Holiday Homes in Southeast Wisconsin

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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Holiday Homes in Southeast Wisconsin

Charming 5-bedroom house in Cedarburg
Enjoy cooking in this well-equipped kitchen with a central island, oven, and sink.

Charming 5-bedroom house in Cedarburg

10.0 out of 10, Exceptional, (4)
"Great property in the heart of Cedarburg. Loved walking to all the local restraunts."
The price is NZ$980
includes taxes & fees
5 Aug - 6 Aug
Charming 5-bedroom house in Cedarburg
Luxury 8-br Lake Home with Pool, Cinema, and Arcade in Oconomowoc on LacLaBelle
Dining

Luxury 8-br Lake Home with Pool, Cinema, and Arcade in Oconomowoc on LacLaBelle

10.0 out of 10, Exceptional, (1)
"We had the most amazing family getaway at this beautiful lakefront house! The location was perfect, right on the water with a huge backyard. We spent so much time relaxing by the pier, lounging in comfy chairs, and taking out the canoes and paddleboat on the lake. The large patio was a favorite spot, where we enjoyed making s’mores around the firepit.The kids had an absolute blast in the game room, which had everything we could have wanted—like a mini Chuck E. Cheese right at the house! There...
Luxury 8-br Lake Home with Pool, Cinema, and Arcade in Oconomowoc on LacLaBelle
Three bedrooms upstairs
Stunning hallway with a dining area, bookcase, and ornate frames.

Three bedrooms upstairs

9.6 out of 10, Exceptional, (66)
"Style is amazing I liked it, good place."
The price is NZ$435
includes taxes & fees
27 July - 28 July
Three bedrooms upstairs
Captain Cook: Walk to Lake, Hot Tub, Sleeps 9
Surrounded by lush greenery and a serene body of water, this residential area offers a peaceful community setting with well-maintained homes and clear roadways.

Captain Cook: Walk to Lake, Hot Tub, Sleeps 9

10.0 out of 10, Exceptional, (23)
"The house was exactly as listed and the location couldn't be beat. Very comfortable and clean. We loved our stay and will return for sure 😊❣️"
Captain Cook: Walk to Lake, Hot Tub, Sleeps 9
Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva
Kitchen equipped with a stove, microwave, dishwasher, and toaster.

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$543
includes taxes & fees
27 July - 28 July
Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva
3-bedroom vacation home just a short walk to Lake Michigan
Relax on the patio with a comfortable sectional sofa and enjoy a barbecue.

3-bedroom vacation home just a short walk to Lake Michigan

9.2 out of 10, Wonderful, (25)
"We were really looking forward to the stay, and it exceeded our expectations significantly. I appreciate how they turned a small house that could have just been a bit rundown into a very lovely space all around. "
The price is NZ$442
includes taxes & fees
11 Aug - 12 Aug
3-bedroom vacation home just a short walk to Lake Michigan
#2 Tamarack aka Como Escape · Como Escape 4 bed 3 bath by LAKE
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and oven, along with ample counter space.

#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$1,019
includes taxes & fees
29 July - 30 July
#2 Tamarack aka Como Escape · Como Escape 4 bed 3 bath by LAKE
Green bean casserole
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, light cabinetry, and a patterned rug.

Green bean casserole

Green bean casserole
Quiet House
Kitchen features a central island, sink, stove, and white countertop.

Quiet House

9.0 out of 10, Wonderful, (2)
"Great stay for attending Summerfest. Short trip to the festival. Place was tidy and comfortable."
The price is NZ$409
includes taxes & fees
6 Aug - 7 Aug
Quiet House
Warm spacious midsize home w/ comfort and fun
Enjoy a relaxing evening on the covered patio with a warm ambiance.

Warm spacious midsize home w/ comfort and fun

8.4 out of 10, Very good, (5)
"We enjoyed the location, easy to walk to places. The property had a lot of room but needed to be professionally cleaned before renting."
Warm spacious midsize home w/ comfort and fun
Private Country House near Lake Geneva, Como and Williams Bay
Enjoy a serene forest view from this deck with a table and chairs.

Private Country House near Lake Geneva, Como and Williams Bay

10.0 out of 10, Exceptional, (85)
"Several families stayed at this well-appointed property as part of a family reunion. We were 11 adults and 10 kids (ages 5-16), and this home worked so perfectly! Playground nearby. Stocked kitchen worked well. Plenty of comfy, spacious bedrooms, but the real winner is the large living room and sunroom! "
Private Country House near Lake Geneva, Como and Williams Bay
Stunning Upscale Retreat - Steps From Everything
Enjoy meals in the kitchen with a central island, oven, and stainless steel range hood, complemented by a dining area with a table and bench.

Stunning Upscale Retreat - Steps From Everything

9.8 out of 10, Exceptional, (27)
"Great location and super clean property. Highly recommend."
The price is NZ$888
includes taxes & fees
31 July - 1 Aug
Stunning Upscale Retreat - Steps From Everything
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
Escape to a serene courtyard oasis, surrounded by lush plants and a warm fire pit.

Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find

9.4 out of 10, Exceptional, (60)
"Clean, nice area, clise to restaurants and downtown"
The price is NZ$650
includes taxes & fees
31 July - 1 Aug
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
LAKEFRONT HIDDEN GEM !
Enjoy serene lakeside views from our picnic tables, positioned to take in the tranquil surroundings and picturesque dock.

LAKEFRONT HIDDEN GEM !

9.6 out of 10, Exceptional, (34)
"Greatly enjoyed our time here."
The price is NZ$2,350
includes taxes & fees
27 July - 28 July
LAKEFRONT HIDDEN GEM !
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
Stunning living area with a spiral staircase, comfortable sofa, and a large potted plant.

NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

2.0 star property
9.8 out of 10, Exceptional, (12)
"We stayed here with family and had a great time. The home is lovely and well furnished! Neighborhood safe and close to all the popular spots!"
The price is NZ$910
includes taxes & fees
18 Aug - 19 Aug
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle
Step outside to this inviting porch, featuring a comfortable chair and table, perfect for relaxing.

Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle

10.0 out of 10, Exceptional, (35)
"We had a wonderful stay at Maison La Belle - perfect location and plenty of space. Will definitely book again!"
Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle
Fully renovated lake front home on Delavan’s North Shore
Enjoy a spacious room with a large window offering a view of the surrounding area, a dining table, and a foosball table for entertainment.

Fully renovated lake front home on Delavan’s North Shore

9.0 out of 10, Wonderful, (2)
"Zach as a host was exceptional! Very responsive from start to finish. He was also very accommodating to our requests. The house was very clean and well stocked which is so important. We will definitely be back to enjoy Zach’s house and the lake. Thank you!! "
Fully renovated lake front home on Delavan’s North Shore
Waterfront Lake Cottage - Upper Nemahbin Lake
Relax in this inviting living room with a sofa, coffee table, and potted plant, offering a view of the lake through a sliding glass door.

Waterfront Lake Cottage - Upper Nemahbin Lake

9.6 out of 10, Exceptional, (27)
"We loved our stay. The home is cozy. Lake and pier and great. The owners are great with communicating. Would definitely come back!"
The price is NZ$1,486
includes taxes & fees
6 Aug - 7 Aug
Waterfront Lake Cottage - Upper Nemahbin Lake
Beach Theme Burlington Retreat
Relax in this stylish living room with a flat-screen TV, comfortable sofa, and dining area.

Beach Theme Burlington Retreat

9.8 out of 10, Exceptional, (22)
"We came into town for a wedding and had a great stay! Our family of 4 was comfortable and pleased! "
The price is NZ$512
includes taxes & fees
28 July - 29 July
Beach Theme Burlington Retreat
Does your dog need a vacation? We are people and pet friendly!
Enjoy meals in the open-plan living and dining area, complete with a dining table and comfortable seating.

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!
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 Southeast Wisconsin Hotel Reviews

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

10/10 Excellent
"The staff was so so accommodating. "
Coleen 2-night trip
Posted 1 day ago
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham