Downtown Gloucester Vacations

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Price found within the past 48 hours. Click for updated prices.
  • Aug 6 - Aug 10

    Hotel Ivy Boston Common + Flight

    Bay Village
    4 nights
    2.5 star property
    8.4/10 - Very Good (1,450 reviews)
    "Dirty, noisy, exorbitantly overpriced."
    Reviewed May 17, 2026
    Roundtrip Osaka (KIX) - Boston (BOS)
    KIX - BOS1 stop BOS - KIX1 stop
    ¥454,573
    ¥349,275
    per traveler
    found 1 day ago
    Hotel Ivy Boston Common
  • Aug 6 - Aug 10

    Boston Harbor Hotel + Flight

    North End
    4 nights
    5.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    "clean and great staff "
    Reviewed May 8, 2026
    Roundtrip Osaka (KIX) - Boston (BOS)
    KIX - BOS1 stop BOS - KIX1 stop
    ¥625,888
    ¥413,362
    per traveler
    found 1 day ago
    Boston Harbor Hotel
  • Aug 6 - Aug 10

    Mandarin Oriental, Boston + Flight

    Back Bay
    4 nights
    5.0 star property
    9.4/10 - 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, 2026
    Roundtrip Osaka (KIX) - Boston (BOS)
    KIX - BOS1 stop BOS - KIX1 stop
    ¥667,768
    ¥505,560
    per traveler
    found 1 day ago
    Mandarin Oriental, Boston
  • Aug 6 - Aug 10

    The Langham, Boston + Flight

    Downtown Boston
    4 nights
    5.0 star property
    9.8/10 - Exceptional (1,003 reviews)
    "Right in heart of town"
    Reviewed May 12, 2026
    Roundtrip Osaka (KIX) - Boston (BOS)
    KIX - BOS1 stop BOS - KIX1 stop
    ¥537,449
    ¥421,805
    per traveler
    found 1 day ago
    The Langham, Boston
  • Aug 6 - Aug 10

    Meco Hotel - Hostel + Flight

    West End
    4 nights
    2.0 star property
    8.6/10 - 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, 2026
    Roundtrip Osaka (KIX) - Boston (BOS)
    KIX - BOS1 stop BOS - KIX1 stop
    ¥480,142
    ¥380,990
    per traveler
    found 1 day ago
    Meco Hotel - Hostel

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

Downtown Gloucester Hotel Deals

Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
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

Beauport Hotel Gloucester
The Highliner Hotel

The Highliner Hotel

2 out of 5
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

The Highliner Hotel
Harborview Inn

Harborview Inn

3.5 out of 5
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

Harborview Inn
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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.