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Weddings

About

Caroline Winn is a wedding, portrait and lifestyle photographer based out of Boston, MA and serving couples all over New England. She started her business in 2013 and absolutely loves every minute of what she does. Her style is light, airy, and classic- with the goal that her couple’s images withstand the test of time. Outside of photography, Caroline loves to run, watch Friends reruns, eat tacos and travel with her husband, Dan.

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Frequently asked questions

Which of the following are included in the starting price?

Engagement Shoot
High-Res Images
One Event / Day
Digital Files

Which of the following are included in the price of your most popular wedding package?

2nd Shooter
Add'l Hours
Engagement Shoot
High-Res Images
One Event / Day
Albums
Digital Files

What primary photographic style do you identify with?

Contemporary
Natural
Photojournalism

What photography services do you offer?

Additional Hours
Destination / Travel
Engagement Shoot
High-Res Images
One Event / Day
Second Shooter

What photography items do you offer?

Albums
Canvas
Digital Files
Flush Mount
Matted Prints
Negatives
Prints
Proofs
Save the Date
Thank You Cards

Reviews of Caroline Winn Photography

Keara
Keara Sent on 01/05/2026
5 out of 5 rating

Treasured Memories Captured Beautifully

We worked with Caroline from our engagement photos all the way through our wedding day, and had a great experience the whole way through. (Engagement photos were actually included as part of our wedding package which was a huge plus!) Aside from capturing absolutely gorgeous photos, Caroline was also organized, responsive, and extremely helpful at managing our wedding party and families for photos. My husband and I opted to not do a first look, which can make things more complicated for photographers/videographers and scheduling, but Caroline made sure we got all the photos we wanted and still made it to the end of our cocktail hour. She also recommended a second photographer in order to enable my husband and I to stay separate until the ceremony. I will treasure the memories Caroline was able to capture forever. Gorgeous photos ranging from posed formals to more candid shots that really highlight the emotions of the day. We highly recommend working with Caroline!
E
Emma Sent on 09/19/2025
5 out of 5 rating

Perfect Wedding Photos!!

We had the absolute BEST experience with Caroline as our wedding photographer this summer! Throughout all the months leading up to the wedding, Caroline was attentive, professional, prompt and kind - sending notes of encouragement about the planning process and answering any and all questions we had. Her detailed timeline was amazing, and was sent to us way in advance in case any changes were needed. On our wedding day Caroline was the perfect calming and knowledgeable presence - we stayed exactly on time and the day flowed so smoothly from start to finish. We are SO incredibly happy with all of the photos we received - they allowed us to relive the day so beautifully, and will truly treasure them forever! They are the perfect blend of formal shots and candids of us and our guests, and we are so happy with how many small, intimate moments she was able to capture throughout the day. Thank you so much Caroline for everything you did to make our wedding (and all the photographic memories) perfect!!
N
Nicole Sent on 07/01/2024
5 out of 5 rating

Wedding Pictures

Caroline was an absolute pleasure to work with. She was responsive, flexible, and professional. She took the time to get to know us during the engagement pictures and answered all my questions leading up the wedding, which helped reduce the stress and anxiety around planning a wedding! She had calm, confident energy on the wedding day. Her assistant was also a delight to work with and did a fantastic job capturing additional moments. I love the way she edited the photos and they were really easy to access and download. I will forever cherish the pictures that Caroline took and am grateful that she was part of my wedding journey.
T
Taylor Sent on 02/23/2024
5 out of 5 rating

Hiring Caroline will be the best decision you make!

Caroline somehow does it all ... she was everything we didn't even know we needed and can't say enough great things about her!
If you look at her work and photos, I think they speak to her level of talent that you won't regret but for us, having Caroline there on our day was the TRUE gift.
She's calm in any setting with ability to quickly adapt to anyone or situation thrown at her. During a time that can be stressful and chaotic, Caroline's professionalism is always authentic, she gave us the chance to laugh, have fun and enjoy the time spent taking photos with all of our loved ones.
Our entire wedding party and family continued to come up to us throughout the day to let us know how great she was... we neglected to realize how much of an impact your wedding photographer has on the day.
If you want to hire someone that will give you the chance to look back on your wedding and feel every emotion all over again through photos ... hiring Caroline is a no brainer.
M
Michelle Sent on 07/17/2023
5 out of 5 rating

Caroline is the best!

Caroline was an absolute delight to work with. From our engagement photos to the wedding day, she made us feel so comfortable in front of the camera and was able to capture these special moments so beautifully! She delivered both sets of our photos way earlier than we expected. She was professional, sweet, fun and helped to make our day so special!
C
Celeste Sent on 12/20/2022
5 out of 5 rating

Highly Recommend!!

Hiring Caroline as our wedding photographer was one of the best decisions we made through our whole wedding process & we cannot recommend her highly enough!! Caroline brings a wonderful combination of calm and excitement to the process. Through both our engagement & wedding photos, she made my husband and me feel relaxed, but also was someone we really enjoyed chatting with and getting to know! It ultimately felt like we had a friend by our side through all of the photos, making us feeling very at ease. Caroline carefully listened to everything we wanted to capture on our big day and was extremely thorough in all her prep. She constantly checked in during our wedding day to make sure we were capturing the moments that were important to us. She was never intrusive or distracting with her photos, which is amazing because she captured such intimate moments without us even realizing. We are SO pleased with how the photos came out. Caroline also brought a lot of knowledge to wedding planning and thoughtfulness. We also were navigating a large range of Covid comfort levels among our guests and Caroline could not have been more accommodating and empathetic. I would highly recommend her & we look forward to working with her to document other milestones in the future! Thank you, Caroline!!
E
Emily Sent on 11/18/2022
5 out of 5 rating

The best wedding planning decision we made

I can not say enough good things about Caroline! She photographed our wedding and engagement pictures and working with her was one of the best decisions we made when planning our wedding! For so many reasons -

Caroline is incredibly organized. We were living in California while planning our wedding in Massachusetts, which often made the planning logistically challenging, but because of Caroline the photography was never something we had to worry about. She was pretty much the quarterback of our wedding day! She checked in with us at regular intervals, had an incredibly detailed and thorough approach to planning the wedding timeline, and was so understanding and flexible with our difficult schedules. She fit us in for an engagement session just 2 weeks before our wedding day and despite it being peak wedding season, she still had our pictures to us just a few days later so we could enjoy them before the wedding.

Caroline herself is just a genuinely awesome person! You spend a lot of time with your photographer on your wedding day and Caroline is fun, easygoing, and relaxed, while still being super on top of everything. She was able to get through all of our portraits quickly and get us back to enjoying time with our guests without compromising the quality of the photos at all. During our engagement session she helped us relax and have fun while giving us just enough direction so that our photos came out amazing but somehow still looked so natural.

The photos Caroline takes really speak for themselves. All of her work is truly stunning and we could not be more in love with the end result. We’re so grateful to have had our wedding day captured so beautifully and we would absolutely recommend Caroline to anyone!
J
Jacky Sent on 11/03/2022
5 out of 5 rating

Caroline Winn Photography

I cannot say enough wonderful things about Caroline as our wedding photographer! If you're questioning whether or not to book her for your wedding… BOOK HER! Her gorgeous photos speak for themselves (I could honestly get lost on her website and Instagram for days), but it should also be noted that she was amazing to work with throughout the entire wedding process. Caroline is organized and efficient with a calming demeanor which is an ideal presence to have around on your wedding day. She executed our complicated timeline with multiple locations and venue time constraints with ease. She delivered a GIANT gallery of photos as soon as we returned from our honeymoon with so many beautiful shots from our favorite day. Trusting someone to capture one of the most important days of your life is a big decision, but one I never doubted having hired Caroline!
M
Meagan Sent on 08/10/2022
5 out of 5 rating

Caroline Caroline Caroline!

Caroline Winn is the most talented, kind, professional, creative photographer in the industry. I absolutely could not recommend her more to anyone who is interested in capturing life's most important moments - from weddings, to engagements to maternity and family photos. For me, she balanced all the "mayhem" of our wedding day perfectly, and made me feel like I had a true friend capturing it all. When we delayed our wedding an entire year because of the pandemic, she re-scheduled. When we wanted to take our bridal portraits on my family's boat, she was down. When our ceremony was on the side of a fairly steep hill overlooking the ocean, she climbed it to capture the whole scene. She is the kind of human who makes you feel at ease and you know she's got it all under control. The way she plays with light and captures personalities and highlights natural beauty in her art is why her photography caught our eye many years ago, and we've been following her on IG ever since. When it came time to plan our own wedding, she was our first choice. Her second photographer, Hallie, was also absolutely amazing! Thank you, Caroline and Hallie, for going so far above and beyond to ensure we have the best wedding album we could have ever asked for. XOXO
Amy
Amy S. Sent on 07/17/2022
5 out of 5 rating

The BEST wedding photographer!!

If you're looking for a wedding photographer, I can't recommend Caroline enough! From the moment we spoke with her on the phone, we knew we had to have her for our wedding day. Caroline was so attentive and organized throughout the planning process leading up to our wedding day. She was there for us every step of the way, crafting us the perfect timeline and staying in touch for all of our last-minute questions before the big day. On the day of the wedding, she did an amazing job keeping everyone on schedule and capturing every photo we had on our list. She was such a calming presence, and she and her second-shooter made sure our entire family and wedding party were looking their best for every single picture. Our final photographs are absolutely stunning, elegant, and timeless-- there is truly not a bad photo in the entire collection! Our family and friends can't stop talking about how beautiful they are. Caroline is the most incredible photographer, and we can't wait to work with her again in the future!
We're all about trust. Our community relies on honest reviews to help you make those big decisions with ease.

Awards

65
WeddingWire Couples' Choice Awards 2023 Winner
WeddingWire Couples' Choice Awards 2022 Winner
WeddingWire Couples' Choice Awards 2020 Winner
WeddingWire Couples' Choice Awards 2019 Winner
WeddingWire Couples' Choice Awards 2018 Winner
WeddingWire Couples' Choice Awards 2017 Winner
WeddingWire Couples' Choice Awards 2016 Winner

Map

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Caroline Winn Photography frequently asked questions

Caroline Winn Photography includes the following photography services in the starting price:
  • Engagement Shoot
  • High-Res Images
  • One Event / Day
  • Digital Files
Caroline Winn Photography includes the following photography services in their most popular wedding package:
  • 2nd Shooter
  • Add'l Hours
  • Engagement Shoot
  • High-Res Images
  • One Event / Day
  • Albums
  • Digital Files
Caroline Winn Photography offers the following photography styles:
  • Contemporary
  • Natural
  • Photojournalism
Caroline Winn Photography offers the following photography services for weddings:
  • Additional Hours
  • Destination / Travel
  • Engagement Shoot
  • High-Res Images
  • One Event / Day
  • Second Shooter
Caroline Winn Photography offers the following photography materials for weddings:
  • Albums
  • Canvas
  • Digital Files
  • Flush Mount
  • Matted Prints
  • Negatives
  • Prints
  • Proofs
  • Save the Date
  • Thank You Cards
Caroline Winn Photography is recommended by 100% of couples who have used their services. Their overall rating is 5.0, with the same score awarded for quality of service, flexibility, value, professionalism and average response time.
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