Gloucester Vacations from $295

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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.
Even Hotels Manchester Airport by IHG

Even Hotels Manchester Airport by IHG

3.5 out of 5
South End
Save 100% on your flight
per person
Oct 29 - Nov 3
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8.8/10 Excellent! (853 reviews)
Nice staff, clean property

Reviewed on Aug 17, 2025

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (2,239 reviews)
The room has a small amount of long hair around and some on the bed I didn’t like that at all

Reviewed on Aug 17, 2025

Hotel 1620 Plymouth Harbor

Hotel 1620 Plymouth Harbor

3 out of 5
Plymouth Downtown Waterfront District
Save 100% on your flight
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.2/10 Very Good! (1,011 reviews)
We loved our stay at the 1620 Hotel. Super Location. Friendly staff. Clean room. Comfy beds. Plenty of free parking. Dog-friendly to boot! The only slight negative - if I had to find one - was that our room was facing the pool area and had no natural daylight. However, since we didn’t come to spend all day in our room, it wasn’t a big deal. All the other positives made more than up for it. I would stay there again, no question.

Reviewed on Aug 17, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
The Boston Harbor Hotel continues to be my absolute favorite place to stay in Boston, and my recent visit reminded me exactly why. From the moment I walked through the doors, I was greeted by the same welcoming and professional staff that makes this property truly special. The team went above and beyond by upgrading me to a suite, which was an unexpected and much-appreciated gesture that really enhanced my stay. The suite itself was beautifully appointed and comfortable, providing the perfect retreat after busy days exploring the city. What really sets this hotel apart is its unbeatable location. You simply cannot find a better spot in Boston - it's perfectly positioned for both business and leisure activities, with easy access to everything the city has to offer while maintaining that sense of waterfront tranquility. Every stay here has been delightful, and the consistency in service quality is remarkable. The Boston Harbor Hotel has earned my loyalty through their attention to detail and genuine hospitality. I'm already looking forward to my next visit!

Reviewed on Aug 11, 2025

DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 3
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8/10 Very Good! (2,069 reviews)
Very nice place to stay

Reviewed on Aug 17, 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
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

$50
per traveler
Massachusetts: Smartphone-Based Audio Tour Bundle
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
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 20 to Aug 21
$180 total
Aug 20 - Aug 21
Total includes taxes and fees
8.2/10 Very Good! (1,005 reviews)
Motor Inn rooms are pretty basic
"Motor Inn portion, while renovated still has very small bathroom, window AC unit and not much lighting. It was fine for a one night stay near family"

Reviewed on Aug 15, 2025

Castle Manor Inn
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
$344 nightly
The price is $384 total per night from Sep 9 to Sep 10
$384 total
Sep 9 - Sep 10
Total includes taxes and fees
9.6/10 Exceptional! (874 reviews)
"Above and beyond my expectations"

Reviewed on Aug 16, 2025

Beauport Hotel Gloucester
Atlantis Oceanfront Inn

Atlantis Oceanfront Inn

3 out of 5
125 Atlantic Road, Gloucester, MA
Fully refundableReserve now, pay when you stay
$230 nightly
The price is $257 total per night from Sep 7 to Sep 8
$257 total
Sep 7 - Sep 8
Total includes taxes and fees
9.4/10 Exceptional! (430 reviews)
"The staff was extremely nice. Check in and out was a breeze. Great location with amazing ocean view."

Reviewed on Aug 15, 2025

Atlantis Oceanfront Inn
See all 1,796 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 $295 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.