Gloucester Holidays

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Top Flight + Hotel Deals in Gloucester

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

YOTEL Boston

4 out of 5
Seaport District
per person
18 Sept - 22 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
8.6/10 Excellent! (2,098 reviews)
The only issue I had was they hit us with an amenity fee. Maybe I missed that part when I made the reservation but still I don’t like that just charge everything up front so i know what I’m paying.

Reviewed on 2 Aug 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
18 Sept - 22 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
Favorite hotel in Boston amazing pool and gym

Reviewed on 2 Aug 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
1 Sept - 8 Sept
found 13 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8.8/10 Excellent! (1,009 reviews)
Beautiful hotel located right in the heart of the city! Nice big room with a big bathroom. Located near all the shopping and great restaurants. Also very close to the T station and very safe!

Reviewed on 28 Jul 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
1 Sept - 8 Sept
found 13 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8.8/10 Excellent! (234 reviews)
We enjoyed having the bistro on site.

Reviewed on 17 Jul 2025

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave

2 out of 5
South End
per person
1 Sept - 8 Sept
found 13 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
7.4/10 Good! (114 reviews)
Property is located in a very nice area. No frill, what they advertise, you get.

Reviewed on 23 May 2025

Gloucester Beach Holiday

The smell of fresh sea air and fabulous ocean views are just the start of things to look forward to during your Gloucester holiday. 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 0.32 kilometres from the city centre 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 holiday homes are another top choice for people planning a holiday 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 holiday deals, you can see more impressive attractions like these.

Top hotels in Gloucester

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is €155 per night from 3 Aug to 4 Aug
€155
3 Aug - 4 Aug
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Very friendly staff !!! Very nice and clean rooms. Feels like home away from home, with gorgeous views outside seating highly recommend"

Reviewed on 30 Jul 2025

Castle Manor Inn
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
9.6/10 Exceptional! (866 reviews)
"This is a beautiful property and friendly staff. Food was excellent. Rooftop pool deck was amazing, although, a little crazy at times."

Reviewed on 1 Aug 2025

Get rates
Beauport Hotel Gloucester
Atlantis Oceanfront Inn

Atlantis Oceanfront Inn

3 out of 5
125 Atlantic Road, Gloucester, MA
The price is €231 per night from 2 Sept to 3 Sept
€231
2 Sept - 3 Sept
includes taxes & fees
9.4/10 Exceptional! (427 reviews)
"Oceanview"

Reviewed on 26 Jul 2025

Atlantis Oceanfront Inn
See all 1,777 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.

Popular places to visit

Wingaersheek Beach

Wingaersheek Beach

Why not spend a care-free afternoon at Wingaersheek Beach during your travels in Gloucester? While you're in the area, stroll along the seaside.

Wingaersheek Beach
Good Harbor Beach

Good Harbor Beach

If a restful holiday is part of your travel plans, Good Harbor Beach might be the perfect place to visit during your trip to Gloucester. While you're in the area, stroll along the seaside.

Good Harbor Beach
Maritime Gloucester

Maritime Gloucester

You can spend an afternoon studying the exhibits at Maritime Gloucester during your trip to Gloucester. Wander through the beautiful beaches and seaside in this family-friendly area.

Maritime Gloucester

What to do in Gloucester

Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

€15
per traveller
100% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

€15
per traveller
80% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
Salem: Pirate Museum with Authentic Treasures Entry Ticket

Salem: Pirate Museum with Authentic Treasures Entry Ticket

€19
per adult
Salem: Pirate Museum with Authentic Treasures Entry Ticket
See all activities in Gloucester

Frequently asked questions

How much does a Gloucester holiday package cost?
Offering great value package deals from €818 on Expedia, you'll be thrilled with how little a holiday to Gloucester costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Gloucester?
You're likely to find lower rates and greater availability in January, February and March. Explore our cheap Gloucester holiday packages and you could score some excellent off-season deals.
How many days is enough for Gloucester?
Typically, a few days is great for a Gloucester holiday. With a well-organised schedule, you can check out all the best sights such as Cressy Beach, as well as explore some hidden treasures along the way.
Is it worth booking a holiday package to Gloucester?
Gloucester has everything you need for an amazing trip. Begin your Gloucester holiday on a high note by exploring major attractions like Capt Bill & Sons Whale Watch.
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 holiday package as soon as possible.
Is it cheaper to book a Gloucester holiday as a package?
Expedia holiday 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 holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday 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 your dates: What you'd like to do in Gloucester and your favourite season will help you decide when to get away.
  2. Budget wisely: As well as the cost of your hotel, you'll need to consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may come up during your trip to Gloucester.
  3. Decide how long to go away for: Now that you're up to speed on Gloucester, you can figure out the perfect length of your break. Create a rough itinerary and allocate enough time to cover everything you want to see.
  4. Combine your airfare and accommodation: Once you've nailed down your travel dates and duration, lock in the right Gloucester holiday package for you.

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