Annisquam Vacation Packages

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Top Holiday Package Deals in Annisquam

Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Price was CA $917, price is now CA $633 per person
CA $633
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (2,156 reviews)
Absolutely loved it all- hip new vibe. Easy going staff at the ready. Gorgeous rooms and the ‘down the hall bathroom’ was across from room and all amenities perfect. Private bathroom suites. Parking right around the corner. Such a good 24 hours in Boston!

Reviewed on Sep 13, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,848, price is now CA $1,666 per person
CA $1,666
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (159 reviews)
Staff went above and beyond everyday! The dining options and location were amazing.

Reviewed on Sep 2, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was CA $1,306, price is now CA $862 per person
CA $862
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (1,001 reviews)
It’s still the best hotel in Cambridge

Reviewed on Sep 12, 2025

The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

4 out of 5
Back Bay
Price was CA $1,365, price is now CA $918 per person
CA $918
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (1,334 reviews)
Great service! From the moment we checked in till the time we checked out we had an amazing experience.

Reviewed on Sep 13, 2025

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Price was CA $1,058, price is now CA $716 per person
CA $716
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,015 reviews)
Great place for families to stay when moving your young adults to Boston for college or from one apartment to another. Located close to Harvard, MIT, Boston University, Tufts University, Cambridge, Allston, Storrow Drive easy access to drive to Boston MFA and Isabella Stewart Gardner Museum

Reviewed on Sep 13, 2025

Annisquam Hotel Deals

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 $209 per night from Sep 21 to Sep 22
CA $209
CA $234 total
Sep 21 - Sep 22
includes taxes & fees
8.4/10 Very Good! (1,010 reviews)
"I am not a fan of the rooms not being cleaned daily. While I thought the rooms were relatively clean, the 1st room we got when we walked in, the bedding was all wrinkled and disheveled looking and when I went to put my water bottles in the fridge it was filled with the previous occupants left over ..."

Reviewed on Sep. 9, 2025

Sonesta Select Boston Danvers
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 $222 per night from Sep 21 to Sep 22
CA $222
CA $248 total
Sep 21 - Sep 22
includes taxes & fees
8/10 Very Good! (2,056 reviews)
"Always enjoy this property! Great staff and quality rooms!"

Reviewed on Sep. 9, 2025

DoubleTree by Hilton Boston North Shore
Hawthorne Hotel

Hawthorne Hotel

3.5 out of 5
18 Washington Square W, Salem, MA
9.4/10 Exceptional! (1,425 reviews)
"very centric to everything! Food at the tavern was great!"

Reviewed on Sep. 9, 2025

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Hawthorne Hotel
See all 1,434 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 CA $633. 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

If a restful vacation is part of your travel plans, Good Harbor Beach might be the perfect place to seek out during your trip to Gloucester. While you're in the area, stroll along the seaside.

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

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

CA $62
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

CA $23
per traveller
100% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

CA $23
per traveller
80% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
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.