Chicago, IL

Enjoy Boston to the Fullest with Destination Sitters: Your Trusted Babysitting Service

Traveling to Boston with your little ones is an adventure filled with history, culture, and plenty of family-friendly fun. However, every parent deserves a bit of downtime to explore the city on their own terms. Whether it’s a romantic dinner in the North End, an evening stroll along the Charles River, or catching a Red Sox game at Fenway, you deserve to enjoy these experiences without worry. This is where Destination Sitters steps in, offering reliable, professional, and fully vetted babysitting services right in your hotel, or vacation rental.

What’s Popular in Boston

While your children are in good hands, take the opportunity to explore some of Boston’s top attractions. Here are a few must-visit spots that offer the perfect blend of history, culture, and leisure:

The Freedom Trail

Home of Chicago Cubs

Take a walk-through American history by following the Freedom Trail. This 2.5-mile route winds through 16 significant historic sites, including the Paul Revere House, Old North Church, and Boston Common. It’s a perfect way to immerse yourself in the city’s revolutionary past.

The North End

Expression of Bosotn

Experience the flavors of Italy in Boston’s North End. This charming neighborhood is known for its authentic Italian cuisine, cozy cafes, and historic sites like the Old North Church. Be sure to save room for a cannoli at Mike’s Pastry!

Museum of Fine Arts

Beautiful outdoor spaces

Indulge in some culture at the Museum of Fine Arts, which houses an impressive collection of art from around the world. From ancient Egyptian artifacts to contemporary pieces, there’s something here for every art lover.

Newbury Street

Iconic Newbury Street shopping

If shopping is on your agenda, Newbury Street is the place to be. This historic street is lined with boutiques, art galleries, and high-end stores, making it a perfect destination for some retail therapy.

Destination SItters babysitter

Boston Hotel Babysitting Service

Professional fully screened childcare

Visiting the Boston with your child(ren)? Not a problem! Let’s help you get some time off our professional childcare providers are here to ensure your little ones are safe, always engaged, and well cared for! We come to your destination, whether at it’s your hotel, vacation rental, or Airbnb!

Boston is a city rich in history and culture, offering countless experiences that deserve your full attention. With Destination Sitters, you can explore these attractions with complete peace of mind, knowing that your children are safe, happy, and well-cared for. So go ahead, make those dinner reservations, book those tickets, and immerse yourself in everything Boston has to offer—while we take care of the rest.

Destination Sitters Babysitting Reviews

I loved the initial customer service. Alex made sure to find the right sitter for our six-month-old twins. Maria was excellent. Our babies were fed, changed, and completely asleep when we returned. She also updated us with texts.

Jennifer Davis

Wow. I would do anything to have a sitter like Martha at home. She was beyond qualified, the kids absolutely loved her (which made it easy for us to be away, knowing they were so happy). She was kind and gentle and so loving to the kids. And so knowledgeable. It was such a comfort having her there!

Cathy Pandila

What a great resource Destination Sitters’ provides, for parents like me who want the peace of mind of leaving the kids with a safe and responsible young adult, who is also so much fun that the kids are happy to go with them. It gave me a few hours to enjoy the La Costa resort in ways that I couldn’t do with the kids. They said their sitter was “awesome.” I felt confidence to leave them with him, and I got the rejuvenation I wanted from a few hours at the spa! I will definitely be calling you again!

Sharon Josepho

Love the ease of making the reservation. Simple, straight-forward price where it is only an hourly fee. No extra or “hidden” additional costs. Greatly appreciate Yvonne making the reservation with the same sitter (Lauren) for the day where Lauren came in the morning for 4 hours then return to the hotel in the evening for another 4 hours. This really helped my 2year old adjust easily with Lauren. Just wanted to add that Lauren Crites is fantastic! My 2-year old can have stranger anxiety where if I’m not there, she would not want to stay with a sitter. Let me just say, my daughter immediately adjusted with Lauren. There were no tears. I was able to easily leave her in the hands of Lauren without any worry. Lauren is very calm, flexible, easy-going, extremely attentive to my 2 year-old and would even interact/play with my 5year old (he didn’t feel left out) while at Camp Pelican. Thank you for making our visit enjoyable. Now I have a reason to return to the area again!

Julie Chen

The convenience of booking and paying with a credit card (I don’t like carrying a lot of cash on vacation), the sitter did a great job with our son and he had a wonderful time and was talking about the fun he had for days.

Alan Lynn

I want to thank you for the chance to have an adult evening out on our trip. Rebecca was wonderful! A lot of people can be overwhelmed by our triplet boys- but she seemed comfortable right away. And our boys were at ease with her immediately as well. They all had a good night! You are lucky to have Rebecca. Please give her our kindest regards.

Sherri Simonetti

Libbie was absolutely amazing with my son. He had such a great time, and I felt so comfortable leaving him with her.

Zena Gardner

Extremely friendly and efficient service through the booking process.
Gabby was great – my daughter had a great time with her and was great
to have peace of mind while travelling in another country. Thank you :)

Amie Shaw
destination-sitter

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