Portland Cottage Rentals & Holiday Homes
Find the best cottages in Portland - We found 109 exact matches
About Portland Luxury Rental on Trailride
Searching for cottages to rent near Portland? Trailride features more than 109 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. Trailride’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? Trailride’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.
Trailride boasts of 109 holiday cottages and places to stay in Portland. The site provides unique Airbnb, VRBO, Trailride-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:
- Carefully Restored Wilsonville Farmhouse next to Parks & Trails, 1 Mile to I-5
- Historic Vista Cottage- Portland Heights -Featured in the Oregonian
- Charming 1-bedroom cottage in Oregon City
- recently constructed eco-cottage, heart of SE Belmont/Hawthorne, walk everywhere
- Cozy Cottage settled in the heart of beautiful Yamhill Valley wineries.
- Welcome to the Farmhouse Retreat!
- Mossy Cobbles: Romantic Cottage in a Wooded Setting
- Charming home within walking distance of gourmet dining, wine tasting & shopping
- Portland Oasis! Close in country renovated cottage with Exc WIFI
- Songbirds Landing- a charming cottage by George Fox -1 block to shops and dining
How much does it cost to rent a cottage in Portland?
The average cost for a cottage rental in Portland is $206 per night. Trailride 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.
Are there any cottages in Portland that allow pets?
Yes, here are the top cottage rentals in Portland that allow you to bring your pet:
- Zen Cottage in Close In NE Alberta Arts Area, Sleeps 2 Private and Sanitized!
- Tiny Digs Cottage House
- Historical Portland Home < 2 Mi to Downtown!
- Two Stories Cottage in SE Portland Oregon
See all pet-friendly vacation rentals in Portland on Trailride
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 Trailride shows that there are Over 109 private swimming pools or cottages with indoor pools in the Portland area along with other great amenities.
