Gloucester Vacations from $310

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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 $635, price is now $310 per person
$310
per person
Nov 1 - Nov 3
found 9 hours ago
Roundtrip flight included
Chicago (ORD) 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 $1,068, price is now $622 per person
$622
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,679 reviews)
I would stay here again in a heartbeat. They were efficient, extremely friendly, clean and fun environment. The location is excellent and the Irish pub in the adjacent location to the lobby was super convenient. This is what Boston is all about!

Reviewed on Aug 19, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $3,070, price is now $1,840 per person
$1,840
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
Awesome hotel. Staff is great. Best hotel in Boston! And I've stayed at alot of em.

Reviewed on Aug 11, 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 $505, price is now $321 per person
$321
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.8/10 Excellent! (471 reviews)
Clean and comfortable. Very easy to park.

Reviewed on Aug 5, 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Save 100% on your flight
Price was $1,328, price is now $845 per person
$845
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (1,102 reviews)
This is our go-to in Boston. Super convenient, clean and modern!

Reviewed on Aug 19, 2025

Don't see what you're looking for?
See all available trips from Columbus to Gloucester
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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 21 to Aug 22
$180 total
Aug 21 - Aug 22
Total includes taxes and fees
8.2/10 Very Good! (1,012 reviews)
"Don't know about the large main house facilities, but the "50s motel" units are terrible & not worth the money"

Reviewed on Aug 18, 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
The Vista

The Vista

2.5 out of 5
22 Thatcher Rd., Gloucester, MA
$246 nightly
The price is $275 total per night from Sep 1 to Sep 2
$275 total
Sep 1 - Sep 2
Total includes taxes and fees
9.2/10 Wonderful! (384 reviews)
Great place
"Friendly, very clean and easy access! The breakfast was awesome"

Reviewed on Jul 15, 2025

The Vista
See all 1,768 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 $310 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.