Discover Your Perfect Gloucester Resorts

Gloucester Resorts

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10.0 (7 Reviews)
House
The Buoys
  • Air Conditioner
  • Parking
  • View
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9.6 (316 Reviews)
Bed & Breakfast
Harborview Inn
  • Air Conditioner
  • Parking
  • TV
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10.0 (3 Reviews)
House
Stay at Rocky Neck
  • Air Conditioner
  • Parking
  • Security/Safety
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More Top-Rated Resorts in Gloucester Area

Why Choose Rent By Owner for your Gloucester Resorts?

What makes our Resorts special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Gloucester Resorts

Where are the best neighborhoods to stay in Gloucester?

When visiting Gloucester, Massachusetts, you’ll find charming neighborhoods that offer a variety of options for a relaxing stay. The waterfront area provides stunning views and easy access to local attractions, making it an ideal choice for those seeking a scenic getaway. Alternatively, the downtown district offers a vibrant atmosphere with convenient amenities, perfect for travelers looking to explore the cultural side of this historic city.

Annisquam

Here, you can enjoy a peaceful retreat within a charming community that offers easy access to scenic coastal views, making it an ideal choice for those seeking relaxing resorts in the region. This destination provides a serene setting perfect for unwinding and experiencing the natural beauty of the area.

View 310+ Rentals in Annisquam

Best Times to Visit Gloucester

When should you plan your Resorts stay?

Determining the ideal time to visit this destination ensures you experience its scenic beauty and local charm at their best, whether you're seeking vibrant seasonal activities or a peaceful retreat within the region’s welcoming atmosphere.

Peak Season Highlights

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Summer (June to August)

During the summer months, you can experience warm weather and an active coastal atmosphere that attracts visitors seeking outdoor activities and seaside relaxation.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 65°F
autumn
Autumn (September to October)

Early fall offers mild temperatures and vibrant foliage, making it a popular time for enjoying scenic views and local events in the area.

Average Temperature Daytime: 65°F to 70°F - Nighttime: 50°F to 55°F

Off-Season Highlights

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Winter (December to February)

The quiet winter months bring cooler temperatures and fewer visitors, providing a peaceful setting for those looking to escape the crowds.

Average Temperature Daytime: 35°F to 45°F - Nighttime: 25°F to 30°F
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Spring (March to May)

Late spring sees the region awakening with blooming flora and gradually rising temperatures, offering a serene environment for tranquil getaways.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 40°F to 45°F

Weekly Weather Forecast for Gloucester

How to Book Your Gloucester Resorts

What's our booking process?

Our platform allows you to browse a curated selection of resorts. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Gloucester

More Top-Rated Resorts in Gloucester Area

Common Resorts Amenities

What amenities can you expect?

Our Resorts are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor patio or balcony to take in the fresh sea breeze and scenic views.
  • Take advantage of well-maintained gardens or landscaped yards that enhance your stay near the coast.
  • Relax by an outdoor swimming pool, perfect for cooling off after exploring the region.
  • Utilize outdoor grilling areas or barbecue setups for memorable cookouts with family and friends.
  • Make use of dedicated fire pits or outdoor fireplaces to gather around during cooler evenings.
  • Benefit from access to nearby beaches or water-front locations for outdoor activities like kayaking or paddleboarding.
  • Take advantage of on-site or nearby tennis courts, golf courses, or other outdoor recreation facilities available here.

Top Attractions Around Gloucester

What attractions are nearby?

Within this charming region, you can enjoy a variety of outdoor activities and scenic attractions that highlight the natural beauty and maritime heritage, making it an ideal destination for those seeking relaxation and adventure close to your preferred Gloucester, Massachusetts resort accommodation.

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Family Activities

  • Visit the Cape Ann Museum: Discover local history and art that provides an engaging cultural experience for the entire family here in Gloucester.
  • Explore Good Harbor Beach: Relax and enjoy the sandy shores and gentle waves at one of the region’s most popular family-friendly beaches, just a short drive away.
  • Take a Whale Watching Tour: Embark on a memorable adventure to spot whale and marine life along the stunning coastline nearby, perfect for inspiring young explorers.
  • Enjoy the Fishermen’s Memorial:** Pay tribute at this touching site dedicated to the region’s maritime heritage, offering educational insights and scenic views for all ages.
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Adult Activities

  • Whale Watching Tours: Embark on an unforgettable adventure by taking a whale watching tour, experiencing the region’s rich marine life firsthand.
  • Fishing Charters: Enjoy a day out on the water with a fishing charter, perfect for anglers seeking to make the most of this coastal destination.
  • Sailing Experiences: Discover the scenic beauty of nearby waters through sailing excursions that offer both relaxation and adventure.
  • Coastal Hiking: Explore the area's stunning coastline along scenic hiking trails that showcase the natural beauty of this maritime region.

Other Places to Stay in Gloucester, MA

Dogtown
Explore 543 Properties
Good Harbor Beach
Explore 458 Properties
Plum Cove Beach
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Northeast Hospital Corporation - Addison Gilbert Campus
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Annisquam
Explore 310 Properties
Cape Ann Museum
Explore 286 Properties
Cape Ann Historical Museum
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Sargent House Museum
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Schooner Adventure
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Gloucester Unitarian Universalist Church
Explore 280 Properties
Lucky 7 Arcade
Explore 279 Properties
Magnolia
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Gloucester Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take advantage of the region's fresh seafood and charming eateries to experience authentic flavors unique to the area.
  • Stroll Along Scenic Waterfronts: Enjoy leisurely walks along Gloucester’s picturesque harbors to immerse yourself in the natural beauty of this coastal destination.
  • Visit Nearby Cultural Attractions: Discover local art galleries and historical sites that offer insight into the area's rich maritime heritage.
  • Plan Outdoor Activities: Make the most of your stay by engaging in outdoor adventures like kayaking or fishing, which showcase the region’s outdoor appeal.

Transportation Options

  • Driving: Renting a car allows you to explore the region at your own pace, especially helpful for reaching remote beaches and scenic spots.
  • Public Transit: Commuting via local buses provides an economical and eco-friendly way to navigate around here without the hassle of parking.
  • Taxi and Rideshare Services: Convenient options like taxis or rideshare apps offer quick and reliable transportation directly to your chosen resort or nearby attractions.
  • Bike Rentals: Cycling along designated trails and scenic routes gives you a healthy, environmentally friendly way to enjoy the area's natural beauty.

Local Customs Options

  • Salutation Customs: Greeting others with a handshake or a friendly nod is common when meeting locals in Gloucester, reflecting the area's warm and welcoming community.
  • Celebration of Seafood Festivals: Participating in regional seafood festivals showcases the area's maritime heritage and offers an authentic way to experience local culture.
  • Fishing Traditions: Respect for fishing customs, such as sustainable practices and traditional methods, is deeply ingrained in the local way of life here on the coast.
  • Seasonal Holiday Observances: Celebrations like the local Christmas and Fourth of July events highlight the community's festive spirit and regional pride during your stay.

Frequently Asked Questions About Gloucester Resorts

1. What are the top Resorts in Gloucester?

There are a lot of options in Gloucester. If you plan on staying in the Gloucester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Resorts in Gloucester:

2. How many Resorts are available in Gloucester?

Currently, the total number of properties listed by RBO in 2026 is over 368 in the Gloucester area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Gloucester. 

3. What is the cancellation policy for resorts in Gloucester, Massachusetts?

Cancellation policies vary depending on the specific resort you choose. It is recommended to review the individual listing details or contact the property owner directly for the most accurate and up-to-date information.

4. Are there any special amenities available at resorts in this region?

Amenities offered by resorts can differ, so it’s best to check each listing for specific features such as pools, spa services, or outdoor activities. Contact the owner if you have particular requirements.

5. How do I secure the best rates when booking a resort here?

To find competitive rates, consider booking in advance or during off-peak seasons. Keep an eye on last-minute deals and special offers listed on the site, and reach out to the property owner for potential discounts.

6. What are the check-in and check-out procedures at resorts in this destination?

Check-in and check-out times are set by each property and are detailed in the listing. For specific instructions or early/late arrival requests, contact the owner directly to ensure a smooth experience.

7. Is there a flexible cancellation or refundable deposit policy for bookings?

Refundability and deposit policies depend on the individual resort’s terms. Review the reservation details carefully or contact the owner to confirm the cancellation options and any associated fees.

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More Top-Rated Resorts in Gloucester Area