Title: Gloucester Vacation Packages 2026 from $343 | Expedia.com [Gloucester Travel Guide](https://expedia.com/Gloucester.dx8008)[Hotels in Gloucester](https://expedia.com/Gloucester-Hotels.d8008.Travel-Guide-Hotels)[Vacation Rentals in Gloucester](https://expedia.com/Gloucester-Vacation-Rentals.d8008.Travel-Guide-VacationRentals)[Flights to Gloucester](https://expedia.com/Cheap-Flights-To-Gloucester.d8008.Travel-Guide-Flights)[Things to do in Gloucester](https://expedia.com/Things-To-Do-In-Gloucester.d8008.Travel-Guide-Activities)[Car Rentals in Gloucester](https://expedia.com/Car-Rentals-In-Gloucester.d8008.Car-Rental-Guide) ![](https://images.trvl-media.com/place/553248621532667409/fda0f2a2-9a66-4e87-a0d4-6552f49b1eaf.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Gloucester Vacations from $343 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Your Gloucester Vacation Say farewell to the worries of planning and hello to a Gloucester vacation package. With your travel details organized before you leave, you can focus on discovering the best of this city, starting with Great Neck, which is great for walking, nature and views. Eager to explore your new surroundings? [Cape Ann](https://www.expedia.com/Cape-Ann-Rockport.d3000463815.Vacation-Attraction), [Good Harbor Beach](https://www.expedia.com/Good-Harbor-Beach-Gloucester.d553248621532667409.Vacation-Attraction) and [Wingaersheek Beach](https://www.expedia.com/Wingaersheek-Beach-Gloucester.d553248621532667334.Vacation-Attraction) are just a few of the leading places to visit during a trip to Gloucester. No matter your travel plans or the size of your budget, organizing a tailored Gloucester vacation is a cinch with Expedia. ## The Latest Gloucester vacation packages Price found within the past 48 hours. Click for updated prices. ![The Wylie Inn and Conference Center at Endicott College](https://images.trvl-media.com/lodging/2000000/1890000/1886900/1886884/e13dffe5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wylie Inn and Conference Center at Endicott College Save 100% on your flight $343 per person Apr 3 - Apr 7 found 1 day ago Roundtrip flight included Chicago (CHI) to Boston (BOS) 9.2/10 Wonderful! (1,160 reviews) Courteous staff, great work out room, nice rooms! Reviewed on Mar 1, 2026 ![AutoCamp Cape Cod](https://images.trvl-media.com/lodging/50000000/49180000/49175900/49175859/da4b66b1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### AutoCamp Cape Cod Save 100% on your flight $577 per person May 19 - May 24 found 20 hours ago Roundtrip flight included Chicago (ORD) to Boston (BOS) 9.4/10 Exceptional! (305 reviews) We had a wonderful stay here on Valentine’s Day weekend. It was the first time we stayed at a camp ground and definitely the first time staying in an AirStream. The clubhouse was sooo nice! Staff were great. Good menu options and merch as well. Picked up an AutoCamp beanie! Live music was awesome. My only complaint is we had no hot water! That was tough being that we are in the middle of the winter and it was already freezing outside. Hot showers would have been nice! Other than that we’re planning for a summer weekend here Reviewed on Feb 17, 2026 ![The Inn at Hastings Park, Relais & Chateaux - Boston](https://images.trvl-media.com/lodging/8000000/7990000/7980700/7980601/8dcd0e80_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn at Hastings Park, Relais & Chateaux - Boston Save 100% on your flight $871 per person Apr 3 - Apr 7 found 24 hours ago Roundtrip flight included Chicago (CHI) to Boston (BOS) 9.6/10 Exceptional! (247 reviews) Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room. Reviewed on Oct 21, 2025 ![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boston Harbor Hotel North End Save 100% on your flight $726 per person Apr 3 - Apr 5 found 1 day ago Roundtrip flight included Chicago (CHI) to Boston (BOS) 9.8/10 Exceptional! (1,005 reviews) Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem. Reviewed on Jan 25, 2026 ![Furnished Apartment near BMC](https://images.trvl-media.com/lodging/125000000/124400000/124390600/124390547/c5a347c8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Furnished Apartment near BMC South End $1,272 per person May 16 - May 23 found 3 hours ago Roundtrip flight included Miami (MIA) to Boston (BOS) No reviews Don't see what you're looking for? See all available trips from Columbus to Gloucester [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-03/2026-04-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_8008) ## Where to stay in Gloucester Find the best Gloucester areas and neighborhoods for the activities you enjoy most. [Learn more about Gloucester](https://expedia.com/Gloucester.dx8008) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### 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. [Find hotel + flight trips in East Gloucester](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=East%20Gloucester&DestID=988950575026716672&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Gloucester 2 out of top 10 points of interest in this area While visiting Downtown Gloucester, you might make a stop by sights like Cape Ann Museum and Capt Bill & Sons Whale Watch. [Find hotel + flight trips in Downtown Gloucester](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Gloucester&DestID=988950093891813376&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Annisquam Light, Gloucester, Massachusetts, USA; Shutterstock ID 161751743](https://images.trvl-media.com/place/553248635975257320/e8be7e48-f2a6-42d0-b81c-dd477a50772c.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### 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. [Find hotel + flight trips in Annisquam](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Annisquam&DestID=553248635975257320&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Rocky Neck 1 out of top 10 points of interest in this area If you're spending some time in Rocky Neck, Rocky Neck Art Colony and Bryan Gallery are top sights worth seeing. [Find hotel + flight trips in Rocky Neck](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Rocky%20Neck&DestID=988950237638844416&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Beautiful place to walk and enjoy the views. This foggy noon created the atmosphere of an unreal world.](https://images.trvl-media.com/place/8008/5147534c-4020-4b19-8522-3f89d8edc342.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### 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. [Find hotel + flight trips in Magnolia](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Magnolia&DestID=6340902&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ### Discover the most popular places to visit in Gloucester ![Wingaersheek Beach featuring rugged coastline](https://images.trvl-media.com/place/553248621532667334/f266a0de-f3f4-41b3-a53e-7e5aa912d50e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wingaersheek Beach Offering fun in the sun, this coastal playground has calm water and everything you need for a day by the sea. [](https://expedia.com/Wingaersheek-Beach-Gloucester.d553248621532667334.Vacation-Attraction) ![Good Harbor Beach which includes a sunset and a coastal town](https://images.trvl-media.com/place/553248621532667409/f7438f55-8c31-4a48-8a51-cf3f9e28dca7.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Good Harbor Beach 4.5/5(18 reviews) With a reputation as Gloucester’s prettiest beach, this curve of white sand lapped by rolling waves sets the scene for soaking up the sun. [](https://expedia.com/Good-Harbor-Beach-East-Gloucester.d553248621532667409.Vacation-Attraction) ![Hammond Castle which includes heritage elements, general coastal views and a sunset](https://images.trvl-media.com/place/6092287/dd2dc56d-f84b-4508-8a14-a47ce5b37e9c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Hammond Castle 4.5/5(8 reviews) A medieval-style castle overlooking the blue ocean waters in Gloucester features a spellbinding collection of art, artifacts and quirky inventions. [](https://expedia.com/Hammond-Castle-Gloucester.d6092287.Vacation-Attraction) ### What to do in Gloucester ![Real Pirates Salem Museum General Admission Ticket](https://mediaim.expedia.com/localexpert/5005330/6a81d910-26d6-4767-8020-d7b7342bb88f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Real Pirates Salem Museum General Admission Ticket $22 per adult **84%** of travellers recommend [](https://expedia.com/things-to-do/real-pirates-salem-museum-general-admission-ticket.a5005330.activity-details) ![Freedom Trail and Salem and The Witch Trail Self-Guided Walking Tour Bundle](https://mediaim.expedia.com/localexpert/46291372/aae6fdbd-f871-42a2-ae4a-c7ae6352419c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Freedom Trail & Salem Witch: Self-Guided Walking Tour Bundle $25 per traveler **100%** of travellers recommend [](https://expedia.com/things-to-do/freedom-trail-salem-witch-self-guided-walking-tour-bundle.a46291372.activity-details) ![Salem: Fantasy Studio Photography Experience](https://mediaim.expedia.com/localexpert/48696822/5a584805-fa33-4805-890e-59788cfb0b1d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Salem: Witch Costume Photo Studio Experience $149 per adult [](https://expedia.com/things-to-do/salem-witch-costume-photo-studio-experience.a48696822.activity-details) [See all activities in Gloucester](https://expedia.com/things-to-do/search?rid=8008) ## Gloucester Hotel Deals ![Beauport Hotel Gloucester](https://images.trvl-media.com/lodging/16000000/15380000/15379900/15379825/70af0ced_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Beauport Hotel Gloucester 55 Commercial Street Gloucester MA $199 nightly $223 total Mar 10 - Mar 11 Total with taxes and fees 9.6/10 Exceptional! (933 reviews) Room was great, beds comfy. Great bloody mary in the bar and awesome sunrise. Reviewed on Feb 15, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F10%2F2026&endDate=3%2F11%2F2026&selected=15379825&PinnedHotelID=15379825&HadPinnedHotel=true®ionId=8008) ![Castle Manor Inn](https://images.trvl-media.com/lodging/12000000/11680000/11678300/11678212/08fc8a74_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Castle Manor Inn 141 Essex Avenue Gloucester MA 8.4/10 Very Good! (1,000 reviews) The room was clean, but the outside of the building our room was in, behind the inn, was run down and the back of the inn was in disrepair. Not a very pleasant experience. Reviewed on Jan 19, 2026 [Get rates](https://expedia.com/Hotel-Search?startDate=3%2F17%2F2026&endDate=3%2F18%2F2026&selected=11678212&PinnedHotelID=11678212&HadPinnedHotel=true®ionId=8008) [](https://expedia.com/Hotel-Search?startDate=3%2F17%2F2026&endDate=3%2F18%2F2026&selected=11678212&PinnedHotelID=11678212&HadPinnedHotel=true®ionId=8008) ![DoubleTree by Hilton Boston North Shore](https://images.trvl-media.com/lodging/1000000/20000/15400/15355/3d84ffb8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Boston North Shore 50 Ferncroft Rd Danvers MA Fully refundableReserve now, pay when you stay $116 nightly $129 total Mar 29 - Mar 30 Total with taxes and fees 8.2/10 Very Good! (2,415 reviews) Everyone had a good time Reviewed on Mar 1, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=15355&PinnedHotelID=15355&HadPinnedHotel=true®ionId=8008) [See all 1,766 properties in Gloucester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F4%2F2026&endDate=3%2F5%2F2026®ionId=8008) 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. ## Find the Best Gloucester Vacation Packages ### Things to do in and around Gloucester Gloucester, Massachusetts, is a fantastic destination for beach lovers and outdoor enthusiasts alike. Visitors can enjoy a variety of activities including music concerts, exploring local arts centers, and engaging in educational experiences. Outdoor activities such as bird watching and audio tours provide opportunities to discover the scenic beauty of Gloucester and its rich history. Whether you're relaxing on the beach or exploring the vibrant local culture, Gloucester has something for everyone. **Shopping** In Gloucester, visit local shops and boutiques for unique gifts. For a broader selection, if you're up for a drive, check out [Todd Farm Flea Market](https://www.expedia.com/Todd-Farm-Flea-Market-Rowley.d553248635975698117.Vacation-Attraction) and [Bewitched in Salem](https://www.expedia.com/Bewitched-In-Salem-Downtown-Salem.d553248621532667448.Vacation-Attraction), both 13 miles away, or head to [MarketStreet Lynnfield](https://www.expedia.com/MarketStreet-Lynnfield-Boston.d553248635975698163.Vacation-Attraction), 20 miles away, for entertainment and family-friendly shopping. **Recreation** Experience the [Shalin Liu Performance Center](https://www.expedia.com/Shalin-Liu-Performance-Center-Rockport.d553248621532667415.Vacation-Attraction) for captivating music concerts that uplift your spirit. At [North Shore Music Theatre](https://www.expedia.com/North-Shore-Music-Theatre-Boston.d553248621532667302.Vacation-Attraction), immerse yourself in cultural performances perfect for a romantic night out. For tranquility, stroll along the [Waterfront Promenade Park](https://www.expedia.com/Waterfront-Promenade-Park-Newburyport.d6274378.Vacation-Attraction), where you can unwind and enjoy nature's beauty. **Adventure** Experience the thrill of whale watching with [Capt Bill & Sons Whale Watch](https://www.expedia.com/Capt-Bill-Sons-Whale-Watch-Gloucester.d553248621533117279.Vacation-Attraction) in Gloucester, where you can encounter majestic marine life. Hike the scenic trails of [Dogtown](https://www.expedia.com/Dogtown-Gloucester.d6092281.Vacation-Attraction) for breathtaking views and natural beauty. For family fun, visit the [Water Park of New England](https://www.expedia.com/Water-Park-Of-New-England-Boston.d553248621532667299.Vacation-Attraction), located 16 miles from Gloucester. **Nightlife** Gloucester's nightlife offers a unique charm, highlighted by the Park-9 Dog Bar, a vibrant drinking pub 25 miles away. Enjoy a lively atmosphere filled with entertainment and romance vibes, perfect for unwinding after a day of exploration. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Find the best attractions in and around Gloucester Gloucester, Massachusetts, is a perfect destination for beach lovers and outdoor enthusiasts, offering stunning coastal scenery and a rich cultural experience. Explore beautiful beaches, historic homes, and interesting museums that cater to diverse interests. Whether you're looking for a relaxing beach vacation or eager to discover the local culture, Gloucester has something for everyone to enjoy. - **[Wingaersheek Beach: ](https://www.expedia.com/Wingaersheek-Beach-Gloucester.d553248621532667334.Vacation-Attraction)** Enjoy the serene beauty of Wingaersheek Beach, where soft sands meet gentle waves. This picturesque beach is perfect for sunbathing, swimming, and beachcombing, offering a relaxing atmosphere for visitors of all ages. - **[Cape Ann: ](https://www.expedia.com/Cape-Ann-Rockport.d3000463815.Vacation-Attraction)** Just 4 miles from Gloucester, Cape Ann boasts stunning coastal scenery with breathtaking views. Explore its charming beaches and rugged cliffs, making it an ideal spot for hiking, photography, and enjoying the great outdoors. - **[Hammond Castle: ](https://www.expedia.com/Hammond-Castle-Gloucester.d6092287.Vacation-Attraction)** Nestled in Gloucester, Hammond Castle offers a romantic glimpse into the past with its medieval architecture and rich cultural history. Wander through the beautiful gardens and explore the fascinating exhibits that celebrate art and innovation. ### Best time to go to Gloucester The best time to visit Gloucester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 31.1°F (-0.5°C) | Light Rain | Mostly Sunny | Moderately Low | Slightly Low | | February | 31.8°F (-0.1°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | March | 36.7°F (2.6°C) | Light Rain | Mostly Sunny | Average | Average | | April | 45.1°F (7.3°C) | Light Rain | Mostly Sunny | Average | Average | | May | 54.3°F (12.4°C) | Light Rain | Mostly Sunny | Average | Slightly High | | June | 62.4°F (16.9°C) | Light Rain | Mostly Sunny | Moderately High | Average | | July | 69.6°F (20.9°C) | Light Rain | Mostly Sunny | Moderately High | Average | | August | 69.4°F (20.8°C) | Light Rain | Mostly Sunny | Moderately High | Average | | September | 64.0°F (17.8°C) | Light Rain | Mostly Sunny | Average | Slightly High | | October | 55.2°F (12.9°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 45.1°F (7.3°C) | Light Rain | Mostly Sunny | Moderately Low | Average | | December | 37.4°F (3.0°C) | Light Rain | Mostly Sunny | Moderately Low | Slightly Low | ### Tips to save on your trip to Gloucester - Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Gloucester. - Consider traveling to Gloucester during the low season (December to February) for more affordable options. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ## Gloucester Beach Vacation The smell of fresh sea air and fabulous ocean views are just the start of things to look forward to during your Gloucester vacation. 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 0.2 miles from the city center 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](https://www.expedia.com/d8008-tBeachHotel.Travel-Guide-Filter-Hotels?lang=en&rfrr=ATG.LP.BodyContent). Nothing beats staying with walking distance of the ocean. - Private vacation homes are another top choice for people planning a vacation in Gloucester. Some great examples are [Castle Manor Inn](https://www.expedia.com/Gloucester-Hotels-Castle-Manor-Inn.h11678212.Hotel-Information) and [The Hotel at Cape Ann Marina](https://www.expedia.com/Gloucester-Hotels-Cape-Anns-Marina-Resort.h13279212.Hotel-Information). - 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](null) 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 vacation deals, you can see more impressive attractions like these. ## Gloucester Essential Information | Language | English | | --------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Logan Intl. Airport (BOS) | | Population | 29,800 | | Max Temp Winter | 35ºF | | Max Temp Summer | 70ºF | | Top Sights | [Wingaersheek Beach](https://www.expedia.com/Wingaersheek-Beach-Gloucester.d553248621532667334.Vacation-Attraction), [Good Harbor Beach](https://www.expedia.com/Good-Harbor-Beach-Gloucester.d553248621532667409.Vacation-Attraction) and [Hammond Castle](https://www.expedia.com/Hammond-Castle-Gloucester.d6092287.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Gloucester vacation package cost? ### What are the cheapest months to go to Gloucester? ### How many days is enough for Gloucester? ### Is it worth booking a vacation package to Gloucester? ### How to find the best Gloucester package deals? ### Is it cheaper to book a Gloucester vacation as a package? ### When to book a vacation package to Gloucester? ### How to plan a trip to Gloucester? > 1. Choose when to get away: Check your diary and pack your bags. Your favorite time of year and the type of activities on offer will also help you decide when to visit Gloucester. > 2. Work out your budget: Ensure you have enough money to cover everything from transportation and meals to flights and activities. Your hotel will probably be the biggest expense during your trip to Gloucester. > 3. Use Expedia's [trip planning tool](https://www.expedia.com/why/trip-planning) to explore Gloucester: Research every aspect of your trip to Gloucester with this handy planner. Invite your friends and family to collaborate on a group trip, search for hotels or things to do and make bookings. > 4. Set the duration of your trip: Start by compiling a list of the sights and activities you'd like to get to in Gloucester. Then, estimate how long you'll need for each, including any travel time. > 5. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Gloucester vacation package that brings all your bookings together. > 6. Book activities and experiences in advance: Whether it's a ticket to a big attraction or a walking tour, you won't have to worry about missing out on Gloucester's best offerings. Find all the incredible [things to do in Gloucester](https://www.expedia.com/Things-To-Do-In-Gloucester.d8008.Travel-Guide-Activities) with our dedicated travel guide. ### Does Expedia offer Book Now, Pay Later Gloucester vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [Hotels near Sargent House Museum ](https://www.expedia.com/Sargent-House-Museum-Hotels.0-l6092285-0.Travel-Guide-Filter-Hotels) - [Hotels near Gloucester Unitarian Universalist Church ](https://www.expedia.com/Gloucester-Unitarian-Universalist-Church-Hotels.0-l553248635975257319-0.Travel-Guide-Filter-Hotels) - [Hotels near Cape Ann Historical Museum ](https://www.expedia.com/Cape-Ann-Historical-Museum-Hotels.0-l553248621533117278-0.Travel-Guide-Filter-Hotels) - [Hotels near Capt Bill & Sons Whale Watch ](https://www.expedia.com/Capt-Bill-Sons-Whale-Watch-Hotels.0-l553248621533117279-0.Travel-Guide-Filter-Hotels) - [Hotels near Cape Ann Museum ](https://www.expedia.com/Cape-Ann-Museum-Hotels.0-l553248621532667408-0.Travel-Guide-Filter-Hotels) - 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[Long Beach ](https://www.expedia.com/Long-Beach-Massachusetts.d6340941.Vacation-Attraction) - [North Shore Vacations ](https://www.expedia.com/North-Shore.d6047672.Destination-Travel-Guides) - [Mount Ann Park ](https://www.expedia.com/Mount-Ann-Park-Gloucester.d553248621532667314.Vacation-Attraction) - [Visit North Shore ](https://www.expedia.com/North-Shore.dx6047672) - [Car rentals near Cape Ann Museum ](https://www.expedia.com/Car-Rentals-In-Cape-Ann-Museum.d553248621532667408.Car-Rental-Guide) - [Car rentals near North Shore ](https://www.expedia.com/Car-Rentals-In-North-Shore.d6047672.Car-Rental-Guide) - [Enterprise Rental Cars in North Shore ](https://www.expedia.com/Enterprise-Car-Rentals-In-North-Shore.d6047672-c15.Car-Rental-Guide-Suppliers) - [Luxury Car Rentals in North Shore ](https://www.expedia.com/Luxury-Car-Rentals-In-North-Shore.d6047672-tLuxury.Car-Rental-Guide-Class) - [Avis Rental Cars in North Shore ](https://www.expedia.com/Avis-Car-Rentals-In-North-Shore.d6047672-c41.Car-Rental-Guide-Suppliers) - [North Shore Vacation Rentals ](https://www.expedia.com/North-Shore-Vacation-Rentals.d6047672.Travel-Guide-VacationRentals) - [Things to do in North Shore ](https://www.expedia.com/Things-To-Do-In-North-Shore.d6047672.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app