Vacation to Gloucester

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Gloucester Flight and Hotel Deals

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston

5 out of 5
Downtown Boston
Price was $1,913, price is now $1,222 per person
per person
Aug 10 - Aug 14
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
8.6/10 Excellent! (240 reviews)
Perfect location, very comfortable, cozy atmosphere

Reviewed on Apr 3, 2023

Residence Inn by Marriott Boston Harbor on Tudor Wharf

Residence Inn by Marriott Boston Harbor on Tudor Wharf

3 out of 5
Charlestown
Save 100% on your flightPrice was $1,760, price is now $1,295 per person
per person
Aug 1 - Aug 6
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.8/10 Excellent! (1,001 reviews)
Our room was extremely clean with comfy beds. We loved the breakfast as well as the customer service the chef and other staff around the buffet treated us! Everything was perfect. The parking was a bit pricy and I wasn’t allowed to leave my car there for the day after I checked out… but overall I would stay here again, it is a great hotel.

Reviewed on May 11, 2023

Marriott Boston Quincy

Marriott Boston Quincy

3.5 out of 5
Price was $1,018, price is now $754 per person
per person
Aug 10 - Aug 14
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
8.4/10 Very Good! (1,012 reviews)
We loved the room we stayed in however the shower liner was dirty.

Reviewed on May 31, 2023

Hampton Inn Boston - Logan Airport

Hampton Inn Boston - Logan Airport

3 out of 5
Price was $724, price is now $544 per person
per person
Aug 10 - Aug 14
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
7.8/10 Good! (3,201 reviews)
Great value for Boston. Can stay here and get to city meeting easily by can or Uber

Reviewed on Jun 6, 2023

Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
Save 100% on your flightPrice was $1,552, price is now $1,192 per person
per person
Jul 20 - Jul 26
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
8.8/10 Excellent! (1,012 reviews)
Breakfast was good. Building needs updates. Very old.

Reviewed on Jun 4, 2023

Gloucester Beach Vacation

There's nothing more enjoyable than a Gloucester vacation. 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 Harbor Beach, situated just 2 miles (3 km) from downtown. However, you'll also discover plenty of Gloucester vacation packages close to Wingaersheek Beach and Niles Beach, two other superb nearby options.

Your Gloucester Vacation

The best way to experience this city is with a custom-made Gloucester vacation package. Base yourself in the neighborhood of Great Neck, which is great for watersports, walking and nature or choose someplace else — our packages are all about you. If taking in sights is on the cards during your trip to Gloucester, stop by big attractions like Cape Ann, Wingaersheek Beach and Good Harbor Beach. Whoever you're traveling with and whatever the size of your budget, your dream Gloucester vacation is just clicks away with Expedia.

Gloucester Hotel Deals

DoubleTree by Hilton Boston North Shore
DoubleTree by Hilton Boston North Shore
4 out of 5
50 Ferncroft Rd, Danvers, MA
Fully refundableReserve now, pay when you stay
The price is $89 per night from Jun 25 to Jun 26
$89
per night
Jun 25 - Jun 26
7.6/10 Good! (1,183 reviews)
"Very quiet"

Reviewed on Jun 5, 2023

DoubleTree by Hilton Boston North Shore
Castle Manor Inn
Castle Manor Inn
2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is $208 per night from Jun 22 to Jun 23
$208
per night
Jun 22 - Jun 23
8/10 Very Good! (627 reviews)
"Very clean and spacious. The staff was very friendly and made us feel welcome."

Reviewed on Jun 4, 2023

Castle Manor Inn
Lakeside Inn
Lakeside Inn
2 out of 5
595 North Ave, Wakefield, MA
Fully refundableReserve now, pay when you stay
The price is $105 per night from Jun 11 to Jun 12
$105
per night
Jun 11 - Jun 12
6.8/10 (1,054 reviews)
"Good, no frills property Clean and quiet"

Reviewed on Jun 5, 2023

Lakeside Inn
See all 1,337 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?
Starting from a low $544, a package is your passport to affordable travel. Custom make your Gloucester trip by picking from our extensive range of hotels, airfares and rental cars.
If I'm not able to travel, can I cancel my Gloucester vacation package?
You can. We realize life doesn’t always go to plan, so we’re happy to help if you need to make changes to your Gloucester vacation package. It may be possible to cancel or amend your itinerary at no cost if you’ve booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees.
How do I get a cheap travel package to Gloucester?
Bundle your bookings with Expedia to save big on your next exciting adventure. With more than 550 airlines and 1,000,000 properties across the world, your Gloucester vacation package can be customized exactly to suit your budget. With all that extra cash, why not throw in a few fun tours and activities? It’s an easy way to unlock even more savings. The vacation you’ve always dreamed of in Gloucester is closer than you thought!
Where should I stay in Gloucester?
With popular attractions such as Good Harbor Beach and Hammond Castle in this area, look for a hotel located near either of them. Wingaersheek Beach is another Gloucester sight that lures the crowds.
What are the top hotels in Gloucester?
One of the most sought-after places to stay in Gloucester is Beauport Hotel Gloucester, in the neighborhood of Annisquam. Explore the city by day and then rest your head in this comfortable option at night.
How far in advance should I book my Gloucester vacation?
Reward yourself with the widest variety at the lowest prices by booking your trip to Gloucester early. Air carriers usually sell tickets anywhere up to 12 months before departure, so start locking things in ASAP. Having said that, Expedia is dedicated to giving you the best bargains around, so there’s never a bad time to book your dream vacation!
What does an Expedia Gloucester travel package include?
It all comes down to what type of escape you have in the works. Gloucester travel deals can include car rentals, hotels and flights. You can mix and match to find the package that suits your style and budget. You can also add on activities and experiences after you’ve booked to get even bigger discounts.
What should I know before booking a Gloucester travel package?
Whether it’s adventure or relaxation you’re craving, a Gloucester vacation package lets you plan your escape your way. Plus, you’ll score great discounts just for combining your accommodations with your flights and rental car. The more you bundle, the more you’ll save!
Can I choose my airline with a Gloucester Expedia vacation package?
The choice is all yours! Expedia has access to more than 550 airlines around the world, so you can tailor your Gloucester trip according to your needs and budget.
Does Expedia offer Book Now, Pay Later Gloucester vacation packages?
If your reason for travel has suddenly cropped up, Expedia can help to reduce any financial stress. Working in partnership with online lender Affirm, we provide a Book Now, Pay Later solution for all vacation package bookings. It’s easy to set up a payment arrangement for your travel that works for you.

Popular places to visit

Image for Wingaersheek Beach

Wingaersheek Beach

Offering fun in the sun, this coastal playground has calm water and everything you need for a day by the sea.

Wingaersheek Beach
Image for Good Harbor Beach

Good Harbor Beach

4.5/5(18 reviews)

With a reputation as Gloucester’s prettiest beach, this curve of white sand lapped by rolling waves sets the scene for soaking up the sun.

Good Harbor Beach
Image for Hammond Castle

Hammond Castle

4.5/5(8 reviews)

A medieval-style castle overlooking the blue ocean waters in Gloucester features a spellbinding collection of art, artifacts and quirky inventions.

Hammond Castle

Things to do

Image for Scenic Cape Ann Self-Guided Driving Tour in Gloucester & Rockport

Scenic Cape Ann Self-Guided Driving Tour in Gloucester & Rockport

$15
Per adult
Scenic Cape Ann Self-Guided Driving Tour in Gloucester & Rockport
Image for Ultimate Cape Ann Self-Guided Driving Audio Tour in Gloucester and Rockport

Ultimate Cape Ann Self-Guided Driving Audio Tour in Gloucester and Rockport

$15
Per adult
80% of travellers recommend
Ultimate Cape Ann Self-Guided Driving Audio Tour in Gloucester and Rockport
Image for History and Hauntings of Salem Guided Walking Tour

History and Hauntings of Salem Guided Walking Tour

$33
Per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
See all activities in Gloucester

More trip options