Holly Bailey Photography

Holly Bailey Photography Couples. Seniors. Maternity. Portraits. Families. Lifestyle. Engagement 📸

✨ The Jones ✨ 08.22.2026 ✨This entire day was literally magic, and I mean that with my whole heart. There was so much lo...
08/24/2026

✨ The Jones ✨ 08.22.2026 ✨
This entire day was literally magic, and I mean that with my whole heart. There was so much love everywhere and I felt so honored Peter & Maddy trusted me to capture this monumental moment in their lives.

From the moment they asked me to do their photos I was beyond excited. Their engagement session was literally one of my favorite shoots I’ve ever done. Capturing love really is one of my favorite things to do - however I was transitioning out of wedding photography - but these two convinced me to do theirs very quickly. I could instantly tell they were end game.

I’ve known Maddy for a long time and she is truly one of the sweetest people out there & I didn’t think she could possibly be any more beautiful but dang girl you were breathtaking on your wedding day. Peter - don’t ever stop being you; you are a good man with a good heart.

The venue was S T U N N I N G & I mean stunnnnning. The Barn At Hatch Point ya’ll know what you are doing.

Every part of this day was incredible. Location. The couple. Family. Friends. From the first look with her dad and brother, to her speech to her mom & entire family slow dance, Peter with the captain hat on. This day couldn’t have been more perfect. A few sprinkles for good measure and a beautiful cloudy sky for photos 🤍

Wishing you all the best guys I absolutely adore you and I know that you will build a beautiful life together. Love you both 🥹🤍

Thank you for a picture perfect day & my last ‘big wedding’ is in the books 🤍

✨ H A N N A H ✨ MDIHS Class of 2027 ✨Holy smokes this girl knocked this outta the park (slight pun intended) but in all ...
08/22/2026

✨ H A N N A H ✨ MDIHS Class of 2027 ✨
Holy smokes this girl knocked this outta the park (slight pun intended) but in all seriousness, I had such a blast at this shoot. It’s so wild to photograph ‘kids’ in this phase of life but you keep picturing them as a little 8 year old but here she is; all grown up and absolutely stunning.
Hannah - you are gorgeous and have such a strong head on your shoulders. I cannot wait to see what you do in life, live it to the fullest - & you have got one hell of a mama in your corner who will have your back forever 🤍

My son the entire time I was editing these could not stop saying ‘wow she is pretty, she has such a pretty smile’ and he is so right.

Aiden; MDIHS Senior Class of 2027.He absolutely set the tone for my senior boys this year; he was up for anything I said...
08/20/2026

Aiden; MDIHS Senior Class of 2027.
He absolutely set the tone for my senior boys this year; he was up for anything I said; even was about to put the tall grass in his mouth to fit the cowboy vibe but thought better of it because... he is allergic 🤣 We had a blast and I'm so glad I was able to capture this time for him.

✨S O P H I E✨ Senior MDIH Class of 2027. This girl could not have rocked this senior session more than she did. From hor...
08/07/2026

✨S O P H I E✨ Senior MDIH Class of 2027.
This girl could not have rocked this senior session more than she did. From horses, to old Fords, to the beach - absolutely blew me away. We had a blast and I literally have been waiting for this day since this girly was a freshman. I was like Em, I call DIBS on that one hahaha. Not only is she sweet, and STUNNING, but she is salt of the earth kind of people. I can not wait to see where this girly goes in life but she has an amazing crew behind her.
I could not possibly narrow it down any more than this.

✨ P E N N Y ; MDIHS class of 2027 ✨Senior season is in full swing and I couldn’t be happier. This sweet girl blew me awa...
07/27/2026

✨ P E N N Y ; MDIHS class of 2027 ✨
Senior season is in full swing and I couldn’t be happier. This sweet girl blew me away. Beautiful, kind, sweet, down to earth. We had a blast and so glad we held out for a better weather day, absolutely worth the wait ✨ Elephanté made a guest appearance and literally warmed my heart so much. Absolutely adore this family so very much. 🤍 thank you for allowing me to capture this precious time.

Hiiiiiii! Mid-summer update! I am booooooked until September solid. So if you have not gotten on my schedule and would l...
07/20/2026

Hiiiiiii! Mid-summer update!
I am booooooked until September solid. So if you have not gotten on my schedule and would like to please, please don’t wait! I don’t want to have to turn anyone away but it does get very busy juggling my full time job, my part time job, and family 🤍
Selfie with my mini me 🏁

Elli - MDIHS Senior Class of 2027 🤍 It's officially my favorite photography season; SENIOR SEASON! Beyond happy this bea...
07/15/2026

Elli - MDIHS Senior Class of 2027 🤍
It's officially my favorite photography season; SENIOR SEASON! Beyond happy this beautiful, sweet, smart, gentle and kind soul was the first one of the year.

I don't know who had more fun during this shoot, but we laughed the whole time. To say this one didn't make me feel old would be an understatement as this is one of my High School best friends 'little' sisters; how did this happen so fast?!
Elli - you are STUNNING and it was an absolute pleasure capturing this milestone for you. I have not a single doubt in my mind that you will go far in life; whatever path you may choose. I'm not sure I've met such a solid 17 year old but she comes from such a wonderful family so it isn't a surprise to me at all.

SENIORS CLASS OF 2027 ! ! ! Please don't wait if you are hoping to book with me; my schedule is filling up and if we hav...
06/19/2026

SENIORS CLASS OF 2027 ! ! !
Please don't wait if you are hoping to book with me; my schedule is filling up and if we haven't confirmed a date/taken a deposit you are not secured in my schedule!
Seniors are 110% my passion and I want to fit as many of you in as I can, but my schedule is getting very busy and I don't want to miss any of you!
PLEASE PLEASE PLEASE reach out to confirm & book if you are hoping to!

Lupine season is always my favorite, no explanation needed. This family is so near and dear to my heart and I'm here for...
06/19/2026

Lupine season is always my favorite, no explanation needed.

This family is so near and dear to my heart and I'm here for all the moments. The giggles, the silly faces, the wild & free spirits. We had a blast on an absolutely beautiful, private property running through the lupine, sliding through the grass. My love for this family is endless and I'm always happy to capture the memories. These boys give THE BEST hugs ever, thankful to be their 'Auntie Holly'.

No matter what I believe it is so important to capture the moments; worried your kids will run wild? They will, but it's absolutely okay - we will take wiggle breaks. The point of capturing memories is freezing a point in time and when you look back at the photos you'll remember that silly face Allan made, the wiggly tooth Otto had, Denali Schnoody Van-Doodle with her beautiful floral collar and 17 names she answers to.

Book the session, the only regret you will have is not doing it.

🫶🏼 this photo lit my creative soul on fire 🔥Two besties ending one journey and starting another together. 🥹Lauren & Audr...
06/05/2026

🫶🏼 this photo lit my creative soul on fire 🔥
Two besties ending one journey and starting another together. 🥹
Lauren & Audrey thanks for choosing me and congrats you beautiful girlies. 🤍

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Southwest Harbor, ME
04679

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(207) 460-3488

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