Holiday rentals near Downtown City Square
We found 189 holiday rentals — enter your dates for availability
If you'd like to stay close to Downtown City Square, scroll through and discover private holiday rentals to find the perfect home base for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the amenities that you need and want, which might include air conditioning and a pool. At the end of the day, you'll be able to choose a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Downtown City Square
Showing deals for:7 Nov - 14 Nov
Image gallery for THE LAKESIDE EAGLE'S NEST NEAR THE TRAIL
9.69.6 out of 10 rating
Exceptional
(23 reviews)
THE LAKESIDE EAGLE'S NEST NEAR THE TRAIL
Hurley, WI
12% off
Price is NZ$2,713
NZ$2,713
NZ$388 per night
includes taxes & fees
Image gallery for Stunning Log Cabin Getaway at The Hannu Haus
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Stunning Log Cabin Getaway at The Hannu Haus
Ironwood, MI
8% off
Price is NZ$6,167
NZ$6,167
NZ$881 per night
includes taxes & fees
Image gallery for Ironwood Trailside Adventures
1010 out of 10 rating
Exceptional
(16 reviews)
Ironwood Trailside Adventures
Ironwood, MI
12% off
Price is NZ$1,785
NZ$1,785
NZ$255 per night
includes taxes & fees
Image gallery for Large home walking distance to town and trails. 10 minutes to ski resorts.
1010 out of 10 rating
Exceptional
(38 reviews)
Large home walking distance to town and trails. 10 minutes to ski resorts.
Ironwood, MI
12% off
Price is NZ$3,226
NZ$3,226
NZ$461 per night
includes taxes & fees
Image gallery for "Dad's Garage" Cozy 2-bdrm house w/ Sauna, Fireplace, King Bed, WiFi & AC
1010 out of 10 rating
Exceptional
(41 reviews)
"Dad's Garage" Cozy 2-bdrm house w/ Sauna, Fireplace, King Bed, WiFi & AC
Ironwood, MI
16% off
Price is NZ$1,590
NZ$1,590
NZ$227 per night
includes taxes & fees
Image gallery for Cozy Cottage ~ Your U.P Home Base!
1010 out of 10 rating
Exceptional
(6 reviews)
Cozy Cottage ~ Your U.P Home Base!
Ironwood, MI
7% off
Price is NZ$2,081
NZ$2,081
NZ$297 per night
includes taxes & fees
Image gallery for Trails Edge Escape- On the Ironwood/Hurley Border
1010 out of 10 rating
Exceptional
(13 reviews)
Trails Edge Escape- On the Ironwood/Hurley Border
Ironwood, MI
8% off
Price is NZ$5,365
NZ$5,365
NZ$766 per night
includes taxes & fees
Image gallery for Serenity POW! Indoor Hot Tub, A/C & 3 Acres!
1010 out of 10 rating
Exceptional
(6 reviews)
Serenity POW! Indoor Hot Tub, A/C & 3 Acres!
Bessemer, MI
8% off
Price is NZ$5,230
NZ$5,230
NZ$747 per night
includes taxes & fees
Image gallery for Beautiful 4 season getaway in the scenic northwoods of the Western UP!
1010 out of 10 rating
Exceptional
(30 reviews)
Beautiful 4 season getaway in the scenic northwoods of the Western UP!
Bessemer, MI
8% off
Price is NZ$2,051
NZ$2,051
NZ$293 per night
includes taxes & fees
Image gallery for Trailside Vacation Home with One of the Best Views in the U.P. of Ski Slopes
9.69.6 out of 10 rating
Exceptional
(30 reviews)
Trailside Vacation Home with One of the Best Views in the U.P. of Ski Slopes
Bessemer, MI
12% off
Price is NZ$4,479
NZ$4,479
NZ$640 per night
includes taxes & fees
Image gallery for Cabin on 25 Acres of Forest
1010 out of 10 rating
Exceptional
(22 reviews)
Cabin on 25 Acres of Forest
Bessemer, MI
13% off
Price is NZ$1,492
NZ$1,492
NZ$213 per night
includes taxes & fees
Image gallery for Mountain Top Chalet ~ A/C & Close to Rec Trails!
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Mountain Top Chalet ~ A/C & Close to Rec Trails!
Bessemer, MI
7% off
Price is NZ$4,253
NZ$4,253
NZ$608 per night
includes taxes & fees
Image gallery for Close to Hurley, Trail access, near The Gile Flowage with Central Air & King Bed
1010 out of 10 rating
Exceptional
(36 reviews)
Close to Hurley, Trail access, near The Gile Flowage with Central Air & King Bed
Gile, WI
12% off
Price is NZ$2,475
NZ$2,475
NZ$354 per night
includes taxes & fees
Image gallery for Cozy Home in Ironwood, MI
1010 out of 10 rating
Exceptional
(53 reviews)
Cozy Home in Ironwood, MI
Ironwood, MI
8% off
Price is NZ$1,792
NZ$1,792
NZ$256 per night
includes taxes & fees
Image gallery for Swiss Hut Unit 1
1010 out of 10 rating
Exceptional
(11 reviews)
Swiss Hut Unit 1
Bessemer, MI
16% off
Price is NZ$1,415
NZ$1,415
NZ$202 per night
includes taxes & fees
Image gallery for Spacious 4 BR 2BA Home with Bar and Fenced Yard
9.89.8 out of 10 rating
Exceptional
(33 reviews)
Spacious 4 BR 2BA Home with Bar and Fenced Yard
Ironwood, MI
8% off
Price is NZ$2,810
NZ$2,810
NZ$401 per night
includes taxes & fees
Image gallery for Unique Industrial 4 season recreational basecamp centrally located!
1010 out of 10 rating
Exceptional
(22 reviews)
Unique Industrial 4 season recreational basecamp centrally located!
Bessemer, MI
8% off
Price is NZ$1,772
NZ$1,772
NZ$253 per night
includes taxes & fees
Image gallery for Snowy River @ big Powderhorn
1010 out of 10 rating
Exceptional
(17 reviews)
Snowy River @ big Powderhorn
Bessemer, MI
8% off
Price is NZ$2,147
NZ$2,147
NZ$307 per night
includes taxes & fees
Image gallery for Authenic Amish built log cabin on 3,300 acre Gile Flowage. All Modern Amenities
1010 out of 10 rating
Exceptional
(113 reviews)
Authenic Amish built log cabin on 3,300 acre Gile Flowage. All Modern Amenities
Montreal, WI
9% off
Price is NZ$3,364
NZ$3,364
NZ$481 per night
includes taxes & fees
Image gallery for Trailside Home on Alpen Trail with Hot Tub & Allows Dogs
8.48.4 out of 10 rating
Very good
(41 reviews)
Trailside Home on Alpen Trail with Hot Tub & Allows Dogs
Bessemer, MI
12% off
Price is NZ$6,570
NZ$6,570
NZ$939 per night
includes taxes & fees
Image gallery for A Comfortable & Spacious Retreat in the Powderhorn Village
9.89.8 out of 10 rating
Exceptional
(50 reviews)
A Comfortable & Spacious Retreat in the Powderhorn Village
Bessemer, MI
12% off
Price is NZ$4,525
NZ$4,525
NZ$646 per night
includes taxes & fees
Image gallery for Beautiful, historic, Craftsman style home, near all you love about the UP !
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Beautiful, historic, Craftsman style home, near all you love about the UP !
Bessemer, MI
8% off
Price is NZ$3,528
NZ$3,528
NZ$504 per night
includes taxes & fees
Image gallery for Mountain View Home
1010 out of 10 rating
Exceptional
(10 reviews)
Mountain View Home
Bessemer, MI
12% off
Price is NZ$1,402
NZ$1,402
NZ$200 per night
includes taxes & fees
Image gallery for Downtown "Green Room" at Villages on Aurora
9.89.8 out of 10 rating
Exceptional
(38 reviews)
Downtown "Green Room" at Villages on Aurora
Ironwood, MI
8% off
Price is NZ$2,484
NZ$2,484
NZ$355 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Downtown City Square
Lake Gogebic Private Cabin Hotel Room
Sleeps 3 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
Black River Retreat (Dog Friendly!)
Sleeps 8 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
268 reviews(268 reviews)
Horsehead Lake Retreat (Big Discounts in June Call 414-378-7273)
Sleeps 10 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
21 reviews(21 reviews)
Dog-friendly lakefront home with a private beach, dock, firepit, & kayaks
Sleeps 6 · 3 bedrooms · 1+ bathroom
9.09.0 out of 10
Wonderfulwonderful
18 reviews(18 reviews)
U.P. A-Frame - Near Ski Resort, Trails, FP, sauna
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
53 reviews(53 reviews)
Lakefront vacation home with 300 ft. of private, South West facing, shoreline.
Sleeps 12 · 6 bedrooms · 3 bathrooms
9.09.0 out of 10
Wonderfulwonderful
16 reviews(16 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