Gloucester Vacations

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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 SAR 879 per night from Apr 8 to Apr 9
SAR 879
SAR 981 total
includes taxes & fees
8 Apr - 9 Apr
9.6/10 Exceptional! (830 reviews)
"Love the fact that it’s located right on the water. Beautiful views everywhere. Always love staying at The Beauport."

Reviewed on 31 March 2025

Beauport Hotel Gloucester
Beach Life Bliss - steps to the beach
Beach Life Bliss - steps to the beach
Gloucester
9.8/10 Exceptional! (27 reviews)
Great place for a getaway
"Loved this comfortable home! Well located and great host."

Reviewed on 16 March 2025

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Beach Life Bliss - steps to the beach
The Vista
The Vista
2.5 out of 5
22 Thatcher Rd., Gloucester, MA
The price is SAR 596 per night from Apr 6 to Apr 7
SAR 596
SAR 665 total
includes taxes & fees
6 Apr - 7 Apr
9.2/10 Wonderful! (361 reviews)
Great place
"Great relaxing place to stay with amazing views. And lovely kind staff."

Reviewed on 19 November 2024

The Vista
See all 1,690 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 vacation package cost?
Offering great value package deals on Expedia, you’ll be thrilled with how little a vacation 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 vacation packages and you could score some excellent off-season deals.
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 vacation package as soon as possible.
Is it cheaper to book a Gloucester vacation as a package?
Expedia vacation 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 vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation 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 favorite 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 accommodations: Once you’ve nailed down your travel dates and duration, lock in the right Gloucester vacation package for you.

Discover the most popular places to visit in Gloucester

Good Harbor Beach which includes a sunset and a coastal town

Good Harbor Beach

4.5/5(18 reviews)

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

Good Harbor Beach
Wingaersheek Beach featuring rugged coastline

Wingaersheek Beach

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

Wingaersheek Beach
Hammond Castle which includes heritage elements, general coastal views and a sunset

Hammond Castle

4.5/5(8 reviews)

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

Hammond Castle