Gloucester Vacations from $502
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Your Gloucester Vacation
Say farewell to the worries of planning and hello to a Gloucester vacation package. With your travel details organized before you leave, you can focus on discovering the best of this city, starting with Great Neck, which is great for walking, nature and views. Eager to explore your new surroundings? Cape Ann, Good Harbor Beach and Wingaersheek Beach are just a few of the leading places to visit during a trip to Gloucester. No matter your travel plans or the size of your budget, organizing a tailored Gloucester vacation is a cinch with Expedia.
The Latest Gloucester vacation packages
Price found within the past 48 hours. Click for updated prices.
The Inn at Hastings Park, Relais & Chateaux - Boston
per person
Sep 4 - Sep 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)
Reviewed on Jun 6, 2025
Discover the most popular places to visit in Gloucester
Wingaersheek Beach
Offering fun in the sun, this coastal playground has calm water and everything you need for a day by the sea.
Good Harbor Beach
4.5/5(18 reviews)
With a reputation as Gloucester’s prettiest beach, this curve of white sand lapped by rolling waves sets the scene for soaking up the sun.
Hammond Castle
4.5/5(8 reviews)
A medieval-style castle overlooking the blue ocean waters in Gloucester features a spellbinding collection of art, artifacts and quirky inventions.
What to do in Gloucester
Massachusetts Highlights: Freedom Trail, Salem & More Tour
$50
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
$42
per traveler
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
$17
per traveler
80% of travellers recommend
Gloucester Hotel Deals
Castle Manor Inn
141 Essex Avenue, Gloucester, MA
$153 nightly
The price is $171 total per night from Jul 10 to Jul 11
$171 total
Jul 10 - Jul 11
Total includes taxes and fees
8.2/10 Very Good! (979 reviews)
Overnight
"Overnight stay for the star gazing trip out of the harbor.Had to scenic view room which was lovely large and a view.Would have appreciated a small fridge in room to keep drinks .The bathroom was small but andclean.Overall would stay again-quiet beautiful ."
Reviewed on Jun 28, 2025
Ocean House Hotel at Bass Rocks
107 Atlantic Rd, Gloucester, MA
Fully refundableReserve now, pay when you stay
$345 nightly
The price is $386 total per night from Jul 14 to Jul 15
$386 total
Jul 14 - Jul 15
Total includes taxes and fees
9/10 Wonderful! (710 reviews)
"Beautiful view from our room! Loved having private lounge area outside our room to relax and look at the view. Very nice hotel and very clean. We hope to return soon!"
Reviewed on Jun 27, 2025
Atlantis Oceanfront Inn
125 Atlantic Road, Gloucester, MA
Fully refundableReserve now, pay when you stay
$324 nightly
The price is $362 total per night from Jul 6 to Jul 7
$362 total
Jul 6 - Jul 7
Total includes taxes and fees
9.4/10 Exceptional! (420 reviews)
"Wonderful staff… Unbeatable views of the Rocky coast and Atlantic Ocean… Perfect location easy to get anywhere on the Cape. The breakfast are beyond amazing one of best breakfast spots in North America."
Reviewed on Jun 21, 2025
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.
Find the Best Gloucester Vacation Packages
Gloucester Beach Vacation
The smell of fresh sea air and fabulous ocean views are just the start of things to look forward to during your Gloucester vacation. If you're eager to save on your trip to Gloucester, we'll let you in on a secret — choose one of our Gloucester packages. Grab one close to Pavilion Beach, only 0.2 miles from the city center and a must-do while here. Alternatively, select a package that puts you closer to Cressy Beach, another gorgeous coastline. Whichever you choose, you'll be left with extra dollars in your travel budget to have fun with.
Things You Should Know About Gloucester
- Drift off to sleep to the gentle sounds of the sea in one of our Gloucester beach hotels. Nothing beats staying with walking distance of the ocean.
- Private vacation homes are another top choice for people planning a vacation in Gloucester. Some great examples are Castle Manor Inn and The Hotel at Cape Ann Marina.
- Roughly 29,800 people reside in Gloucester. If you want some tips about things to see and do here, why not start a conversation with some of the friendly locals? Our Gloucester things to do page is also a handy source of information.
- Don't head home without exploring Cape Ann, Capt Bill & Sons Whale Watch and Dogtown. With the cash you save through our Gloucester vacation deals, you can see more impressive attractions like these.
Gloucester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Logan Intl. Airport (BOS) |
Population | 29,800 |
Max Temp Winter | 35ºF |
Max Temp Summer | 70ºF |
Top Sights | Wingaersheek Beach, Good Harbor Beach and Hammond Castle |
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- Hotels near Sargent House Museum
- Hotels near Gloucester Unitarian Universalist Church
- Hotels near Cape Ann Historical Museum
- Hotels near Capt Bill & Sons Whale Watch
- Hotels near Cape Ann Museum
- Hotels near Maritime Gloucester
- Hotels near Fishermen's Memorial Monument
- Hotels near Gloucester Station
- Condo Rentals in Gloucester Station
- Hotels near Schooner Adventure
- Hotels near Rocky Neck Art Colony
- Hotels near Ten Pound Lighthouse
- Hotels near The Gorton Theatre
- Hotels near Half Moon Beach
- Hotels near Stage Fort Park
- Boston Hotels
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- Hotels near Good Harbor Beach
- Hotels near Dogtown
- Hotels near Ravenswood Park
- Hotels near West Gloucester Station
- Hotels near Eastern Point Lighthouse
- Hotels near Hammond Castle
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- Hammond Castle
- Sargent House Museum
- Gloucester Unitarian Universalist Church
- Maritime Gloucester
- Cape Ann Historical Museum
- Capt Bill & Sons Whale Watch
- Fishermen's Memorial Monument
- Good Harbor Beach
- Schooner Adventure
- Rocky Neck Art Colony
- Half Moon Beach
- Stage Fort Park
- Niles Beach
- Dogtown
- Wingaersheek Beach
- Ravenswood Park
- Eastern Point Lighthouse
- Long Beach
- North Shore Vacations
- Mount Ann Park
- Visit North Shore
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.