Annisquam Vacation Packages 2026 from $495

Plan, book, travel with confidence
Better together
Save up to $2,000 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

Your Annisquam Vacation

Annisquam is beckoning! Whatever type of getaway you're planning, you can see and experience the best of this neighborhood with an Annisquam vacation package. Your trip to Annisquam wouldn't be complete without a stop at popular attractions nearby such as Wingaersheek Beach, Cape Ann Museum and Plum Cove Beach. Whatever your ideal Annisquam vacation looks like, you can make it a reality with Expedia.

The Latest Annisquam Vacation Packages

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

Boston Lodge and Suites

Dorchester

$495

per person

Nov 3 - Nov 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

8.4/10 Very Good! (190 reviews)

Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.

Reviewed on May 19, 2026

Four Seasons Hotel Boston

Bay Village

$1,992

per person

Nov 21 - Nov 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.4/10 Exceptional! (484 reviews)

Mandarin Oriental, Boston

Back Bay

$1,753

per person

Nov 21 - Nov 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.4/10 Exceptional! (451 reviews)

Great hotel in great location. Staff earned five star status.

Reviewed on Sep 6, 2026

The Mansion at Ocean Edge

Save 100% on your flight

$847

per person

Nov 11 - Nov 14

just found

Roundtrip flight included

Chicago (CHI) to Boston (BOS)

8.2/10 Very Good! (1,002 reviews)

Kyung and his team delivered on a special weekend get away for my wife’s 40th birthday! This is now our next favorite place on the cape and we look forward to many more memories being made @ Ocean Edge! Thank you all! The Contino’s

Reviewed on Sep 6, 2026

Boston Harbor Hotel

North End

Save 100% on your flight

$1,592

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.8/10 Exceptional! (1,014 reviews)

Everything about this hotel is wonderful! We would definitely stay here again.

Reviewed on Sep 8, 2026

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

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.

A statue of a man with a wheel, surrounded by a stone base with an inscription, in a public square with houses and cars in the background.

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.

A lighthouse on a rocky shore with a wooden walkway leading to it.

Rocky Neck

While Rocky Neck might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Rocky Neck Art Colony and Maritime Gloucester.

A garden with purple flowers and a foggy coastline.

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

Best Western Plus North Shore Hotel

50 Dayton St Danvers MA

Fully refundableReserve now, pay when you stay

$149 nightly

$166 total

Sep 20 - Sep 21

Total with taxes and fees

9/10 Wonderful! (1,000 reviews)

"Newer mattresses, especially room 402, bed 1—you can feel the steel coils."

Reviewed on Sep 8, 2026

DoubleTree by Hilton Boston North Shore

50 Ferncroft Rd Danvers MA

Fully refundableReserve now, pay when you stay

$109 nightly

$122 total

Sep 13 - Sep 14

Total with taxes and fees

Sonesta Select Boston Danvers

275 Independence Way Danvers MA

Fully refundableReserve now, pay when you stay

$151 nightly

$168 total

Sep 23 - Sep 24

Total with taxes and fees

See all 1,520 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.