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San Mateo County Cottage Rentals & Holiday Homes
Find the best cottages in San Mateo County - We found 47 exact matches
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About San Mateo County Cottage Rentals on Stay If You Dare
Searching for cottages to rent near San Mateo County? Stay If You Dare features more than 47 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 San Mateo County 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. Stay If You Dare’s cottage listings come in all shapes and sizes for large groups, friends, or couples in San Mateo County.
Are you planning to travel to the lakeside, beach, or mountain area? Stay If You Dare’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.
Stay If You Dare boasts of 47 holiday cottages and places to stay in San Mateo County. The site provides unique Airbnb, VRBO, Stay If You Dare-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 San Mateo County Cottage Rentals
What are the top rated Cottage Rentals in San Mateo County?
There are a lot of options in San Mateo County. If you plan on staying in the San Mateo County area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in San Mateo County:
- The Cottages Hotel
- Coastal Zen Cottage - Walk To Beach
- Private Cottage House - Walk to Beaches HarborFood Trials so much more
- Entire Mountain Cottage Home - Restaurants Amazing Hiking & Biking Trails
- Steps to Ocean: Luxe Family Home in Half Moon Bay!
- Marbella Lane - 3BR House Dtwn RWC Parking
- Marbella Lane - 2BR Guest House Dtwn RWC Pking
- Charming 2-bedroom cottage less than one mile to Montara beach
- Charming 1-bedroom cottage with WiFi, AC in tranquil San Carlos
- Peaceful Studio Cottage In the Heart Of Silicon Valley
How much does it cost to rent a cottage in San Mateo County?
The average cost for a cottage rental in San Mateo County is $485 per night. Stayifyoudare has a wide list of great cottages near San Mateo County that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in San Mateo County that allow pets?
Yes, here are the top cottage rentals in San Mateo County that allow you to bring your pet:
- OCEAN FRONT Beach Cottage with Panoramic Views!
- Exquisite luxury executive cottages
- Marbella Lane - 2BR Guest House Dtwn RWC Pking
- Private and charming Bay Area home. Centrally located to all Bay Area cities!
See all pet-friendly vacation rentals in San Mateo County on Stayifyoudare
Do you have any rental cottages in San Mateo County that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in San Mateo County to find one that works for you.
Are there quality cottages in San Mateo County that have indoor swimming pools?
As of 2026, the data from Stayifyoudare shows that there are Over 47 private swimming pools or cottages with indoor pools in the San Mateo County area along with other great amenities.
