Gloucester Holidays from £763

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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.
Studio Allston Hotel
The Inn at Hastings Park, Relais & Chateaux - Boston
The Whitney Hotel
The Newbury Boston
Maverick Suites at 245 Newbury St

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

2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is £134 per night from 22 Jul to 23 Jul
£134
22 Jul - 23 Jul
includes taxes & fees
8.2/10 Very Good! (992 reviews)
"Beautiful property. The rooms are nice but the air conditioning is quite noisy. Overall very nice experience!"

Reviewed on 13 Jul 2025

Castle Manor Inn
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

4 out of 5
107 Atlantic Rd, Gloucester, MA
The price is £311 per night from 29 Jul to 30 Jul
£311
29 Jul - 30 Jul
includes taxes & fees
9/10 Wonderful! (718 reviews)
"Grounds are beautiful. Amazing view. Pool, jacuzzi, fire pit. Benches across the way to sit and enjoy thw ocean. Had a breath taking view of the moon rising above the ocean. Room was spacious and clean. Bed was super comfortable. Plenty of parking right by the room. Overall a lovely stay."

Reviewed on 14 Jul 2025

Ocean House Hotel at Bass Rocks
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is £394 per night from 21 Jul to 22 Jul
£394
21 Jul - 22 Jul
includes taxes & fees
9.6/10 Exceptional! (862 reviews)
"Great property. It's right on the beach. You can get a ride anywhere nearby. You can walk to restaurants and the memorial boardwalk. The room is very simple for almost $600..It just overlooked the sandy parking lot and nearby college.,but the rooftop pool was warm and amazing. It changed colors and ..."

Reviewed on 12 Jul 2025

Beauport Hotel 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

What to do 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.

* 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.