Gloucester Trip

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Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.
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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 3 kilometres from downtown. However, you'll also discover plenty of Gloucester holiday packages close to Wingaersheek Beach and Niles Beach, two other superb nearby options.

Find the Best Gloucester Vacation Packages

Gloucester Hotel Deals

Beauport Hotel Gloucester
Beauport Hotel Gloucester
3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is ₹16,447 per night from 24 Nov to 25 Nov
₹16,447
₹18,372 total
includes taxes & fees
24 Nov - 25 Nov
9.6/10 Exceptional! (789 reviews)
"Was a wonderful hotel. Everyone so nice & it is so attractive. We had a room on the ocean & it was gorgeous. Only minor complaint was the gym was too small. The food was EXCELLENT!!"

Reviewed on 19 Nov 2024

Beauport Hotel Gloucester
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 ₹10,647 per night from 2 Dec to 3 Dec
₹10,647
₹11,892 total
includes taxes & fees
2 Dec - 3 Dec
8.2/10 Very Good! (661 reviews)
"I liked staying at a marina and I liked the little deck, pool, food, staff, parking. I think an updated remodel is in order. Thank you"

Reviewed on 13 Nov 2024

The Hotel at Cape Ann Marina
Castle Manor Inn
Castle Manor Inn
2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is ₹13,507 per night from 30 Nov to 1 Dec
₹13,507
₹15,087 total
includes taxes & fees
30 Nov - 1 Dec
8.2/10 Very Good! (947 reviews)
"Chef Dan and Kamden made our morning breakfast buffet experience even more enjoyable! Food was delicious and we loved how hospitable they were. John greeted us upon arrival and made some great recommendations about restaurants and touring Gloucester. We stayed in the Inn in room Sunnyside up on third ..."

Reviewed on 17 Nov 2024

Castle Manor Inn
See all 1,636 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.

Frequently asked questions

How much does a Gloucester holiday package cost?
Our Gloucester packages, which begin at just , are an awesome way to save money. Select your favourite hotels, flights and rental car to create your dream itinerary.
How do I get a cheap travel package to Gloucester?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Hotels, rental cars, flights and activities — we’ve got them all covered. Pick and choose a combination that suits your style and see your savings stack up. Of course, a package deal is never one-size-fits-all. That’s why we offer more than 550 airlines and 1,000,000 properties globally, which lets you customize your Gloucester getaway.
Where should I stay in Gloucester?
Stay where the action is. Many travellers like to book hotels within easy reach of top attractions, such as Wingaersheek Beach, Good Harbour Beach and Hammond Castle.
What are the top hotels in Gloucester?
Castle Manor Inn in the Annisquam neighbourhood is an excellent choice for a Gloucester escape. Stay here and you’ll be in a perfect position to explore all that this happening city has to offer.
How far in advance should I book my Gloucester holiday?
To land rock-bottom prices, book nice and early. Air carriers typically release tickets, along with some of the lowest fares, nearly 12 months in advance. Hotels, experiences and car rental should also be booked well in advance to avoid disappointment. If you’ve decided on a last-minute getaway to Gloucester, there are always plenty of great deals on Expedia. Book something in today!
What does an Expedia Gloucester travel package include?
With Expedia, you can choose a combination of car rentals, flights and hotels to build your ideal Gloucester travel package. Once you’ve made your booking, you can add on the fun stuff like tours and experiences. Don’t forget — the more you bundle, the bigger the savings!
What should I know before booking a Gloucester travel package?
Tailor deals that match your budget with an Expedia package. Hotels, flights, rental cars — we’ve got them all. You’ll save precious dollars just for bundling your bookings. Whether you’re heading away on a winter adventure or drinking cocktails on a beach, your ideal getaway is only a few clicks away.
Can I choose my airline with a Gloucester Expedia holiday package?
With a holiday package, you’re the one in charge. Whether you’re looking to fly to Gloucester in coach or first class, simply choose from the available airline options. Expedia has access to over 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Gloucester holiday package?
You can. We totally understand that life doesn’t always go to plan, so we’re happy to help if you need to make changes to your Gloucester holiday package. You may be able to cancel or change your itinerary at no cost if you’ve booked within 24 hours. Your airline, hotel or car rental company may impose a fee if you booked more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Gloucester

Hammond Castle

Hammond Castle

You can browse the exhibits at Hammond Castle, a museum with a story of its own, during your holiday in Gloucester. Wander the beautiful beaches and seaside in the area.

Hammond Castle

Rocky Neck Art Colony

You can enjoy some culture when you stop by Rocky Neck Art Colony in Gloucester. Wander through the beautiful beaches and seaside in this family-friendly area.

Rocky Neck Art Colony

Plum Cove Beach

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

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