Gloucester Vacations from $308

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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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $633, price is now $308 per person
$308
per person
Nov 1 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,104, price is now $654 per person
$654
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,679 reviews)
“The air conditioning was not working properly and was extremely loud. The bathroom door did not close properly, and the room felt very outdated.”

Reviewed on Aug 25, 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Save 100% on your flight
Price was $1,364, price is now $877 per person
$877
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (1,108 reviews)
Beautiful, well located and clean hotel but very noisy (especially at night). I could hear a lot of noise from sirens and cars honking. It seems like windows need to be double or even triple paned.

Reviewed on Aug 25, 2025

DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Save 100% on your flight
Price was $882, price is now $569 per person
$569
per person
Nov 1 - Nov 7
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8/10 Very Good! (2,072 reviews)
Good value for the price and our family of 5. I would prefer rooms with no carpet. It was fine, but questionable as I smelled chorine. Overall, it was fine. The front desk was helpful and the service was very good.

Reviewed on Aug 21, 2025

Fairfield Inn & Suites by Marriott Plymouth

Fairfield Inn & Suites by Marriott Plymouth

2.5 out of 5
Save 100% on your flight
Price was $603, price is now $390 per person
$390
per person
Nov 12 - Nov 17
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
8.8/10 Excellent! (474 reviews)
Clean and comfortable. Very easy to park.

Reviewed on Aug 5, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Gloucester

Wingaersheek Beach featuring rugged coastline

Wingaersheek Beach

Offering fun in the sun, this coastal playground has calm water and everything you need for a day by the sea.

Wingaersheek Beach
Good Harbor Beach which includes a sunset and a coastal town

Good Harbor Beach

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.

Good Harbor Beach
Hammond Castle which includes heritage elements, general coastal views and a sunset

Hammond Castle

A medieval-style castle overlooking the blue ocean waters in Gloucester features a spellbinding collection of art, artifacts and quirky inventions.

Hammond Castle

What to do in Gloucester

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

$50
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

$17
per traveler
80% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

$50
per traveler
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Gloucester

Gloucester Hotel Deals

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
$161 nightly
The price is $180 total per night from Aug 27 to Aug 28
$180 total
Aug 27 - Aug 28
Total with taxes and fees
8.2/10 Very Good! (1,011 reviews)
"The stay was amazing! We loved the area and the location was beautiful. John was great and attentive. 1000% recommend!"

Reviewed on Aug 23, 2025

Castle Manor Inn
The Hotel at Cape Ann Marina

The Hotel at Cape Ann Marina

3.5 out of 5
75 Essex Avenue, Gloucester, MA
$210 nightly
The price is $235 total per night from Sep 16 to Sep 17
$235 total
Sep 16 - Sep 17
Total with taxes and fees
8.2/10 Very Good! (725 reviews)
Lovely Getaway
"The staff was great, our room was lovely. Had dinner at Mile Marker 1, and it was delicious with a great view."

Reviewed on Aug 15, 2025

The Hotel at Cape Ann Marina
Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

2.5 out of 5
138 Eastern Avenue, Gloucester, MA
$165 nightly
The price is $184 total per night from Aug 27 to Aug 28
$184 total
Aug 27 - Aug 28
Total with taxes and fees
9/10 Wonderful! (412 reviews)
"Room was very clean, the shower was hot with water pressure and bed was comfortable. Win, win, win!"

Reviewed on Aug 22, 2025

Sea Lion Motel and Cottages
See all 1,764 properties in Gloucester
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.

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.

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Frequently asked questions

How much does a Gloucester vacation package cost?
Offering great value package deals from $308 on Expedia, you'll be thrilled with how little a vacation to Gloucester costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Gloucester?
If you'd like to snag a cheap Gloucester vacation package, consider planning a trip in November, December and January. You'll typically find lower rates on accommodations and flights during these months — perfect for travelers wishing to save money.
How many days is enough for Gloucester?
Typically, a few days is enough for a Gloucester vacation. With a detailed itinerary, you can go to all the top attractions including Hammond Castle, as well as explore some hidden gems along the way.
Is it worth booking a vacation package to Gloucester?
Gloucester offers everything you need for an amazing escape. Get your Gloucester vacation off to a flying start by visiting popular attractions like Wingaersheek Beach.
How to find the best Gloucester package deals?
Use Expedia's filters to find some great Gloucester package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Gloucester package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Gloucester vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component separately. And you'll still have the freedom to create a tailored Gloucester vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Gloucester?
If you're considering a spontaneous Gloucester getaway, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Gloucester?

  1. Choose when to get away: Check your diary and pack your bags. Your favorite time of year and the type of activities on offer will also help you decide when to visit Gloucester.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and meals to flights and activities. Your hotel will probably be the biggest expense during your trip to Gloucester.
  3. Use Expedia's trip planning tool to explore Gloucester: Research every aspect of your trip to Gloucester with this handy planner. Invite your friends and family to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Set the duration of your trip: Start by compiling a list of the sights and activities you'd like to get to in Gloucester. Then, estimate how long you'll need for each, including any travel time.
  5. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Gloucester vacation package that brings all your bookings together.
  6. Book activities and experiences in advance: Whether it's a ticket to a big attraction or a walking tour, you won't have to worry about missing out on Gloucester's best offerings. Find all the incredible things to do in Gloucester with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Gloucester vacation packages?
If you're like us, you love exploring new places but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Gloucester trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.