Why should I book my Gloucester holiday with Expedia?

Expedia has you covered for all aspects of your Gloucester holiday. You'll always land the best deals around, but when you bundle your flights, hotel and/or hire car into a holiday package, you'll score even more savings. Looking to really make the most of your break? Add some fun tours and activities to your customised package. Expedia offers flexible cancellation policies on most bookings, so there's no need to worry if your travel plans change. Visit our Customer Service Portal link to learn more.

When is the best time of year to holiday in Gloucester?

Gloucester draws the crowds in June, July and August. If you want a more relaxed getaway, visit in November, December and January. To get an idea of what type of weather you can experience, the average temperature during the day in January, the coolest month in Gloucester, is 0ºC. The warmest period here is July, when temperatures average 20ºC.

What are the top hotels for my holiday in Gloucester?

Castle Manor Inn will make an ideal base for your Gloucester getaway. Located in Annisquam, it's one of this area's best hotels.

How do I get a cheap holiday to Gloucester?

Booking a hotel and flight together with Expedia won't just save valuable time — it'll save you a tidy sum too. A Gloucester holiday makes it simple to create the ideal trip. With more than 400 airlines all over the world to choose from, finding convenient flights that suit your schedule won't be an issue. On top of that, we've got over 321,000 hotel options globally to select from. Talk about choice! No matter who you are, Expedia can show you the world. Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.

What should I do on my Gloucester holiday?

Ensure your holiday in Gloucester is one to remember by checking out its well-known attractions. Good Harbour Beach , Cape Ann , Hammond Castle and Wingaersheek Beach are some of the things to put on your itinerary while you're in the area.

What is the best area to stay in when on holiday in Gloucester?

If you'll be visiting Good Harbour Beach, maximise your time sightseeing and book a stay close by. It's one of the most popular attractions in Gloucester.

Do I need a visa for my Gloucester holiday?

Visa requirements for Gloucester vary based on your nationality and the reason for your visit. It's best to check official government websites to determine if you need a visa for your holiday. Here you'll also find the most up-to-date information, including details about application procedures or any supporting documentation that may be necessary. Research your visa requirements well ahead of time to ensure a travel experience that's hassle free. Also check to see that your passport is valid for a further six months from your return date.

What should I wear on my Gloucester holiday?

Do a little research into the types of things people in Gloucester wear, and maybe even check out social media fashion pages for inspiration. Whatever your look, try to create a versatile wardrobe with pieces that work for your destination and show off your personal style. Check the weather forecast so you can pack accordingly. The warmest time of year in Gloucester is July, with average daily temperatures of 20ºC. If you plan to visit during the coolest month of January, the mercury averages 0ºC during the day.

What does an Expedia Gloucester holiday include?

Flights, car hires and hotels, or any combination of the three — it's your choice. Whether you're headed to Gloucester with the entire family or travelling by yourself, there's a package to fit your style and budget. Once you've made your booking, why not add on a few tours as well? Discover an excellent range of property types and select one that matches your travel needs. The most sought-after holiday rentals here are private holiday homes and apartments. With Expedia, you can easily tailor-make your Gloucester retreat the way you like.

Does Expedia offer Book Now, Pay Later Gloucester holidays?

Your bank balance shouldn't prevent you from going on holiday, so Expedia has come up with a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book your dream getaway without making a dent in your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your break. Consider one of these flexible payment options: Pay monthly holidays : Escape on that dream holiday sooner with Klarna's manageable instalment plans. If paying bite-sized amounts each month sounds right for you, pick this option during the checkout process. No-deposit holidays : If not paying ahead of time for your trip makes pressing that "book now" button more stress-free, choose a no-deposit holiday plan from Klarna so that you can Book Now, Pay Later!

Can I choose my airline with a Gloucester Expedia holiday?

Yes, you can. Expedia has access to more than 400 airline partners globally, so opt for the carrier that best suits your budget and travel needs.

Gloucester Holidays 2025 from $365

Top Gloucester Flight + Hotel Deals

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

Club Quarters Hotel Faneuil Hall, Boston

Downtown Boston

Save 100% on your flight

per person

25 Oct - 1 Nov

found 6 hours ago

Return direct flight included

Dublin (DUB) to Boston (BOS)

9/10 Wonderful! (2,696 reviews)

Great food next door at Elephant and Castle . The potato and leek casserole was excellent. The elevator is small and the rooms are very close together. It gets loud if you have noisy neighbors.

Reviewed on 5 Aug 2025

Boston Harbor Hotel

North End

Save 100% on your flight

per person

19 Sept - 24 Sept

found 20 hours ago

Return direct flight included

Edinburgh (EDI) to Boston (BOS)

9.8/10 Exceptional! (1,001 reviews)

Wonderful high end hotel in a fantastic area. Loved being able to walk to the north end!

Reviewed on 3 Aug 2025

Raffles Boston

Back Bay

Save 100% on your flight

per person

25 Oct - 1 Nov

found 6 hours ago

Return direct flight included

Dublin (DUB) to Boston (BOS)

9.6/10 Exceptional! (132 reviews)

I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on 5 Aug 2025

Beacon Hill Hotel

Beacon Hill

Save 100% on your flight

per person

18 Sept - 25 Sept

found 1 day ago

Return direct flight included

Edinburgh (EDI) to Boston (BOS)

8.8/10 Excellent! (234 reviews)

We enjoyed having the bistro on site.

Reviewed on 17 Jul 2025

Global Luxury Suites Downtown Boston

Chinatown

Save 100% on your flight

per person

25 Oct - 1 Nov

found 6 hours ago

Return direct flight included

Dublin (DUB) to Boston (BOS)

8/10 Very Good! (569 reviews)

Washer/Dryer did not work properly. Despite 2 calls and 1 email to customer service, the issue was not resolved. The washer didn’t rinse clothing out and they remained sopping wet. They required extensive drying time as a result ( over 4 hours). This was extremely inconvenient.

Reviewed on 2 Aug 2025

Things to do in and around Gloucester

Gloucester, Massachusetts, is an ideal destination for beach lovers and outdoor enthusiasts. Visitors can enjoy music concerts, walking tours, and exciting adventures amidst stunning scenery. The town offers a variety of attractions and seasonal activities, making it perfect for weekend getaways. Whether you're seeking relaxation at a resort or educational experiences, Gloucester has something to suit every traveller's taste.

Shopping

For a unique shopping experience, visit Todd Farm Flea Market, a lively public market 20.9km away. If you're up for a drive, Bewitched in Salem and MarketStreet Lynnfield offer diverse shopping options, with the latter being 32.2km away and featuring entertainment and family-friendly vibes.

Recreation

Experience the enchanting sounds at the Shalin Liu Performance Center, just 6.4km from Gloucester, where the atmosphere is filled with vibrant entertainment. Alternatively, unwind at Halibut Point Reservation, a serene spot perfect for relaxation, or enjoy cultural performances at the Gorton Theatre, fostering romance and family connections.

Adventure

Experience the thrill of whale watching with Capt Bill & Sons Whale Watch, immersing yourself in the majestic ocean. Hike the scenic trails of Dogtown, surrounded by beautiful landscapes. For family fun, visit the Water Park of New England, offering exciting rides and entertainment 25.7km from Gloucester.

Nightlife

For a lively night out in Gloucester, visit the Park-9 Dog Bar, a charming drinking pub 40.2km away. With its vibrant atmosphere and romantic vibes, it’s the perfect spot to unwind, socialise, and enjoy some entertainment after a day of exploring the area.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Gloucester

Gloucester, Massachusetts, offers a delightful blend of beach and outdoor experiences, perfect for your holiday. Explore the scenic Gloucester docks and Gloucester quays, visit the historic Gloucester Cathedral, and enjoy local parks in Gloucestershire. With a variety of attractions including museums and historic houses, this charming town invites you to immerse yourself in its rich culture and stunning scenery.

Good Harbor Beach: Experience the stunning soft sands and vibrant beach vibes of Good Harbor Beach, a perfect spot for sunbathing, swimming, and beachcombing. The picturesque views of the Atlantic Ocean make it a delightful escape.
Cape Ann: Just 6.4km from Gloucester, Cape Ann offers breathtaking scenery, with rugged coastlines and charming seaside towns. Explore its serene beaches and enjoy picturesque landscapes that showcase the beauty of New England.
Castle Hill on the Crane Estate: Located 12.9km away, this historic estate boasts exquisite architecture and beautifully landscaped gardens. Immerse yourself in the rich culture and history as you wander through its stunning grounds and enjoy sweeping views of the ocean.

Best time to go to Gloucester

The best time to visit Gloucester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Gloucester falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Gloucester falls in January, visitor numbers are moderately low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	31.1°F (-0.5°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
February	31.8°F (-0.1°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	36.7°F (2.6°C)	Light Rain	Mostly Sunny	Average	Average
April	45.1°F (7.3°C)	Light Rain	Mostly Sunny	Average	Average
May	54.3°F (12.4°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	62.4°F (16.9°C)	Light Rain	Mostly Sunny	Moderately High	Average
July	69.6°F (20.9°C)	Light Rain	Mostly Sunny	Moderately High	Average
August	69.4°F (20.8°C)	Light Rain	Mostly Sunny	Moderately High	Average
September	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	55.2°F (12.9°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	45.1°F (7.3°C)	Light Rain	Mostly Sunny	Moderately Low	Average
December	37.4°F (3.0°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low

Tips to save on your trip to Gloucester

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Gloucester.
Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Gloucester.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Language	English
Currency	U.S dollars
Closest Airport	Logan Intl. Airport (BOS)
Population	29,800
Max Temp Winter	2ºC
Max Temp Summer	21ºC
Top Sights	Wingaersheek Beach, Good Harbour Beach and Crane Beach

Language

English

Currency

U.S dollars

Closest Airport

Logan Intl. Airport (BOS)

Population

29,800

Max Temp Winter

2ºC

Max Temp Summer

21ºC

Top Sights

Wingaersheek Beach, Good Harbour Beach and Crane Beach

Top hotels in Gloucester

Castle Manor Inn

141 Essex Avenue, Gloucester, MA

£135

13 Aug - 14 Aug

includes taxes & fees

8.2/10 Very Good! (1,002 reviews)

"Very very happy with our stay. Great location, room was very nice, clean, the bed was comfortable. The Inn was exactly what we hoped for.. we will definitely return in the future."

Reviewed on 5 Aug 2025

Beauport Hotel Gloucester

55 Commercial Street, Gloucester, MA

£399

3 Sept - 4 Sept

includes taxes & fees

9.6/10 Exceptional! (869 reviews)

"My daughter and I have spent a few days here for the past several years. We enjoy the ease of going to Good Harbor beach or spending a day at the roof top pool. The rooms are spacious and clean - the turn down service leaves the most delicious milk chocolate nonpareils on the bed! The food at the ..."

Reviewed on 5 Aug 2025

Ocean House Hotel at Bass Rocks

107 Atlantic Rd, Gloucester, MA

£251

1 Sept - 2 Sept

includes taxes & fees

9/10 Wonderful! (722 reviews)

"Gorgeous views."

Reviewed on 22 Jul 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.