Holiday rentals near Sky Trail
We found 969 holiday rentals — enter your dates for availability
If you want to to stay within easy reach of Sky Trail, take a look at holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include parking and a fireplace. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Sky Trail
Showing deals for:19 Sept - 26 Sept
Image gallery for Beautiful English Mansion, 1/4 mile from Lake and close to Arts & Entertainment
1010 out of 10 rating
Exceptional
(85 reviews)
Beautiful English Mansion, 1/4 mile from Lake and close to Arts & Entertainment
Milwaukee, WI
8% off
Price is AU$15,196
AU$15,196
AU$2,171 per night
includes taxes & fees
Image gallery for Whitefish Bay 3Bedroom Entire House Sleeps 4
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Whitefish Bay 3Bedroom Entire House Sleeps 4
Milwaukee, WI
22% off
Price is AU$2,954
AU$2,954
AU$422 per night
includes taxes & fees
Image gallery for Newly Renovated Full Family House in Bayview!
9.49.4 out of 10 rating
Exceptional
(11 reviews)
Newly Renovated Full Family House in Bayview!
Milwaukee, WI
12% off
Price is AU$3,651
AU$3,651
AU$522 per night
includes taxes & fees
Image gallery for 4BD House, Your Central Suburban Oasis, City Lights, Quiet Nights
9.29.2 out of 10 rating
Wonderful
(14 reviews)
4BD House, Your Central Suburban Oasis, City Lights, Quiet Nights
Milwaukee, WI
11% off
Price is AU$3,609
AU$3,609
AU$516 per night
includes taxes & fees
Image gallery for Eclectic, Stylish, and Cozy Milwaukee Home!
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Eclectic, Stylish, and Cozy Milwaukee Home!
Milwaukee, WI
15% off
Price is AU$10,243
AU$10,243
AU$1,463 per night
includes taxes & fees
Image gallery for New built w/free parking off Brady St. Fiserv Forum, Summer Fest and Lakefront!
1010 out of 10 rating
Exceptional
(8 reviews)
New built w/free parking off Brady St. Fiserv Forum, Summer Fest and Lakefront!
Milwaukee, WI
8% off
Price is AU$5,036
AU$5,036
AU$719 per night
includes taxes & fees
Image gallery for Charming Pet-Friendly 3-BR Home, Backyard, Firepit, A/C, Centrally Located
1010 out of 10 rating
Exceptional
(10 reviews)
Charming Pet-Friendly 3-BR Home, Backyard, Firepit, A/C, Centrally Located
Milwaukee, WI
7% off
Price is AU$3,243
AU$3,243
AU$463 per night
includes taxes & fees
Image gallery for Rare East Side Gem! Walk > Lake Michigan. Historic Flat by Beach, UWM, Lake Park
1010 out of 10 rating
Exceptional
(5 reviews)
Rare East Side Gem! Walk > Lake Michigan. Historic Flat by Beach, UWM, Lake Park
Milwaukee, WI
8% off
Price is AU$6,449
AU$6,449
AU$921 per night
includes taxes & fees
Image gallery for Kasa | Kickback and Relax, 1BD with Amenity Access | Milwaukee
1010 out of 10 rating
Exceptional
(15 reviews)
Kasa | Kickback and Relax, 1BD with Amenity Access | Milwaukee
Milwaukee, Wisconsin
7% off
Price is AU$2,362
AU$2,362
AU$337 per night
includes taxes & fees
Image gallery for The Best Bungalow in Riverwest Parking onsite
9.69.6 out of 10 rating
Exceptional
(12 reviews)
The Best Bungalow in Riverwest Parking onsite
Milwaukee, WI
7% off
Price is AU$2,787
AU$2,787
AU$398 per night
includes taxes & fees
Image gallery for Stylish 3-bd place with back yard & free parking
1010 out of 10 rating
Exceptional
(9 reviews)
Stylish 3-bd place with back yard & free parking
Milwaukee, WI
7% off
Price is AU$2,135
AU$2,135
AU$305 per night
includes taxes & fees
Image gallery for Charming Riverfront Home l 4 BR l King Beds I Free Parking I Outdoor Haven
1010 out of 10 rating
Exceptional
(11 reviews)
Charming Riverfront Home l 4 BR l King Beds I Free Parking I Outdoor Haven
Milwaukee, WI
7% off
Price is AU$4,698
AU$4,698
AU$671 per night
includes taxes & fees
Image gallery for Lake Drive Mansion ~ Downtown ~ Art Museum ~ Lakefront
1010 out of 10 rating
Exceptional
(10 reviews)
Lake Drive Mansion ~ Downtown ~ Art Museum ~ Lakefront
Milwaukee, WI
8% off
Price is AU$12,254
AU$12,254
AU$1,751 per night
includes taxes & fees
Image gallery for *New Listing!* East Side Spa Retreat Near Lake
1010 out of 10 rating
Exceptional
(13 reviews)
*New Listing!* East Side Spa Retreat Near Lake
Milwaukee, WI
7% off
Price is AU$2,787
AU$2,787
AU$398 per night
includes taxes & fees
Image gallery for 3Kings, Renovated, FenceYard, Games, Ctr Loc
9.89.8 out of 10 rating
Exceptional
(9 reviews)
3Kings, Renovated, FenceYard, Games, Ctr Loc
Milwaukee, WI
7% off
Price is AU$3,057
AU$3,057
AU$437 per night
includes taxes & fees
Image gallery for Spacious house, yard, hot tub & games — 1 mile to Downtown and the East Side
1010 out of 10 rating
Exceptional
(37 reviews)
Spacious house, yard, hot tub & games — 1 mile to Downtown and the East Side
Milwaukee, WI
15% off
Price is AU$7,081
AU$7,081
AU$1,012 per night
includes taxes & fees
Image gallery for Newly renovated 3 bedroom home
1010 out of 10 rating
Exceptional
(17 reviews)
Newly renovated 3 bedroom home
Franklin, WI
8% off
Price is AU$4,277
AU$4,277
AU$611 per night
includes taxes & fees
Image gallery for Vine Street Home
1010 out of 10 rating
Exceptional
(47 reviews)
Vine Street Home
Milwaukee, WI
15% off
Price is AU$1,868
AU$1,868
AU$267 per night
includes taxes & fees
Image gallery for Best Location in Milwaukee!
9.89.8 out of 10 rating
Exceptional
(30 reviews)
Best Location in Milwaukee!
Milwaukee, WI
8% off
Price is AU$10,363
AU$10,363
AU$1,480 per night
includes taxes & fees
Image gallery for Brady St. Retreat - Where Families & Groups Gather
1010 out of 10 rating
Exceptional
(7 reviews)
Brady St. Retreat - Where Families & Groups Gather
Milwaukee, WI
8% off
Price is AU$7,769
AU$7,769
AU$1,110 per night
includes taxes & fees
Image gallery for 3 bedroom Bayview house. Located in quiet residential area.
1010 out of 10 rating
Exceptional
(15 reviews)
3 bedroom Bayview house. Located in quiet residential area.
Milwaukee, WI
8% off
Price is AU$2,761
AU$2,761
AU$394 per night
includes taxes & fees
Image gallery for Pink Door Place with fenced yard in a walkable area & 2 miles from Fiserv Forum
1010 out of 10 rating
Exceptional
(5 reviews)
Pink Door Place with fenced yard in a walkable area & 2 miles from Fiserv Forum
Milwaukee, WI
9% off
Price is AU$2,536
AU$2,536
AU$362 per night
includes taxes & fees
Image gallery for Modern Victorian-Walk to Brady St-Family Friendly
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Modern Victorian-Walk to Brady St-Family Friendly
Milwaukee, WI
7% off
Price is AU$3,436
AU$3,436
AU$491 per night
includes taxes & fees
Image gallery for Brady St Home with a Private Outdoor Bar and Deck!
1010 out of 10 rating
Exceptional
(7 reviews)
Brady St Home with a Private Outdoor Bar and Deck!
Milwaukee, WI
12% off
Price is AU$8,853
AU$8,853
AU$1,265 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Sky Trail
Family Retreat, private, large, great for multi-family, company retreat, wedding
Sleeps 36 · 11 bedrooms · 5+ bathrooms
1010 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
Wooded Hills/Indoor Pool/Hot Tub/Arcade
Sleeps 12 · 5 bedrooms · 3+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
17-acre Private Oasis estate with, an indoor pool, and private lake, sleeps 16
Sleeps 16 · 7 bedrooms · 6+ bathrooms
8.08.0 out of 10
Very goodvery good
1 review(1 review)
Lake Vacation/Hunters Lake in Dousman,WI, Milwaukee, Delafield, Oconomoc, Wales
Sleeps 5 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
80 reviews(80 reviews)
Waterfront Lake Cottage - Upper Nemahbin Lake
Sleeps 6 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!
Sleeps 12 · 4 bedrooms · 1+ bathroom
9.69.6 out of 10
Exceptionalexceptional
159 reviews(159 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value