Gloucester Accommodations

Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck

Highly Rated

House

Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck

10.0

Exceptional

(135 Reviews)

2 Bedrooms 1 Bath 5 Guests 1100 ft²

AU $605/Night 7 Nights - AU $4,233

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House

The Buoys

10.0

Exceptional

(7 Reviews)

3 Bedrooms 1 Bath 6 Guests 1001.04 ft²

AU $560/Night 7 Nights - AU $3,919

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Apartment

Long Beach Suites: Steps To Beach, Newly Built

10.0

Exceptional

(5 Reviews)

2 Bedrooms 1 Bath 6 Guests

AU $643/Night 7 Nights - AU $4,503

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Luxury Accommodations in Quiet Seaside Village

Highly Rated

Apartment

Luxury Accommodations in Quiet Seaside Village

10.0

Exceptional

(130 Reviews)

1 Bedroom 1 Bath 2 Guests 600 ft²

AU $407/Night 7 Nights - AU $2,851

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House

Stay at Rocky Neck

10.0

Exceptional

(3 Reviews)

3 Bedrooms 3 Baths 7 Guests 1194.79 ft²

AU $1,546/Night 7 Nights - AU $10,822

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WALK TO BEACH! Great Location! Booking 2026! Close to Salem!

Highly Rated

House

WALK TO BEACH! Great Location! Booking 2026! Close to Salem!

10.0

Exceptional

(72 Reviews)

2 Bedrooms 1 Bath 6 Guests

AU $593/Night 7 Nights - AU $4,151

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1 Mi to Beach! Family Gloucester Gem w/Yard

House

1 Mi to Beach! Family Gloucester Gem w/Yard

10.0

Exceptional

(2 Reviews)

2 Bedrooms 2 Baths 6 Guests 1377.78 ft²

AU $540/Night 7 Nights - AU $3,777

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House

Single Level Home - Steps to Downtown Gloucester & A/C throughout

10.0

Exceptional

(49 Reviews)

2 Bedrooms 1 Bath 4 Guests 1150 ft²

AU $550/Night 7 Nights - AU $3,847

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Cranberry Hill | 9 BR 22 Acre Estate | Sleeps 24

House

Cranberry Hill | 9 BR 22 Acre Estate | Sleeps 24

10.0

Exceptional

(1 Review)

9 Bedrooms 7 Baths 16 Guests 8664.95 ft²

AU $2,809/Night 7 Nights - AU $19,661

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Apartment

WATERFRONT 1BDRM SPACIOUS STUDIO APARTMENT

10.0

Exceptional

(48 Reviews)

1 Bedroom 1 Bath 2 Guests 650 ft²

AU $338/Night 7 Nights - AU $2,368

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Fish & Ships on River Steps to Ocean, Blvd, Park

Apartment

Fish & Ships on River Steps to Ocean, Blvd, Park

10.0

Exceptional

(1 Review)

2 Bedrooms 1 Bath 5 Guests 753.47 ft²

AU $1,272/Night 7 Nights - AU $8,906

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House

1 Mi to Beach! Family Gloucester Gem w/Yard

10.0

Exceptional

(35 Reviews)

2 Bedrooms 2 Baths 6 Guests 1376 ft²

AU $658/Night 7 Nights - AU $4,603

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More Top-Rated Accommodations in Gloucester Area

Why Choose Rent By Owner for your Gloucester Accommodations?

What makes our Accommodations special?

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Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Gloucester Accommodations

Where are the best neighborhoods to stay in Gloucester?

In Gloucester, Massachusetts, choosing to stay in the downtown Gloucester area offers easy access to local shops and waterfront views, making it a convenient base for exploring the city. For a more relaxed atmosphere, the Fisherman's Wharf neighborhood provides charming surroundings and proximity to maritime activities, perfect for an authentic experience. Whichever area you select, you'll find dependable and comfortable accommodations that ensure a memorable visit to this historic Massachusetts coastal town.

Annisquam

This charming neighborhood offers a tranquil retreat where you can enjoy the natural beauty of the area. Staying here provides easy access to scenic views and peaceful surroundings, making it an ideal choice for a relaxing getaway.

View 333+ Rentals in Annisquam

Best Times to Visit Gloucester

When should you plan your Accommodations stay?

To make the most of your visit, consider planning your stay during the shoulder seasons or off-peak times when the area offers a more relaxed atmosphere and better availability of quality accommodations here in Gloucester, Massachusetts.

Peak Season Highlights

Summer (June to August)

During the warm summer months, the area experiences peak visitation, making it an ideal time for beach activities and exploring local culture.

Average Temperature Daytime: 75°F to 80°F - Nighttime: 60°F to 65°F

Fall (September to October)

Autumn offers stunning foliage and a lively atmosphere as visitors enjoy the region's scenic beauty and harvest festivals.

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

Off-Season Highlights

Winter (December to February)

Quiet winter months attract travelers seeking tranquility and seasonal serenity, often with fewer crowds.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F

Spring (March to May)

Early spring sees fewer visitors as the area begins to bloom, offering a peaceful retreat before the busy summer season.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Gloucester

How to Book Your Gloucester Accommodations

What's our booking process?

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

Booking Steps

Search Properties

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

Select a Rental

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

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 Accommodations in Gloucester Area

Common Accommodations Amenities

What amenities can you expect?

Our Accommodations 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

You can enjoy a private outdoor patio or deck for relaxing and dining al fresco.
Expect well-maintained gardens or landscaped yards that add to the scenic charm of your stay.
Many properties feature access to a kayaking or boating area along the picturesque waterfront.
A grilling station or outdoor barbecue setup is often available for cookouts with family and friends.
Look for spacious lawns perfect for outdoor activities or simply soaking up the sunshine.
Some accommodations include a fire pit, ideal for cozy evenings under the stars.
Seaside views and proximity to beaches provide prime outdoor experiences right outside your door.

Top Attractions Around Gloucester

What attractions are nearby?

While staying in this charming destination, you can enjoy a variety of outdoor activities and cultural experiences nearby, making it an ideal choice for exploring the best of Gloucester, Massachusetts; from scenic coastal walks to local art galleries, there’s something to suit every interest in this vibrant region.

Family Activities

Cape Ann Whale Watch Tours Embark on a family-friendly boat tour to observe majestic whales and marine life in the surrounding waters.
Fishermen’s Memorial Museum Discover local maritime history and honor those who worked at sea, offering an educational experience for all ages.
Good Harbor Beach Enjoy a day of swimming, building sandcastles, and picnicking at this scenic beach known for its soft sands and gentle waves.
Gloucester Fishermen's Memorial Visit this iconic monument that celebrates the region’s rich fishing heritage and offers panoramic views of the harbor.

Adult Activities

Whale Watching Tours: Embark on a guided excursion to witness the majestic humpback and minke whales that frequent the waters off Gloucester, Massachusetts, offering an unforgettable maritime experience.
Fishing Charters: Spend a day deep-sea fishing with experienced captains in the area known for its rich fishing heritage, perfect for those looking to enjoy the region’s maritime traditions.
Coastal Kayaking: Explore the scenic coastline and hidden coves by kayak, providing a peaceful way to appreciate the natural beauty of this coastal destination.
Historic Maritime Tours: Discover the area's rich seafaring history through guided boat tours that highlight Gloucester's storied fishing industry and maritime heritage.

Other Places to Stay in Gloucester, MA

Gloucester Travel Tips

How Can You Make the Most of Your Stay?

Plan Ahead Book your stay well in advance to secure the best properties and enjoy a variety of options in this coastal area.
Explore Local Cuisine Take advantage of the region’s renowned seafood and dine at local eateries to experience authentic flavors in Gloucester.
Visit Beaches Early Arrive early at nearby beaches to find the perfect spot and make the most of sunny days along the coastline.
Discover Hidden Gems Ask locals or do some research to uncover lesser-known spots and activities that showcase the area's natural beauty and maritime charm.

Transportation Options

Gloucester Harbor Cruises Experience scenic boat tours that provide a relaxing way to explore the area's maritime heritage and stunning coastline.
Public Transportation The regional transit authority offers bus services connecting you conveniently to popular spots around Gloucester and beyond.
Taxi and Rideshare Services Easily accessible options like taxis and rideshare apps ensure quick and flexible transportation throughout this coastal destination.
Car Rentals Renting a vehicle is a practical choice for exploring the region at your own pace, with various rental agencies available nearby.

Local Customs Options

Gurnet Point Fish Fry Tradition: During your stay, you might observe locals celebrating the long-standing tradition of fresh seafood festivals, which highlight the region's maritime heritage.
Clamoring for Clams: It’s common here to see residents and visitors alike participating in clam digging or enjoying clams freshly harvested from the area's abundant coastal waters.
Celebration of the Maritime Heritage: The community often honors its rich seafaring history through local events that showcase traditional boat races and seaside festivals.
Respect for the Environment: Visitors are encouraged to partake in eco-friendly practices, reflecting the area's deep-rooted respect for its natural coastal surroundings and maritime environment.

Frequently Asked Questions about Gloucester Accommodations

1. What are the top Accommodations 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 Accommodations in Gloucester:

2. How many Accommodations are available in Gloucester?

Currently, the total number of properties listed by RBO in 2026 is over 349 in the Gloucester area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Gloucester. 

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

Cancellation policies vary by property; you should review the specific listing details or contact the owner directly to understand the terms and any applicable fees.

4. Are there any additional fees I should be aware of when booking here?

Additional fees such as cleaning, service charges, or taxes may apply. Please check the listing details or contact the property owner for a complete fee breakdown.

5. How do I secure my reservation and what are the deposit requirements?

Reservation and deposit requirements differ between properties. You will find this information in the listing description or can inquire with the owner for confirmation.

6. What amenities are typically included in accommodations in this region?

Amenities vary by property but often include essentials like Wi-Fi, parking, and kitchen facilities. Detailed amenities are listed on each property’s page; reaching out to the owner can provide further clarification.