1. USA
  2. Maryland
  3. Frederick
  4. Middleburg
  5. Cottage Rentals

Middleburg Cottage Rentals & Holiday Homes

Find the best cottages in Middleburg - We found 4 exact matches

About Middleburg Cottage Rentals on Anderson Island Living

Searching for cottages to rent near Middleburg? Anderson Island Living features more than 4 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 Middleburg 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. Anderson Island Living’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Middleburg.

Are you planning to travel to the lakeside, beach, or mountain area? Anderson Island Living’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.

Anderson Island Living boasts of 4 holiday cottages and places to stay in Middleburg. The site provides unique Airbnb, VRBO, Anderson Island Living-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 Middleburg Cottage Rentals

What are the top rated Cottage Rentals in Middleburg?

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

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

The average cost for a cottage rental in Middleburg is $304 per night. Andersonislandliving has a wide list of great cottages near Middleburg that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Middleburg that allow pets?

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

See all pet-friendly vacation rentals in Middleburg on Andersonislandliving

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

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

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

As of 2026, the data from Andersonislandliving shows that there are Over 4 private swimming pools or cottages with indoor pools in the Middleburg area along with other great amenities.