Deals on vacations and trips to Gloucester

Save when you book Gloucester package deals

Choose two or more items and save on your trip:

Gloucester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Aug 8 - Aug 12
found 4 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Boston (BOS)
This luxury hotel features a casino, a full-service spa, and a nightclub. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Free self parking is free for guests, and you can enjoy a meal in one of the 15 restaurants.
The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 1 - Aug 8
found 7 hours ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Families will appreciate the onsite laundry facilities and in-room childcare. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Aug 1 - Aug 8
found 7 hours ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a garden, and a lobby fireplace are also offered.
The Dagny Boston

The Dagny Boston

4 out of 5
Downtown Boston
Save 100% on your flight
per person
Aug 1 - Aug 8
found 7 hours ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A coffee shop, a grocery/convenience store, and a library are also on offer.
The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
per person
Aug 1 - Aug 8
found 7 hours ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Boston (BOS)
A full-service spa, 3 restaurants, and a 24-hour gym are all featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Self parking, limo/town car service, and a snack bar/deli are also offered.

Top Gloucester hotels deals

The Hotel at Cape Ann Marina

The Hotel at Cape Ann Marina

3.5 out of 5
75 Essex Avenue, Gloucester, MA
Free Cancellation
Reserve now, pay when you stay
The price is $199 per night
$199
per night
Jun 23 - Jun 24
A marina and a restaurant are featured at this hotel. Relax with a drink at the bar/lounge and enjoy free perks like continental breakfast and free self parking. Free WiFi in public areas, a picnic area, and laundry facilities are also on offer.
Breakfast included
Parking included
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is $395 per night
$395
per night
Jun 24 - Jun 25
This hotel features a restaurant, a gym, and a bar/lounge. Take the free beach shuttle and relax with beach umbrellas. Enjoy the a rooftop terrace and perks like free WiFi and a free beach shuttle.
Pool
Free WiFi
Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is $189 per night
$189
per night
Jun 23 - Jun 24
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.
Parking included
Free WiFi
The Vista

The Vista

2.5 out of 5
22 Thatcher Rd., Gloucester, MA
The price is $293 per night
$293
per night
Jun 24 - Jun 25
An outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.
Pool
Breakfast included
Lakeside Inn

Lakeside Inn

2 out of 5
595 North Ave, Wakefield, MA
Free Cancellation
Reserve now, pay when you stay
The price is $93 per night
$93
per night
Jun 30 - Jul 1
This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Free self parking, a terrace, and express check-out are also offered.
Parking included
Free WiFi
Ashworth by the Sea

Ashworth by the Sea

3 out of 5
295 Ocean Blvd, Hampton, NH
Free Cancellation
Reserve now, pay when you stay
The price is $236 per night
$236
per night
Jun 27 - Jun 28
This smoke-free hotel includes 3 restaurants, an indoor pool, and a gym. You'll appreciate the a rooftop terrace, bar/lounge, and snack bar/deli.
Pool
Pet friendly
Don't see what you're looking for?
See all available properties in Gloucester
View all properties
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.

Popular places to visit

Image for 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
Image for Good Harbor Beach

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
Image for Hammond Castle

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

Photos of local treasures

Browse Gloucester vacation photos for more inspiration

Half Moon Beach which includes a beach, general coastal views and a sunset

Frequently asked questions

How much are vacation packages to Gloucester?
Enjoy a fulfilling travel experience in Gloucester with a vacation package starting at $1,005. Booking flights, tours and hotels through Travelocity is so simple. And even better, our packages will leave you with more money in your pocket for fun times.
How long should my Gloucester vacation be?
Generally, 2 nights is how long most visitors spend checking out the attractions of Gloucester. Worried that won’t be enough time to fit in everything on your travel itinerary? Stay an extra night or two so you don’t miss a thing.
Where can I get the best vacation package deals for Gloucester?
No matter your adventure, Travelocity can help you lock in an unbeatable Gloucester package deal. All you need to do is select a combination from our 400 partner airlines and 1,000,000 worldwide properties.
Why should I purchase my Gloucester vacation bundle with Travelocity?
Because life is all about the journey, and we have all you need to get you on your way. With our superb service and Price Match Guarantee, you can organize your trip with confidence. Plus, you can sleep easy while you’re away knowing you can reach us with our round-the-clock support.
Will I save money on my Gloucester car rental if I combine it with hotels and flights?
Absolutely — combine your hotel, flight and car into a Gloucester vacation package and you’ll save plenty. With so many things to do in and around Gloucester, having your own wheels will make it easy to explore. Once you’re behind the wheel, turn up the stereo and cruise toward Plymouth Rock, a famous attraction about 45 mi from Gloucester.
What is the best time of year to go to Gloucester?
If a limited budget is what’s driving your travel plans, you’ll score the best deals in . is often the costliest time of year. Most tourists head to this location around June, July and August. If you prefer to avoid the busiest time, it’s likely to be quieter in November, December and January.
Which airport is best for Gloucester?
For many, heading to Gloucester means passing through Logan Intl. Airport (BOS). This busy airport is located 25 mi southwest of the city center. You could also fly into Manchester-Boston Regional Airport (MHT) (45 mi away from central Gloucester) or Provincetown Municipal Airport (PVC) (45 mi away from central Gloucester).
What is there to do in Gloucester?
Gloucester is full of sights to check out, such as Wingaersheek Beach and Good Harbor Beach. These two impressive attractions top most tourists’ must-see lists.
Where should I stay when visiting Gloucester?
The Castle Manor Inn is the top choice of many visitors. Book as soon as possible before it’s too late.