Gloucester Holidays from £1,056

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £335 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Packages with flights are ATOL protected

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.
The Wylie Inn and Conference Center at Endicott College
Raffles Boston
The Langham, Boston
The Whitney Hotel
Life House, Nantucket

Where to stay in Gloucester

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

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

Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street Gloucester MA
The price is £172 per night from 22 Apr to 23 Apr
£172
22 Apr - 23 Apr
includes taxes & fees
9.6/10 Exceptional! (943 reviews)
Nice waterview king room! Had a great dinner as well to cap off a great stay.

Reviewed on 10 Apr 2026

Beauport Hotel Gloucester
Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue Gloucester MA
The price is £149 per night from 18 Apr to 19 Apr
£149
18 Apr - 19 Apr
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
The room was clean, but the outside of the building our room was in, behind the inn, was run down and the back of the inn was in disrepair. Not a very pleasant experience.

Reviewed on 19 Jan 2026

Castle Manor Inn
The Hotel at Cape Ann Marina

The Hotel at Cape Ann Marina

3.5 out of 5
75 Essex Avenue Gloucester MA
Fully refundableReserve now, pay when you stay
The price is £179 per night from 12 Apr to 13 Apr
£179
12 Apr - 13 Apr
includes taxes & fees
8.4/10 Very Good! (781 reviews)
We were pleasantly surprised. The staff was helpful. We loved our room. The restaurant was a bit small but we happened to be there when there was a live performance so it was hopping. Hot tub was welcome relief. Would definitely go back.

Reviewed on 29 Mar 2026

The Hotel at Cape Ann Marina
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

What to do in Gloucester

Explore a world of travel with Expedia

* 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.