwaukee Museum of Art."
The price is AU$302
includes taxes & fees
29 Dec - 30 Dec
The Plaza Hotel

Kasa Westown Milwaukee

4.0 star property
9.0 out of 10, Wonderful, (66)
"Would've preferred a tv in the bedroom too and an additional comforter for the sofa bed. Other than that, it was pretty good. "
The price is AU$198
includes taxes & fees
6 Jan - 7 Jan 2025
Kasa Westown Milwaukee

Mill Creek Hotel

2.5 star property
9.2 out of 10, Wonderful, (1147)
"Could use updating "
The price is AU$271
includes taxes & fees
29 Dec - 30 Dec
Mill Creek Hotel

New Years!! Hot Tub, Fishing Pond, Events! Winter Discounts! Weddings, Pool

9.8 out of 10, Exceptional, (194)
"We stayed here for the weekend and it was wonderful! The kids loved the playset outside and the game room! Definitely would recommend to other groups and families. "
New Years!! Hot Tub, Fishing Pond, Events! Winter Discounts! Weddings, Pool

Amazing Five Bedroom Milwaukee Vacation Home!!

10.0 out of 10, Exceptional, (40)
"I went to detox, relax, and swim for a few days and did not bring family, but this is a terrific place for a family getaway with amazing pool, video games, plenty of beds, etc. Pleasant neighborhood as well. "
Amazing Five Bedroom Milwaukee Vacation Home!!

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$808
includes taxes & fees
2 Jan - 3 Jan 2025
Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking

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

10.0 out of 10, Exceptional, (26)
"Glamping Loft is a beautiful place for a ladies' getaway. The ambiance is warm and like a fairytale. It has everything you need if you want to bring in your own food and drinks or if you'd rather hit the town, Lake Geneva is right out the front door. I would definitely go back again. "
The price is AU$1,331
includes taxes & fees
22 Jan - 23 Jan 2025
Experience Stay at the Glamping Loft Lake Geneva |Group Stays |12 Stylish Tent Suites |Kitchen & Bar

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

9.2 out of 10, Wonderful, (7)
"The house was great. The pool temp was very warm when we arrived we did our best to cool it down. We really enjoyed the stay."
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

Charming Riverwest Retreat

9.4 out of 10, Exceptional, (16)
"Which the property had off street parking. The kitchen did not have pot-holders and tissues. Nice property."
Charming Riverwest Retreat

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

9.0 out of 10, Wonderful, (95)
"The property was beautiful, great location for walking. Love the decor. The bed was so comfy. Thank you for a great anniversary! "
NEWLY Updated! Cove of Lake Geneva, Private Luxury Resort Pool View

Step right up, step right up! Welcome to the grand, the unique, the unparalleled

9.8 out of 10, Exceptional, (67)
"The house was very roomy and lots of places to hang out with family and friends. It was awesome that it was close to the lake. The owner had forgotten we were coming and didn’t have the refrigerator cleaned out and our check-in process was a little awkward because we didn’t have the keypad information. "
Step right up, step right up! Welcome to the grand, the unique, the unparalleled

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

10.0 out of 10, Exceptional, (232)
"I booked this property for a reunion with some old friends, with the intention that we would be spending a lot of time hanging out. This property was perfect for that -- lots of beds and bathrooms. A beautiful view of the lake from the main living area and two of the bedrooms. Lots of amenities/activities including a pool table, ping pong, a fire pit, etc. But perhaps the best feature was the openness of the kitchen/dining room/pool table/family room, which meant that you feel connected to...
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

Historical Downtown Geneva Bungalow |Upper Unit |Parking for 3 |Walkable |Near Shops & Restaurants

10.0 out of 10, Exceptional, (53)
"Stayed there for a business retreat...loved the space. Very cozy and comfortable. Would definitely stay there again."
The price is AU$708
includes taxes & fees
1 Jan - 2 Jan 2025
Historical Downtown Geneva Bungalow |Upper Unit |Parking for 3 |Walkable |Near Shops & Restaurants

Indoor Kidquariam, Large Group Equipped, EnglishPrairieBnB

10.0 out of 10, Exceptional, (35)
"Our family had a blast! Everyone from ages 4 months to 64 years old had a great time. This house was perfect for hosting a large multi-family gathering. Rainy weather did not ruin our trip since there was so much to do inside. The kids enjoyed the bounce house, the digital game table, board games, and of course the pool! The host went above and beyond with special touches including having burp cloths, a soothing noise machine, and a nursery room set up! They even had an extra place to put the...
Indoor Kidquariam, Large Group Equipped, EnglishPrairieBnB

Poolside Lookout at the Cove Hotel |Downtown Lake Geneva |Hot Tub |Walkable |Resort Game Room & Gym

8.6 out of 10, Excellent, (14)
"This condo was the perfect size for our family and great location to food and shopping. "
The price is AU$590
includes taxes & fees
28 Dec - 29 Dec
Poolside Lookout at the Cove Hotel |Downtown Lake Geneva |Hot Tub |Walkable |Resort Game Room & Gym

SuMMeR IS HeRe BrinG ur boat and tie to dock, Tavern, huge DECK, KIDS jungle gym

8.6 out of 10, Excellent, (11)
"Enjoyed the spaces for young adults and parents to hang out together and separately. Had a fantastic time at the cabin and enjoyed the lake access for water sports."
SuMMeR IS HeRe BrinG ur boat and tie to dock, Tavern, huge DECK, KIDS jungle gym

Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!

10.0 out of 10, Exceptional, (16)
"The property was a good place to stay at! I will say it was what we needed for everyone to stay and have a place to sleep. The only issue with was trying to fit a vehicle in the garage. We took my friends Tahoe and it was a tough spot to fit in the garage, which we can tell it’s meant for smaller vehicles. And there were a pair of eyelashes set out on the coffee table. But overall for anyone with a bigger family or group of friends that need somewhere to stay I would recommend this location!"
The price is AU$881
includes taxes & fees
29 Dec - 30 Dec
Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!

Ground- Level Lake Geneva Villa!

9.0 out of 10, Wonderful, (62)
"Weekend trip to enjoy the outdoors. Lots of places for walking "
The price is AU$619
includes taxes & fees
6 Jan - 7 Jan 2025
Ground- Level Lake Geneva Villa!

Private Country House near Lake Geneva, Como and Williams Bay

10.0 out of 10, Exceptional, (74)
"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
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 types of properties in Southeast Wisconsin you may be interested in

The Pfister Hotel

4.5 star property
9.6 out of 10, Exceptional, (1574)
"My daughter had a wonderful time celebrating her birthday! "
The price is AU$279
includes taxes & fees
19 Jan - 20 Jan 2025
The Pfister Hotel

Saint Kate - The Arts Hotel

4.0 star property
9.8 out of 10, Exceptional, (2044)
"Lovely hotel"
The price is AU$244
includes taxes & fees
16 Jan - 17 Jan 2025
Saint Kate - The Arts Hotel

Hyatt Regency Milwaukee

4.0 star property
8.4 out of 10, Very good, (1120)
"Close to the arena "
The price is AU$179
includes taxes & fees
6 Jan - 7 Jan 2025
Hyatt Regency Milwaukee
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.