A beach with a lifeguard tower, waves, and a large house with a tower on a rocky shore.

Gloucester Holidays from £1,253

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Top Gloucester flight + hotel deals

Price found within the past 48 hours. Click for updated prices.
  • 8 Oct - 13 Oct

    Good Hotels Boston + Flight

    South End
    5 nights
    2.0 star property
    8.0/10 - Very good (55 reviews)
    "This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order."
    Reviewed May 23, 2026
    Return London (LON) - Boston (BOS)
    LHR - BOS1 stop BOS - LHR1 stop
    Save 100% on your flight
    £1,750
    £1,253
    per traveller
    found 1 day ago
    Good Hotels Boston
  • 12 Oct - 18 Oct

    Boston Harbor Hotel + Flight

    North End
    6 nights
    5.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    "I loved to view from our room. The room smelled fresh and pretty. Everything was impeccable. The amenities were fantastic. I love that there was a golf simulator in the Health Club. Staff were amazing and everyone was friendly. The location was great. I didn’t want to leave! Jose, the bellhop was very helpful and informative when he brought our luggage to our room. Housekeeping was amazing as well. We had a wonderful stay in Boston!"
    Reviewed July 23, 2026
    Return London (LHR) - Boston (BOS)
    LHR - BOSDirect BOS - LHRDirect
    Save 100% on your flight
    £3,532
    £2,217
    per traveller
    found 1 day ago
    Boston Harbor Hotel
  • 27 Sept - 3 Oct

    The Atlas Hotel + Flight

    Allston
    6 nights
    4.5 star property
    9.4/10 - Exceptional (223 reviews)
    Return London (LON) - Boston (BOS)
    LHR - BOSDirect BOS - LGW1 stop
    Save 100% on your flight
    £2,044
    £1,377
    per traveller
    found 7 hours ago
    The Atlas Hotel
  • 12 Oct - 18 Oct

    The Godfrey Hotel Boston + Flight

    Downtown Boston
    6 nights
    4.0 star property
    9.6/10 - Exceptional (5,124 reviews)
    Return London (LHR) - Boston (BOS)
    LHR - BOSDirect BOS - LHRDirect
    Save 100% on your flight
    £2,175
    £1,513
    per traveller
    found 1 day ago
    The Godfrey Hotel Boston
  • 8 Oct - 13 Oct

    The Whitney Hotel + Flight

    Beacon Hill
    5 nights
    4.0 star property
    9.6/10 - Exceptional (592 reviews)
    "We could not sleep. The upstairs guest was stomping from 12am-2am. When I made a noise complaint around 1am the issue was not mitigated. We were again woken up at 6am by the neighbor continuing on with stomping. The hotel phone line didn’t work so I had to connect via my cell and go through prompts to even make the original complaint."
    Reviewed July 21, 2026
    Return London (LON) - Boston (BOS)
    LHR - BOS1 stop BOS - LHR1 stop
    Save 100% on your flight
    £2,147
    £1,498
    per traveller
    found 1 day ago
    The Whitney Hotel

Where to stay in Gloucester

Find the best Gloucester areas for the activities you enjoy most. Learn more about Gloucester
Learn more about Gloucester

East Gloucester

If you're spending some time in East Gloucester, Good Harbor Beach and Niles Beach are top sights worth seeing.

Downtown Gloucester

While visiting Downtown Gloucester, you might make a stop by sights like Cape Ann Museum and Capt Bill & Sons Whale Watch.

Annisquam

Though Annisquam may not have many top sights, you can venture to the surrounding area to see attractions like Wingaersheek Beach and Plum Cove Beach.

Rocky Neck

While visiting Rocky Neck, you might make a stop by sights like Rocky Neck Art Colony and Bryan Gallery.

Magnolia

You'll enjoy the beaches and restaurants in Magnolia. You might want to make time for a stop at Gray Beach or Massachusetts Bay.

Discover the most popular places to visit in Gloucester

What to do in Gloucester

Gloucester Hotel Deals

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.

Frequently Asked Questions

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.

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Things to do in and around Gloucester

Gloucester offers an ideal vacation for beach lovers and outdoor enthusiasts, featuring exciting activities such as music concerts and visits to local arts centres. Enjoy weekend getaways with scenic walking tours and thrilling adventures, alongside numerous attractions and seasonal events that showcase the town's charm. Dive into Gloucester's vibrant culture and natural beauty for a memorable experience.

Shopping

In Gloucester, you can visit the Todd Farm Flea Market for unique finds. If you're up for a drive, Bewitched in Salem and MarketStreet Lynnfield offer a mix of shopping and entertainment 13 and 32.2km away, respectively, with a variety of shops and family-friendly activities.

Recreation

The Shalin Liu Performance Center offers an uplifting musical experience, just a short distance from Gloucester, perfect for entertainment and relaxation. Meanwhile, Halibut Point Reservation is a beautiful natural area ideal for unwinding amidst stunning coastal views. Don’t miss the Gorton Theatre for a blend of culture and family fun in Gloucester.

Adventure

Embark on an exhilarating whale-watching adventure with Capt Bill & Sons Whale Watch, immersing yourself in the marine wonders of Gloucester. For a picturesque hike, explore Dogtown's scenic trails. For family fun, visit the Water Park of New England, a mere 25.7km from Gloucester, offering thrilling rides and entertainment.

Nightlife

For a lively evening in Gloucester, visit the Park-9 Dog Bar, located 40.2km away. This charming drinking pub offers a delightful mix of entertainment and romantic vibes, perfect for a relaxed night out with friends or a special someone.

Find the best attractions in and around Gloucester

Gloucester, Massachusetts, is a charming coastal destination perfect for beach and outdoor enthusiasts. Visitors can explore a variety of attractions, including the Gloucester Museum, historic houses, and the picturesque Gloucester Docks. The area offers stunning scenery and cultural experiences, making it ideal for those seeking both relaxation and adventure. Don’t miss the nearby parks and the renowned Gloucester Cathedral for a taste of local heritage.

  • Wingaersheek Beach: Experience the stunning sandy shores and tranquil waters of Wingaersheek Beach, known for its picturesque views and relaxed beach vibes. Ideal for sunbathing, swimming, and beachcombing, this local gem is perfect for a peaceful day by the sea.
  • Castle Hill on the Crane Estate: Discover the rich history and cultural significance of Castle Hill, an elegant historic house located 12.9km from Gloucester. Explore its beautifully landscaped gardens and enjoy breathtaking views of the Atlantic, making it a perfect spot for history enthusiasts and nature lovers alike.
  • Eastern Point Lighthouse: Visit the charming Eastern Point Lighthouse, a historic landmark within Gloucester. This iconic structure offers a glimpse into maritime history and stunning coastal scenery, providing an excellent backdrop for photography and contemplation.

Best time to go to Gloucester

The best time to visit Gloucester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is mostly sunny with light rain.

Tips to save on your trip to Gloucester

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Gloucester during the low season (December to February) for more affordable options.
  • 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.

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