Gloucester Holidays from £735

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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.

The Latest Gloucester Holiday Deals

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

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
7 Aug - 10 Aug
found 1 day ago
Return direct flight included
London (LON) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Beautiful property and health club

Reviewed on 30 Jun 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
13 Sept - 19 Sept
found 1 day ago
Return direct flight included
London (LHR) to Boston (BOS)
9.4/10 Exceptional! (347 reviews)
The staff were very helpful. The hotel is exceptionally clean and well appointed.

Reviewed on 6 Jun 2025

Global Luxury Suites East Boston

Global Luxury Suites East Boston

4 out of 5
East Boston
Save 100% on your flight
per person
22 Sept - 30 Sept
found 8 hours ago
Return direct flight included
London (LHR) to Boston (BOS)
7/10 Good! (145 reviews)
Amazing location right by the water, quiet building and clean. But the furniture is really uncomfortable, particularly the couch which is the only seating, it’s a pull out bed so the entire sofa sinks in low. The bed isn’t solid and easily slides off the frame just by sitting on it. We also had a delivery order stolen from the front desk area.

Reviewed on 25 Jun 2025

Hotel Veritas

Hotel Veritas

3.5 out of 5
Mid-Cambridge
Save 100% on your flight
per person
13 Sept - 19 Sept
found 18 hours ago
Return direct flight included
London (LHR) to Boston (BOS)
9/10 Wonderful! (1,006 reviews)
Clean, friendly, professional boutique hotel. Easy to walk to Harvard Square and Harvard for shops and restaurants.

Reviewed on 29 Jun 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
7 Aug - 10 Aug
found 1 day ago
Return direct flight included
London (LON) to Boston (BOS)
9.6/10 Exceptional! (1,000 reviews)
Wonderful hotel, in a great location. Beautiful with many amenities and excellent dining. Highly recommend! I’d give it 10 stars if I could!

Reviewed on 1 Jul 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
per person
6 Aug - 13 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Boston (BOS)
8/10 Very Good! (562 reviews)
Very clean and nice! I love that Boston is rennovating building space for airport use - very needed.

Reviewed on 10 Jun 2025

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

Our pick of the best Gloucester Hotel Deals

Castle Manor Inn
Castle Manor Inn
2.5 out of 5
141 Essex Avenue, Gloucester, MA
Stay at this hotel in Gloucester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in their ...
8.2/10 Very Good! (979 reviews)
Overnight
"Overnight stay for the star gazing trip out of the harbor.Had to scenic view room which was lovely large and a view.Would have appreciated a small fridge in room to keep drinks .The bathroom was small but andclean.Overall would stay again-quiet beautiful ."

Reviewed on 28 Jun 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
Stay at this 4-star golf hotel in Gloucester. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
9/10 Wonderful! (710 reviews)
"Beautiful view from our room! Loved having private lounge area outside our room to relax and look at the view. Very nice hotel and very clean. We hope to return soon!"

Reviewed on 27 Jun 2025

Ocean House Hotel at Bass Rocks
Atlantis Oceanfront Inn
Atlantis Oceanfront Inn
3 out of 5
125 Atlantic Road, Gloucester, MA
Stay at this 3-star beach motel in Gloucester. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
9.4/10 Exceptional! (421 reviews)
"Wonderful staff… Unbeatable views of the Rocky coast and Atlantic Ocean… Perfect location easy to get anywhere on the Cape. The breakfast are beyond amazing one of best breakfast spots in North America."

Reviewed on 21 Jun 2025

Atlantis Oceanfront Inn
See all 1,769 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

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.

Discover the most popular places to visit in Gloucester

Wingaersheek Beach

Wingaersheek Beach

Why not spend a care-free afternoon at Wingaersheek Beach during your travels in Gloucester? While you're in the area, stroll along the seaside.

Wingaersheek Beach
Half Moon Beach

Half Moon Beach

If a restful holiday is part of your travel plans, Half Moon Beach might be the perfect place to visit during your trip to Gloucester. While you're in the area, stroll along the seaside.

Half Moon Beach
Eastern Point Lighthouse

Eastern Point Lighthouse

Learn about the local history of Gloucester when you spend time at Eastern Point Lighthouse. Wander through the beautiful beaches and seaside in this family-friendly area.

Eastern Point Lighthouse

Unmissable things to do in Gloucester

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

£33
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

£13
per traveller
100% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

£37
per traveller
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Gloucester

* 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.