Vacation rentals in Greenfield

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Top-rated vacation rentals in Greenfield

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

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Guest favorite
A living room is presented with a gray sofa, a minimalist table, and wooden chairs. Natural light enters through large windows, accentuated by decorative curtains. A patterned area rug covers the floor, while a ceiling fan hangs above, contributing to the room's comfortable ambiance.
Apartment in West Allis
4.95 out of 5 average rating, 214 reviews

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!

Top guest favorite
The exterior of a two-story brick duplex is shown, featuring a welcoming entrance. Lush green lawns are bordered by manicured flower beds. Steps lead to the front door, flanked by hanging flower baskets and illuminated by wall-mounted lanterns. A concrete pathway curves gently through the yard.
Bungalow in Wauwatosa
4.98 out of 5 average rating, 254 reviews

Wauwatosa/MKE “Inglewood Place” Historic Place

Great location! Near all Milwaukee attractions and village of Wauwatosa.Cozy, upper two-bedroom duplex with keyless entry in quiet east Tosa. Extras such as ironed sheets, snacks and personal items are included. Walk to popular restaurants and bars 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. Near AmFam Field (Brewers stadium) and the lakefront. 4 miles to downtown Milwaukee.

Top guest favorite
Apartment in Milwaukee
4.98 out of 5 average rating, 44 reviews

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.

Top guest favorite
The exterior of a vintage two-story home in a sunlit setting is shown, featuring a soft yellow façade and green window trims. A white picket fence outlines a landscaped area, while mature trees provide shade along the walkway leading to the entrance.
Home in Greendale
5 out of 5 average rating, 66 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.

Superhost
A spacious living area features a blue sectional sofa and a yellow accent chair, offering an inviting seating arrangement. A brown coffee table sits on a patterned rug, while large windows allow for natural light. A desk with a chair is positioned nearby for work or leisure.
Home in West Allis
4.86 out of 5 average rating, 113 reviews

West Allis Oasis

Welcome to our cozy 2-bedroom, 1-bathroom home on a quiet street in a fantastic neighborhood. Dog-friendly and perfect for families or solo travelers, enjoy easy access to I-94 and the State Fair Park just a few blocks away. Our home offers a peaceful retreat with comfortable furnishings, a fully equipped kitchen, cozy bedrooms, and large fenced in yard. Relax and unwind in a tranquil environment after a day of exploring. Book your stay today for the perfect blend of comfort and convenience!

Guest favorite
A dining area features a round table surrounded by black chairs with plush white cushions. Sunlight filters through large windows, highlighting the vintage sideboard and plant. An inviting living space is visible through an archway, showcasing a blend of decor and natural light.
Bungalow in West Milwaukee
4.97 out of 5 average rating, 194 reviews

Adorn Abode

Charming upper level hygge bungalow (2 unit home total). Ten minutes from anywhere. Tucked away in the quiet village of West Milwaukee. Full of natural light and curated vintage decor. Walking distance to a few restaurants and bars, as well as the American Family Field. Enjoy a cocktail on the front balcony and watch the sunset while indulging in a classic vinyl collection. Small balcony off of the kitchen to watch the sunrise and enjoy a cup of coffee. Perfect for adventuring or relaxing.

Top guest favorite
The exterior of the vintage 1938 home features a white façade with multiple windows and a welcoming porch adorned with decorative railings. Natural light creates playful shadows on the walls, highlighting the architectural details and lush greenery surrounding the property.
Townhouse in Greendale
4.91 out of 5 average rating, 105 reviews

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.

Top guest favorite
A cozy sleeping area features a wrought iron bed with white linens and several pillows. Two nightstands with lamps are placed on either side. A fan is mounted on the ceiling, while emerald green curtains frame a window beside a floral wall art piece.
Apartment in West Allis
4.97 out of 5 average rating, 115 reviews

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

Guest favorite
Home in West Allis
4.87 out of 5 average rating, 180 reviews

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

Top guest favorite
A single-story ranch-style home is presented, featuring a well-maintained exterior with a light-colored stone façade. Green grass surrounds the property, complemented by neatly trimmed bushes and a paved walkway leading to the front door. The roof is covered with gray shingles under a partly cloudy sky.
Home in Wauwatosa
4.92 out of 5 average rating, 104 reviews

Relax close to everything in Milwaukee

Ranch Style home in a quiet Neighborhood. You will feel at home and comfortable! The home is well maintained and very clean. In the winters you could cozy up to a nice fire upstairs and relax with a glass of wine. Downstairs is a second fireplace you have going and play a game of pool. In The summer you can enjoy the three seasons room, with looking a cup of coffee and look at the planted flower garden. Close to the Wauwatosa village down town. Even closer to Elm Grove Village.

Guest favorite
Townhouse in Waukesha
4.93 out of 5 average rating, 186 reviews

Pet-Friendly | Large Yard | Fire pit | Sleeps 5

Wake up to the sunrise over a peaceful backyard and enjoy your favorite blend on your private balcony. Evenings are perfect by the fire pit under a starry sky. This renovated home has gas stove/oven, microwave, coffee maker, full-size fridge/freezer, in-unit washer & dryer, smart TV, and Wi-Fi - ideal for couples, small families, or traveling professionals. Only 1 mile from I-94 and 20 minutes from Milwaukee, blending quiet comfort with city convenience.

Top guest favorite
Home in Greenfield
4.95 out of 5 average rating, 21 reviews

Cozy, Cute, & Clean !

Cozy, Cute, and Clean! SHORT TERM fully furnished rental available in a quiet neighborhood of Greenfield! 20 minutes or less drive to: Downtown Milwaukee, Lake Michigan, Brady Street, Am-Fam Field, UW-Milwaukee, Marquette University; Advocate-Aurora, Ascension, & Froedtert Hospitals, stores, restaurants, and just 40 mins from the IL border! Utilities included In-Unit Washer/Dryer **Perfect for Travel Nurses/Techs, and Business Professionals**

Popular amenities for Greenfield vacation rentals

When is the best time to visit Greenfield?

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Frequently Asked Questions

  • 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.

  • 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.

  • 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.

  • 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 Hawley Farms, over 50 vacation rentals in Euclid Park, and over 90 vacation rentals in Mount Olivet.

  • 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 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 wifi?

    Absolutely! We offer over 40 house rentals with wifi 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.

  • 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 a kitchen, over 40 homes with air conditioning, over 30 homes with free parking, over 40 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Greenfield

  • Total vacation rentals

    Explore 60 vacation rentals in Greenfield

  • Nightly prices starting at

    Greenfield vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 1,750 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Greenfield vacation rentals include wi-fi 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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