
Holiday rentals in Greenfield
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Top-rated holiday rentals in Greenfield
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Sunny State Fair Sojourn!
Newly renovated upper unit in a 1902 Victorian home. 2 bedroom, one bath, kitchen, dining area, living room, and office space! Less than one block from Wisconsin State Fair Park, The Milwaukee Mile and local bus routes! Minutes from American Family Field, Milwaukee County Zoo, and more! Local shuttle to Summerfest and other concerts and sporting events withing walking distance! Private balcony, free parking for one car, private laundry in the unit. Owner occupied lower for over 25 years!

Mid-Century Modern Apartment
This stylish and spacious apartment provides the perfect stay. Experience convenience and comfort in this freshly updated one-bedroom apartment. Centrally located, with easy access to many attractions & amenities. The property is well located within 5 minutes from multiple freeway interchanges. Downtown Milwaukee is a quick 15 minute commute, while the American Family Field is a mere 10 minutes away. Apartment is situated on the second floor of a 3-unit building. Dedicated workspace provided.

Beautiful Bay View MKE Flat - w/parking!
This is a bright, sunny apartment on the upper level of a sweet little 1870's "Polish Flat" in the heart of Bay View, one of the city's most desirable neighborhoods! We are just steps away from some of Milwaukee's best restaurants, bars, taprooms, boutiques and coffee shops. The space features an efficiency kitchenette, living room, beautiful bedroom and renovated bathroom with walk-in shower! Close to East Side, Walker’s Point, Historic Third Ward, Summerfest, Mitchell Park and the airport.

★Cozy Beach Themed Home★2 Beds★Spacious Parking★
Welcome to this cozy beach themed home located in the heart of West Allis. Close to public transportation and a few minutes driving to State Fair Park, Milwaukee County Zoo, Potawatomi Hotel & Casino, bars, restaurants, and more! Peaceful and quiet residential spot with plenty of parking on premises (up to 3 cars.) Amenities include: Spacious Parking, Smart TV, WiFi, Self Check in, Fresh Sheets and Towels, Shampoo & Conditioner, Soap & Hand Sanitizer, Fully Stocked Kitchen, and much more!

Funky 2BR in Prime Bay View - w/ Parking
Perfectly located on the main strip of KK in MKE's eclectic Bay View directly next to restaurants and bars. Minutes from downtown, Summerfest, art museum. You’ll have the entire first floor of this sunny duplex. Stylishly designed - 2 bedrooms with Casper mattresses, a bright kitchen with seating area, record player, a work space in the master, and a comfy living room with a smart TV. The space has a small backyard area, an in-unit washer & dryer as well as 1 off-street parking space.

Entire historic home, ideal for families & pets.
Entire cozy, historic 1938 home. No cleaning or guest service fee! Family & Pet (dog/cat) 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; Laundry, Central AC, Hi Speed Wi-Fi; ample work space. Free off street parking. Plush towels and toiletries in bathrooms. Enjoy your visit to this historic garden community. Sleeps 7. Over 70 “5 Star” 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!

Nice 1 BR Apt, WIFI & Office, Near State Fair
This beautifully furnished upper duplex offers a cozy and comfortable living space in a safe and peaceful neighborhood. The kitchen comes fully equipped with all the necessary supplies for cooking and dining, and the garage and driveway provide convenient parking options. Stay connected with the included WIFI and watch YouTube TV. Nice Office space. Conveniently located near major freeways, downtown, hospitals, and the State Fair Grounds. Book now for a stress-free and enjoyable stay

KING BED/Amazing Location/Free parking/Wi-Fi
Enjoy a fun and relaxing stay with family or friends in this stylish, cozy, and comfortable lower unit, which features: 2 bedrooms (1 king, 1 queen ) 1 bathroom Fully equipped kitchen with dining table and designated coffee bar Living room with a 65” smart TV (Netflix included) Home office space Free parking spot Located just a short drive (4 min) from I94, this home offers easy access to all the city's major attractions * the ideal base for exploring the best of Milwaukee

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.

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.

Charming 1BR Loft • Parking + Walkable Location
Welcome to your stylish Milwaukee retreat! This 1BR loft blends historic Cream City charm with modern comfort. Soaring 15-ft ceilings, exposed brick, and oversized windows create a bright, open space. Enjoy a spacious king bed, fully stocked kitchen, and free off-street parking — rare in this neighborhood. Walk to the Third Ward, Walker’s Point, and Milwaukee’s best restaurants, breweries, shops, and the vibrant riverfront. Perfect for both work and play.
Popular amenities for Greenfield holiday rentals
Stay near Greenfield's top sights
Other great holiday rentals in Greenfield

Green space to stay

Elegant charm!

Historic Hawthorne House

Centrally-Located Modern Mid-Century Modern Apt

Historic Greendale, Milwaukee Attractions

Charming retro one-bedroom upper

Spacious 3-Bedroom Townhouse

Charming Milwaukee upper duplex near downtown.
When is the best time to visit Greenfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $161 SGD | $161 SGD | $181 SGD | $186 SGD | $199 SGD | $192 SGD | $204 SGD | $204 SGD | $194 SGD | $150 SGD | $127 SGD | $192 SGD |
| Avg. temp | -4°C | -3°C | 3°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 12°C | 5°C | -1°C |
Frequently Asked Questions
Do house rentals in Greenfield have a kitchen?
Absolutely! We offer over 40 house rentals with a kitchen in Greenfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Greenfield have free parking?
Absolutely! We offer over 30 house rentals with free parking in Greenfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Greenfield have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Greenfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Greenfield have wifi?
Absolutely! We offer over 40 house rentals with wifi in Greenfield. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Greenfield?
Greenfield has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Greenfield?
Yes! Work meets play with ease at over 30 vacation rentals in Greenfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Greenfield?
Make yourself at home in Greenfield by choosing from our most frequently booked neighborhoods. We have over 90 vacation rentals in Mount Olivet, over 90 vacation rentals in Hawley Farms, and over 50 vacation rentals in Euclid Park.
What are the most popular amenities for House Rentals in Greenfield?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with wifi, over 40 homes with air conditioning, over 30 homes with free parking, over 40 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Greenfield?
Four-legged friends are welcome in Greenfield. Choose from more than 10 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Greenfield?
Experience the best of Greenfield with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Quick stats about holiday rentals in Greenfield

Total holiday rentals
Explore 60 holiday rentals in Greenfield

Nightly prices starting at
Greenfield holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 1,750 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Greenfield holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Greenfield rentals

4.8 Average rating
Greenfield stays are highly rated by guests – averaging 4.8 out of 5!
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- Six Flags Great America
- Alpine Valley Resort
- Wilmot Mountain Ski Resort
- Erin Hills Golf Course
- Illinois Beach State Park
- Milwaukee County Zoo
- Riverside Theater
- Bradford Beach
- Sunburst
- Discovery World
- Milwaukee Public Museum
- Kettle Moraine State Forest - Northern Unit
- Betty Brinn Children's Museum
- Baird Center
- Little Switzerland Ski Area
- American Family Field
- Marquette University
- Lake Park
- Naval Station Great Lakes
- Gurnee Mills
- Lake Geneva Public Library
- Lake Geneva Cruise Line
- Racine Zoo
- Lake Geneva Ziplines & Adventures




