A statue of a man with a wheel, surrounded by a stone base with an inscription, in a public square with houses and cars in the background.

Downtown Gloucester Vacations from $609

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The Latest Downtown Gloucester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • An indoor swimming pool with a wooden ceiling and tiled floor.
    Jan 22 - Jan 25

    Brewster Green Resort + Flight

    Brewster
    3 nights
    3.5 star property
    9.4/10 - Exceptional (153 reviews)
    Roundtrip • Los Angeles (LAX) - Boston (BOS)
    LAX - BOS • Nonstop BOS - LAX • Nonstop
    $813
    $609
    per traveler
    found 9 hours ago
    Brewster Green Resort
  • A rooftop dining area with a round table set for two, surrounded by plush seating and potted plants.
    Dec 8 - Dec 13

    The Newbury Boston + Flight

    Back Bay
    5 nights
    5.0 star property
    9.4/10 - Exceptional (747 reviews)
    "Beautiful hotel and the staff was wonderful. They gave us a corner room with a great view of the city. The room was spacious with a comfortable seating area."
    Reviewed November 7, 2026
    Roundtrip • Los Angeles (LAX) - Boston (BOS)
    LAX - BOS • Nonstop BOS - LAX • 1 stop
    $2,574
    $1,494
    per traveler
    found 1 day ago
    The Newbury Boston
  • A spacious hotel lobby with a dining area, seating, large windows, and a chandelier.
    Dec 11 - Dec 14

    Boston Harbor Hotel + Flight

    North End
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,006 reviews)
    Roundtrip • Dallas (DFW) - Boston (BOS)
    DFW - BOS • Nonstop BOS - DFW • 1 stop
    $1,652
    $979
    per traveler
    found 1 day ago
    Boston Harbor Hotel
  • A spacious, elegantly designed dining area with high ceilings, chandeliers, and classic decor.
    Jan 11 - Jan 14

    The Langham, Boston + Flight

    Downtown Boston
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,003 reviews)
    "Coffee machine in our room did not work and unfortunately our room located near the stair exit was not the most quiet. Other than that, was a very nice hotel with lovely staff."
    Reviewed November 7, 2026
    Roundtrip • Dallas (DAL) - Boston (BOS)
    DAL - BOS • Nonstop BOS - DAL • Nonstop
    $1,308
    $975
    per traveler
    found 22 hours ago
    The Langham, Boston
  • A room with a wooden floor, a white dresser, a bean bag, and a bench.
    Dec 23 - Dec 26

    The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat + Flight

    East Wareham
    3 nights
    3.0 star property
    10/10 - Exceptional (11 reviews)
    "We had a great experience staying in the crab house. The cottage was well maintained and had everything we needed to enjoy our stay. The staff was friendly, helpful, and genuinely care. Ken was fantastic, you can really tell he cares about ensuring guests have a great experience. 10/10 experience, would recommend this spot to anyone looking for a great stay on the cape."
    Reviewed July 27, 2026
    Roundtrip • San Juan (SJU) - Boston (BOS)
    SJU - PVD • Nonstop PVD - SJU • 2 stops
    $2,175
    $1,629
    per traveler
    found 1 day ago
    The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

Where to stay in Downtown Gloucester

Find the best Downtown Gloucester areas and neighborhoods for the activities you enjoy most.
A lighthouse, a white building with a red roof, and a stone walkway leading to the water.

East Gloucester

If you're spending some time in East Gloucester, Good Harbor Beach and Niles Beach are top sights worth seeing.

A lighthouse on a rocky shore with a wooden walkway leading to it.

Rocky Neck

While Rocky Neck might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Rocky Neck Art Colony and Maritime Gloucester.

A coastal landscape with a lighthouse, rocky shoreline, and a beach.

Annisquam

While Annisquam might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Wingaersheek Beach and Plum Cove Beach.

A garden with purple flowers and a foggy coastline.
Photo by Katia Bers
Open Photo by Katia Bers

Magnolia

Nestled in Gloucester, this small village boasts its own library, restaurants, and shops. Enjoy Gray Beach at Coolidge Reservation or take in scenic views of Kettle Cove at Surf Park.

Discover the most popular places to visit in Downtown Gloucester

A bustling harbor with a red building, a maritime heritage center sign, and a crowd of people.

Maritime Gloucester

9.4/10 (63 reviews)
Discover Gloucester’s maritime history at the historic working waterfront with an aquarium, a scenic pier and educational programs on marine sciences.
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What to do near Downtown Gloucester

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)

$50
per adult
0% of travelers recommend
Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)
See all activities near Downtown Gloucester

Downtown Gloucester Hotel Deals

Two individuals in white robes by a window overlooking a body of water with a distant shoreline.

Beauport Hotel Gloucester

Beauport Hotel Gloucester
3.5 star property
Downtown Gloucester
9.6 out of 10, Exceptional, (1,002 reviews)
$239 nightly
The price is $267
Dec 8 - Dec 9
Total with taxes and fees
Beauport Hotel 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.
See all properties in Downtown Gloucester
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.