Caledonia Holiday Rentals

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Holiday Rentals in Caledonia

Heated Pool, Hot Tub, Fishing Pond, Game Room, Events!! Fall Discounts! Weddings
Outdoor pool, a heated pool

Heated Pool, Hot Tub, Fishing Pond, Game Room, Events!! Fall Discounts! Weddings

9.8 out of 10, Exceptional, (193)
"Me and 9 of my friends rented this space it was very affordable for all the amenities that it came with. Robert was very responsive to messaging before and during our stay. The property is huge and built for all kinds of activities. Can’t wait to book again! "
Heated Pool, Hot Tub, Fishing Pond, Game Room, Events!! Fall Discounts! Weddings
The Plaza Hotel
Classic Room, 2 Queen Beds

The Plaza Hotel

3.0 star property
8.6 out of 10, Excellent, (1050)
"Love this hotel. Its so cute and in the middle of everything. Breakfast is amazing "
The price is AU$290
includes taxes & fees
1 Dec - 2 Dec
The Plaza Hotel
Kasa Westown Milwaukee
Fireplace

Kasa Westown Milwaukee

4.0 star property
9.0 out of 10, Wonderful, (64)
"Loved it very clean and beautiful room most definitely coming back"
The price is AU$155
includes taxes & fees
8 Dec - 9 Dec
Kasa Westown Milwaukee
Charming Riverwest Retreat
Living area

Charming Riverwest Retreat

9.4 out of 10, Exceptional, (16)
"Which the property had off street parking. The kitchen did not have pot-holders and tissues. Nice property."
Charming Riverwest Retreat
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River
Pool

Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

10.0 out of 10, Exceptional, (321)
"Great house for being in the lake. Has a nice backyard that is fenced in and was perfect for our dogs. "
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Property grounds

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

10.0 out of 10, Exceptional, (231)
"I booked this property for a reunion with some old friends, with the intention that we would be spending a lot of time hanging out. This property was perfect for that -- lots of beds and bathrooms. A beautiful view of the lake from the main living area and two of the bedrooms. Lots of amenities/activities including a pool table, ping pong, a fire pit, etc. But perhaps the best feature was the openness of the kitchen/dining room/pool table/family room, which meant that you feel connected to...
The price is AU$934
includes taxes & fees
4 Dec - 5 Dec
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Step right up, step right up! Welcome to the grand, the unique, the unparalleled
Exterior

Step right up, step right up! Welcome to the grand, the unique, the unparalleled

9.8 out of 10, Exceptional, (67)
"The house was very roomy and lots of places to hang out with family and friends. It was awesome that it was close to the lake. The owner had forgotten we were coming and didn’t have the refrigerator cleaned out and our check-in process was a little awkward because we didn’t have the keypad information. "
Step right up, step right up! Welcome to the grand, the unique, the unparalleled
Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!
Fridge, microwave, oven, stovetop

Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!

10.0 out of 10, Exceptional, (14)
"The property was a good place to stay at! I will say it was what we needed for everyone to stay and have a place to sleep. The only issue with was trying to fit a vehicle in the garage. We took my friends Tahoe and it was a tough spot to fit in the garage, which we can tell it’s meant for smaller vehicles. And there were a pair of eyelashes set out on the coffee table. But overall for anyone with a bigger family or group of friends that need somewhere to stay I would recommend this location!"
The price is AU$826
includes taxes & fees
30 Nov - 1 Dec
Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!
Sleeps up to 30 people comfortably, there's karaoke pool table and so much more.
Exterior

Sleeps up to 30 people comfortably, there's karaoke pool table and so much more.

8.0 out of 10, Very good, (9)
"We were unable to check in until several hours after the check in time due to a plumbing issue the host did not proactively communicate about. Host did not use the entry keypad code they requested we set. The listing indicated 7 bedrooms for a total of 2 king beds, 1 queen, 10+ twin beds, and additional futons. On arrival there was only 1 double bed, 10 twin beds, a couple of futons. We had to make alternate accommodations for half our group. The host did not respond to outreach at all the first...
The price is AU$1,307
includes taxes & fees
27 Nov - 28 Nov
Sleeps up to 30 people comfortably, there's karaoke pool table and so much more.
Historic House, Frank Lloyd Wright-Designed House In Milwaukee, WI
Dining

Historic House, Frank Lloyd Wright-Designed House In Milwaukee, WI

9.6 out of 10, Exceptional, (232)
"Communication with the property manager was excellent. Fabulous opportunity to experience a FLW home. The property could be challenging for seniors because there are no handrails associated with the steps in and outside the house."
Historic House, Frank Lloyd Wright-Designed House In Milwaukee, WI
Urban Oasis minutes to Fiserv, Summerfest & more
Interior

Urban Oasis minutes to Fiserv, Summerfest & more

8.8 out of 10, Excellent, (13)
"Great location, lovely, plant-filled space. Bummer that the shampoo and soap were empty in bathroom and there was nothing complimentary in kitchen beyond salt and pepper. Coffee filters, but no coffee or tea or anything. Very minimalist. Clean a d super comfortable."
The price is AU$365
includes taxes & fees
1 Dec - 2 Dec
Urban Oasis minutes to Fiserv, Summerfest & more
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (53)
"Home was large and well appointed. Great central location for all the Milwaukee activities we did. "
The price is AU$617
includes taxes & fees
2 Dec - 3 Dec
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
Booth Upper · Amazing view, Modern Space
Exterior

Booth Upper · Amazing view, Modern Space

10.0 out of 10, Exceptional, (35)
"Loved everything about this place. Spacious, nice, well stocked, great view of the city. Really liked how it was close enough to the city to get there in 10 minutes, but far enough to have some quiet and privacy. Not sure if I’ll ever visit Milwaukee again but I will definitely look for this place again if I do."
Booth Upper · Amazing view, Modern Space
Nice three 3 bedroom unit with free parking and wi-fi
Fridge, microwave, oven, stovetop

Nice three 3 bedroom unit with free parking and wi-fi

6.0 out of 10, (18)
"Could use updated, but was clean and comfortable."
The price is AU$313
includes taxes & fees
1 Dec - 2 Dec
Nice three 3 bedroom unit with free parking and wi-fi
15 minutes to anywhere in and around Milwaukee.
Exterior

15 minutes to anywhere in and around Milwaukee.

10.0 out of 10, Exceptional, (29)
"Each summer two of my adult children and I go on a baseball excursion to a baseball stadium we haven't been to before. This was walking distance from American Family Park. Our hosts were friendly and helpful and our stay was comfortable. We had easy access by car to restaurants and entertainment venues. It was a great place to stay., "
15 minutes to anywhere in and around Milwaukee.
MKE Mansion - Both Wings
Outdoor dining

MKE Mansion - Both Wings

9.8 out of 10, Exceptional, (12)
"The house is exactly as listed. There were some small functional issues with the house that the landlord responded to immediately. All around great stay. "
The price is AU$2,270
includes taxes & fees
1 Dec - 2 Dec
MKE Mansion - Both Wings
Walker's Point House Near Downtown Milwaukee
Outdoor dining

Walker's Point House Near Downtown Milwaukee

9.8 out of 10, Exceptional, (31)
"We were all very pleased with the property and the owner was very helpful. "
Walker's Point House Near Downtown Milwaukee
Safe location lively Wauwatosa and within 10 min of what Milwaukee has to offer.
Terrace/patio

Safe location lively Wauwatosa and within 10 min of what Milwaukee has to offer.

9.2 out of 10, Wonderful, (23)
"As listed, clean and perfect communication. Located a short walk from the shops on 68th and Wells, and a short drive to Marquette and downtown Milwaukee. "
The price is AU$574
includes taxes & fees
23 Dec - 24 Dec
Safe location lively Wauwatosa and within 10 min of what Milwaukee has to offer.
Stunning Lake Michigan Cottage
Interior

Stunning Lake Michigan Cottage

9.6 out of 10, Exceptional, (25)
"Host was extremely responsive and easy to work with"
Stunning Lake Michigan Cottage
Quaint Three-Bedroom Upper Level Duplex Apartment
Fridge, microwave, oven, stovetop

Quaint Three-Bedroom Upper Level Duplex Apartment

9.6 out of 10, Exceptional, (15)
"Unit was good size and clean. Enjoyed our trip!"
Quaint Three-Bedroom Upper Level Duplex Apartment
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.
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Other types of properties in Caledonia you may be interested in

Heated Pool, Hot Tub, Fishing Pond, Game Room, Events!! Fall Discounts! Weddings
Outdoor pool, a heated pool

Heated Pool, Hot Tub, Fishing Pond, Game Room, Events!! Fall Discounts! Weddings

9.8 out of 10, Exceptional, (193)
"Me and 9 of my friends rented this space it was very affordable for all the amenities that it came with. Robert was very responsive to messaging before and during our stay. The property is huge and built for all kinds of activities. Can’t wait to book again! "
Heated Pool, Hot Tub, Fishing Pond, Game Room, Events!! Fall Discounts! Weddings
Hilton Milwaukee
Lobby

Hilton Milwaukee

4.0 star property
8.2 out of 10, Very good, (1063)
"Good location! Walkable to Fiserv Forum and restaurants. It is a historic hotel, so do not expect it to be modern and up to date. The lobby is nice and the room was adequate. The pub in the hotel is great! Highly recommend. "
The price is AU$169
includes taxes & fees
22 Dec - 23 Dec
Hilton Milwaukee
Saint Kate - The Arts Hotel
Premium bedding, down duvets, in-room safe, blackout curtains

Saint Kate - The Arts Hotel

4.0 star property
9.8 out of 10, Exceptional, (1987)
"Beautiful hotel!! Loved the stay "
The price is AU$236
includes taxes & fees
25 Dec - 26 Dec
Saint Kate - The Arts Hotel
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Frequently asked questions

Are there holiday rentals in Caledonia?

Yes, there are holiday rentals close to the most popular sights in Caledonia, or you can select a more secluded option if you're looking for a relaxing stay. Caledonia is known for its parks.

What are some of the best holiday rentals that Caledonia has to offer?

Heated Pool, Hot Tub, Fishing Pond, Game Room, Events!! Fall Discounts! Weddings: This highly rated holiday home rental in Caledonia is located on the beach, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

What can I see and do in Caledonia?

While exploring the area, visit family-friendly sights like Henry W. Maier Festival Park, or get outside and enjoy nature at Boerner Botanical Gardens. In the wider area, you’ll find Milwaukee County Sport Complex and Rock Snow Park.

What are holiday rentals like in Caledonia?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Caledonia. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.