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Vacation rentals in Greendale

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Top-rated vacation rentals in Greendale

Guests agree: these stays are highly rated for location, cleanliness, and more.

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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!

Oct 5 – 12

G$18,028 GYD per night

Townhouse in Greendale

4.87 out of 5 average rating, 47 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 !

Dec 2 – 9

G$27,154 GYD per night

Guest suite in Brookfield

4.99 out of 5 average rating, 183 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!

Sep 9 – 16

G$31,176 GYD per night

Apartment 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/

Sep 15 – 22

G$21,063 GYD per night

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!

May 2 – 9

G$37,916 GYD per night

Home in Greendale

5.0 out of 5 average rating, 38 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.

Sep 6 – 13

G$34,396 GYD per night

Home in Greendale

4.83 out of 5 average rating, 52 reviews

Designer Home in Walkable Historic Greendale

Situated in an ideal walkable location, the Villager on Arrowwood is an absolute gem in the heart of the historic Village of Greendale. Freshly updated with a modern style and mid century touches. Work from the office which includes a fold-out couch. Enjoy dual outdoor spaces with the front screened porch and large backyard with patio. Just steps from Village's inviting downtown shops and restaurants - the perfect place to experience the unique charm and history of Greendale!

May 6 – 13

G$30,213 GYD per night

Apartment in Wauwatosa

4.83 out of 5 average rating, 263 reviews

Tosa Village Studio Apartment

Tosa Village Studio. (Wauwatosa is the first suburb west of Milwaukee). Walk to the Village and explore the boutique shops, restaurants and bars. Enjoy summer concerts in Hart Park. Miller Park (Milwaukee County Stadium - Home of the Brewers) only 3.5 miles away. Close to the Medical Complex, Froedert and Children's Hospitals. 6.5 miles to the Fiserv Forum (Home of the Milwaukee Bucks). Six miles to downtown Milwaukee. Enjoy Summerfest at the Lake Michigan shore.

Oct 2 – 9

G$17,002 GYD per night

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!

Aug 9 – 16

G$24,670 GYD per night

Apartment in West Allis

4.91 out of 5 average rating, 253 reviews

The Cheese House

Large well appointed two bedroom, living room, dining room, kitchen, and private balcony. Apartment is located on the second floor right above the award winning West Allis Cheese & Sausage Shoppe. Each stay includes 4 breakfast sandwiches and house coffee vouchers for the cheese store cafe. The rental is centrally located minutes from Pettit National Ice Center, Milwaukee County Zoo, Wisconsin State Fair, and Brewers Stadium not to mention local restaurants.

Jan 18 – 25

G$28,116 GYD per night

Home in Greendale

4.97 out of 5 average rating, 71 reviews

The Robin's Roost LLC

Relax with the whole family at this peaceful place to stay. Located within walking distance to the Fabulous Rock Sports Complex. You can also enjoy Luxe Golf Bays, a high tech, 250 yd turf driving range with 57 bays equipped with Track management range technology. You can also dine here, or at the other 2 restaurants. You will be just 2 miles from, Historic Downtown Greendale, featuring unique shops, boutiques, restaurants and cafés.

Mar 16 – 23

G$34,474 GYD per night

Apartment in Elkhorn

4.95 out of 5 average rating, 330 reviews

FarmWise Country Stay by Alpine Valley/Lake Geneva

Retreat to a quiet countryside experience at this all organic farm, where you can sit back, relax, and enjoy the country charm of your private space inside the main farm house. Optional for you are joining us for early morning chores in the barn. If you tell me the night before, you can try milking Carmel, the cow by hand, feeding the pig, collecting eggs from the chicken coop and more. Most loved of all are our friendly cats!

Nov 30 – Dec 7

G$19,805 GYD per night

Vacation rentals for every style

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Popular amenities for Greendale vacation rentals

Free parking on premises

Air conditioning

Stay near Greendale's top sights

Southridge Mall15 locals recommend

The Rock Sports Complex3 locals recommend

Ricardo's Pizza6 locals recommend

Panther Pub & Eatery3 locals recommend

Joey Gerard's - A Bartolotta Supper Club5 locals recommend

Blüm Coffee Garden3 locals recommend

Other great vacation rentals in Greendale

Townhouse in Greenfield

4.9 out of 5 average rating, 21 reviews

Spacious 3-Bedroom Townhouse

Sep 26 – Oct 3

G$32,735 GYD per night

Home in West Allis

4.92 out of 5 average rating, 12 reviews

Green Valley Homes - Updated Lower Apartment

Mar 7 – 14

G$19,348 GYD per night

Guest suite in Cudahy

4.94 out of 5 average rating, 69 reviews

RARE Private Butler’s Suite in Historic Home

Jul 29 – Aug 5

G$17,895 GYD per night

Home in Milwaukee

5.0 out of 5 average rating, 13 reviews

Entire Cozy Cottage! Pet Friendly, No Cleaning Fee

Dec 8 – 15

G$27,462 GYD per night

Home in West Allis

5.0 out of 5 average rating, 29 reviews

Pet Friendly, Calm + Near It All

May 15 – 22

G$27,012 GYD per night

Home in Oak Creek

4.9 out of 5 average rating, 49 reviews

Spacious Ranch Home Oak Creek close to Airport

May 5 – 12

G$29,959 GYD per night

Apartment in Cudahy

5.0 out of 5 average rating, 82 reviews

Cudahy Gem. 1 bdr apt. near airport & downtown MKE

May 20 – 27

G$21,325 GYD per night

Home in Milwaukee

4.96 out of 5 average rating, 70 reviews

Charming Milwaukee Bungalow Apartment

Sep 8 – 15

G$13,433 GYD per night

Destinations to explore