Vacation rentals in Upper Gresham Lake

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Top-rated vacation rentals in Upper Gresham Lake

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Ramsay

4.97 out of 5 average rating, 122 reviews

Happy Hippie Shack! Good U.P. Vibes Hike/Bike/Ride

Hippies Retreat!! Self check in with a door code and let the Good Vibes and Adventures begin! Our place is designed for guests with an open mind, free spirit and great Hippie sense of humor. You will have a Groovy pad to land after exploring the U.P. and are only minutes from Indianhead, Blackjack, Big Powderhorn & Mt. Zion Ski hills. A bit further away, but worth the drive, are Whitecap Mountain and Porcupine Mountains. Also, close to ABR x-c skiing, the Iron Belle Trail, and Lake Superior.

Dec 16 – 23

G$27,538 GYD per night

Guest favorite

Guesthouse in Sayner

4.97 out of 5 average rating, 152 reviews

Zen out & Sauna at LandsEndattheEdge Loft!

QUIET private zenny retreat! Covered deck in treetops overlooks NHAL state forest wilderness. Ponder a skyline of pines & a plethora of stars! Howling wolves & birdwatching; a vist by Woody, our resident pileated woodpecker sure to stop by. BBQ on gas grill, sit by firetable, or suhwing! Rustic sauna WIFI elect FP kitch 2kayaks. 5min to LostCanoe Lake, WhiteSand Lake BoatLaunch&Beach, Lumberjack/Escanaba StateTrls, 15min to HeartofVilas paved 52+mi Trl. Semi-secluded yet 8mi to BJ restaurants!

Oct 22 – 29

G$25,701 GYD per night

Guest favorite

Cabin in Harshaw

4.97 out of 5 average rating, 186 reviews

Secluded cabin in the woods surrounded by nature

Cozy home features warm lighting & paint colors and creative Northwoods decorating with a modern touch. Amenities include high speed internet, stainless appliances, coffee maker, front load washer and dryer, streaming services/Apple TV, 3 flat screen TV's, 2 fireplaces , central AC and a high efficiency furnace. The home is situated on 4 wooded acres (not lakefront) off a well maintained gravel road. Very private. No neighbors in sight. Wildlife is abundant. Dogs are OK w/approval & fee.

Mar 28 – Apr 4

G$34,809 GYD per night

Guest favorite

Cabin in Ironwood

4.95 out of 5 average rating, 420 reviews

The Shell Cabin at Rockhound Hideaway

An outdoor enthusiasts dream awaits at Rockhound Hideaway's Shell Cabin, with opportunities for hiking, biking, fishing, boating and everything in between. Take in the views from your back deck, relax around the bonfire, enjoy walk to Lake Superior, hike or snowshoes the North Country Trail to waterfalls or take a day trip to the Porkies. Don't forget to visit Downtown Ironwood and experience its charm for yourself. Amazing star gazing and Northern Lights potential! 420 Friendly for 21&up.

Jul 15 – 22

G$26,635 GYD per night

Guest favorite

Cabin in Boulder Junction

4.98 out of 5 average rating, 108 reviews

Middle Gresham Get-a-way Your year round Getaway

We are located on Middle Gresham Lake, this is a semi private lake, very quite lake with no public access. The fishing is great. Includes use of a row boat, canoe and two kayaks, boat motor available-extra charge. Rustic cabin feel with pristine views, a fire pit for roasting marsh mellows. Centrally located between Minocqua and Boulder Junction. Please note that an invoice for Room Tax will also be sent upon booking , as Airbnb only collects Wisconsin sales tax with your reservation.

Sep 24 – Oct 1

G$38,565 GYD per night

Guest favorite

Apartment in Arbor Vitae

4.92 out of 5 average rating, 215 reviews

Retreat C on Little Spider Lake (Towering Pines)

Our property offers a Peaceful Getaway in a Resort Setting on a Quiet Lake. "Great Location", "Amazing Views", "Clean", "Cozy", "Perfect", "Peaceful", "Comfortable", and "Relaxing" are what we repeatedly hear from our guests after their stay. The Heart of Vilas County Bike Trails and numerous Hiking trails are just minutes away. The #5 Snowmobile/ATV trail runs across the front of the property along Hwy 51 and we are surrounded by many area lakes and the Northern Highland State Forest.

Mar 31 – Apr 7

G$25,414 GYD per night

Guest favorite

Guesthouse in Arbor Vitae

5.0 out of 5 average rating, 11 reviews

Full kitchen at Studio 517

Full kitchen. 517 square foot studio guest house on 3 acre lake property surrounded by state forest - just north of Minocqua, WI. Private Guest house suite newly remodeled! Lovely decor - Navy and White. Snowmobile trails just down the lane. Winter Park x country ski trails close by. Clean, white snow on our lake as there only 8 full time families Full kitchen with new appliances. One queen bed . Lovely gardens, 150 acre quiet and peaceful lake. Smoke Free and Bark Free Property

Dec 23 – 30

G$35,949 GYD per night

Guest favorite

Tiny home in Saxon

5.0 out of 5 average rating, 136 reviews

Parker Creek Tiny House

Come stay on our hobby farm with us! We are in a great central location to multiple hiking trails and gorgeous falls. We have had many guests visit the sea caves in Cornucopia, spend the day in Bayfield, or hike the Porcupine Mountains. We also are only a few miles from the ATV trails if you would rather spend the day riding the trails. We have multiple places to mountain bike or kayak. We have more things to do listed in our details section! Feel free to message me with questions.

Apr 5 – 12

G$26,925 GYD per night

Guest favorite

Tiny home in Arbor Vitae

4.94 out of 5 average rating, 277 reviews

The croquet cabin your year round romantic escape

FYI our cozy cabin is perfect for snowmobiling. The floors are heated in the main part and the shower has an on-demand heater, so the hot water never runs out trail 51 is less than a mile down the road from the driveway along with the number one snowmobile stop! There’s room for your trailer and gear so hopefully we’ll see you out here this season. This cozy cabin is a perfect choice for a couple’s romantic getaway! Celebrate any special occasion in this peaceful secluded cabin!

Dec 24 – 31

G$37,632 GYD per night

Guest favorite

Home in Ironwood

4.99 out of 5 average rating, 187 reviews

"Bakery Bungalow" -Sweet Accommodations & Nature !

Completely remodeled from head to toe! Located within half mile of trail system, 2 miles from historic downtown shops, on the outskirt of town (Ironwood Township=great drinking water) minutes from Big Powderhorn Mountain & Copper Peak, walking distance to Gogebic College & Mount Zion, 17 miles from Lake Superior, large private wooded yard with fire pit in summer, private parking, 1 stall garage if needed in winter. A light Bakery breakfast included with your stay!

Apr 3 – 10

G$27,503 GYD per night

Superhost

Home in Boulder Junction

5.0 out of 5 average rating, 15 reviews

Completely remodeled home at the end of peninsula

This home was completely remodeled in 2017 with a new kitchen, baths, flooring, etc. It is located at the end of peninsula, creating a private setting with north and west views of the lake. There is a sandy frontage, great for swimming, fishing and boating. A short distance from the shops and restaurants of Manitowish Waters and Downtown Boulder Junction, but far enough away from everything to create a peaceful, relaxing setting for your Northwoods vacation.

Aug 21 – 28

G$123,867 GYD per night

Guest favorite

Guest suite in Rhinelander

4.99 out of 5 average rating, 101 reviews

Quiet Family Suite on River near Lakes and Trails

Family-size guest suite offers all the comforts of home within 15 min. of Minocqua, Rhinelander, and premier outdoor experiences. Inside find bright spaces, full log beams, and a hobbiton feel; open concept living area with fully stocked kitchen, table, bunk beds, large couch, TV and Wi-Fi; bedroom with queen bed and stowed air mattress; full bath; play room. Suite is fully enclosed with separate entrance from the attached private log house.

Aug 7 – 14

G$27,678 GYD per night