Top Gloucester Hotel Deals

Make the Most of Your Gloucester Stay

Cultural heritage on the harbor

Gloucester stands as America's oldest seaport, where the working waterfront remains as vital today as it was in 1623. The iconic Fisherman's Memorial statue faces the harbor, honoring the estimated 10,000 fishermen lost at sea over centuries of maritime tradition. Rocky Neck, one of the country's oldest continuously operating art colonies, draws you into galleries and studios where the creative energy that attracted Milton Avery and Childe Hassam still thrives. The Cape Ann Museum houses the world's largest collection of works by maritime painter Fitz Henry Lane.

Coastal sophistication and dining

Beyond the authentic fishing industry downtown, distinct villages like Annisquam and Magnolia reveal a different character entirely. Annisquam's narrow roads wind past white clapboard houses and the historic harbor lighthouse, while Magnolia showcases Gilded Age grandeur at Hammond Castle, the medieval-style home of inventor John Hays Hammond Jr. The dining scene has evolved considerably, with Tonno bringing elegant coastal Italian cuisine and Talise offering romantic farm-to-table experiences. Good Harbor Beach provides white sand and views of Thacher Island's twin lighthouses.

Practical access and exploration

The MBTA Commuter Rail connects Gloucester Station directly to Boston's North Station. Private car services offer reliable transfers from Logan Airport, approximately 40 minutes south. Nearby Rockport and Salem make excellent additions to your visit, while whale-watching charters depart to Stellwagen Bank National Marine Sanctuary.

Frequently Asked Questions about Gloucester

Can I use my miles on Delta Stays to book hotels in Gloucester?

Yes, you can book your hotel stay in Gloucester using your Delta miles, either for the total amount or in combination with money to reserve your stay. Simply log in to your SkyMiles® account, where you will also discover Member-only offers at select properties that could enhance your travel experience.

What is the benefit of booking my Gloucester hotel directly on Delta Stays?

As a SkyMiles Member, you will earn 2 miles per $1 spent on completed hotel stays and vacation rentals reserved through Delta Stays. Plus, you will receive access to Member promotions at select properties, along with the option to complete payment using miles, cash, or a combination. To ensure you earn your miles, simply sign in to your SkyMiles account or enter your SkyMiles number at checkout when paying with cash. Please allow up to 8 weeks after completing a stay for miles to appear in the SkyMiles account provided. Please also note that if you use miles to pay for any portion of your stay, you will not earn miles on that reservation, including any amount paid with cash.

Is it possible to change or cancel my hotel booking made through Delta Stays?

Cancellation policies differ depending on the property you choose. We recommend reviewing the specific cancellation policy displayed under each hotel's details before finalizing your reservation. Some rates are fully refundable while others are non-refundable. Any modifications or cancellations to your reservation may affect the number of miles you earn and receive in your account.

Can I use my Delta SkyMiles® American Express® Card to book?

As a Delta SkyMiles® Gold, Platinum, or Reserve American Express® Cardholder, you enjoy the advantage of earning additional miles alongside numerous valuable benefits, including an annual statement credit of up to $200 applicable toward prepaid accommodations booked through Delta Cars and Stays. Terms apply. To explore all the benefits available with your card, please visit the Delta SkyMiles® American Express Credit Cards page for complete details.

Can I earn MQDs on Delta Stays hotel bookings?

Periodically, Delta Stays provides special promotions for SkyMiles Members to earn Medallion® Qualification Dollars on accommodations reserved through their booking service. We encourage you to visit the Delta Stays MQD Offer page to check for the latest MQDs offers and review their specific terms and conditions.

Do I need to have a Delta SkyMiles account to book hotels on Delta Stays?

No, anyone can book hotels through Delta Stays. However, only SkyMiles Members can earn miles and access Member-only prices and offers. As a Member, you will earn 2 miles per $1 you spend on Delta Cars and Stays (excluding taxes and other fees). The best part is that SkyMiles is free to join. Register today by going to the delta.com.

Can I book a vacation rental through Delta Stays?

Absolutely, Delta Stays features an extensive collection of vacation rentals in addition to traditional hotel accommodations. Explore the variety of homes, condos, and unique accommodations powered by Vrbo on the Vacation Rentals page.

What hotels in Gloucester have high ratings?

You will find 12 hotels in Gloucester to choose from when you book on Delta Stays. Beauport Hotel Gloucester has a guest rating of 9.6 out of 10, and features a beachfront setting and a restaurant. Another top-rated hotel is Ocean House Hotel at Bass Rocks, where you can enjoy a seasonal outdoor pool and a hot tub. The Hotel at Cape Ann Marina has a rating of 8.4 including good ratings for the restaurant. The hotel has a bar/lounge and couples/private dining.

What is a good area in Gloucester to book for my trip?

Gloucester is filled with plenty of interesting neighborhoods beloved by travelers and locals alike.

East Gloucester draws artists and visitors to its dramatic rocky shores, where the same luminous coastal light that captivated Winslow Homer illuminates the historic Rocky Neck Art Colony, one of America's oldest working artist communities, alongside fresh seafood spots with authentic harbor views. Ocean House Hotel at Bass Rocks is a popular hotel here.

What's a good time of year to visit Gloucester?

To experience Gloucester during great weather, consider a visit in July when the temperature averages 70°F and the skies are mostly sunny with warm beach conditions. For off-peak prices and more deals on hotels, consider visiting during November when temperatures reach a cooler 45°F with fewer crowds and significantly lower pricing.

Which hotels in Gloucester are near Wingaersheek Beach?

White sands meet shallow waters at this family-friendly beach known for unique rock formations. Arrive at low tide to explore the expansive sandbars and discover tide pools. Popular hotels include Ocean House Hotel at Bass Rocks which is a short drive away.

Which hotels in Gloucester are located near Good Harbor Beach?

Good Harbor Beach stretches along the Atlantic with soft white sand where you can walk to Salt Island at low tide. Gentle waves and summer lifeguards make it welcoming for families. Popular hotels include Ocean House Hotel at Bass Rocks which is an 18-minute walk.

Which hotels in Gloucester are located near Hammond Castle?

This 1920s medieval-style castle showcases inventor John Hays Hammond Jr.'s collection of Roman and Renaissance artifacts. The ocean-facing grounds offer dramatic coastal views. One popular hotel is Ocean House Hotel at Bass Rocks which is a short drive away.

*Terms and conditions:

Mileage Offer:

SkyMiles Members will earn two (2) miles per US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Opens in a new window on the base hotel rate for a completed hotel stay. Base hotel rate is the cost of the hotel room, before taxes and fees, charged at the time of booking or upon checkout. Taxes and fees, gratuities, room service other booking charges, or any bookings which are paid or reduced by miles, redemption vouchers or discount codes are excluded from mileage credit. For clarity, if miles are used as a form of payment (whether for all or a portion of the booking), no portion of the booking will be eligible to earn miles under this offer. Except with respect to the Hertz Mileage offer (listed below), SkyMiles Members will earn two (2) miles per eligible US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Cars on the base car rental rate for a completed car qualifying rental booking (“Qualifying Dollars”). A qualifying rental booking includes rentals at a participating location for one or more days at rates other than travel industry rates or discounts, wholesale of tour package rates or discounts, wholesale tour package rates, insurance/dealer replacement rates, corporate and government rates, group travel discounts, or rentals in conjunction with a frequent flyer car award, or other corporate agreements applicable to the respective car company. Calculation of the applicable standard mileage offer is listed below by car rental company. Qualifying Dollars include the base car rental rate, which is the cost of the car rental before taxes and fees, charged at the time of booking. Taxes, fees, other incidental charges, or other booking charges or any bookings which are paid or reduced by redemption vouchers or discount codes are excluded from mileage credit and are not included in the Qualifying Dollars.

This mileage offer does not apply to stays or car rentals booked through Delta Vacations or any cruises booked through Delta Cruises.

Standard mileage offer for car rentals booked at https://www.delta.com/Opens in a new window or https://carsandstays.delta.com/Opens in a new window:

Hertz Reservations:

• General SkyMiles Members earn 4 miles per Qualifying Dollar

• Silver Medallions earn 5 miles per Qualifying Dollar

• Gold Medallions earn 6 miles per Qualifying Dollar

• Platinum Medallions earn 7 miles per Qualifying Dollar

• Diamond Medallions earn 8 miles per Qualifying Dollar

Dollar and Thrifty Reservations:

• All SkyMiles Members earn 4 miles per Qualifying Dollar

Alamo, Enterprise, National, Avis, Budget, Payless and SIXT Reservations:

• All SkyMiles Members earn 2 miles per Qualifying Dollar