Holiday rentals in Greendale

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Top-rated holiday rentals in Greendale

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Superhost

Townhouse in Greendale

4.79 out of 5 average rating, 58 reviews

Historic Greendale, Milwaukee Attractions

A Greendale "original" designated historic dwelling within walking distance of the quaint village of downtown Greendale. Walk to Ricardo's pizza, a local wine bar, frozen custard shop, upscale Joey Gerard's, bar and grill and BBQ restaurants. Also, local boutique shops. Greendale also hosts some local festivals year-round, outdoor concerts at the Gazebo and Farmer's market. A short drive from Milwaukee and all this great city has to offer. Newly renovated porcelain tile flooring in kitchen!

7–14 Oct

$118 SGD per night

Guest favourite

Home in Milwaukee

4.95 out of 5 average rating, 133 reviews

Bay View Beau - Near 3rd Ward, Summerfest, Fiserv

Beautifully appointed 2 bedroom, 1 bath with all of the comforts of home! Fast internet, private space, great for remote working. Lower unit in duplex, built in 1906, has been lovingly updated to reflect current design sensibilities while preserving the house’s historic character. Perfect for groups or a couple that wants to stretch out. Great location, next to Humboldt Park and short walk to all that Bayview has to offer. Short drive to 3rd Ward, Fiserv, Festival Park. Sorry No Parties please.

4–11 May

$209 SGD per night

Guest favourite

Townhouse in Greendale

4.87 out of 5 average rating, 46 reviews

Entire home, ideal for families & pets.

Entire cozy, historic 1938 home. Family, pet friendly; steps from playground or historic Village Center w/shopping, dining, wine bar; 15 min to downtown MKE or Airport; 6 min from Rock Sports Complex or WI State Fair Park. Full kitchen with new cookware; Laundry, AC, Hi Speed Wi-Fi; ample work space. Plush towels in bathrooms and toiletries available if you forgot yours. Bring your bikes, kids, pets and enjoy the paths of this garden community. Sleeps 7. No extra cleaning or guest service fee !

23–30 Oct

$177 SGD per night

Guest favourite

Guest suite in Brookfield

4.99 out of 5 average rating, 182 reviews

In the Canopy (beautiful Brookfield/Milwaukee)

Relax "in the Canopy" of beautiful maples! We’re a Superhosted, verified Guest Favorite, available for the GOP Convention! A comfortable retreat in a tree-filled neighborhood, just a few minutes from all the best Milwaukee has to offer. Perfect location for quick access to the city, or to Lake Country to the west. Quiet, comfortable, safe, surrounded by beautiful gardens. We’re in a perfect launching spot to visit Summerfest, Brewers/Bucks games, or Milwaukee's western suburbs. Bring the kids!

30 May – 6 Jun

$155 SGD per night

Guest favourite

Flat in Milwaukee

4.89 out of 5 average rating, 193 reviews

Bay View Historic Home-1/2 block from Lake

This old Victorian home is perfect for an urban experience with the charm of an old home. A 1/2 block from the lake, the location offers lakefront walks in the heart of Milwaukee's trendiest neighborhood. Around the corner is an Italian grocery, Indy music venue, and numerous trendy restaurants. Downtown attractions are 10 minutes away by car & easilyaccessible by bus. Here's a link to a very fast moving video tour of the neighborhood: https://www.visitmilwaukee.org/neighborhoods/bay-view/

1–8 Nov

$110 SGD per night

Superhost

Home in Greendale

4.92 out of 5 average rating, 12 reviews

Cozy, historic home in walkable Greendale village

Your family will be close to everything when you stay at this centrally-located, original but renovated 3 bedroom/1.5 bath in the Historic Village of Greendale. Enjoy a stroll through the walkways connecting various parks, shopping and dining on just a few blocks away on Broad Street. You'll love the friendly village vibe. Just an easy 15 minute drive from downtown/lakefront, if you are in the mood for a city vibe. We hope you enjoy this cozy home and the village of Greendale as much as we do!

26 Apr – 3 May

$248 SGD per night

Guest favourite

Home in Greendale

5.0 out of 5 average rating, 37 reviews

A Showplace of Greendale History on Apple Court

This entire 3 bedroom home is a vintage gem in Historic Greendale, Wisconsin — and it's all yours! • NO extra charge for cleaning! • FREE on-site parking for two cars • An EASY walk to charming boutiques & eateries • Located in a National Historic Landmark district • Steeped in 1930s History with Eleanor Roosevelt design features Features stylish, functional layout as part of FDR’s 1930s New Deal. Includes high speed Internet, central air conditioning, private patio for outdoor enjoyment.

24–31 Aug

$225 SGD per night

Guest favourite

Home in Wauwatosa

4.98 out of 5 average rating, 177 reviews

Wauwatosa/Milwaukee 10 Minutes from Downtown

Great location near all Milwaukee attractions. Cozy upper two bedroom duplex with keyless entry in quiet Tosa. Extras such as ironed sheets, snacks and personal items are included. Walk to popular bars and restaurants in the village and along North Ave. Full kitchen and new beds make this a home away from home. 10 min to Froedtert & The Medical College of WI & Children’s Hospital of WI. Near Am Fam Field (Brewers stadium) and the lakefront. 4 miles to downtown Milwaukee. COME STAY WITH US!

22–29 Jan

$177 SGD per night

Guest favourite

Townhouse in Milwaukee

4.94 out of 5 average rating, 363 reviews

Vintage Bay View - Big Backyard, Big 1 Bedroom

Welcome to your Milwaukee getaway! Located in the Bay View area, you're walking distance from the best farm-to-table restaurants, music venues, art fairs, and craft beer in the city. Not only that, but Lake Michigan's beaches, Miller Park, and downtown are a short drive away. The location is ideal. The place was created with a 70's midwestern feel, with wood-paneled furniture pieces and mod design. It also boasts a giant kitchen and backyard with grill. We can't wait for you to visit!

24–31 May

$115 SGD per night

Guest favourite

Guest suite in Brookfield

4.88 out of 5 average rating, 107 reviews

Family Friendly - Entire Guest suite

The lower level of our single family home is perfect for families of all kinds . It will give you all the comforts of home, including a spacious backyard, free parking, full-size kitchen, trampoline, fire pit, and a basketball hoop! Our home is 10 mins or less from: the Milwaukee County Zoo, Am Fam Field, STATE FAIR PARK; 15-25 min to downtown, Lake Michigan, numerous inland lakes including Pewaukee; 20 mins to airport; 35 mins to Alpine Valley & 15 MINS TO SUMMERFEST!

9–16 Aug

$173 SGD per night

Superhost

Flat in West Allis

4.78 out of 5 average rating, 269 reviews

Kegel's Inn - Studio - Classic Apartment #3

Quaint little studio with lots of old-world character. This one-room studio has original hardwood floors, heavy wood ceiling beams and 1930's tile work in the bathroom. The apartment looks down on 59th street, which for the summer months between May and November, hosts the Kegels Beer Garden on the street! We're one of the last Authentic German restaurants and Inn's left in country and the studio apartment is right above it! We hope you love this place as much as we do!

3–10 May

$130 SGD per night

Superhost

Flat in West Allis

4.79 out of 5 average rating, 154 reviews

Station No 06 Inn

Very spacious two bedroom condo style apartment completely remolded and updated. Located behind Wild Roots restaurant which offers fine dining in a casual setting. The Award Wining West Allis Cheese & Sausage Shoppe (deli & cafe), Station No 06 beer garden, and Becher Meats are across the street. Once you arrive you won't need to leave, and you get two free breakfast sandwiches and house coffee per adult per stay at the cheese shop are amazing!

7–14 Nov

$128 SGD per night