Essex Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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Your Essex Vacation

The coastal scenery and spectacular views are just the beginning of the things Essex has to offer. Experience the sights and sounds of this interesting city your way with a personalized Essex vacation package. Eager to get out and explore? Wingaersheek Beach, Castle Hill on the Crane Estate and Hammond Castle are a few of the most popular places to visit during your trip to Essex. Don't delay exploring this destination any longer. Your perfect Essex vacation is only a few clicks away with Expedia.

Top Essex Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $2,410, price is now CA $651 per person
CA $651
per person
Dec 17 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,071, price is now CA $1,119 per person
CA $1,119
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,477, price is now CA $1,015 per person
CA $1,015
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
Perfect

Reviewed on Nov 14, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $1,077, price is now CA $774 per person
CA $774
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,636 reviews)

The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Price was CA $1,059, price is now CA $787 per person
CA $787
per person
Dec 17 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (1,036 reviews)

Ready to book your vacation to Essex?

 

Choose your dates

Essex Hotel Deals

Hampton Inn Boston - Logan Airport

Hampton Inn Boston - Logan Airport

3 out of 5
230 Lee Burbank Hwy Revere MA
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Nov 25 to Nov 26
CA $139
CA $155 total
Nov 25 - Nov 26
includes taxes & fees
8.2/10 Very good! (5,530 reviews)
"Everything was excellent"

Reviewed on Nov 13, 2026

Hampton Inn Boston - Logan Airport
enVision Hotel Boston Everett

enVision Hotel Boston Everett

2 out of 5
1834 Revere Beach Pkwy Everett MA
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Nov 29 to Nov 30
CA $146
CA $163 total
Nov 29 - Nov 30
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
"Great hotel and nice staff. On a busy street so could hear traffic at night but nothing overwhelming."

Reviewed on Nov 14, 2026

enVision Hotel Boston Everett
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
50 Ferncroft Rd Danvers MA
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Nov 22 to Nov 23
CA $132
CA $148 total
Nov 22 - Nov 23
includes taxes & fees
8.2/10 Very good! (2,611 reviews)
"Excellent staff and breakfast"

Reviewed on Nov 13, 2026

DoubleTree by Hilton Boston North Shore
See all 2,137 properties in Essex
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Essex attractions

Essex River

9.6/10 (35 reviews)
Commune with nature and explore the great outdoors at Essex River during your travels in Essex. Wander the beautiful beaches and seaside in the area.
See properties

Frequently asked questions

How much does an Essex vacation package cost?
You can grab a vacation package to this top destination from CA $651 on Expedia. But how much your vacation to Essex costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Essex?
The off-season is the best time to head to Essex if you're hoping to keep costs down. Another tip for finding cheap Essex vacation packages? Try to avoid visiting during public holidays and any major events.
How many days is enough for Essex?
Allow around 2 days for your Essex vacation if you want to immerse yourself in all that makes this place special. Wander around key neighbourhoods, including Great Neck and Annisquam. Then make a beeline for major sights such as Essex River and Graves Beach. With a well-organized itinerary, you'll be kept busy with room for some rest and relaxation too. Want to travel outside of Essex? Consider squeezing in an excursion or two.
Is it worth booking a vacation package to Essex?
Essex offers everything you need for an amazing escape. Begin your Essex vacation on a high note by checking out major attractions like Essex River.
How to find the best Essex package deals?
Finding a cheap Essex package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, add a couple of filters and see what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Essex package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book an Essex vacation as a package?
You can enjoy significant savings on your Essex break by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Essex?
Enjoy incredible discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Essex escape.
How to plan a trip to Essex?

  1. Choose your dates: What you want to do in Essex and your favourite season can help you decide when to travel.
  2. Set your budget: Factor in expenses like flights, food and transportation when working out how much to put aside for your trip to Essex. Then, choose a hotel that works with your budget, whether that's a wallet-friendly option or a more luxurious getaway.
  3. Decide how long to go for: Now that you're more familiar with Essex, you can figure out the perfect length of your vacation. Pull together a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a customized Essex vacation package.

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