Annisquam Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Holiday Package Deals in Annisquam
Price found within the past 48 hours. Click for updated prices.
Chatham Bars Inn
CA $4,357
per person
Oct 7 - Oct 12
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.2/10 Wonderful! (857 reviews)
The food wasn’t great. It’s not like it looks in the pictures We stayed in the cottage. It really was not a difference to any room. The kids club was great.
I don’t feel I need to go back
Reviewed on Aug 21, 2026
Pier 7 Condominiums
Bass River
CA $936
per person
Sep 26 - Oct 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (22 reviews)
The property was small and very intimate. Close to downtown Hyannis, Barnstable, and Dennis.........I, definitely, got a great experience with seeing alot in such a small community. Piers are a hop, skip, and a jump away!
The room was nice, upgraded, and super clean! The only thing missing from the kitchenette was a stove. Other than that, I would stay here again!
Reviewed on Aug 24, 2026
Where to stay in Annisquam
Find the best Annisquam areas and neighborhoods for the activities you enjoy most. Learn more about Annisquam
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.
Downtown Gloucester
3 out of top 10 points of interest in this area
While visiting Downtown Gloucester, you might make a stop by sights like Cape Ann Museum and Capt Bill & Sons Whale Watch.
Rocky Neck
1 out of top 10 points of interest in this area
If you're spending some time in Rocky Neck, Rocky Neck Art Colony and Bryan Gallery are top sights worth seeing.
Magnolia
Nestled in Gloucester, this small village boasts its own library, restaurants, and shops. Enjoy Gray Beach at Coolidge Reservation or take in scenic views of Kettle Cove at Surf Park.
Annisquam Hotel Deals
DoubleTree by Hilton Boston North Shore
50 Ferncroft Rd Danvers MA
Fully refundableReserve now, pay when you stay
CA $154
CA $172 total
Sep 7 - Sep 8
includes taxes & fees
8.2/10 Very good! (2,549 reviews)
"Was told I could check in early and then when I arrived I was told there was nothing available, had to wait around for 4 hours. Rooms smelled funny, fridge didn’t keep food cold, toilet wouldn’t flush. Arcade and pool hours closed early. The waterpark part was great, staff there were great and very ..."
Reviewed on Aug 25, 2026
Holiday Inn Hotel & Suites Boston - Peabody by IHG
1 Newbury St Peabody MA
Fully refundable
CA $169
CA $189 total
Aug 30 - Aug 31
includes taxes & fees
Sonesta Select Boston Danvers
275 Independence Way Danvers MA
Fully refundableReserve now, pay when you stay
CA $169
CA $189 total
Aug 30 - Aug 31
includes taxes & fees
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.
Frequently asked questions
How much does an Annisquam vacation package cost?
Custom build your Annisquam vacation package from as little as CA $823. 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
Salem, MA: History and Hauntings Guided Walking Tour
CA $51
per adult
86% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
CA $51
per adult
98% of travellers recommend
Real Pirates Salem Museum General Admission Ticket
CA $30
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.