Gloucester, MA Rentals by Owner

Gloucester Rentals by Owner

House

Perfect 4-bedroom beach house second row on private beach

4 Bedrooms 2 Baths 9 Guests

US $1,173/Night 7 Nights - US $8,210

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House

The Buoys

10.0

Exceptional

(7 Reviews)

3 Bedrooms 1 Bath 6 Guests 1001.04 ft²

US $396/Night 7 Nights - US $2,772

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Highly Rated

Apartment

Long Beach Suites

9.2

Exceptional

(64 Reviews)

1 Bedroom 1 Bath 4 Guests

US $341/Night 7 Nights - US $2,385

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House

Waterway View; Steps to Ocean, Beach, Blvd, Park

4 Bedrooms 2 Baths 9 Guests

US $1,123/Night 7 Nights - US $7,860

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House

Stay at Rocky Neck

10.0

Exceptional

(3 Reviews)

3 Bedrooms 3 Baths 7 Guests 1194.79 ft²

US $1,094/Night 7 Nights - US $7,655

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Apartment

Elevated Fish & Ships on Canal: Walk to Beach,Park

2 Bedrooms 1 Bath 5 Guests

US $477/Night 7 Nights - US $3,339

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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

US $382/Night 7 Nights - US $2,672

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New

Apartment

Cozy Apartment at Green Landing - AC - No Cleaning Fee - Hassle Free Check Out

1 Bedroom 1 Bath 2 Guests

US $264/Night 7 Nights - US $1,845

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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

US $1,987/Night 7 Nights - US $13,908

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Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester

Highly Rated

House

Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester

10.0

Exceptional

(135 Reviews)

2 Bedrooms 1 Bath 5 Guests 1100 ft²

US $387/Night 7 Nights - US $2,711

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Elegant Gloucester Beach Getaway with Ocean Views!

House

Elegant Gloucester Beach Getaway with Ocean Views!

10.0

Exceptional

(1 Review)

5 Bedrooms 2 Baths 10 Guests 2497.23 ft²

US $589/Night 7 Nights - US $4,123

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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

US $243/Night 7 Nights - US $1,698

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More Top-Rated Rentals by Owner in Gloucester Area

Why Choose Rent By Owner for your Gloucester vacation rental?

What makes our Rentals by Owner special?

Verified Listings

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 Rentals by Owner

Where are the best neighborhoods to stay in Gloucester?

When choosing where to stay in Gloucester, Massachusetts, exploring its diverse neighborhoods can enhance your visit. Whether you prefer a cozy seaside retreat or a lively area close to local attractions, each neighborhood offers a unique experience. Located along the scenic coast of Gloucester, these neighborhoods provide easy access to the region’s natural beauty and charming community vibe. As you search for rental by owner options through Rent By Owner, you'll find a variety of properties that suit different preferences, all within convenient distances to the area's top destinations. Trust in our seamless booking process to help you discover the perfect neighborhood for an authentic Gloucester experience.

Annisquam

In this charming neighborhood, you can enjoy a tranquil coastal retreat while staying within easy reach of local attractions. It’s an ideal spot for those seeking a peaceful getaway in the Gloucester area with vacation rentals by owner.

View 333+ Rentals in Annisquam

Best Times to Visit Gloucester

When should you plan your Rentals by Owner stay?

Choosing the ideal time to vacation in Gloucester ensures you experience this destination's unique charm at its best, allowing you to enjoy a memorable stay when the weather and local events align perfectly for your preferences.

Peak Season Highlights

Summer (June to August)

This is when the area experiences its warmest weather, making it ideal for enjoying outdoor activities and exploring the scenic coastline. Booking your rental here during summer guarantees a lively atmosphere and long daylight hours.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F

Fall (September to November)

During early fall, this destination offers breathtaking foliage and pleasant temperatures, attracting visitors seeking scenic drives and outdoor adventures. Securing accommodations in advance ensures you enjoy the region’s vibrant autumn scenery at its best.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F

Off-Season Highlights

Winter (December to February)

The quiet winter months bring colder temperatures and fewer tourists, providing a peaceful retreat for those looking to experience the region’s serene beauty. Booking during this time often comes with better rates and greater availability.

Average Temperature Daytime: 35°F to 45°F - Nighttime: 25°F to 35°F

Spring (March to May)

In early spring, the area begins to awaken with new growth and milder weather, perfect for avoiding the crowds while still enjoying the emerging natural beauty of this coastal destination.

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

Weekly Weather Forecast for Gloucester

How to Book Your Gloucester vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Rentals by Owner in Gloucester Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 outdoor dining spaces perfect for savoring the fresh sea air and scenic views.
Take advantage of private patios or decks to relax after a day exploring the coast.
Make use of spacious yards or gardens ideal for outdoor activities or gatherings.
Benefit from outdoor grilling areas to prepare meals with local ingredients.
Revel in stunning waterfront views from your outdoor seating area or balcony.
Step outside onto lush lawns suited for picnics or outdoor games.
Utilize designated fire pits or fireplaces to enjoy cozy evenings under the stars.

Top Attractions Around Gloucester

What attractions are nearby?

In this charming coastal area, you can enjoy a variety of outdoor activities such as boating, fishing, and exploring scenic beaches just moments from your rental here in Gloucester, Massachusetts.

Family Activities

Cape Ann Whale Watch Tours: Experience an unforgettable family adventure on a whale watching tour that showcases the region’s rich marine life and natural beauty.
Cape Ann Museum: Discover the area's maritime history and local art collections, offering engaging exhibits for visitors of all ages in this cultural hub.
Good Harbor Beach: Relax and play on one of the area’s most popular sandy beaches, perfect for swimming, picnicking, and building sandcastles with your family.
Trafton’s Saltwater Farm Museum: Explore a historical farm that offers interactive displays and activities, making it an educational outing for children and adults alike.

Adult Activities

Whale Watching Tours: Embark on an unforgettable adventure to see majestic whales in the waters off this renowned coastal destination.
Fishing Charters: Experience sportfishing in the region’s rich Atlantic waters, perfect for a day of angling and marine exploration.
Historic Harbor Walks: Explore the area's maritime history through scenic walks along the harbor, offering stunning views and cultural insights.
Seafood Dining Experiences: Savor the region’s fresh catch at local eateries, highlighting the area's vibrant seafood cuisine scene.

Other Places to Stay in Gloucester, MA

Dogtown

Explore 543 Properties

Good Harbor Beach

Explore 458 Properties

Annisquam

Explore 333 Properties

Plum Cove Beach

Explore 323 Properties

Northeast Hospital Corporation - Addison Gilbert Campus

Explore 316 Properties

Cape Ann Museum

Explore 286 Properties

Cape Ann Historical Museum

Explore 284 Properties

Sargent House Museum

Explore 283 Properties

Schooner Adventure

Explore 282 Properties

Gloucester Unitarian Universalist Church

Explore 280 Properties

Lucky 7 Arcade

Explore 279 Properties

Magnolia

Explore 90 Properties

More Places to Stay Near Gloucester

Gloucester Travel Tips

How Can You Make the Most of Your Stay?

Explore Local Dining and Fresh Seafood: Take advantage of the region’s renowned seafood scene by trying local eateries to enjoy authentic flavors during your stay.
Visit the Coastal Areas and Beaches: Make time for relaxing on the area's scenic beaches and coastal spots to fully experience the seaside charm.
Utilize the Area’s Natural Parks and Outdoor Spaces: Discover nearby parks and outdoor areas that offer excellent opportunities for hiking, picnicking, and enjoying nature.
Plan Your Activities Around Seasonal Events: Check the local calendar for seasonal festivals and events that can enrich your visit and provide a taste of regional culture.

Transportation Options

Gloucester Harbor Cruises: Explore the scenic coastline and harbor views by boat, offering a relaxing and picturesque transportation option in this maritime region.
Local Bus Services: Utilize regional bus routes to conveniently navigate the area without the hassle of driving, making it easy to reach popular destinations nearby.
Taxi and Rideshare Services: Access reliable taxis and rideshare options for quick and direct travel throughout here, ideal for flexible movement during your stay.
Car Rentals from Local Providers: Rent a vehicle directly in the area to enjoy the freedom to explore Gloucester and its surroundings at your own pace.

Local Customs Options

Sea Shanty Singing Traditions: Embrace the maritime spirit by participating in or observing local sea shanty singing sessions that celebrate the area's rich fishing heritage.
Clamming and Seafood Harvesting: Respect the community’s traditional clamming practices, which are an essential part of the region’s coastal livelihood and culinary culture.
Maritime Festivals: Engage with annual maritime festivals that showcase the area’s fishing history and foster a sense of local pride and camaraderie.
Respectful Coastal Navigation: When exploring the coastline, observe local customs of respectful navigation and conservation to preserve the region's natural beauty and marine life.

Gloucester Rentals by Owner Frequently Asked Questions

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 are available in Gloucester?

Currently, the total number of properties listed by RBO in 2026 is over 339 in the Gloucester area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Vacation Rentals in Gloucester. 

3. What is the cancellation policy for a rental by owner in Gloucester, Massachusetts?

The cancellation policy varies depending on the individual host. You should review the specific listing details or contact the owner directly to understand the terms and any potential fees associated with cancellations.

4. How do I confirm the availability of a rental property by owner in Gloucester, Massachusetts?

Availability calendars are typically provided on each listing. For real-time confirmation, it’s best to reach out directly to the owner through the booking platform to ensure the dates you desire are open.

5. Are there any additional fees or charges for staying in a rental by owner here?

Additional fees such as cleaning or service charges are usually listed on the property page. To get a complete understanding of the total cost, review the detailed pricing information or contact the host for clarification.

6. What amenities can I expect when booking a rental by owner in Gloucester, Massachusetts?

Amenities vary by property but generally include essentials like Wi-Fi, kitchen facilities, and linens. Specific amenities are listed on each rental page—be sure to check these details or ask the owner directly.

7. How can I ensure my booking with a rental owner in Gloucester is secure and reliable?

To guarantee a secure booking experience, use the official booking platform’s messaging system, read reviews from previous guests, and communicate directly with the owner to clarify any questions before confirming your reservation.