Northwoods Vacation Rentals
Chalets, condos, and single family homes for rent in and around the Northwoods area.

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Visit Northwoods
Welcome to Northwoods, Wisconsin, where breathtaking beauty and outdoor adventure await! Immerse yourself in pristine lakes, dense forests, and charming small towns. Experience thrilling activities like fishing, hiking, and kayaking. Delight in the region’s abundant wildlife and enjoy the tranquility of this nature lover’s paradise.
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Tipler, WI
Long Lake, WI
Long Lake, WI
Tipler, WI
Featured Northwoods
Vacation Rentals


Long Lake
Enjoy a day on the water, fishing for walleye, bass, and panfish. Rent a boat or bring your own and cruise along the 3,300-acre lake, known for its crystal-clear waters and abundant fish population. Grab your binoculars and keep an eye out for majestic bald eagles, white-tailed deer, and playful otters.

Hiking
Lace up your hiking boots and embark on the scenic trails of the Chequamegon-Nicolet National Forest. Don’t miss the Hemlock Creek Trail, offering breathtaking views of cascading waterfalls and lush greenery.

Penokee Mountain Range
Venture north of Long Lake to explore the picturesque Penokee Mountain Range. Hike to the summit of Mt. Whittlesey for panoramic vistas of the surrounding forests and lakes.

Snowmobiling and Cross-Country Skiing
During winter, Long Lake transforms into a winter wonderland. Enjoy thrilling snowmobile rides on the well-groomed trails or glide through the snowy landscapes on cross-country skis.

Granite Peak Ski Area
Granite Peak is Wisconsin’s number one ski area. It boasts 200 acres of skiable terrain spread over nearly 60 trails. Granite Peak claims the fastest lift system in the state, including the only six-pack in Wisconsin. Thrill seekers will love the impressive 700-foot vertical drop! Granite Peak also some of the best night skiing in the region.

Whitecap Mountain Resort
Whitecap Mountain Resort is one of Wisconsin’s largest ski areas, located in the heart of the Penokee Mountains. Choose from the three mountains, Thunderhead, Eagle’s Nest and Whitecap Mountain. There’s a large variety of run types that cater to every ability level.
Check-In Instructions
Check-in is 4:00pm CST and check-out is 10:00am CST. A check-in instructions email will be distributed to guests 7 days prior to arrival date containing directions and access information for the property. In most cases guests will access a property via a lockbox or smart lock using the given access code. Early check-ins can only be confirmed on the day of arrival.
Guests must depart the property by the check-out time unless a late checkout has been coordinated and confirmed with the SkyRun office. Late check-outs must be coordinated directly with the SkyRun office no later than 9am on the day of departure; please note that if we have an incoming guest we will not be able to accommodate a late checkout. We ask that guests remove major trash from the unit, return the furniture to it’s original location, and load and run the dishwasher.
Parking
Parking may be limited. The check-in instructions email will contain information regarding parking at your property. Any parking fines assessed to your vehicles during your stay will be billed to you if they are billed to us. Parking fines can be significant.
Property Damage Waiver
Enjoy peace-of-mind with our incidental damage protection.
SkyRun includes a property damage protection waiver on each reservation. The damage waiver covers damage to the property up to $1,500 so long as the damage is accidental and reported to SkyRun prior to your departure. It does not cover damage that is willful, the result of negligence, or damaged caused by the misuse of household items. It also doesn’t cover unreported damage. SkyRun doesn’t charge our guests a refundable damage deposit in lieu of the waiver. Unlike a refundable damage deposit, the damage protection waiver is non-refundable.
If during your rental of our property, you damage the real or personal property assigned to that property, SkyRun will cover the cost of repairs or the cost to replace the property up to an amount not to exceed $1,500. Should the cost of the damage exceed $1,500 or does not meet the criteria for a “covered loss”, and the property owner’s insurance policy also does not cover the loss, then you shall be responsible for the full amount of the damage which will be charged to the credit card on file. Coverage is provided to you and all travelling companions that are staying in the home overnight during your stay.
Coverage is not provided for loss due to:
- Your intentional acts or gross negligence.
- Any damage that occurs if you are in violation of the terms and conditions (including but not limited to having more than maximum occupancy or having a party).
- Loss, theft or damage to any personal effects owned by you or brought on the covered stay by you.
- Loss, theft or damage caused by any person other than you or your traveling companions with whom you share the property reservation unless substantiated by a police report.
Your Duties in the Event of Damage. You must:
- Take all reasonable, necessary steps to protect the property and prevent further damage to it.
- Report the loss in writing (email ok) prior to check-out to the SkyRun staff.
- Provide us documentation such as pictures to substantiate the claim.
Travel Insurance
Nationwide® Travel Insurance protects your vacation investment against unforeseen events like a hurricane, sickness, injury, flight cancellation, job loss and much more.
Group coverage protects everyone in your traveling party for one low price.
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