Gloucester Vacations

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Find the Best Gloucester Vacation Packages

Gloucester Hotel Deals

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is AED 618 per night from Nov 13 to Nov 14
AED 618
AED 691 total
13 Nov - 14 Nov
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
Staff was extremely courteous, advising us to take the train to Salem and giving us a train schedule. 100% would recommend. Great accommodations.

Reviewed on 29 October 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
Fully refundableReserve now, pay when you stay
The price is AED 476 per night from Nov 10 to Nov 11
AED 476
AED 618 total
10 Nov - 11 Nov
includes taxes & fees
9/10 Wonderful! (782 reviews)
Clean comfortable room. Beautiful view.

Reviewed on 1 November 2025

Ocean House Hotel at Bass Rocks
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
9.6/10 Exceptional! (894 reviews)
Great stay!

Reviewed on 6 November 2025

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Beauport Hotel Gloucester
See all 1,748 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.

Discover the most popular places to visit in Gloucester

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
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
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

Frequently asked questions

How do I find cheap flights to Gloucester that have flexible change policies?
By using our nifty "No change fee" filter, that's how. Just enter your dates and other details, click the "Search" button, then click the checkbox directly under the "Flexible change policies" subheading (top left-hand side of your screen). Expedia makes it a cinch to find inexpensive, flexible tickets to Gloucester.
Which airlines fly to Gloucester?
You can choose from a variety of airlines that service Gloucester. Some of the best of them are:

  • Delta Air Lines - 3,701 flights to or near Gloucester each month, including 3,701 flights to Logan Intl. Airport (BOS) per month.
  • JetBlue Airways - 3,407 flights to or near Gloucester each month, including 3,407 flights to Logan Intl. Airport (BOS) per month.
  • American Airlines - 2,106 flights to or near Gloucester each month, including 2,106 flights to Logan Intl. Airport (BOS) per month.

How can I find cheap tickets to Gloucester?
Book well in advance, fly in or out of nearby airports, avoid peak travel periods — you're not short of ways! One more is to take advantage of Expedia's "flexible dates" function. Search for your Gloucester flight, then compare the prices for nearby dates. In the last seven days, the lowest price for a flight to Gloucester was .
How much is a flight to Gloucester?
In the last seven days, return tickets to Gloucester sold for as low as and peaked at . For one-way fares taking off from (), the lowest amount paid during this time was only .
What are the most popular airports to fly into in Gloucester?
Zip up your suitcase and fly into Logan Intl. Airport (BOS), Gloucester's major flight hub. Book a ticket on one of the 12,948 flights that land at this awesome destination every month.
When is the cheapest time to fly to Gloucester?
Consider leaving earlier in the week to get a bargain airfare to Gloucester. Tuesday is generally the most affordable day to fly, with Monday a close second. Saturday typically has the most expensive ticket prices. This is because many people like to begin their break on a weekend.
How much is a plane ticket to Gloucester?
In the last seven days, fares to Gloucester fluctuated from to .
What months are the cheapest to book a flight to Gloucester?
February is the top month to bag cheap flights to Gloucester. Keep in mind that the most expensive time to purchase tickets in the U.S. Isn't during the peak of summer, but the festive month of December.
How long is a flight to Gloucester?
Whether or not you'll have time to read one chapter of your favorite book or a few depends on where you're traveling from. To make planning your trip a little easier, here are the average flight times for three top domestic routes to Gloucester:

  • Washington, DC (DCA-Ronald Reagan Washington National) to Logan Intl. Airport (BOS) - 1 hour and 48 minutes
  • New York, NY (LGA-LaGuardia) to Logan Intl. Airport (BOS) - 1 hour and 35 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Logan Intl. Airport (BOS) - 1 hour and 25 minutes