Gloucester Holidays from £850

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Your Gloucester Holiday

Say farewell to the worries of planning and hello to a Gloucester holiday package. With your travel details organised 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 Harbour 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, organising a tailored Gloucester holiday is a cinch with Expedia.

Top Gloucester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Sonesta Simply Suites Boston Burlington

Sonesta Simply Suites Boston Burlington

£850
per person
12 Oct - 15 Oct
found 1 day ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
8.8/10 Excellent! (443 reviews)
Buena

Reviewed on 7 Sept 2026

Arcadian Hotel

Arcadian Hotel

Coolidge Corner
£964
per person
12 Oct - 15 Oct
found 1 day ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
8/10 Very good! (4,465 reviews)
The room was clean. The staff were alright. Pool did not try. WiFi was excellent.

Reviewed on 7 Sept 2026

Residence Inn Boston Dedham

Residence Inn Boston Dedham

£927
per person
12 Oct - 15 Oct
found 1 day ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
8.4/10 Very good! (564 reviews)
Quality Inn Boston - Revere

Quality Inn Boston - Revere

£914
per person
12 Oct - 15 Oct
found 1 day ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
7.6/10 Good! (1,014 reviews)
The room wasn’t clean

Reviewed on 7 Sept 2026

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St

Beacon Hill
£1,023
per person
12 Oct - 15 Oct
found 1 day ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
7.8/10 Good! (142 reviews)

Where to stay in Gloucester

Find the best Gloucester areas and neighborhoods for the activities you enjoy most. Learn more about Gloucester
A lighthouse, a white building with a red roof, and a stone walkway leading to the water.

East Gloucester

3 out of top 10 points of interest in this area

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

Find hotels in East Gloucester
A statue of a man with a wheel, surrounded by a stone base with an inscription, in a public square with houses and cars in the background.

Downtown Gloucester

3 out of top 10 points of interest in this area

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

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A coastal landscape with a lighthouse, rocky shoreline, and a beach.

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.

Find hotels in Annisquam
A lighthouse on a rocky shore with a wooden walkway leading to it.

Rocky Neck

While Rocky Neck isn't home to many top sights, Rocky Neck Art Colony and Maritime Gloucester are some notable places to visit nearby.

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A garden with purple flowers and a foggy coastline.

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.

Find hotels in Magnolia

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.

*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, 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.1°F (-0.5°C)Light RainMostly SunnyModerately LowSlightly Low
February31.8°F (-0.1°C)Light RainMostly SunnyAverageSlightly Low
March36.7°F (2.6°C)Light RainMostly SunnyAverageAverage
April45.1°F (7.3°C)Light RainMostly SunnyAverageAverage
May54.3°F (12.4°C)Light RainMostly SunnyAverageSlightly High
June62.4°F (16.9°C)Light RainMostly SunnyModerately HighAverage
July69.6°F (20.9°C)Light RainMostly SunnyModerately HighAverage
August69.4°F (20.8°C)Light RainMostly SunnyModerately HighAverage
September64.0°F (17.8°C)Light RainMostly SunnyAverageSlightly High
October55.2°F (12.9°C)Light RainMostly SunnyAverageSlightly High
November45.1°F (7.3°C)Light RainMostly SunnyModerately LowAverage
December37.4°F (3.0°C)Light RainMostly SunnyModerately LowSlightly Low

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.

Gloucester Beach Holiday

There's nothing more enjoyable than a Gloucester holiday. Whether you're treating yourself to delicious cocktails at a local hot spot or flipping through a book along the water's edge, your trip to Gloucester is the perfect time to live out those beachy daydreams. Many like to stay close to Good Harbour Beach, situated just 2 miles from downtown. However, you'll also discover plenty of Gloucester holiday packages close to Wingaersheek Beach and Niles Beach, two other superb nearby options.

Gloucester Essential Information

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

Castle Manor Inn

141 Essex Avenue Gloucester MA
£158
14 Sept - 15 Sept
includes taxes & fees
Castle Manor Inn
Beauport Hotel Gloucester

Beauport Hotel Gloucester

55 Commercial Street Gloucester MA
£226
21 Sept - 22 Sept
includes taxes & fees
Beauport Hotel Gloucester
Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

138 Eastern Avenue Gloucester MA
£143
14 Sept - 15 Sept
includes taxes & fees
9.2/10 Wonderful! (483 reviews)
"It was a wonderful stay. Clean and comfortable!. We look forward to staying in the future again."

Reviewed on 2 Sept 2026

Sea Lion Motel and Cottages
See all 1,881 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.
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Stay near popular Gloucester attractions

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

Good Harbor Beach

9.2/10 (191 reviews)
Stroll along Good Harbour Beach's pristine white sands, walking to Salt Island at low tide. Reserve summer parking in advance to enjoy this Atlantic gem with its gentle surf and family-friendly atmosphere.
See properties
A rocky shoreline with large boulders and calm water.

Wingaersheek Beach

9.4/10 (83 reviews)
This pristine beach captivates with white sands, clear shallow waters, and dramatic rock formations. Visit at low tide to explore expansive sandbars and discover hidden tide pools teeming with marine life.
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A stone archway with a view of the sea.

Hammond Castle

9.4/10 (86 reviews)
Explore this 1920s medieval-style castle built by inventor John Hays Hammond Jr. on Massachusetts' coast. Wander through grand halls filled with Roman and Renaissance artefacts while enjoying dramatic ocean views.
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An art gallery with wooden flooring and paintings on the walls.

Cape Ann Museum

9.0/10 (23 reviews)
You can spend an afternoon exploring the galleries in Cape Ann Museum in Gloucester. Wander through the beautiful beaches and seaside in this family-friendly area.
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A coastal town with rocky shores, a prominent church, and a clear blue sky.

Stage Fort Park

9.2/10 (71 reviews)
After visiting Stage Fort Park, make a plan to see the other sights and activities in Gloucester. Wander through the beautiful beaches and seaside in this family-friendly area.
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A beach with clear water, sandy shore, and green foliage.

Half Moon Beach

9.0/10 (45 reviews)
This crescent-shaped cove offers calm waters and golden sand within historic Stage Fort Park. Explore the rocky cliffs for picturesque views of Gloucester Harbour while enjoying the tranquil atmosphere.
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A coastal scene with clear blue water, rocky shoreline, and several sailboats anchored in the distance.

Niles Beach

8.0/10 (8 reviews)
This serene harbour beach offers calm waters and gentle waves perfect for families with young children. Visit at sunset to witness breathtaking golden light while collecting sea glass along the shore.
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A group of people in naval uniforms on a wooden deck, with a ship's rigging and a clear blue sky in the background.

Maritime Gloucester

9.4/10 (63 reviews)
Maritime Gloucester showcases the oldest operating marine railway in the US alongside interactive exhibits of local marine life. Explore the historic Dory Shop or sail the harbour aboard the traditional Schooner Ardelle.
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What to do in Gloucester

Salem, MA: History and Hauntings Guided Walking Tour

Salem, MA: History and Hauntings Guided Walking Tour

£26
per adult
88% of travellers recommend
Salem, MA: History and Hauntings Guided Walking Tour
Freedom Trail and Salem and The Witch Trail Self-Guided Walking Tour Bundle

Freedom Trail & Salem Witch: Self-Guided Walking Tour Bundle

£18
per traveller
100% of travellers recommend
Freedom Trail & Salem Witch: Self-Guided Walking Tour Bundle
History and Hauntings of Salem Guided Walking Tour

History and Hauntings of Salem Guided Walking Tour

£26
per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
See all activities in Gloucester

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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.