The Retreats at Grace Cottage
2026 Collection
At Work. In Love. At Home.
Some experiences are enjoyable. Others are defining. Our retreats at Grace Cottage are both.
Welcome to The Retreats at Grace Cottage, a curated series of intimate retreats offered across the year for women who are ready to be more deliberate about their work, love and home lives and who want to have fun while doing it.
We're now accepting participant applications for 2026. (Yes, you have to apply)
Early Bird Rate $3,200
Our retreats are not one-size-fits-all.
Each gathering brings together accomplished, thoughtful women for weekends that are equal parts fun, learning, coaching, and grounding.
Our retreats are intimate by design. Each experience is limited to six thoughtfully selected guests, ensuring depth, connection, and space to fully engage.
Held at Grace Cottage, a private lakeside home in South Haven, Michigan, the series is built to ensure every woman leaves more aligned with her aspirations, passions and equally inspired by what she's learned as well as the company she’s kept.
The Retreat Experience
From the moment you arrive, everything is handled.
This is not a vacation. It’s an intimate, high-touch experience designed for women who know that attention is the real luxury.
Here, value isn’t measured by how many days you’re away, but by the quality of attention and intention devoted to you. Every detail of the experience is designed around who you are and what you need next, not what works for the masses.
With only six women per retreat, there is no blending into a crowd. We know your name. We know your story. We help you recognize your patterns and the blind spots that keep showing up and holding you back, even though you’re accomplished, capable, and outwardly successful.
This is five-star hospitality with depth. Beautiful surroundings, private chef-prepared meals, and thoughtfully paced days allow you time to rediscover yourself.
While vacations or excursions may offer more days and more distractions, this experience offers something rarer: space. Space to think. Space to be honest. Space to do the work that actually moves your life or passion forward. You are guided, supported, and challenged in ways that feel grounded, personal, and lasting. The kind of work you don’t get to do on a vacation.
This is the experience women choose when burnout is no longer an option, when where you're headed next matters, and when you're ready to hone in on your passion or destiny by investing in yourself.
You don’t leave with just memories and Instagrammable moments. You leave feeling that you've been thoughtfully guided, with insights about yourself you'll never forget and a renewed sense of purpose and passion for your life.
Specifically, each retreat includes:
• Three days and two nights of beautifully appointed lodging with access to a private lake and thoughtfully designed spaces that support reflection, conversation, and connection
• Private chef-prepared meals designed to nourish and delight so every gathering around the table feels special
• Intimate coaching or hands-on tablescaping sessions led by a certified executive coach and professional tablescaper.
• A personalized goal-setting roadmap or keepsake workbook you’ll continue using long after the weekend ends
• A minimum of three curated sessions led by trusted experts, created exclusively for the retreat
• Unstructured time to explore town, shop, wander, or simply do nothing at all
• A thoughtfully curated gift bag filled with customized, meaningful gifts, not-throwaway, indulgences
Early registration is highly recommended because word is spreading fast about how fabulous each retreat is!
Apply now for the 2026 retreat of your choosing.
Meet the Founder
Welcome to Grace Cottage!
I’m Cheryl Grace, founder of Powerful Penny LLC, a leadership development and executive coaching firm.
Having spent more than 25 years in the corporate sector, I’ve attended just about every retreat, summit, and offsite imaginable. Too many felt big, impersonal, cliquish, or one-dimensional. Everything we do at my firm is grounded in three pillars: at work, in love, and at home, because life isn’t lived in silos. It felt only fitting that the retreats hosted at my private vacation home reflect that same philosophy.
Each experience is thoughtfully designed
to elevate the whole of you.
We focus on your full self.
At Work
Focused on your professional life, these retreats help you refine your individual or company goals, sharpen your direction, and step back into your work, business, or Life 2.0 with renewed focus and authority.
In Love
Held just once a year, our love retreat creates a safe space to look honestly at the love you desire, the boundaries you’ve set, and the unintentional walls you’ve built that may be quietly standing between you and the relationship you say you want. Think of it as a boot camp for the heart!
At Home
Centered on women who love to entertain, these retreats are about the art of tablescaping, hosting, creating beauty, and moments people remember long after the dishes are cleared.
Retreats by Date
2026 retreat schedule by date:
🗓 April 24th - 26th The Host Within (II)
🗓 June 5th - 7th The Ascension Weekend Retreat Alumni Experience
🗓 July 10th -12th The Relationship Readiness Retreat
🗓 August 14th - 16th The Host Within (III)
🗓 September 18th - 20th The Host Within (IV)
🗓 November 6th - 8th Her Boss Era, THE Retreat for Women Who Mean Business
🗓 December 11th-13th Your Life By Design Goal Setting Retreat (III)
The Retreats by Pillar
at Work
The Ascension Weekend Retreat Alumni Experience
June 5 - 7, 2026
This summer weekend is designed exclusively for women who have previously completed the Your Life By Design (YLBD) Goal Setting Retreat and are ready for a thoughtful mid-year recalibration at a higher level.
You’ll rekindle friendships, may reconnect with your accountability partner in person, and enjoy the kind of easy, unforced camaraderie that comes from being in the right room with the right women. The setting is relaxed and intentional, reminding you that this work does not have to feel heavy or lonely. You’ll revisit your roadmap with fresh eyes and leave with renewed direction that feels grounded, focused, and doable for the rest of the year.
Her Boss Era: THE Retreat for Women Who Mean Business
November 6–8
This is a working retreat for women who have been in business five years or less, or who are running a side hustle that’s ready to grow up. You’re good at what you do, but the business itself still feels messy, reactive, overwhelming, or too dependent on you.
This practical, hands-on business experience is rooted in everything we deliver inside our Grace Start program. In one weekend, we help you put real structure in place, clearly define what you sell so people understand why they should buy from you, and learn how to speak directly to your ideal audience without sounding salesy or scattered. You’ll also identify a lead magnet aligned with your clients’ core problem areas and set up a simple sales funnel you can replicate long after you leave the retreat.
In just three days you’ll walk away with a clear, executable 60-day plan that would have taken you months (if not years) to figure out the YouTube way. This retreat is priceless to a business owner.
SAVE YOUR SPOT
Your Life by Design Goal Setting Retreat
December 11-13, 2026
This is our signature retreat experience for women who are ready to stop reacting to life and start designing it with intention.
Over three thoughtfully structured days, you get out of your own head and do real work that actually moves your life forward. There’s no rushing, no fixing everyone else’s problems, and no pretending you are fine when you’re not.
You let go of the thinking that has been quietly holding you back and use the Five-Step Eat Pink Elephants Framework™ to focus on what you want next and map out how to make it happen without burning yourself out.
There’s something powerful about being in a room where no one needs you to explain yourself. Amidst conversation and laughter, you’ll create a vision board based on actual goals, and be part of the kind of honest dialogue you rarely get to have at home or at work because everyone is too busy or too polite.
You’ll leave with your Your Life By Design Roadmap, created specifically for you, with a clear, easy-to-implement plan for what comes next.
in Love
Love, Intentionally – The Relationship Readiness Retreat
July 10-12, 2026
This is not a sit-in-a-circle-and-cry-about-your-ex retreat. It’s a summer reset for single women who want real love and still want to enjoy the process.
Over this playful, eye-opening weekend, you step out of the noise and into honest reflection around how you love, how you protect yourself, and what you actually want in a relationship at this stage of your life. We talk honestly about the beliefs you’ve picked up along the way, the habits that keep sneaking into your dating life, and the invisible walls that once felt protective but may now be blocking the good stuff. Expect plenty of laughter and “ohhh… that makes sense” moments along the way.
You’ll learn how to flirt with confidence, spot frogs without making them mean anything about you, and free yourself to date in a way that feels fun instead of exhausting. Think less “What’s wrong with me?” and more “Ohhh, that’s my pattern.”
at Home
Host Within Retreat
April 24-26; August 14-16; September 18-20
So popular we’re offering it several times this year! The Host Within Retreat is an interactive, high-energy experience for women who genuinely love hosting and want to take their lives and tables from “nice” to truly memorable. This is not a watch-and-listen weekend. You roll up your sleeves, get creative, and play.
You’ll learn the tricks of the trade that elevate a table instantly, from building layered centerpieces and working with florals, to choosing the right napkin size, tablecloth proportions, and finishing details that make guests say, “Wow!” You’ll sharpen your eye for what works, what doesn’t, and understand why certain choices elevate a table while others fall flat.
Then you’ll put it all into action during a fun, competitive tablescape challenge that lets you test your instincts, stretch your creativity, and see how small choices make a big impact.
Expect laughter, friendly rivalry, and plenty of hands-on experimentation. You’ll leave with sharper hosting skills and a new appreciation for hosting as an experience.
SAVE YOUR SPOT
Early Consideration
Each retreat is intentionally limited to preserve the quality of the experience and the dynamic in the cottage.
You’re encouraged to apply early so we can thoughtfully consider your fit for the retreats that resonate most with you. Many weekends reach capacity before wider promotion begins. Once accepted, all retreats must be paid in full no later than 30 days prior to the first day of the retreat.
If you already know this is the kind of experience you value, now is the time to get in early.
Grace Cottage is waiting.
