Discover Your Perfect Gloucester Vacation Homes

Gloucester Luxury Rentals

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9.0 (333 Reviews)
Hotel
The Vista
  • Air Conditioner
  • Parking
  • Pool
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Gloucester Pet Friendly Vacation Rentals

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9.1 (53 Reviews)
Apartment
Retreat near Beaches
  • Air Conditioner
  • Parking
  • Pet Friendly
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Why Choose Rent By Owner for your Gloucester Vacation Rental Homes?

What makes our Vacation Rentals 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 Vacation Rentals

Where are the best neighborhoods to stay in Gloucester?

Discover the charm of Gloucester, Massachusetts, by choosing a neighborhood that aligns with your ideal vacation experience. Whether you prefer staying close to the bustling harbor area or in a peaceful residential community, each neighborhood offers unique access to local attractions and scenic views. Selecting the right area to stay ensures you enjoy the authentic coastal atmosphere while enjoying the convenience and comfort of quality vacation rentals. With a variety of options available, you can easily find a welcoming place that makes your visit to Gloucester both memorable and effortless.

Annisquam

Located in the scenic region of Gloucester, this neighborhood offers a peaceful retreat where you can enjoy a serene coastal atmosphere. Here, your choice of vacation rentals provides easy access to charming seaside views and tranquil surroundings.

View 270+ Rentals in Annisquam

Best Times to Visit Gloucester

When should you plan your Vacation Rentals stay?

Choosing the best time to visit here depends on your preferences for weather and local events, ensuring you experience the region’s charm at its most appealing throughout the year.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, you can enjoy warm weather and long daylight hours, making it ideal for exploring the scenic coastline and local attractions. The region welcomes many visitors seeking a lively atmosphere and outdoor activities.

Average Temperature Daytime: 75°F - 80°F - Nighttime: 60°F - 65°F
autumn
Fall (September to November)

Autumn brings colorful foliage and pleasant temperatures, inviting you to experience the area's natural beauty. This season is perfect for enjoying peaceful coastal views and seasonal events in the region.

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

Off-Season Highlights

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Winter (December to February)

Winter offers a quieter retreat with crisp air and fewer visitors, providing a cozy atmosphere for your stay. You can experience the region’s charm without the crowds, especially if you prefer a more relaxed vacation.

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

As the region begins to thaw, early spring delivers mild temperatures and blooming landscapes. This period offers a peaceful escape with fewer tourists before the busy summer season starts.

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

Weekly Weather Forecast for Gloucester

How to Book Your Gloucester Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. 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 Vacation Rentals in Gloucester Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals 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 deck, perfect for relaxing and taking in the sea breezes.
  • Take advantage of well-maintained barbecue grills for outdoor cooking during your stay.
  • Relish the scenic views from a spacious yard or garden area, ideal for gatherings or quiet contemplation.
  • Make the most of convenient parking spaces for easy access to your rental property.
  • Utilize outdoor dining areas that provide a charming setting for meals with a view.
  • Discover nearby walking trails or access to natural preserves for outdoor exploration.
  • Secure outdoor storage for outdoor gear, ensuring your equipment stays organized and protected.

Top Attractions Around Gloucester

What attractions are nearby?

While staying here, you'll have the opportunity to explore nearby beaches, scenic harbor walks, and charming coastal attractions that showcase the best of Gloucester’s maritime heritage and natural beauty.

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Family Activities

  • Fishermen’s Memorial Sanctuary: Discover a peaceful spot where you can enjoy scenic views of the harbor and learn about Gloucester's rich maritime history with your family.
  • Cape Ann Museum: Explore local art, history, and culture that highlight the area's artistic heritage, perfect for engaging the whole family.
  • Eastern Point Lighthouse: Take a short drive or walk to this historic lighthouse for picturesque vistas and an educational experience about the region’s nautical significance.
  • Good Harbor Beach: Relax on soft sands and play in the gentle surf at one of the most popular family-friendly beaches here, ideal for sunny days and picnics.
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Adult Activities

  • Whale Watching Tours: Experience the thrill of spotting majestic whales along the coast, a must-do activity that highlights the region’s rich marine life.
  • Historic Fishery Museum: Explore the area's fishing heritage through engaging exhibits that offer insight into Gloucester's maritime history.
  • Scenic Coastal Walks: Enjoy leisurely strolls along scenic shoreline trails, offering breathtaking views and a peaceful retreat within the region.
  • Cuisine at Local Seafood Restaurants: Savor fresh, locally caught seafood dishes at celebrated eateries that showcase the area’s culinary traditions.

Other Places to Stay in Gloucester, MA

Dogtown
Dogtown Vacation Rentals
Good Harbor Beach
Good Harbor Beach Vacation Rentals
Plum Cove Beach
Plum Cove Beach Vacation Rentals
Annisquam
Annisquam Vacation Rentals
Northeast Hospital Corporation - Addison Gilbert Campus
Northeast Hospital Corporation - Addison Gilbert Campus Vacation Rentals
Sargent House Museum
Sargent House Museum Vacation Rentals
Cape Ann Historical Museum
Cape Ann Historical Museum Vacation Rentals
Cape Ann Museum
Cape Ann Museum Vacation Rentals
Gloucester Unitarian Universalist Church
Gloucester Unitarian Universalist Church Vacation Rentals
Lucky 7 Arcade
Lucky 7 Arcade Vacation Rentals
Schooner Adventure
Schooner Adventure Vacation Rentals
Magnolia
Magnolia Vacation Rentals
More Places to Stay Near Gloucester

Gloucester Travel Tips

How Can You Make the Most of Your Stay?

  • Discover Local Cuisine: Dive into the region's fresh seafood offerings by visiting local eateries to enhance your authentic experience here.
  • Explore Ocean Currents: Take advantage of guided tours or self-driven excursions along the coast to fully appreciate the area's maritime charm.
  • Plan Outdoor Activities: Make the most of the scenic landscape by scheduling outdoor adventures like hiking or beach days during your stay.
  • Engage with the Community: Attend local events or visit community spots to connect deeply with this destination’s welcoming atmosphere.

Transportation Options

  • Gloucester Municipal Airport: This regional airport offers convenient domestic flights, making it easy for you to access the area from various parts of the country.
  • MBTA Commuter Rail: Connecting you to Boston and other key cities, the commuter rail provides a reliable transportation option for exploring the region's urban attractions.
  • Local Bus Services: Local transit options serve the area well, allowing you to easily navigate within Gloucester and its neighboring communities.
  • Taxis and Rideshare Services: For flexible and direct transportation, taxis and rideshare apps offer a convenient way to get around here, especially when carrying luggage or exploring at your own pace.

Local Customs Options

  • Seafood Festivals: Participating in local seafood festivals allows you to experience the region's rich maritime heritage firsthand.
  • Traditional Clam Digging: Engaging in clam digging is a cherished activity here, connecting visitors with the area's longstanding coastal traditions.
  • Harbor Celebrations: Attending harbor celebrations offers insight into the community’s deep-rooted connection with the sea and fishing industry.
  • Historical Maritime Customs: Respect for maritime history is reflected in various local customs, from boat parades to historic ship displays that add charm to your stay.

Frequently Asked Questions About Gloucester?

1. What are the top vacation rentals 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 Vacation Rentals in Gloucester:

2. How many vacation rentals have private pools in Gloucester?

There are 3 vacation rentals with private pools near Gloucester. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Gloucester are best for families?

If you are looking for a family-friendly vacation home in Gloucester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Gloucester:

4. How many Rentbyowner vacation rentals are available in Gloucester?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 348 in the Gloucester area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Gloucester. 

5. What is the cancellation policy for vacation rentals in this area?

The cancellation policy varies depending on the property owner. To ensure you understand the specific terms, please review the cancellation details listed on the property page or contact the owner directly before booking.

6. Are there any additional fees I should be aware of when booking a property here?

Additional fees such as cleaning fees, service charges, or security deposits are often specified in the listing. It's recommended to read the property details thoroughly or reach out to the host for clarification before finalizing your reservation.

7. How do I find the best vacation rental deals in this destination?

To secure the best rates, consider filtering search results by price, dates, and amenities. Early bookings and flexible travel dates can also help you access promotional offers. For personalized assistance, contacting the property owner can provide insights into current discounts.

8. Is there a minimum stay requirement for renting a property in this region?

Many listings have minimum night requirements, which vary by property. Be sure to check the individual listing details for this information or inquire with the host directly to confirm your stay duration.

9. What should I know about check-in and check-out procedures at vacation homes here?

Check-in and check-out procedures differ per property. Details are usually provided in the listing or communicated by the host. It’s best to review these instructions beforehand or contact the owner for guidance to ensure a smooth arrival and departure process.