Gloucester Vacation Packages

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Your Gloucester Vacation

Say farewell to the worries of planning and hello to a Gloucester vacation package. With your travel details organized before you leave, you can focus on discovering the best of this city, starting with Great Neck, which is great for walking, nature and views. Eager to explore your new surroundings? Cape Ann, Good Harbor Beach and Wingaersheek Beach are just a few of the leading places to visit during a trip to Gloucester. No matter your travel plans or the size of your budget, organizing a tailored Gloucester vacation is a cinch with Expedia.

Top Gloucester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Seaport District
Save 100% on your flight
per person
Jun. 9 - Jun. 12
found 13 hours ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9/10 Wonderful! (1,805 reviews)
Clean, convenient, cordial staff

Reviewed on Mar. 25, 2025

The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
Save 100% on your flight
per person
May 7 - May 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.2/10 Very Good! (1,002 reviews)
Property was lovely. Enjoyed how quiet it was. Beach close by shuttle service very convenient. Everyone was friendly. Room was clean. Would stay here again.

Reviewed on Mar. 16, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jun. 8 - Jun. 11
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Boston (BOS)
9.4/10 Exceptional! (332 reviews)
We had a wonderful stay at Mandarin Oriental Hotel. They upgraded us because the room we booked was not ready yet. The hotel is safe and connects to the Prudential mall for shopping and more dining options. The staff and service were exemplary. We will definitely stay again.

Reviewed on Feb. 26, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Jun. 9 - Jun. 12
found 13 hours ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
I felt very safe as a solo female traveler, anything you could ever want they can make available for you with a list of extra amenities that can be requested. Staff were kind and professional with good recommendations. I could easily walk to most things- The Harbor for my harbor cruise and north end for my tour I did out there. Overall very good stay, will stay again.

Reviewed on Mar. 18, 2025

Riverview Resort

Riverview Resort

3 out of 5
Bass River
Save 100% on your flight
per person
May 7 - May 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.2/10 Wonderful! (156 reviews)
I'll definitely be back!!!

Reviewed on Oct. 30, 2024

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 3 kilometres from downtown. However, you'll also discover plenty of Gloucester vacation packages close to Wingaersheek Beach and Niles Beach, two other superb nearby options.

Ready to book your vacation to Gloucester?

 

Choose your dates

Gloucester Hotel Deals

Beauport Hotel Gloucester
Beauport Hotel Gloucester
3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is CA $290 per night from Apr. 6 to Apr. 7
CA $290
CA $324 total
includes taxes & fees
Apr 6 - Apr 7
9.6/10 Exceptional! (832 reviews)
"The Beauport was a perfect late winter getaway. The hotel staff were kind and helpful; the seafood was amazing - all meals and drinks were top of the line - the room and common spaces were impeccable clean and beautiful. Bed comfortable and decor just beautiful - a yearly tradition in the off season ..."

Reviewed on Mar. 20, 2025

Beauport Hotel Gloucester
Beach Life Bliss - steps to the beach
Beach Life Bliss - steps to the beach
Gloucester
9.6/10 Exceptional! (26 reviews)
Short weekend stay
"Quick weekend trip to see our daughter in college. Beautiful little cottage and communication was great. Very clean and cozy"

Reviewed on Feb. 9, 2025

Get rates
Beach Life Bliss - steps to the beach
Harborview Inn
Harborview Inn
3.5 out of 5
71 Western Avenue, Gloucester, MA
The price is CA $270 per night from Apr. 6 to Apr. 7
CA $270
CA $301 total
includes taxes & fees
Apr 6 - Apr 7
9.4/10 Exceptional! (291 reviews)
Great stay
"This is a very special property. Quaint, right on the water, owned and operated by John Orlando and wife. He is a very interesting host, lifetime resident and interesting to get to know. I highly recommend a stay here. Room was just right."

Reviewed on Mar. 14, 2025

Harborview Inn
See all 1,681 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Gloucester vacation package cost?
Offering great value package deals from CA $1,014 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 many days is enough for Gloucester?
Typically, a few days is great for a Gloucester vacation. With a well-organized 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 vacation package to Gloucester?
Gloucester has everything you need for an amazing trip. Begin your Gloucester vacation 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 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

Good Harbor Beach

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

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

Hammond Castle

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

What to do in Gloucester

Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts Self-Guided Driving and Walking Tours Bundle

CA $72
per adult
Massachusetts Self-Guided Driving and Walking Tours Bundle
Ultimate Cape Ann Self-Guided Driving Audio Tour in Gloucester and Rockport

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

CA $24
per traveller
80% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

CA $22
per traveller
100% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
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.