Eastern Massachusetts Kid friendly Vacations

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Flight and Kid friendly hotel deals in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

CA $768
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Hyannis (HYA)
8.6/10 Excellent! (733 reviews)
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

CA $1,092
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very good! (2,526 reviews)
Sheraton Boston, a Marriott Hotel

Sheraton Boston, a Marriott Hotel

Back Bay
CA $1,108
per person
Nov 25 - Nov 30
found 12 hours ago
Roundtrip flight included
Winnipeg (YWG) to Boston (BOS)
8.8/10 Excellent! (1,917 reviews)
Crowne Plaza Boston - Woburn by IHG

Crowne Plaza Boston - Woburn by IHG

CA $1,158
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Charlottetown Alexander B. Campbell Airport (YYG) to Boston (BOS)
8.6/10 Excellent! (1,086 reviews)
Omni Parker House

Omni Parker House

Downtown Boston
CA $1,095
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9/10 Wonderful! (3,703 reviews)
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3 Night Kid friendly holidays in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

CA $768
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Hyannis (HYA)
8.6/10 Excellent! (733 reviews)
Revere Hotel Boston Common

Revere Hotel Boston Common

Bay Village
CA $1,363
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (2,214 reviews)
Good size room, although the bathroom was a little small

Reviewed on Sep 9, 2026

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

MIT
CA $770
per person
Nov 12 - Nov 15
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (2,618 reviews)
Needed more toilet paper called front desk. It never came. Had to go out and get it from the cleaning staff myself. Then on our last night they had a guy power washing the sidewalk right outside our room window at 9:30pm.

Reviewed on Sep 9, 2026

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4 Night Kid friendly holidays in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.
Aloft by Marriott Lexington

Aloft by Marriott Lexington

CA $1,001
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
8.4/10 Very good! (1,006 reviews)
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

CA $1,645
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Boston (BOS)
8.2/10 Very good! (2,526 reviews)
Revere Hotel Boston Common

Revere Hotel Boston Common

Bay Village
CA $1,212
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (2,214 reviews)
Good size room, although the bathroom was a little small

Reviewed on Sep 9, 2026

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Plan the perfect family-friendly vacation in Eastern Massachusetts with Expedia

What are some benefits of booking a family-friendly vacation?

Whether it's luxurious or cheap, family vacations in Eastern Massachusetts are among the most memorable experiences you'll ever have with your family. It can be a great way to bond and explore new destinations with the people you love most. Plus, it's easy to keep an eye on your little ones without having to worry about how they are with a sitter back home. You may even meet some other families and establish long-lasting friendships.

How can I find the best family-friendly vacations?

Using search filters makes finding the perfect family-friendly vacation easy. You can implement the search filter for family-friendly accommodations specifically, but that's just the beginning. You'll also find search filters for price range along with the desired number of bedrooms, so you can ensure you have enough space for everyone you want to bring to Eastern Massachusetts.

Are there cheap family vacations to Eastern Massachusetts?

Price varies quite a bit, ranging from to . The price you'll be paying depends on a variety of factors, and you can filter for them all. You can implement a filter for your budget limitations and also remove any 4- and 5-star stays from your search. You can even filter by accommodation type, which can present you with cheap alternatives to what is typically considered standard.

When should I book family-friendly vacation packages?

The right time to book family-friendly vacation packages in Eastern Massachusetts depends on what you're looking for. If you're looking to save, booking during least popular month tends to be cheaper compared to the rest of the year, though that's not always a guarantee. Keep in mind that the off-season and the busy season differ from place to place, with family-friendly vacations in Canada being very different compared to options in France and Spain, for example.

Can I book an all-inclusive family vacation in Eastern Massachusetts?

Yes, you'll find plenty of all-inclusive family vacation packages for Eastern Massachusetts. To see what's available, just select the all-inclusive filter on your search.

How can I book the best family activity vacation?

If you're looking to make the most out of the available activities in Eastern Massachusetts, you'll need to consider what your family likes to do. Cater your itinerary to your family's interests, and you'll create memories that you and your kids will hold on to for the rest of your lives whether it's family ski vacations in Eastern Massachusetts or something a bit more relaxed.

Can I find luxury family vacations in Eastern Massachusetts?

If you're looking for a luxury family vacation to Eastern Massachusetts, you can use search filters to find the best options available. Activate the filter for 5-star packages to only see the best of the best. Plus, you'll find a range of first-class flights available to make even the journey there top-of-the-line.

How can I search for family vacation deals?

Finding deals is easy when you take advantage of the array of available search filters. You can set budget limitations and remove 4- and 5-star options from your search. If you don't want to miss out on your favourite amenities, however, you can consider travelling during , which often have lower prices because of the off-season in Eastern Massachusetts.

Can I book a family vacation package that is fully refundable?

If you're looking for a fully refundable reservation, you won't have to look far on Expedia. Quite a few properties in Eastern Massachusetts are fully refundable. You can search for this feature, but always make sure to check the specific property's policies and requirements before booking.

Why should I book my family trip with Expedia?

When you book with Expedia, you can book your accommodation and your flight together, with some discounts available for doing both at once. Additionally, you may be able to enjoy special discounts with Expedia Rewards that will earn you points you can then put toward discounts for subsequent bookings.

Kid friendly Hotels in Eastern Massachusetts

Embassy Suites by Hilton Boston Waltham

Embassy Suites by Hilton Boston Waltham

550 Winter Street Waltham MA
  • 8 min drive from Fenway Park
Book a stay at this business-friendly hotel in Waltham. Enjoy free breakfast, 2 restaurants, and a 24-hour fitness center. Our guests praise the breakfast and ...
Embassy Suites by Hilton Boston Waltham
Bayside Resort Hotel

Bayside Resort Hotel

225 Route 28 West Yarmouth MA
  • 2 hours drive from Fenway Park
Book a stay at this beach hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
8.8/10 Excellent! (1,607 reviews)
"The fire pits outside were great!"

Reviewed on Sep 9, 2026

Bayside Resort Hotel
Hyatt Place Boston/Braintree

Hyatt Place Boston/Braintree

50 Forbes Road Braintree MA
  • 21 min drive from Fenway Park
Book a stay at this business-friendly hotel in Braintree. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hyatt Place Boston/Braintree
See all 16,218 properties in Eastern Massachusetts
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.