Cheltenham Cottage Rentals & Holiday Homes

Find the best cottages in Cheltenham - We found 613 exact matches

About Cheltenham Cottage Rentals on Wailea Vacation Rentals

Searching for cottages to rent near Cheltenham? Wailea Vacation Rentals features more than 613 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 Cheltenham 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. Wailea Vacation Rentals’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Cheltenham.

Are you planning to travel to the lakeside, beach, or mountain area? Wailea Vacation Rentals’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.

Wailea Vacation Rentals boasts of 613 holiday cottages and places to stay in Cheltenham. The site provides unique Airbnb, VRBO, Wailea Vacation Rentals-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 Cheltenham Cottage Rentals

What are the top rated Cottage Rentals in Cheltenham?

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

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

The average cost for a cottage rental in Cheltenham is $508 per night. Waileavacationrentals has a wide list of great cottages near Cheltenham that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

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

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

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

As of 2026, the data from Waileavacationrentals shows that there are Over 613 private swimming pools or cottages with indoor pools in the Cheltenham area along with other great amenities.