Milwaukee Vacation Homes

A city skyline with modern skyscrapers and a river in the foreground.

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Our top choices for Milwaukee holiday homes

1. Quiet House

Milwaukee

Laterrance G.

HK$1,669 total

includes taxes & fees

1 Sept - 2 Sept

Coffee/tea maker, fridge, microwave, oven

2. Remodeled Home - Steps from Brady Street!

Downtown Milwaukee

David M.

HK$2,228 total

includes taxes & fees

7 Sept - 8 Sept

3. Best location in Milwaukee! Upper Duplex Unit

Downtown Milwaukee

Janice B.

HK$1,320 total

includes taxes & fees

2 Sept - 3 Sept

4. The Nohl | A Lake Effect Stay Near Brady Street

Lower East Side

HK$2,103 total

includes taxes & fees

1 Sept - 2 Sept

5. The Pink Lady - Stylish Walker’s Point Home

Fifth Ward

syed a.

HK$2,672 total

includes taxes & fees

8 Sept - 9 Sept

6. The Bentley - Frida's Reign, Heart of Walkers Point w/Garage,Yard

Fifth Ward

Holly B.

HK$2,310 total

includes taxes & fees

28 Sept - 29 Sept

7. 2bed 1.5bath House, Lower Eastside, King Bed, Fire Pit, Sleeps 6

Downtown Milwaukee

Kristen M.

HK$5,757 total

includes taxes & fees

4 Sept - 5 Sept

8. Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions

Lower East Side

Lyndsay K.

HK$3,476 total

includes taxes & fees

1 Sept - 2 Sept

9. Three Bedroom Upper

Riverwest

Crystiana H.

HK$1,854 total

includes taxes & fees

1 Sept - 2 Sept

10. Charming 2-bedroom house with everything you need in the heart of West Allis

West Allis

Renee W.

HK$1,943 total

includes taxes & fees

7 Sept - 8 Sept

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

Lower East Side

Jenna L.

HK$3,264 total

includes taxes & fees

1 Sept - 2 Sept

12. Charming Bungalow / Heart of Bay View / Parking - Central Air - Deck

Bay View

Pamela M.

HK$3,485 total

includes taxes & fees

7 Sept - 8 Sept

13. Modern 4BR Retreat w/ Workspace + Coffee Bar

Milwaukee

"The condo was very clean. Had a very nice coffee bar. Beds were comfortable. The internet was terrible. We count on it for work and we could not access it for the first 5 days of our day. Contacted the management company early in our stay & they were not able to help us. The initial 2 people that I dealt with had no idea where the router was located. Very frustrating! By the time we were able to access it & reboot it is was late in our stay. Even then the signal was weak. Left a day early. If...

Joan B.

HK$3,697 total

includes taxes & fees

1 Sept - 2 Sept

4 bedrooms, desk, iron/ironing board, travel cot

14. Workspace + Fireplace + Coffee Bar + Sleeps 12

Milwaukee

Chris B.

HK$3,690 total

includes taxes & fees

8 Sept - 9 Sept

15. Peaceful East Side-2 min UWM-Dining-Coffee-Parking

Upper East Side

Holly G.

HK$2,351 total

includes taxes & fees

1 Sept - 2 Sept

16. Barclay House in Walker's Point

Fifth Ward

Tom L.

HK$3,180 total

includes taxes & fees

22 Sept - 23 Sept

17. Sunny & Spacious 4BR East Side Stay ¦ Balcony ¦ Family-Friendly

Upper East Side

Mike G.

HK$3,017 total

includes taxes & fees

7 Sept - 8 Sept

18. Tranquil Downtown Haven | 3-Bed, 2-Bath Delight

Downtown Milwaukee

Quinn M.

19. House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

Johnson Woods

Mark K.

HK$2,570 total

includes taxes & fees

9 Sept - 10 Sept

20. Superb cozy 4-bedroom building in vibrant Milwaukee

Milwaukee

HK$2,728 total

includes taxes & fees

7 Sept - 8 Sept

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Top Milwaukee Hotel Reviews

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

10/10 Excellent

"The front desk was amazing and so helpful with checking us in and showing us where to park...we have already booked our next stay!"

AmericInn by Wyndham Glendale/Milwaukee

8/10 Good

"The check in process was good, the staff was friendly, the breakfast was good, there was a good variety of items to choose from. The room was clean. The AC unit was a bit noisy, but we got used to it after a while. The shower had plenty of hot water. The motel is located close to a shopping center in case you want to do a little shopping. All in all, it was a good stay at the AmericInn by Wyndham Glendale/Milwaukee"

The Iron Horse Hotel

8/10 Good

"The Iron Horse Hotel is visually stunning. The lobby and dining areas feature a fantastic industrial design with exposed brick, heavy timber beams, vintage motorcycles, and vibrant artwork. The staff is extremely helpful and welcoming, and the room's bathroom was beautifully designed. However, there are a few areas for improvement. First, the on-site restaurant closes at 10:00 PM, which is too early, especially on weekends. Second, at the outdoor bar, I was served a drink in a noticeably dirty glass. When I asked for a replacement, the bartender simply poured the existing drink from the dirty glass directly into a clean one rather than pouring a fresh drink. Finally, the room itself showed significant wear and tear. The carpeting had a tripping hazard from buckling, dark creases, and a bleached spot. The animal-hide ottoman was heavily worn with a hole on top, and the bathroom vanity had a burnt-out bulb, indicating a lapse in basic maintenance. Despite these issues, the beautiful atmosphere and great staff make this a place I would definitely stay again."

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