Annisquam Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Annisquam

Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $1,530, price is now CA $963 per person
CA $963
per person
Jan 29 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,397, price is now CA $1,548 per person
CA $1,548
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)
The best location and the beat service! The best swimming pool

Reviewed on Nov 9, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $2,234, price is now CA $1,488 per person
CA $1,488
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
Amazing hotel Great rooms and helpful, professional staff. Couldn’t fault it.

Reviewed on Nov 8, 2026

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $1,789, price is now CA $1,298 per person
CA $1,298
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (744 reviews)
Beautiful hotel and the staff was wonderful. They gave us a corner room with a great view of the city. The room was spacious with a comfortable seating area.

Reviewed on Nov 7, 2026

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Price was CA $1,566, price is now CA $1,179 per person
CA $1,179
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (4,278 reviews)

Where to stay in Annisquam

Find the best Annisquam areas and neighborhoods for the activities you enjoy most. Learn more about Annisquam
A lighthouse, a white building with a red roof, and a stone walkway leading to the water.

East Gloucester

2 out of top 10 points of interest in this area

If you're spending some time in East Gloucester, Good Harbor Beach and Niles Beach are top sights worth seeing.

Find hotels in East Gloucester

Annisquam Hotel Deals

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 $131 per night from Nov 22 to Nov 23
CA $131
CA $146 total
Nov 22 - Nov 23
includes taxes & fees
8.2/10 Very good! (2,605 reviews)
"this place is 100/10 the beds are comfortable the place is clean and the over all atmosphere is welcoming and warming i definitely would stay there again in the future"

Reviewed on Nov 8, 2026

DoubleTree by Hilton Boston North Shore
Sonesta Select Boston Danvers

Sonesta Select Boston Danvers

3 out of 5
275 Independence Way Danvers MA
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Nov 15 to Nov 16
CA $151
CA $169 total
Nov 15 - Nov 16
includes taxes & fees
8.6/10 Excellent! (1,203 reviews)
"Great place"

Reviewed on Nov 8, 2026

Sonesta Select Boston Danvers
Holiday Inn Hotel & Suites Boston - Peabody by IHG

Holiday Inn Hotel & Suites Boston - Peabody by IHG

3 out of 5
1 Newbury St Peabody MA
Fully refundable
The price is CA $141 per night from Nov 27 to Nov 28
CA $141
CA $158 total
Nov 27 - Nov 28
includes taxes & fees
7.4/10 Good! (1,025 reviews)
"This was an okay property. It was located right off of the highway - but easy to miss if people are going too quickly by it. The conditions were not the best - though the staff were very kind and down to earth. I’m a bit bummed because I’m sure there was a continental breakfast when I first booked; ..."

Reviewed on Nov 9, 2026

Holiday Inn Hotel & Suites Boston - Peabody by IHG
See all 1,493 properties in Annisquam
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

Frequently asked questions

How much does an Annisquam vacation package cost?
Custom build your Annisquam vacation package from as little as CA $963. Choose from any combination of rental cars, flights and hotels to pull together the getaway you've been dreaming about. Remember to add on a few experiences or tours!
How do I get a cheap travel package to Annisquam?
If you love landing a bargain, bundle your bookings into an Annisquam vacation package. Whether you're looking for flights, hotels, rental cars or day tours, you can book them all in one place. You'll have ample choice at your fingertips as well. Expedia has over 550 partner airlines and 1,000,000 hotel options worldwide to pick from. Fly with who you prefer, book a room where you like and save a tidy sum — now that's the perfect vacation!
Where should I stay in Annisquam?
A trip to Annisquam wouldn't be complete without seeing Wingaersheek Beach, Plum Cove Beach and Cape Ann Museum. Stay close to these top attractions and make sightseeing simple.
How far in advance should I book my Annisquam vacation?
It can be difficult to know exactly when is the perfect time to book your vacation to Annisquam. But typically the earlier you book, the lower the prices. In some cases, you can reserve your flights and hotels up to 12 months prior to departure. If you're thinking of a last-minute getaway, no need to fret! There are unbeatable deals advertised on Expedia every day.
What does an Expedia Annisquam travel package include?
It all comes down to what sort of trip you want to have. Annisquam travel deals can include flights, car rentals and hotels. You can mix and match to find the package that suits your budget and style. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking an Annisquam travel package?
Booking all the parts of your getaway together is a great way to save. Bundle your airfares, rental cars and hotels into a handy package. But you're not restricted to hotels. Expedia has all types of properties, including vacation rentals such as beachfront villas and city apartments. You've got loads of choices!
Can I choose my airline with an Annisquam Expedia vacation package?
You can, and with more than 550 airlines to pick from across the globe, you're spoiled for choice. Have a look through the available options and find out which airline best suits your budget and needs.
If I'm not able to travel, can I cancel my Annisquam vacation package?
We totally get it — life can throw you the odd curveball. If you've locked in an Annisquam vacation package and need to cancel or change it, we can help. We suggest checking out our Customer Service Portal first for information. But in general, if you've booked your package within 24 hours, you may be able to change your itinerary free of charge. If it's been more than 24 hours, your airline, hotel or car rental company may impose a charge.

Things to do

History and Hauntings of Salem Guided Walking Tour

History and Hauntings of Salem Guided Walking Tour

CA $57
per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
Freedom Trail and Salem and The Witch Trail Self-Guided Walking Tour Bundle

Freedom Trail & Salem Witch: Self-Guided Walking Tour Bundle

CA $35
per traveller
100% of travellers recommend
Freedom Trail & Salem Witch: Self-Guided Walking Tour Bundle
Real Pirates Salem Museum General Admission Ticket

Real Pirates Salem Museum General Admission Ticket

CA $30
per adult
84% of travellers recommend
Real Pirates Salem Museum General Admission Ticket
See all activities in Gloucester
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.