Holiday houses in Upper Gresham Lake

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Top-rated holiday rentals in Upper Gresham Lake

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Top Guest favourite
An aerial view of Wanderloft reveals its modern architectural design set against a lush green landscape. The cabin features large windows, a rooftop deck with seating, and a path leading down to the natural surroundings by Manuel Lake.
Cabin in Phelps
4.98 out of 5 average rating, 122 reviews

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 provides stunning 360-degree views from various 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.

Top Guest favourite
The exterior of a modern cabin is visible, featuring a combination of wood and stone materials. A welcoming front porch with a small set of steps leads to the entrance. Flower boxes filled with blooms adorn the windows, enhancing the natural surroundings.
Cabin in Boulder Junction
5 out of 5 average rating, 19 reviews

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.

Guest favourite
A spacious living area features a combination of comfortable seating and rustic decor. A large wooden canoe is mounted on the wall beside an intricately designed staircase that leads to the upper level. Natural light fills the room, highlighting the wooden accents throughout.
Home in Minocqua
4.89 out of 5 average rating, 207 reviews

Minocqua Retreat Home ...7 miles from downtown!!!

Newer home nestled on a wooded water front lot (limited views of Lake Shishibogama). Tastefully decorated with rustic antiques & nostalgia from the past, located 7 mi. from downtown Minocqua. 5 uniquely decorated bedrooms & 3 bathrooms makes a perfect place for large groups- Hot tub/bar/game room. Great for snowmobilers w/room to accommodate large trucks and trailers. The kitchen is fully stocked w/everything you'll need(2 fridges). 4 kayaks and a 2 person Pontoon paddle boat also avaible.

Top Guest favourite
A circular fire pit area is surrounded by six red Adirondack chairs and a wooden bench, all set on a gravel base. The space is framed by trees, and daylight filters through the leaves, illuminating the cozy gathering spot.
Cabin in Park Falls
4.98 out of 5 average rating, 48 reviews

Bolo's Landing (last home on peninsula)

Modern comfort meets rustic charm at Bolo’s Landing on Muskie Lake. With direct trail access, a private pier, kayaks, and stunning lake views, it's your perfect Northwoods getaway year-round. We have room for your trailer and are just off of Iron County Trail 8 and 8a. Enjoy the almost 100-acre PRIVATE lake with included kayaks and rowboat (with life jackets). Cooking your thing? Just bring your food we have the rest. If not, there are 7 restaurants (bar scene to gourmet) within 13 miles.

Top Guest favourite
A large stone fire pit is surrounded by several black wooden chairs, situated on a grassy area. Near the water, a wooden pier is visible alongside a table with an umbrella. Lush trees line the shore, providing a serene lakeside setting.
Cabin in Manitowish Waters
4.91 out of 5 average rating, 102 reviews

The Eagles Nest Cabin on Island Lake

Newly Renovated Galley Kitchen (small, but has all the essentials). located on Island Lake, part of the desired 10 Lake Manitowish Chain. Huge fire pit behind the cabin on the ridge overlooking the lake, pier, and gas grill. Near biking trails, restaurants and shopping. It’s private yet easy to get to right off of Hwy 51. Enjoy beautiful summer sun sets and amazing wild life. My place is good for couples, solo adventurers, and small families. Weekly rentals only mid June to mid August!

Guest favourite
An elevated deck features four outdoor chairs arranged for relaxation, overlooking a peaceful wooded area. Large glass doors reflect the surrounding greenery, allowing natural light into the interior space. The wooden deck surface provides a rustic charm with a welcome mat at the entrance.
Apartment in Arbor Vitae
4.85 out of 5 average rating, 266 reviews

Retreat B 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.

Top Guest favourite
A cozy yurt is nestled among tall trees, with sunlight filtering through the leaves. Vibrant flowers line the path leading to the entrance, creating a serene and inviting outdoor space. The blue sky above contrasts with the greenery, enhancing the tranquil forest setting.
Yurt in Boulder Junction
5 out of 5 average rating, 68 reviews

'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!

Top Guest favourite
A modern cabin is set among tall trees, featuring a spacious wooden deck with stairs leading up to it. Large windows offer views into the interior, while warm lighting creates a welcoming atmosphere as dusk approaches.
Cabin in Park Falls
4.9 out of 5 average rating, 104 reviews

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.

Guest favourite
A modern cabin is surrounded by lush greenery, featuring large windows that provide views of the serene landscape. The structure is set on a grassy area, with trees framing the home and a peaceful atmosphere evident in the natural setting.
Home in Boulder Junction
5 out of 5 average rating, 22 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.

Top Guest favourite
A calm lake at sunset reflects pastel shades of pink and orange across the water's surface. Silhouetted ducks glide peacefully through the gentle ripples, surrounded by lush green trees lining the shore.
Cabin in Boulder Junction
4.98 out of 5 average rating, 130 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. Room Tax is now being collected directly thru Airbnb at 6.75% and remitted to the Town of Boulder Junction.

Top Guest favourite
Home in Lac du Flambeau
5 out of 5 average rating, 9 reviews

Fern and Moss A-frame Lakefront Hot Tub

Fern & Moss – Modern Northwoods Retreat Escape to this stunning A-frame on Moss Lake with panoramic lake views, 2 bedrooms, a bunk room, and 3 full baths. Enjoy 100+ ft of fisherman's frontage, a private dock, hot tub, fire pit, and stylish interiors with vaulted ceilings, a full kitchen, and smart TV. Located near Minocqua with year-round access to outdoor adventures. A perfect blend of modern comfort and lakeside serenity. ✨ Book your getaway today!

Guest favourite
The cabin's exterior features a sturdy stone facade adorned with bright red shutters. A covered porch with comfortable seating is framed by lush greenery and colorful flowers, creating a warm and inviting entrance.
Tiny home in Arbor Vitae
4.93 out of 5 average rating, 323 reviews

Your three-season romantic escape

Escape to The Croquet Cabin—a cozy 1-bed, 1-bath retreat nestled in Wisconsin’s Northwoods. Perfect for couples, this charming cabin features heated floors, a fireplace, full kitchen, Wi-Fi, and outdoor space for grilling or enjoying lake life. Just minutes from Trail 51 and local lakes, it’s ideal for year-round adventures or romantic getaways. Relax, recharge, and enjoy rustic charm with modern comforts. (Owners live on premise)

Popular amenities for Upper Gresham Lake holiday rentals