Vacation rentals in Upper Gresham Lake

Lakeside Loft, Roof Deck + Sauna

Wanderloft, designed by architect David Salmela, combines modern Scandinavian design with the natural beauty of Wisconsin's Northwoods. Located on one of Vilas County's highest points, this cabin offers stunning 360-degree views from multiple levels, overlooking Manuel Lake and 9.4 acres of land. Beyond its striking design, Wanderloft is defined by its profound sense of peace and quiet - where natural beauty and thoughtful architecture create space for rest, creativity, inspiration, and renewal.

Beautiful, newly renovated log lakefront home

Escape to our beautifully updated 3BR, 2BA lakefront log home on LITTLE OXBOW LAKE —perfect for families or friends. 3.6 miles from downtown Presque Isle WI! Enjoy stunning lake views, sunsets, private dock, kayaks, fire pit, fully stocked kitchen, large bedrooms, 2 living rooms, fast Wi-Fi. Relax on the deck, fish, swim, or explore nearby hiking and bike trails and quaint towns with amazing restaurants and shopping. Pontoon rentals available from local marina. Your perfect Northwoods place!!

Lakefront Chalet w/Pontoon

Perfect year-round family getaway! Luxurious 3-story chalet sits on 15+ acres with 770’ of lake frontage on Lucy Lake. 2 kitchens to accommodate large families, dog run/kennel, private walking trails, sandy lake bottom ideal for wading, private dock for fishing, basketball hoop, swimming & kayaking. In winter there's snow shoeing, ice fishing, and sledding (bring your own equipment) on property. Close to cross country skiing/skijoring trails & snow mobile trails. EV Charging Station (NEMA 14-50)

Cottage on High Lake

Dog-Friendly Lakefront Cottage w/ Dock, Kayaks, Canoe, and Snowshoes Experience everything the Boulder Junction area has to offer at this cottage located on beautiful High Lake in Land O’ Lakes. This rental is ideally situated at the gateway to year-round outdoor adventures, whether you're looking to get out on the water, explore the woods, or race through the snow. This home features lakefront access with level fisherman frontage and a private dock. At night, enjoy the wood-burning fireplace.

Waterfront 4 BedRm Near Snowmobile/Bike Trail NEW!

Welcome to our modern and cozy 4-bedroom cabin, nestled on a serene riverfront and navigable to Boulder Junction Lake. Snowmobile straight from the driveway! Area known for it's miles of scenic bike trails. Whether seeking adventure or a peaceful retreat, our cabin blends comfort and nature. Conveniences such as a fully equipped kitchen, washer/dryer, outdoor seating, grill and firepit make you feel right at home! Summer- Pontoon avail for rent to enjoy great fishing or a day in the sun.

Lakefront Retreat | Chain of Lakes | New 3BR

Welcome to The Lighthouse — a newly built lakefront cabin on the Manitowish Waters Chain of Lakes. Wake up to beautiful water views, spend the day boating, fishing, swimming, cross-country skiing, snowmobiling, or exploring the Northwoods, then come home to vaulted ceilings, a cozy fire, and everything you need to unwind. Built in 2024 with comfort in mind, The Lighthouse is your year-round home base for summer lake days, fall getaways, snowy ski weekends, and unforgettable time together.

Charming Cabin on Manitowish Chain of 10 Lakes

This waterfront respite on the beautiful chain of lakes in Manitowish Waters, WI offers a relaxing and adventure-filled visit during any season. In summer enjoy swimming, fishing, and boating. Visit in fall for gorgeous foliage, and gear up for winter activities like ice fishing, snowmobiling, snowshoeing, and skiing. Enjoy miles of paved bike path, hiking, and wildlife throughout the year. The owner/manager lives down the street and responds quickly should any unexpected issues arrive.

'Driftwood' Cozy Luxury Yurt with Sauna & Wi-Fi

Our luxury yurts are fully insulated and equipped with heat, electricity, piping hot water, a full kitchen, bathroom, and a spacious living area. Relax in the 6–8 person sauna just steps away, enjoy the bonfire pit, s’mores, HBO Max, nearby trails, and free delivery for gear rentals. We’re happy to help with reservations, rentals, and personalized recommendations to make your Northwoods stay unforgettable. Furry Friends Allowed! - $40 per pet Inquire about seasonal or group discounts!

National Forest Lakeside Retreat

Escape to this beautiful cabin nestled in the woods on a serene lake. With its cozy layout and large windows, you'll feel right at home surrounded by nature's beauty. Enjoy breathtaking views of the dark sky at night and wake up to the peaceful sounds of the National Forest. Explore endless adventures with hiking, ATV, and snowmobile trails just steps away. Unwind on the deck and take in the tranquility of this hidden gem. Book your getaway now and experience the ultimate retreat.

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.

Lively Lofts at Aqualand - Apt #1

A unique getaway experience awaits you. The lively Lofts of Aqualand are located above the Ale House overlooking the outdoor patio. These unique lofts feature an elegant bedroom with a full kitchen, living room, and bathroom with a jacuzzi tub for relaxation. Located in downtown Boulder Junction with a bike path and snowmobile trails outside your window for easy access. Shopping, art, and other restaurants are within walking distance. Good times await you!

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. Room Tax is now being collected directly thru Airbnb at 6.75% and remitted to the Town of Boulder Junction.