Sussex Holiday Rentals

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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

Our top choices for Sussex holiday rentals

Fridge, microwave, oven, stovetop

Luxury Historic Home - Stellar Location

Luxury Historic Home - Stellar Location
Lower East Side
9.6 out of 10, Exceptional, (27 reviews)
"A lovely historic house with three large bedrooms, a very functional kitchen, beautiful dining room and family room areas and a super fun game room. Great for family get togethers!"
United States
Donna M.
The price is HK$1,763
HK$4,426 total
includes taxes & fees
20 Mar - 21 Mar
Luxury Historic Home - Stellar Location
Dining

Style and Luxury - Unbeatable Location

Style and Luxury - Unbeatable Location
Lower East Side
9.6 out of 10, Exceptional, (13 reviews)
"Great location!"
United States
Mike G.
The price is HK$1,728
HK$4,107 total
includes taxes & fees
22 Mar - 23 Mar
Style and Luxury - Unbeatable Location
Fridge, microwave, oven, stovetop

Quiet Retreat in Morgan Heights, Sleeps 6, 1.5 baths

Quiet Retreat in Morgan Heights, Sleeps 6, 1.5 baths
Milwaukee
10.0 out of 10, Exceptional, (1 review)
"Great host and nice place. "
United States
Tommy G.
The price is HK$1,220
HK$2,926 total
includes taxes & fees
20 Mar - 21 Mar
Quiet Retreat in Morgan Heights, Sleeps 6, 1.5 baths
TV

Charming 3-bedroom house in lovely Milwaukee near DT and Hospitals

Charming 3-bedroom house in lovely Milwaukee near DT and Hospitals
Morgandale
10.0 out of 10, Exceptional, (3 reviews)
"My kids and I had a great stay here! The location was in a cozy and quiet neighborhood, my kids loved the back yard, and the house itself was very well cared for with comfortable furniture. I’ll definitely be staying there again the next time I’m in town!"
United States
Lauren M.
The price is HK$1,685
HK$4,851 total
includes taxes & fees
20 Mar - 21 Mar
Charming 3-bedroom house in lovely Milwaukee near DT and Hospitals
Floor plan

Large Milwaukee Home 4BR Fast Wifi

Large Milwaukee Home 4BR Fast Wifi
3.0 star property
Fifth Ward
The price is HK$1,371
HK$5,566 total
includes taxes & fees
23 Mar - 24 Mar
Large Milwaukee Home 4BR Fast Wifi
Dining

Victorian Hot Tub Oasis steps from Restaurants Pubs Coffee, Grocery & The Beach

Victorian Hot Tub Oasis steps from Restaurants Pubs Coffee, Grocery & The Beach
Shorewood
10.0 out of 10, Exceptional, (4 reviews)
"Great location. 1 block walk to a grocery store, a pharmacy, a great restaurant, AND a great coffee shop. Plenty of space for all."
United States
Nicki U.
The price is HK$3,082
HK$6,761 total
includes taxes & fees
23 Mar - 24 Mar
Victorian Hot Tub Oasis steps from Restaurants Pubs Coffee, Grocery & The Beach
Smart TV, books

Central location, newly remodeled, Backyard, Firepit, Hot Tub, A/C, Pet-Friendly

Central location, newly remodeled, Backyard, Firepit, Hot Tub, A/C, Pet-Friendly
Murray Hill
10.0 out of 10, Exceptional, (15 reviews)
"We had a wonderful stay and appreciate the hospitality! While in town to visit family and our first trip with an infant, the house had everything we needed making it a comfortable and pleasant first trip! The location was fantastic and allowed for us to easily walk to restaurants, the market and enjoy the sights of the lake! "
United States
Christina T.
The price is HK$1,676
HK$4,554 total
includes taxes & fees
22 Mar - 23 Mar
Central location, newly remodeled, Backyard, Firepit, Hot Tub, A/C, Pet-Friendly
Exterior

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, (46 reviews)
"Great location loved the coffee shop downstairs. The place definitely needs some TLC."
United States
Kris J.
The price is HK$1,763
HK$2,578 total
includes taxes & fees
22 Mar - 23 Mar
Downtown Eastside gem near Fiserv Forum Water St Brady St
Dining

Three bedrooms upstairs

Three bedrooms upstairs
Riverwest
9.6 out of 10, Exceptional, (84 reviews)
"Very nice stay in a quaint place. Owner, Ryan, was very nice and hospitable."
United States
Jason D.
The price is HK$1,375
HK$1,843 total
includes taxes & fees
23 Mar - 24 Mar
Three bedrooms upstairs
Exterior detail

Gift yourself a getaway in 2026

Gift yourself a getaway in 2026
Cedarburg
10.0 out of 10, Exceptional, (198 reviews)
"The host was very gracious and the property had all the amenities we needed. The property was clean, and the location was fantastic!"
United States
Theresa Z.
The price is HK$1,199
HK$1,516 total
includes taxes & fees
19 Apr - 20 Apr
Gift yourself a getaway in 2026
Smart TV, books, music library, stereo

Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer

Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer
Bay View
10.0 out of 10, Exceptional, (27 reviews)
"This was our second time staying here and I can’t recommend it enough! The owners are so thoughtful and have left little treats or things for us each time we’ve stayed. They have everything you might need and then some, making it feel like home away from home. We will definitely stay here again. "
United States
Amber T.
The price is HK$1,411
HK$3,483 total
includes taxes & fees
23 Mar - 24 Mar
Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer
Fridge, microwave, oven, stovetop

Stunning Upscale Retreat - Steps From Everything

Stunning Upscale Retreat - Steps From Everything
Lower East Side
9.6 out of 10, Exceptional, (32 reviews)
"It was a great place and close to Brady street! Definitely recommend. "
United States
Hugh L.
The price is HK$1,587
HK$4,218 total
includes taxes & fees
23 Mar - 24 Mar
Stunning Upscale Retreat - Steps From Everything
Exterior

Historic Downtown-Old World Charm-Dining-Coffee

Historic Downtown-Old World Charm-Dining-Coffee
Delafield
10.0 out of 10, Exceptional, (5 reviews)
"Great place to rest and relax on a fun weekend getaway. "
United States
Jeffrey C.
The price is HK$1,215
HK$2,292 total
includes taxes & fees
23 Mar - 24 Mar
Historic Downtown-Old World Charm-Dining-Coffee
Smart TV, books

“Charming West Allis Stay • 3BR • Quiet Block, Close to It All!”

“Charming West Allis Stay • 3BR • Quiet Block, Close to It All!”
West Allis
The price is HK$1,206
HK$3,242 total
includes taxes & fees
20 Mar - 21 Mar
“Charming West Allis Stay • 3BR • Quiet Block, Close to It All!”
Smart TV, ping pong, printers

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, (50 reviews)
"Very clean and nice home.Would definitely recommend "
United States
Glenn T.
The price is HK$1,389
HK$2,657 total
includes taxes & fees
22 Mar - 23 Mar
Historic home - walk to village center. Original features with modern updates.
Beach nearby

Charming home w/ fire pit, walk to Lake Michigan

Charming home w/ fire pit, walk to Lake Michigan
Shorewood
9.8 out of 10, Exceptional, (36 reviews)
"Host communication was excellent. House was clean and perfect for a little weekend getaway!"
United States
Grayson P.
The price is HK$1,301
HK$2,910 total
includes taxes & fees
10 Apr - 11 Apr
Charming home w/ fire pit, walk to Lake Michigan
Smart TV, computer monitors

Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms

Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms
Bay View
10.0 out of 10, Exceptional, (20 reviews)
"Best stay"
United States
Marvin G.
The price is HK$2,821
HK$4,758 total
includes taxes & fees
22 Mar - 23 Mar
Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms
Dining

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
9.6 out of 10, Exceptional, (14 reviews)
"Great place!"
United States
Kathy R.
The price is HK$1,865
HK$3,631 total
includes taxes & fees
25 Mar - 26 Mar
Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers
TV

Near AmFam Field & Pettit |Sleeps 12|4BR + Parking

Near AmFam Field & Pettit |Sleeps 12|4BR + Parking
Bluemound Heights
The price is HK$1,965
HK$5,168 total
includes taxes & fees
22 Mar - 23 Mar
Near AmFam Field & Pettit |Sleeps 12|4BR + Parking
Casino

Stunning Brewers Hill Retreat with 2 bedrooms & 1 bath

Stunning Brewers Hill Retreat with 2 bedrooms & 1 bath
Brewers Hill
10.0 out of 10, Exceptional, (3 reviews)
"The property was lovely and well equipped. The host was responsive and communicative. Great location and easy rideshare to get anywhere. Would absolutely stay again!"
United States
Nuala J.
The price is HK$976
HK$2,528 total
includes taxes & fees
23 Mar - 24 Mar
Stunning Brewers Hill Retreat with 2 bedrooms & 1 bath
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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Top Sussex Hotel Reviews

Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

10/10 Excellent
"Nice place n staff"
Nicole 2-night trip
Posted 4 hours ago
Drury Plaza Hotel Milwaukee Downtown

Find out more about Sussex

Search for holiday rentals in Sussex on Expedia! You can easily find your home rentals, villas, holiday apartments in Sussex using one of the methods below:

  • View our selection of featured holiday rentals in Sussex
  • Use the map to find apartments and other holiday homes in the Sussex neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sussex while they last

Look no further and take a look at our great range of rental properties in Sussex!

Frequently asked questions

Can I find holiday rentals in Sussex?

Yes, there are holiday rentals in Sussex close to Sussex Bowl, or you can select a more secluded option if you're looking for a relaxing stay. Sussex is known for its entertainment choices.

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

Wooded Hills/Indoor Pool/Hot Tub/Arcade: This highly rated holiday home rental in Sussex offers an indoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 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 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Sussex?

Choose from 3 Expedia holiday rentals in Sussex for a memorable holiday.

What can I see and do in Sussex?

Explore the area and cultural attractions such as Sharon Lynne Wilson Center for the Arts, or visit one of the family-friendly sights such as Sussex Bowl. In the wider area, you’ll find Pewaukee Lake and Springs Water Park.

What are holiday rentals like in Sussex?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Sussex. Holiday rentals feature extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family gatherings.