Lake Oswego Cottage Rentals & Holiday Homes
Find the best cottages in Lake Oswego - We found 121 exact matches
About Lake Oswego Luxury Rental on Wine Country Villas
Searching for cottages to rent near Lake Oswego? Wine Country Villas features more than 121 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 Lake Oswego 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. Wine Country Villas’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Lake Oswego.
Are you planning to travel to the lakeside, beach, or mountain area? Wine Country Villas’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.
Wine Country Villas boasts of 121 holiday cottages and places to stay in Lake Oswego. The site provides unique Airbnb, VRBO, Wine Country Villas-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 Lake Oswego Cottage Rentals
What are the top rated Cottage Rentals in Lake Oswego?
There are a lot of options in Lake Oswego. If you plan on staying in the Lake Oswego area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Lake Oswego:
- Lake Oswego Luxury 9 or 10 Bedrooms 9 or 10 Baths
- Condo on the Lake
- Entire Guest House - Lake Oswego
- Oswego Lake Country Club's 9th Fairway nAn ADU for 31+ days - "The Bentley"
- The OMG House that will BLOW YOUR MIND with Unbelievable Cats n Mirrors
- Phenomenal Single Level Home Featuring Incredible Outdoor Golf Option w/Gazebo, Fire-Pit, and Patio
- Stylish Family Retreat w/Patio, & Game Console in Heart of Lake Oswego’s Westlake Neighborhood
- Dog-Friendly Home w/Fast WiFi, Full Kitchen, Gas Fireplace, Private Washer/Dryer
- OSWEGO LAKEFRONT STUDIO
- Lake Oswego Home w/Deck 9 Mi to Downtown Portland
How much does it cost to rent a cottage in Lake Oswego?
The average cost for a cottage rental in Lake Oswego is $422 per night. Winecountryvillas has a wide list of great cottages near Lake Oswego that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Lake Oswego that allow pets?
Yes, here are the top cottage rentals in Lake Oswego that allow you to bring your pet:
- ORIGINAL 1927 COZY LAKEFRONT BUNGALOW WITH WRAP AROUND PORCH
- Lake Oswego Inn
- Fairfield Inn & Suites by Marriott Lake Oswego
- Modern, new and close to lake
See all pet-friendly vacation rentals in Lake Oswego on Winecountryvillas
Do you have any rental cottages in Lake Oswego that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Lake Oswego to find one that works for you.
Are there quality cottages in Lake Oswego that have indoor swimming pools?
As of 2026, the data from Winecountryvillas shows that there are Over 121 private swimming pools or cottages with indoor pools in the Lake Oswego area along with other great amenities.
