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7-Day Aspiring Artist All-inclusive Retreat in Oregon | October 2026

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7-Day Aspiring Artist All-inclusive Retreat in Oregon | October 2026

October 27 - November 2, 2026

Ashland, OR, United States

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Hosted By

Oregon Wellness Retreat

7 followers

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6 nights, 7 days

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7 person retreat

Highlights

  • #1 Artist Retreat in the country!

  • Great for beginners and professionals alike.

  • Feeling creative? Join us for this exclusive trip.

Details

#1 Artist Retreat in the country! Great for beginners and professionals alike. Feeling creative? Join us for this exclusive trip. Have you always wanted to be an artist but need help figuring out where to start? Or do you need an outlet to let your creative juices flow? Check out what our past guests have to say on our website, including celebrity reviews. Stay in luxury accommodations. Eat at the best restaurants and be served by private chefs. All while learning hands-on, diverse techniques from professional artists. Go home with your own completed works and a beautiful "artist tool kit". Learn and try out different mediums and artistic styles. On your own or side by side with one of your favorite people, making friends lasts a lifetime. (O.W.R.'s entire space is devoted, this week only, to you and other "dreaming artist" guests. Class size will be kept under 5 persons (total) As you journey through many artistic realms, you are bound to find the path that speaks to you!

Location

Ashland, OR, United States

Ashland, Oregon (97520), is a charming town in southern Oregon’s Rogue Valley, best known for its vibrant arts scene, natural beauty, and welcoming community. Nestled at the base of the Siskiyou and Cascade mountains, it’s home to the renowned Oregon Shakespeare Festival, which draws visitors from around the world. The town features tree-lined streets, eclectic shops, farm-to-table restaurants, and nearby vineyards, creating a lively yet relaxed atmosphere. Outdoor enthusiasts are drawn to its hiking trails, Lithia Park, and proximity to skiing and rivers, making Ashland a unique blend of cultural richness and scenic adventure.

Venue

Oregon Wellness Retreat

4.9 117 Reviews

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A 14-minute walk from the Oregon Shakespeare Festival, this relaxed bed-and-breakfast in an American Craftsman residence is 2 miles from the Pacific Highway and a mile from Lithia Park. The 6 homey rooms feature sitting areas, en suite or private bathrooms, and free Wi-Fi. Breakfast and parking are complimentary. There's a porch and a garden. Kids aged 10 and over are welcome with prior arrangement. Dogs are allowed for a fee.

A/C in Rooms

A/C in Rooms

Free Wifi

Free Wifi

Towels

Towels

Kitchen

Kitchen

Free Parking

Free Parking

Shower

Shower

TV

TV

Hairdryer

Hairdryer

Fireplace

Fireplace

Bathtub

Bathtub

Accommodation

Single Private Room

3 Rooms Left

Private room for 1

$5,042 USD total

Room for 2 people.

2 Rooms Left

Private room for 2

$4,151 USD / person

Room for 2 people.

2 Rooms Left

Private room for 1

$8,302 USD total

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1 person, having their room to themselves. All of our rooms have en suite full bathrooms, central air/heat. ceiling fans, closets, robes, luxury toiletries, TV with streaming services, luxury bedding, and sitting areas. *Most rooms have 1 queen-size bed. or Save over $1700 when you book for 2 people. Shared room for you and one of your favorite people. (not with a stranger) All of our rooms have en suite full bathrooms and central air/heat. ceiling fans, closets, robes, luxury toiletries, TV with streaming services, luxury bedding, and sitting areas.1 room with a King and Twin bed.

Meals

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Meals provided

Breakfast · Brunch · Lunch · Dinner

Diets catered

Vegan · Vegetarian · Gluten-free · Dairy-free · Nut Allergy Friendly · Diabetic Friendly · Keto Friendly

We will have 17 meals together this week and a Welcome Reception on the first day. We will partake in gourmet meals both on and off-site. Fine dining at award-winning restaurants. Catered and chef-prepared onsite meals. On or off-site dining will depend on each day's class schedules and locations. Dietary Allergies can be accommodated; we will discuss this ahead of time.

Schedule

Multi-course breakfast will be served onsite each morning at 9 am. Optional Movement with Mindfulness sessions Daily art classes will either be held on-site or amongst artists’ studios in town Classes will be given by a local, experienced, and professional artist Each class will take 1/2 to a full day to complete Gourmet lunches and dinners will be diverse We will eat off-site at least once per day Snacks and a 24 coffee/tea bar are on site Instruction and hands-on class time will be 5-7 hours per day Time to rest, chat, or keep creating each evening Explore the town, get a massage, or lie in the hammock during your free time Take your well-deserved rest each night in your climate-controlled private room

Testimonials

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"Josh and I decided on a whim to celebrate our 15th wedding anniversary by going on an art retreat. We found Oregon Wellness Retreat and before we could overthink it…pulled the trigger! Best. Decision. Ever! We had such an incredibly renewing, creative, expanding and delicious experience and made connections with some of the most incredible people we hope to know for the rest of our lives! I can not wait for the next retreat!! Thank you Bayberry Inn we’ll see you at the next one!" -Katherine Heigl "Can be found on her Instagram"

Katherine Heigl, American Actress, Producer,, United States

"A few weeks ago, I treated myself to a lovely art retreat vacation in Ashland, Oregon with Oregon Wellness Retreat at the Bayberry Inn. It was a wonderful week filled with hours of relaxing creativity, new friends, and amazing food. So fun!" -Astronaut Karen Nyberg (Can be found on her Facebook)

Karen Nyberg, American Astronaut, United States

"@katherineheigl and I had a blast on our #artretreat at the @oregon_wellness_retreat @bayberryinn438 last month - inspired, accomplished and well fed !! Katie laughs at this but now I’m into sculpting marble and I love it !! Look into this y’all- whether you’re aspiring or accomplished artists it’s so good for the soul!!" _Josh Kelley ( Can be found on his Instagram)

Josh Kelley, American Musician, United States

What a treat! Attending the Artist Retreat was an extraordinaryrewarding and fun event. The owners Jacqui and Billy were like meeting old friends from the moment I arrived. The took care of everything and were so well organized and extremely helpful. They are both kind and fun to spend time with and I already miss them and the other artists/participants. We were invited to start our morning with a yoga/meditation instructor and a five star gourmet breakfast that was prepared by Billy. Yummy! We then started our art sessions with a different local artist daily. They were all excellent caring teachers. Everyday we would eat lunch and dinner in some great restaurant that our hosts provided. Again, more good food. In the evenings we could have free time or attended other events, a concert, galleries, spa, etc. that were scheduled by Jacqui and Billy. All above was arranged by our extraordinary host and included in our stay at the beautiful and well appointed Bayberry Inn which is located a short walk to downtown Ashland. I give this experience a hundred plus stars! -Pasha Sept 2023

Pasha, United States

I had a wonderful, unforgettable time at the OWR Aspiring Artist's Retreat, and I highly recommend it! The Bayberry Inn is beautiful, and the owners made me feel welcome and pampered from the moment they picked me up at the airport. I loved meeting local artists and stretching my creativity in new ways. And the food was so delicious! I returned home feeling energized, empowered, and grateful for new friends and a fresh perspective. This is a very special place and I can't wait to go back! -Susan Nov 2024

Susan, United States

Location, Fantastic Host, and dream retreat- this artist couldn't ask for more! I was introduced to the Bayberry Inn through their Oregon Wellness Retreat Aspiring Artist Retreat. The Inn was wonderfully appointed and my room (Bayberry Room) had the best view of mountains and trees! Their location is a short easy walk to downtown where you have your choice of parks, shops, restaurants, and entertainment. The breakfast services was so scrumptious and always welcoming! Billy & Jacqui love their Inn and what they do and it shows in the care of they give their guest. I came a stranger and left with a whole new set of friends! The Aspiring Artist Retreat was spectacular! We were introduced to local artist and had a creative adventure every day! I came home with so much art and a new fire was ignited in me to create more! I will be back for more of what they have to offer! -DeeDee Sept 2023

DeeDee, United States

Exceeded my expectations!! I came for an artist retreat and got so much more! Jacqui and Billy were wonderful hostesses. Jacqui accommodated every single need from planning amazing art activities, delicious local restaurants, beautifully appointed rooms and even skin care items!! She was always gracious and kind. Billy is a cook extraordinaire! Every morning we were surprised with a delicious breakfast. I will live my life dreaming of his banana pancakes!! He was engaging and fun and attended to our every need. The town of Ashland city is charming and unique and has everything from outdoor concerts to shopping to lovely bookstores, amazing restaurants, gorgeous hiking, and worldwide acclaimed theater. If you want to relax , rejuvenate and reconnect- then this is your place. I made so many friends💕💕Forever in my heart. Beautiful Ashland City- Wonderful Bayberry Inn!!! - Freedom Sept 2023

Freedom, United States

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Host

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Oregon Wellness Retreat

Ashland, OR 97520, USA

Oregon Wellness Retreat, located at the Bayberry Inn in Ashland, Oregon, has been recognized for eight years as one of the "100 Best Destinations in Oregon" and ranked in the "Top 3% of Hotels Worldwi...

1 language

English

Teaching for 4 months

Joined Insight Timer in Sep 2025

What's Included

Beautiful private guest room

All meals

Professional world-renowned instructors each day

Snacks and drinks 24 hrs

Coffee and Tea bar 24 hrs

Transportaion during retreat

Transportaion to and from MFR airport

Optional mediation or yoga classes

All the professional-grade artist tool kit , to take home with you

Multiple art mediums taught throughout week

Take home your finished projects from each day

Retreat pics and videos will be shared with the group post retreat, with signed release

Personal pre and post retreat care

Some alcoholic drinks

Not Included

Flight costs

Travel Insurance

Visa fees

Additional activities not inlcuded in itineray

Spa treatments

Additional nights ( 6 inlcuded )

FAQs

Guest requirements

  • Must be 18 or older or traveling with an adult

  • Please acknowledge classes will be taught in English

Cancellation policy

The remaining balance for the retreat is due 60 days prior to the start date. If this balance is paid earlier than these 60 days, you are eligible to cancel and receive a full refund of this remaining balance, provided you do so at least 60 days before the retreat begins.