Gloucester Holidays
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Top Flight + Hotel Deals in Gloucester
Price found within the past 48 hours. Click for updated prices.
The Lenox Hotel Boston
Back Bay
Price was €881, price is now €546 per person
€546
per person
25 Feb - 2 Mar
found 1 hour ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (1,218 reviews)
Very nice clean room. I was happy to see the personnel’s attentiveness. The facilities, including the Irving are first rate.
Reviewed on 24 Dec 2025
Boston Harbor Hotel
North End
Price was €2,051, price is now €1,045 per person
€1,045
per person
25 Feb - 2 Mar
found 1 hour ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Everything was wonderful including a delicious breakfast. We will definitely return.
Reviewed on 17 Dec 2025
The Newbury Boston
Back Bay
Price was €1,463, price is now €999 per person
€999
per person
25 Feb - 2 Mar
found 1 hour ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (536 reviews)
Very friendly staff. Amazing location. The room was perfect. Didn’t go to Contessa, but we ran into the Chef in the elevator and he was super fun and courteous. The bar is cool, we ate there a couple nights. We had a very pleasant Thanksgiving week there. Festive and lively hotel. There’s Tatte around the corner and every store you can think of within walking distance. Looking forward to our next stay!
Reviewed on 4 Dec 2025
Where to stay in Gloucester
Find the best Gloucester areas and neighborhoods for the activities you enjoy most. Learn more about Gloucester
East Gloucester
3 out of top 10 points of interest in this area
If you're spending some time in East Gloucester, Good Harbor Beach and Niles Beach are top sights worth seeing.
Gloucester Beach Holiday
The smell of fresh sea air and fabulous ocean views are just the start of things to look forward to during your Gloucester holiday. If you're eager to save on your trip to Gloucester, we'll let you in on a secret — choose one of our Gloucester packages. Grab one close to Pavilion Beach, only 0.32 kilometres from the city centre and a must-do while here. Alternatively, select a package that puts you closer to Cressy Beach, another gorgeous coastline. Whichever you choose, you'll be left with extra dollars in your travel budget to have fun with.
Things You Should Know About Gloucester
- Drift off to sleep to the gentle sounds of the sea in one of our Gloucester beach hotels. Nothing beats staying with walking distance of the ocean.
- Private holiday homes are another top choice for people planning a holiday in Gloucester. Some great examples are Castle Manor Inn and The Hotel at Cape Ann Marina.
- Roughly 29,800 people reside in Gloucester. If you want some tips about things to see and do here, why not start a conversation with some of the friendly locals? Our Gloucester things to do page is also a handy source of information.
- Don't head home without exploring Cape Ann, Capt Bill & Sons Whale Watch and Dogtown. With the cash you save through our Gloucester holiday deals, you can see more impressive attractions like these.
Top hotels in Gloucester
Beauport Hotel Gloucester
55 Commercial Street Gloucester MA
9.6/10 Exceptional! (908 reviews)
Clean and spacious rooms. Staff was awesome
Reviewed on 17 Dec 2025
Castle Manor Inn
141 Essex Avenue Gloucester MA
8.2/10 Very Good! (1,000 reviews)
Beautiful rooms at affordable rates! Highly recommended.
Reviewed on 29 Nov 2025
Ocean House Hotel at Bass Rocks
107 Atlantic Rd Gloucester MA
9/10 Wonderful! (803 reviews)
Wonderful view and rooms.
Reviewed on 14 Dec 2025
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
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.
Good Harbor Beach
Why not spend a care-free afternoon at Good Harbor Beach during your travels in Gloucester? Wander the waterfront or discover the area's sunrises.
Maritime Gloucester
You can spend an afternoon studying the exhibits at Maritime Gloucester during your trip to Gloucester. Wander through the beautiful beaches and seaside in this family-friendly area.
What to do in Gloucester
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
€14
per traveller
80% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
€13
per traveller
100% of travellers recommend
Salem 101 General History Tour (Massachusetts)
€22
per adult
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- Square One Mall
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- Todd Farm Flea Market
- Visit Topsfield
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- Wingaersheek Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
