Gloucester Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Gloucester

Castle Manor Inn
Castle Manor Inn
2.5 out of 5
141 Essex Avenue, Gloucester, MA
8.2/10 Very Good! (978 reviews)
"The staff was super helpful and accommodating with the changes I needed to make the morning of my stay. The rooms were very clean and the property is beautiful. I left my rings there and the staff immediately notified me, which is amazing."

Reviewed on 23 Jun 2025

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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 8.899.439 ₫ per night from 14 Jul to 15 Jul
8.899.439 ₫
10.550.731 ₫ total
14 Jul - 15 Jul
includes taxes & fees
9/10 Wonderful! (707 reviews)
"Wonderful hotel. Cool, clean, well appointed views, breathtaking views from every room. Delightful staff."

Reviewed on 24 Jun 2025

Ocean House Hotel at Bass Rocks
Atlantis Oceanfront Inn
Atlantis Oceanfront Inn
3 out of 5
125 Atlantic Road, Gloucester, MA
Fully refundableReserve now, pay when you stay
The price is 8.193.830 ₫ per night from 30 Jun to 1 Jul
8.193.830 ₫
9.152.560 ₫ total
30 Jun - 1 Jul
includes taxes & fees
9.4/10 Exceptional! (420 reviews)
"Wonderful staff… Unbeatable views of the Rocky coast and Atlantic Ocean… Perfect location easy to get anywhere on the Cape. The breakfast are beyond amazing one of best breakfast spots in North America."

Reviewed on 21 Jun 2025

Atlantis Oceanfront Inn
See all 1,769 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 holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday 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 holiday 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 holiday. With a well-organised 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 holiday package to Gloucester?
Gloucester has everything you need for an amazing trip. Begin your Gloucester holiday 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 holiday package as soon as possible.
Is it cheaper to book a Gloucester holiday as a package?
Expedia holiday 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 holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday 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 favourite 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 accommodation: Once you've nailed down your travel dates and duration, lock in the right Gloucester holiday package for you.

Popular places to visit

Wingaersheek Beach

Wingaersheek Beach

Why not spend a care-free 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 holiday is part of your travel plans, Good Harbor Beach might be the perfect place to visit during your trip to Gloucester. While you're in the area, stroll along the seaside.

Good Harbor Beach
Hammond Castle

Hammond Castle

You can browse the exhibits at Hammond Castle, a museum with a story of its own, during your holiday in Gloucester. Wander the beautiful beaches and seaside in the area.

Hammond Castle