Downtown Gloucester Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
- Hotel Ivy Boston Common
Aug 6 - Aug 10Hotel Ivy Boston Common + Flight
Bay Village4 nights8.4/10 - Very Good (1,450 reviews)"Dirty, noisy, exorbitantly overpriced."Reviewed May 17, 2026Roundtrip • Osaka (KIX) - Boston (BOS)KIX - BOS • 1 stop BOS - KIX • 1 stop￥454,573￥349,275found 1 day agoper traveler - Boston Harbor Hotel
Aug 6 - Aug 10Boston Harbor Hotel + Flight
North End4 nights9.8/10 - Exceptional (1,001 reviews)"clean and great staff "Reviewed May 8, 2026Roundtrip • Osaka (KIX) - Boston (BOS)KIX - BOS • 1 stop BOS - KIX • 1 stop￥625,888￥413,362found 1 day agoper traveler - Mandarin Oriental, Boston
Aug 6 - Aug 10Mandarin Oriental, Boston + Flight
Back Bay4 nights9.4/10 - Exceptional (422 reviews)"This is not a blow, your socks off property by any means! Dated and just ok. You’ll get the same thing for far less expense at a Sheraton, Hilton or Hyatt. Staff waa nice. There was nothing bad but certainly nothing spectacular or memorable to rave about."Reviewed April 29, 2026Roundtrip • Osaka (KIX) - Boston (BOS)KIX - BOS • 1 stop BOS - KIX • 1 stop￥667,768￥505,560found 1 day agoper traveler - The Langham, Boston
Aug 6 - Aug 10The Langham, Boston + Flight
Downtown Boston4 nights9.8/10 - Exceptional (1,003 reviews)"Right in heart of town"Reviewed May 12, 2026Roundtrip • Osaka (KIX) - Boston (BOS)KIX - BOS • 1 stop BOS - KIX • 1 stop￥537,449￥421,805found 1 day agoper traveler - Meco Hotel - Hostel
Aug 6 - Aug 10Meco Hotel - Hostel + Flight
West End4 nights8.6/10 - Excellent (422 reviews)"Great access very cheep. Was not expecting that much for a reasonable price, but was surprised when they had a 24h autolock, well furnished and clean bunkers, and most importantly, well mannerred room mates. Also had a small snack stand, free coffee in the morning which made me very happy. would love to stay here again! "Reviewed May 18, 2026Roundtrip • Osaka (KIX) - Boston (BOS)KIX - BOS • 1 stop BOS - KIX • 1 stop￥480,142￥380,990found 1 day agoper traveler
Where to stay in Downtown Gloucester
Find the best Downtown Gloucester areas and neighborhoods for the activities you enjoy most. Learn more about Downtown 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.
Downtown Gloucester Hotel Deals
Beauport Hotel Gloucester
55 Commercial Street Gloucester MA
The price is ￥43,963 per night from May 26 to May 27
￥43,963
￥49,107 total
May 26 - May 27
includes taxes & fees
9.6/10 Exceptional! (964 reviews)
"Room was nice. Staff was rude"
Reviewed on May 18, 2026
The Highliner Hotel
108 Main St Gloucester MA
The price is ￥42,503 per night from May 25 to May 26
￥42,503
￥72,300 total
May 25 - May 26
includes taxes & fees
10/10 Exceptional! (4 reviews)
"Wonderful room, cool decor and such a neat building. The bed was super comfortable and the space to hang out in the room was relaxing. Location is perfect for browsing the shops and eating out. Using text to communicate with the concierge was also very convenient and easy."
Reviewed on Apr 22, 2026
Harborview Inn
71 Western Avenue Gloucester MA
The price is ￥39,526 per night from May 20 to May 21
￥39,526
￥44,150 total
May 20 - May 21
includes taxes & fees
9.6/10 Exceptional! (322 reviews)
"Wonderful location and sparkling property. John Orlando, the owner, was welcoming and attentive. The room was comfortable with great lighting and the Continental breakfast was good. The only thing missing was a full length mirror: maybe one could be mounted on the bathroom door? All in all however, ..."
Reviewed on Apr 29, 2026
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.
Discover the most popular places to visit in Downtown Gloucester
Fishermen's Memorial Monument
Learn about the local history of Gloucester with a stop at Fishermen's Memorial Monument. Wander the beautiful beaches and seaside in this family-friendly area.
Things to do
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
￥2,666
per traveler
80% of travellers recommend
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
￥7,843
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
￥7,059
per traveler
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.