What are the top rated Cottage Rentals in Highland?

There are a lot of options in Highland. If you plan on staying in the Highland area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Highland: <a href="/property/stunning-serene-rustic-house-in-the-woods-near-spring-green-wisconsin/HA-3211320102" class="class="static-page-link"">Stunning, serene, rustic house in the woods near Spring Green, Wisconsin</a> <a href="/property/amish-built-cabin-in-the-driftless-area/HA-3212660052" class="class="static-page-link"">Amish-Built Cabin in the Driftless Area</a> <a href="/property/elegant-country-retreat-near-spring-green-w-expansive-views-of-driftless-region/HA-3213772957" class="class="static-page-link"">Elegant country retreat near Spring Green w expansive views of Driftless Region</a> <a href="/property/riverside-chalet-llc/HA-3211794767" class="class="static-page-link"">Riverside Chalet, LLC</a> <a href="/property/serenity-awaits-at-this-secluded-riverfront-property/HA-3212981969" class="class="static-page-link"">Serenity awaits at this secluded riverfront property</a> <a href="/property/rustic-elegant-8-000-sq-ft-timber-frame-lodge-in-southwest-wisconsin/HA-321560238" class="class="static-page-link"">Rustic, Elegant 8,000 Sq. Ft. Timber Frame Lodge in Southwest Wisconsin.</a> <a href="/property/silver-birch-retreat-spacious-pet-friendly-country-home/HA-3213685807" class="class="static-page-link"">Silver Birch Retreat. Spacious, pet friendly country home</a> <a href="/property/deerfield-bottom/HA-3214165455" class="class="static-page-link"">Deerfield Bottom</a> <a href="/property/private-ridge-top-cabin-house/HA-3212764368" class="class="static-page-link"">Private Ridge top Cabin/House</a> <a href="/property/upscale-4-bedroom-farmhouse-in-muscoda-on-historic-century-old-farm-w-ac-wi-fi/HA-3214682357" class="class="static-page-link"">Upscale 4-bedroom Farmhouse in Muscoda on Historic Century-Old Farm w/AC, Wi-Fi</a>

How much does it cost to rent a cottage in Highland?

The average cost for a cottage rental in Highland is $240 per night. Renatovillas has a wide list of great cottages near Highland that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Highland that allow pets?

Yes, here are the top cottage rentals in Highland that allow you to bring your pet: Unique! A renovated old railroad depot turned into a cozy cottage. River's Edge Cabin, LLC Eco-Friendly/Sustainable White Oak Savanna Events Farm and Sanctuary Spacious Cabin on the Wisconsin River! AmericInn by Wyndham Dodgeville Best Western Dodgeville Inn & Suites Stunning, serene, rustic house in the woods near Spring Green, Wisconsin <a href="/all/usa/wisconsin/highland" class="class="static-page-link"">See all pet-friendly vacation rentals in Highland on Renatovillas</a>

Do you have any rental cottages in Highland that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Highland to find one that works for you.

Are there quality cottages in Highland that have indoor swimming pools?

As of 2026, the data from Renatovillas shows that there are Over 3 private swimming pools or cottages with indoor pools in the Highland area along with other great amenities.

Highland Cottage Rentals By Owner

Unique! A renovated old railroad depot turned into a cozy cottage.

From US $277

10.0 (125 Reviews)

Cottage

Unique! A renovated old railroad depot turned into a cozy cottage.

Air Conditioner
Parking
TV

Highland Cottage Rentals & Holiday Homes

Find the best cottages in Highland - We found 3 exact matches

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