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Portland Cottage Rentals & Holiday Homes

Find the best cottages in Portland - We found 111 exact matches

About Portland Cottage Rentals on Montgomery Cottages

Searching for cottages to rent near Portland? Montgomery Cottages features more than 111 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 Portland 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. Montgomery Cottages’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Portland.

Are you planning to travel to the lakeside, beach, or mountain area? Montgomery Cottages’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.

Montgomery Cottages boasts of 111 holiday cottages and places to stay in Portland. The site provides unique Airbnb, VRBO, Montgomery Cottages-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 Portland Cottage Rentals

What are the top rated Cottage Rentals in Portland?

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

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

The average cost for a cottage rental in Portland is $214 per night. Montgomerycottages has a wide list of great cottages near Portland that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

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

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

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

As of 2026, the data from Montgomerycottages shows that there are Over 111 private swimming pools or cottages with indoor pools in the Portland area along with other great amenities.