Default HTG hotel image

Greendale Vacation Rentals

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Greendale vacation rentals

A living room with a leather sofa, a round coffee table, and a dining area with a table and chairs.

1. Historic home - walk to village center. Original features with modern updates.

Historic home - walk to village center. Original features with modern updates.
Greendale
9.8 out of 10, Exceptional, (55 reviews)
"Stayed here many times. Great as always."
United States
Kristi T.
$297 nightly
The price is $324
Oct 1 - Oct 2
Total with taxes and fees
Historic home - walk to village center. Original features with modern updates.
A bedroom with a bed, bedside table, nightstand, ceiling fan, potted plant, window with blinds, and artwork on the wall.

2. The Plaza Hotel

The Plaza Hotel
3.0 star property
Downtown Milwaukee
8.8 out of 10, Excellent, (1,251 reviews)
"Parking was reasonable and close by"
United States
Danita
$180 nightly
The price is $213
Oct 13 - Oct 14
Total with taxes and fees
The Plaza Hotel
A living room with a ceiling fan, a sofa, a coffee table, and a dining area with a table and chairs.

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

Charming Bungalow / Heart of Bay View / Parking - Central Air - Deck
Bay View
10.0 out of 10, Exceptional, (39 reviews)
"Great place to stay in Milwaukee! The house was clean and very well stocked with everything we could need! I didn’t realize someone lived upstairs, but there wasn’t any issues with it. The neighborhood was close to many great things to do We would definitely stay here again!"
United States
Jenna H.
$354 nightly
The price is $417
Sep 29 - Sep 30
Total with taxes and fees
Charming Bungalow / Heart of Bay View / Parking - Central Air - Deck
A modern kitchen with light wood cabinets, a stainless steel refrigerator, a stove, and a marble countertop.

4. 3-bedroom bungalow with WiFi vibrant Milwaukee

3-bedroom bungalow with WiFi vibrant Milwaukee
Milwaukee
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful property! We had a great stay!"
United States
VJ P.
$361 nightly
The price is $426
Sep 28 - Sep 29
Total with taxes and fees
3-bedroom bungalow with WiFi vibrant Milwaukee
A modern kitchen with dark cabinets, a white island, blue bar stools, and a window with a view.

5. 6 Mi to Summerfest Park: Home w/ Game Room!

6 Mi to Summerfest Park: Home w/ Game Room!
3.0 star property
Cudahy
$450 nightly
The price is $522
Oct 4 - Oct 5
Total with taxes and fees
6 Mi to Summerfest Park: Home w/ Game Room!
A modern living room with a sectional sofa, a ceiling fan, large windows, and a TV.

6. Babich Building - 3 Bedroom - Upper Apt #4

Babich Building - 3 Bedroom - Upper Apt #4
West Allis
8.6 out of 10, Excellent, (7 reviews)
"Great property, but a little hot and hard to cool down."
United States
Laura
$344 nightly
The price is $376
Sep 28 - Sep 29
Total with taxes and fees
Babich Building - 3 Bedroom - Upper Apt #4
A bedroom with a wooden dresser, a patterned bedspread, a large mirror, and a wardrobe with sliding doors.

7. King Bed • Vintage Urban Oasis • Near MKE Airport

King Bed • Vintage Urban Oasis • Near MKE Airport
Town of Lake
$225 nightly
The price is $266
Sep 28 - Sep 29
Total with taxes and fees
King Bed • Vintage Urban Oasis • Near MKE Airport
A cozy outdoor seating area with wicker furniture and a glass table, set against a stone wall and under string lights.

8. Quincy Estate 5BR/3BA for Family Stays with Fireplace Park Views & Parking

Quincy Estate 5BR/3BA for Family Stays with Fireplace Park Views & Parking
Bay View
9.8 out of 10, Exceptional, (6 reviews)
" Easy check in, well stocked and perfect location. "
United States
robin h.
$588 nightly
The price is $694
Oct 4 - Oct 5
Total with taxes and fees
Quincy Estate 5BR/3BA for Family Stays with Fireplace Park Views & Parking
A bar area with a vintage cash register, a wooden counter, and a menu board.

9. Kegel`s Inn - Studio - Classic Apartment #3

Kegel`s Inn - Studio - Classic Apartment #3
West Allis
9.0 out of 10, Wonderful, (6 reviews)
"Great place"
Canada
Zachary
$168 nightly
The price is $188
Sep 28 - Sep 29
Total with taxes and fees
Kegel`s Inn - Studio - Classic Apartment #3
A deck with a table, chairs, and an umbrella.

10. Luxurious Craftsman Style Home in Famous Bay View with Hot Tub Oasis

Luxurious Craftsman Style Home in Famous Bay View with Hot Tub Oasis
Milwaukee
$443 nightly
The price is $522
Sep 28 - Sep 29
Total with taxes and fees
Luxurious Craftsman Style Home in Famous Bay View with Hot Tub Oasis
A dining area with a long table, pink chairs, and a chandelier.

11. Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers

Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers
Bay View
9.8 out of 10, Exceptional, (28 reviews)
"Best rental I’ve ever stayed at!!! Spacious, clean, cozy and had everything you could possibly need. Even left us some sweet and salty snacks! Highly recommend!!"
United States
Bobbie C.
$315 nightly
The price is $371
Oct 6 - Oct 7
Total with taxes and fees
Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers
Outdoor seating with wicker chairs and red umbrellas, a 'DO NOT ENTER' sign, and a building with 'noodles & company' signage.

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

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Johnson Woods
9.6 out of 10, Exceptional, (47 reviews)
"Nice quite spot close to highway"
United States
Dan K.
$305 nightly
The price is $360
Oct 13 - Oct 14
Total with taxes and fees
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
A courtyard with a wooden fence, a gravel path, and a variety of plants.

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

Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
Lower East Side
9.4 out of 10, Exceptional, (75 reviews)
"Clean, strong communication, great location. Thank you!"
United States
Jenna L.
$329 nightly
The price is $388
Sep 28 - Sep 29
Total with taxes and fees
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
A spacious living room with a spiral staircase, wooden flooring, a large potted plant, and a modern air conditioning unit.

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

Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions
Lower East Side
9.6 out of 10, Exceptional, (41 reviews)
"Great location to Brady Street."
United States
Andrew C.
$350 nightly
The price is $413
Sep 28 - Sep 29
Total with taxes and fees
Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions

15. Mins to State Fair & AmFam Field |Sleeps 12|4BR + Parking

Mins to State Fair & AmFam Field |Sleeps 12|4BR + Parking
Bluemound Heights
9.0 out of 10, Wonderful, (4 reviews)
"Great place to stay!"
United States
Suzanne S.
$472 nightly
The price is $556
Sep 28 - Sep 29
Total with taxes and fees
Mins to State Fair & AmFam Field |Sleeps 12|4BR + Parking
A living room with a brown leather sofa, a patterned rug, a coffee table, and a dining area with wooden chairs and a table.

16. Brewers Bungalow•Wauwatosa Craftsman•2 Bdrm •King Bed • Walk to Coffee & Dining

Brewers Bungalow•Wauwatosa Craftsman•2 Bdrm •King Bed • Walk to Coffee & Dining
Wauwatosa
10.0 out of 10, Exceptional, (4 reviews)
"This was an amazing property with a friendly host in a fun neighborhood. Recommend."
United States
Stephen B.
$253 nightly
The price is $293
Sep 28 - Sep 29
Total with taxes and fees
Brewers Bungalow•Wauwatosa Craftsman•2 Bdrm •King Bed • Walk to Coffee & Dining
A two-story stone building with a central entrance, symmetrical windows, and a small porch area.

17. The Residence at Uplifting Mansion

The Residence at Uplifting Mansion
Merrill Park
10.0 out of 10, Exceptional, (5 reviews)
"Excellent accommodations, but even better hosts!"
United States
Don T.
$348 nightly
The price is $397
Sep 28 - Sep 29
Total with taxes and fees
The Residence at Uplifting Mansion
A modern urban street with multi-story buildings, a traffic light, and a crosswalk.

18. Downtown Eastside gem near Fiserv Forum Water St Brady St

Downtown Eastside gem near Fiserv Forum Water St Brady St
Downtown Milwaukee
9.0 out of 10, Wonderful, (64 reviews)
"Nice condo, very convenient."
United States
Mark W.
$268 nightly
The price is $316
Sep 28 - Sep 29
Total with taxes and fees
Downtown Eastside gem near Fiserv Forum Water St Brady St
A sculpture of a human figure made of interconnected metal pieces, placed on a concrete base with a view of the sunset over the sea.

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

Peaceful East Side-2 min UWM-Dining-Coffee-Parking
Upper East Side
10.0 out of 10, Exceptional, (13 reviews)
"Great location and the host is fabulous!"
United States
Holly G.
$243 nightly
The price is $287
Sep 28 - Sep 29
Total with taxes and fees
Peaceful East Side-2 min UWM-Dining-Coffee-Parking
A modern kitchen with stainless steel appliances, a central island with stools, and wooden cabinetry.

20. New built w/free parking off Brady St. Fiserv Forum, Summer Fest and Lakefront!

New built w/free parking off Brady St. Fiserv Forum, Summer Fest and Lakefront!
Lower East Side
10.0 out of 10, Exceptional, (13 reviews)
"Clean neat, Close to everything"
United States
Kay H.
$316 nightly
The price is $373
Sep 28 - Sep 29
Total with taxes and fees
New built w/free parking off Brady St. Fiserv Forum, Summer Fest and Lakefront!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Greendale Hotel Reviews

Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

10/10 Excellent
"Excellent stay. The hotel was clean, quiet, and pleasant."
Andrea 2-night trip
Posted less than an hour ago
Hyatt Regency Milwaukee

Find out more about Greendale

Everything you need to know about Greendale vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Greendale vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greendale vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greendale vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greendale. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Greendale in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Greendale rentals

At Expedia, we put the best Greendale vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Greendale rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greendale vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greendale. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Greendale?

Yes, there are vacation rentals close to popular local attractions in Greendale, or you can go with a more remote option if you want a relaxing place to stay. Greendale is known for its restaurants.

What are some of the best vacation rentals that Greendale has to offer?

Three Bedroom Upper: This vacation home rental near Greendale is located near the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals will I find in Greendale?

Expedia has 5 vacation rentals for your stay in Greendale.

What’s there to see and do in Greendale?

While exploring the area, visit family-friendly sights like Pettit National Ice Center, or get outside and enjoy nature at Boerner Botanical Gardens. In the larger area, you’ll find Rock Snow Park and American Family Field.

What’s a vacation rental in Greendale like?

Vacation rentals are private properties where you can stay for several days or longer in Greendale. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for small groups.