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

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Price found within the past 48 hours. Click for updated prices.
  • Standard Room, 1 Queen Bed
    Jul 20 - Jul 23

    Hotel Ivy Boston Common + Flight

    Bay Village
    3 nights
    2.5 star property
    8.4/10 - Very good (1,451 reviews)
    "Safe, friendly staff, garage discount, great location. Easy check in and check out."
    Reviewed May 18, 2026
    Roundtrip • Edmonton (YEG) - Boston (BOS)
    YEG - BOS • 1 stop BOS - YEG • 1 stop
    CA $1,650
    CA $1,110
    per traveller
    found 1 day ago
    Hotel Ivy Boston Common
  • Suite, Multiple Beds (John Adams Presidential Suite)
    Jul 20 - Jul 23

    Boston Harbor Hotel + Flight

    North End
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    "clean and great staff "
    Reviewed May 8, 2026
    Roundtrip • Edmonton (YEG) - Boston (BOS)
    YEG - BOS • 1 stop BOS - YEG • 1 stop
    CA $2,976
    CA $1,641
    per traveller
    found 1 day ago
    Boston Harbor Hotel
  • Game room
    Jul 23 - Jul 26

    Meco Hotel - Hostel + Flight

    West End
    3 nights
    2.0 star property
    8.6/10 - Excellent (423 reviews)
    "good"
    Reviewed May 19, 2026
    Roundtrip • Toronto (YTZ) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $1,963
    CA $1,146
    per traveller
    found 1 day ago
    Meco Hotel - Hostel
  • Breakfast meal
    Jun 24 - Jun 30

    By the Sea Guests Bed & Breakfast & Suites + Flight

    Dennis Port
    6 nights
    3.5 star property
    9.2/10 - Wonderful (185 reviews)
    "."
    Reviewed October 16, 2025
    Roundtrip • Toronto (YTZ) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YTZ • Nonstop
    CA $2,487
    CA $1,561
    per traveller
    found 21 hours ago
    By the Sea Guests Bed & Breakfast & Suites
  • Reception
    Jul 5 - Jul 9

    The Inn at Hastings Park, Relais & Chateaux - Boston + Flight

    Lexington
    4 nights
    4.0 star property
    9.6/10 - Exceptional (256 reviews)
    "Splendid bed and breakfast"
    Reviewed April 29, 2026
    Roundtrip • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $2,359
    CA $1,487
    per traveller
    found 1 day ago
    The Inn at Hastings Park, Relais & Chateaux - Boston

Where to stay in Annisquam

Find the best Annisquam areas and neighborhoods for the activities you enjoy most. Learn more about Annisquam
Beautiful sunset of Eastern Point Lighthouse at Gloucester, Massachusetts, USA. The Lighthouse is One of Five iconic lighthouses along the Cape Ann coastline.

East Gloucester

3 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

Hawthorne Hotel

Hawthorne Hotel

3.5 out of 5
18 Washington Square W Salem MA
The price is CA $240 per night from May 25 to May 26
CA $240
CA $268 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (1,554 reviews)
"The Hawthorne never dissapoints! Whenever im in Salem, this is my first choice. The rooms are always clean, comfortable and charming. The food options are incredible and worth the money spent. I have never come across a staff member anywhere in the hotel that isnt polite and or helpful or courteous. ..."

Reviewed on May 19, 2026

Hawthorne Hotel
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
50 Ferncroft Rd Danvers MA
The price is CA $145 per night from May 26 to May 27
CA $145
CA $162 total
May 26 - May 27
includes taxes & fees
8.2/10 Very Good! (2,414 reviews)
"The facility is very old and needs major renovations! Mattresses were very old and uncomfortable. There is absolutely no sounds proof. We couldn’t sleep all night long because next door guests were too loub"

Reviewed on May 18, 2026

DoubleTree by Hilton Boston North Shore
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 $168 per night from May 31 to Jun 1
CA $168
CA $187 total
May 31 - Jun 1
includes taxes & fees
7.2/10 Good! (1,013 reviews)
"Easy check in, clean"

Reviewed on May 19, 2026

Holiday Inn Hotel & Suites Boston - Peabody by IHG
See all 1,476 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.
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Frequently asked questions

How much does an Annisquam vacation package cost?
Custom build your Annisquam vacation package from as little as . 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.

Discover the most popular places to visit in Annisquam

Wingaersheek Beach

Wingaersheek Beach

Why not spend a carefree afternoon at Wingaersheek Beach during your travels in Gloucester? While you're in the area, stroll along the seaside.

Wingaersheek Beach
Good Harbor Beach

Good Harbor Beach

Why not spend a carefree afternoon at Good Harbor Beach during your travels in Gloucester? Wander the waterfront or discover the area's sunrises.

Good Harbor Beach
Hammond Castle

Hammond Castle

You can browse the exhibits at Hammond Castle, a museum with a story of its own, during your trip to Gloucester. Wander the beautiful beaches and seaside in the area.

Hammond Castle

Things to do

History and Hauntings of Salem Guided Walking Tour

History and Hauntings of Salem Guided Walking Tour

CA $49
per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
Salem's Best Ghost Tour

Salem's Best Ghost Tour

CA $34
per adult
90% of travellers recommend
Salem's Best Ghost Tour
Freedom Trail and Salem and The Witch Trail Self-Guided Walking Tour Bundle

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

CA $31
per traveller
100% of travellers recommend
Freedom Trail & Salem Witch: Self-Guided Walking Tour Bundle
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.