Book Ashland Bed & Breakfast

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

B&B in Ashland

Villa DeWolf
Stately brick building with a central entrance and decorative pediment, flanked by two columns.

Villa DeWolf

4.0 star property
10.0 out of 10, Exceptional, (10)
"If you want the kindest hospitality, delicious breakfast and a memorable experience at a gorgeous historical home instead of a generic hotel, you must stay here!"
$275 nightly
The price is $313
Aug 7 - Aug 8
Total includes taxes and fees
Villa DeWolf
Blessings on State Bed & Breakfast
Property grounds

Blessings on State Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (55)
"Excellent property with welcoming staff and cozy, well-appointed rooms. "
Blessings on State Bed & Breakfast
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashland Hotel Reviews

Courtyard by Marriott Springfield

Courtyard by Marriott Springfield

10/10 Excellent
"The room was in great shape, bed comfortable, shower and bathroom very nice, tv worked great. I used the bistro bar in the front everyday for breakfast and coffee. Closely located to main thoroughfare and restaurants. I will stay there again when I come to visit again."
Lawrence 4-night trip
Posted 22 hours ago
Courtyard by Marriott Springfield

Frequently asked questions

What is the nightly rate for a B&B in Ashland?
Prices for B&Bs in Ashland often vary, but you can find a great deal from $313 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Ashland B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Ashland?
The best time to book a B&B in Ashland is during the vibrant spring months of April and May, when the city comes alive with cultural events and beautiful blooms. This period is particularly appealing for travelers who appreciate the arts, as it coincides with the renowned Oregon Shakespeare Festival, drawing theater enthusiasts from around the country.

During these months, visitors can enjoy mild temperatures averaging from the low 40s to mid-70s Fahrenheit, creating a comfortable environment for outdoor activities and leisurely strolls through Lithia Park, where the cherry blossoms are in full bloom. The picturesque landscape and charming downtown area make it an ideal time for sightseeing and indulging in local culinary delights.

For those seeking a more budget-friendly option, consider visiting in the quieter month of November. This time offers a unique charm with fewer crowds, allowing for an intimate experience of the town's rich history and culture, while still enjoying the beautiful fall ambiance.
What is the difference between a Ashland B&B and a hotel?
Every Ashland B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Ashland B&Bs.