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Uptown Cottage Rentals & Holiday Homes

Find the best cottages in Uptown - We found 10 exact matches

About Uptown Luxury Rental on Madison Vacation Rental

Searching for cottages to rent near Uptown? Madison Vacation Rental features more than 10 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Uptown have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Madison Vacation Rental’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Uptown.

Are you planning to travel to the lakeside, beach, or mountain area? Madison Vacation Rental’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

Madison Vacation Rental boasts of 10 holiday cottages and places to stay in Uptown. The site provides unique Airbnb, VRBO, Madison Vacation Rental-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.

Frequently Asked Questions About Uptown Cottage Rentals

What are the top rated Cottage Rentals in Uptown?

There are a lot of options in Uptown. If you plan on staying in the Uptown area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Uptown:

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

The average cost for a cottage rental in Uptown is $167 per night. Madisonvacationrental has a wide list of great cottages near Uptown that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Uptown that allow pets?

Yes, here are the top cottage rentals in Uptown that allow you to bring your pet:

See all pet-friendly vacation rentals in Uptown on Madisonvacationrental

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

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

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

As of 2026, the data from Madisonvacationrental shows that there are Over 10 private swimming pools or cottages with indoor pools in the Uptown area along with other great amenities.