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.
Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
per person
Feb. 13 - Feb. 17
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Boston (BOS)
8.6/10 Excellent! (1,003 reviews)
Interesting property that's full of art. Staff was friendly. One annoying thing; parking is no longer free. Expedia still has hotel under free parking. Wish hotel would be transparent and just disclose this fee on its website / listing.

Reviewed on Nov. 19, 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Dec. 25 - Dec. 30
found 7 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (64 reviews)
Excellent hotel. The only thing was that the AC in our room was so loud when turned on that it was unbearable. The hotel did help us move to another room that did not have the problem. We were only there for a night. We will definitely stay again as it is an excellent hotel otherwise.

Reviewed on Oct. 27, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Dec. 27 - Dec. 30
found 9 hours ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Super place, great service

Reviewed on Nov. 6, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Feb. 13 - Feb. 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (301 reviews)
Brilliant hotel and staff.

Reviewed on Nov. 5, 2024

Sea Mist Resort by VRI Americas

Sea Mist Resort by VRI Americas

3 out of 5
per person
Dec. 26 - Jan. 2
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
8.8/10 Excellent! (105 reviews)
We loved having two full bathrooms and kitchen

Reviewed on Nov. 18, 2024

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.
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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 $272 per night from Nov. 24 to Nov. 25
CA $272
CA $304 total
includes taxes & fees
Nov 24 - Nov 25
9.6/10 Exceptional! (788 reviews)
"Was a wonderful hotel. Everyone so nice & it is so attractive. We had a room on the ocean & it was gorgeous. Only minor complaint was the gym was too small. The food was EXCELLENT!!"

Reviewed on Nov. 19, 2024

Beauport Hotel Gloucester
The Hotel at Cape Ann Marina
The Hotel at Cape Ann Marina
3.5 out of 5
75 Essex Avenue, Gloucester, MA
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Dec. 9 to Dec. 10
CA $176
CA $197 total
includes taxes & fees
Dec 9 - Dec 10
8.2/10 Very Good! (661 reviews)
"I liked staying at a marina and I liked the little deck, pool, food, staff, parking. I think an updated remodel is in order. Thank you"

Reviewed on Nov. 13, 2024

The Hotel at Cape Ann Marina
Castle Manor Inn
Castle Manor Inn
2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is CA $223 per night from Nov. 24 to Nov. 25
CA $223
CA $250 total
includes taxes & fees
Nov 24 - Nov 25
8.2/10 Very Good! (946 reviews)
"Chef Dan and Kamden made our morning breakfast buffet experience even more enjoyable! Food was delicious and we loved how hospitable they were. John greeted us upon arrival and made some great recommendations about restaurants and touring Gloucester. We stayed in the Inn in room Sunnyside up on third ..."

Reviewed on Nov. 17, 2024

Castle Manor Inn
See all 1,636 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?
Our Gloucester packages, which begin at just CA $905, are an awesome way to save money. Select your favorite hotels, flights and rental car to create your dream itinerary.
How do I get a cheap travel package to Gloucester?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Hotels, rental cars, flights and activities — we’ve got them all covered. Pick and choose a combination that suits your style and see your savings stack up. Of course, a package deal is never one-size-fits-all. That’s why we offer more than 550 airlines and 1,000,000 properties globally, which lets you customize your Gloucester getaway.
Where should I stay in Gloucester?
Stay where the action is. Many travelers like to book hotels within easy reach of top attractions, such as Wingaersheek Beach, Good Harbor Beach and Hammond Castle.
What are the top hotels in Gloucester?
Castle Manor Inn in the Annisquam neighborhood is an excellent choice for a Gloucester escape. Stay here and you’ll be in a perfect position to explore all that this happening city has to offer.
How far in advance should I book my Gloucester vacation?
To land rock-bottom prices, book nice and early. Air carriers typically release tickets, along with some of the lowest fares, nearly 12 months in advance. Hotels, experiences and car rental should also be booked well in advance to avoid disappointment. If you’ve decided on a last-minute getaway to Gloucester, there are always plenty of great deals on Expedia. Book something in today!
What does an Expedia Gloucester travel package include?
With Expedia, you can choose a combination of car rentals, flights and hotels to build your ideal Gloucester travel package. Once you’ve made your booking, you can add on the fun stuff like tours and experiences. Don’t forget — the more you bundle, the bigger the savings!
What should I know before booking a Gloucester travel package?
Tailor deals that match your budget with an Expedia package. Hotels, flights, rental cars — we’ve got them all. You’ll save precious dollars just for bundling your bookings. Whether you’re heading away on a winter adventure or drinking cocktails on a beach, your ideal getaway is only a few clicks away.
Can I choose my airline with a Gloucester Expedia vacation package?
With a vacation package, you’re the one in charge. Whether you’re looking to fly to Gloucester in coach or first class, simply choose from the available airline options. Expedia has access to over 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Gloucester vacation package?
You can. We totally understand that life doesn’t always go to plan, so we’re happy to help if you need to make changes to your Gloucester vacation package. You may be able to cancel or change your itinerary at no cost if you’ve booked within 24 hours. Your airline, hotel or car rental company may impose a fee if you booked more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Gloucester

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
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

What to do in Gloucester

Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor Tour: Self-Guided Drive

CA $21
Per adult
100% of travellers recommend
Cape Ann Harbor Tour: Self-Guided Drive
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts Self-Guided Driving and Walking Tours Bundle

CA $70
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 adult
80% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
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.