Gloucester Holidays

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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.

Top hotels in Gloucester

Beauport Hotel Gloucester
Beauport Hotel Gloucester
3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is €216 per night from 5 Mar to 6 Mar
€216
includes taxes & fees
5 Mar - 6 Mar
9.6/10 Exceptional! (828 reviews)
"Excellent experience"

Reviewed on 18 Feb 2025

Beauport Hotel Gloucester
Harborview Inn
Harborview Inn
3.5 out of 5
71 Western Avenue, Gloucester, MA
The price is €201 per night from 6 Mar to 7 Mar
€201
includes taxes & fees
6 Mar - 7 Mar
9.4/10 Exceptional! (288 reviews)
"John welcomed us and was a remarkable host. We stayed in six different accomodations on this trip and this one was by far our favorite. The room was spacious and comfortable. Breakfast was excellent. Parking is free and convenient. John gave us a great dining recommendation which was within an easy ..."

Reviewed on 25 Nov 2024

Harborview Inn
The Vista
The Vista
2.5 out of 5
22 Thatcher Rd., Gloucester, MA
The price is €196 per night from 1 Apr to 2 Apr
€196
includes taxes & fees
1 Apr - 2 Apr
9.2/10 Wonderful! (361 reviews)
Great place
"Great relaxing place to stay with amazing views. And lovely kind staff."

Reviewed on 19 Nov 2024

The Vista
See all 1,660 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?
Offering great value package deals on Expedia, you’ll be thrilled with how little a holiday to Gloucester costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Gloucester?
You’re likely to find lower rates and greater availability in January, February and March. Explore our cheap Gloucester holiday packages and you could score some excellent off-season deals.
How many days is enough for Gloucester?
Typically, a few days is great for a Gloucester holiday. With a well-organised schedule, you can check out all the best sights such as Cressy Beach, as well as explore some hidden treasures along the way.
Is it worth booking a holiday package to Gloucester?
Gloucester has everything you need for an amazing trip. Begin your Gloucester holiday on a high note by exploring major attractions like Capt Bill & Sons Whale Watch.
How to find the best Gloucester package deals?
Use Expedia’s filters to find some great Gloucester package deals. When you begin your search, simply set your maximum budget and then order the results by “Price: low to high.” If you want to save, plan your trip for midweek, or look for Gloucester package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it’s usually best to book your holiday package as soon as possible.
Is it cheaper to book a Gloucester holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You’ll typically get a better deal than booking each component separately. And you’ll still have the freedom to create a tailored Gloucester holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Gloucester?
If you’re considering a spontaneous Gloucester getaway, check out our last-minute deals that can be booked up to a week before you go. Don’t want to leave things to the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Gloucester?

  1. Choose your dates: What you’d like to do in Gloucester and your favourite season will help you decide when to get away.
  2. Budget wisely: As well as the cost of your hotel, you’ll need to consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may come up during your trip to Gloucester.
  3. Decide how long to go away for: Now that you’re up to speed on Gloucester, you can figure out the perfect length of your break. Create a rough itinerary and allocate enough time to cover everything you want to see.
  4. Combine your airfare and accommodation: Once you’ve nailed down your travel dates and duration, lock in the right Gloucester holiday package for you.

Popular places to visit

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
Good Harbor Beach

Good Harbor Beach

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

Good Harbor Beach
Stage Fort Park

Stage Fort Park

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.

Stage Fort Park

What to do in Gloucester

Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts Self-Guided Driving and Walking Tours Bundle

€43
per adult
Massachusetts Self-Guided Driving and Walking Tours Bundle
Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

€16
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

€48
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.