Gloucester Oceanfront Vacation Rentals
New
Apartment
4 Bedrooms
2 Baths
10 Guests
1300 ft²
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
AU $1,029/Night
7 Nights - AU $7,204
Bed & Breakfast
9.6(322 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
AU $393/Night
7 Nights - AU $2,750
House
3 Bedrooms
3 Baths
6 Guests
24757 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $600/Night
7 Nights - AU $4,203
House
10.0(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
1377.78 ft²
- Oceanfront
- Ocean View
- View
Parking
AU $539/Night
7 Nights - AU $3,774
House
10.0(135 Reviews)
2 Bedrooms
1 Bath
5 Guests
1100 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $604/Night
7 Nights - AU $4,228
House
10.0(1 Review)
5 Bedrooms
2 Baths
10 Guests
2497.23 ft²
Private Beach- Oceanfront
Spa- Fireplace/Heating
AU $832/Night
7 Nights - AU $5,823
Apartment
10.0(130 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
AU $382/Night
7 Nights - AU $2,672
House
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
796.53 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $405/Night
7 Nights - AU $2,837
House
10.0(72 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $592/Night
7 Nights - AU $4,147
House
9.8(14 Reviews)
3 Bedrooms
1 Bath
6 Guests
1270.14 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
AU $381/Night
7 Nights - AU $2,669
Apartment
10.0(60 Reviews)
2 Bedrooms
1 Bath
4 Guests
1300 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $319/Night
7 Nights - AU $2,236
Why Choose Rent By Owner for your Gloucester Oceanfront Vacation Rentals?
What makes our Oceanfront Vacation Rentals 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 Oceanfront Vacation Rentals
Where are the best neighborhoods to stay in Gloucester?
When visiting Gloucester, Massachusetts, you might consider staying in neighborhoods that offer stunning ocean views and easy access to the waterfront. The Downtown Gloucester area provides vibrant local charm, perfect for exploring maritime history and seaside dining, while communities along the coast allow you to enjoy peaceful, scenic surroundings right outside your door. Whether you're seeking a lively atmosphere or tranquil shores, these neighborhoods make an ideal base for your oceanfront experience in this historic coastal town.
Annisquam
In this charming area, you can enjoy picturesque ocean views and peaceful seaside surroundings, making it an ideal location for your oceanfront rentals. Here, the region offers a tranquil retreat with easy access to the scenic coastline, perfect for relaxing getaways.
View 333+ Rentals in AnnisquamBest Times to Visit Gloucester
When should you plan your Oceanfront Vacation Rentals stay?
Choosing the right time to visit can greatly enhance your experience, so consider planning your getaway during the warmer months when the area’s natural beauty and outdoor activities are at their best, making it an ideal opportunity to enjoy the stunning oceanfront rentals that this destination offers.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather and longer daylight hours, making it ideal for relaxing with oceanfront rentals by the sea.
Average Temperature Daytime: 75°F - 85°F - Nighttime: 60°F - 70°F
Fall (September to October)
Early fall offers pleasant temperatures and fewer crowds, providing a tranquil setting to experience the region’s natural beauty from your oceanfront rental.
Average Temperature Daytime: 65°F - 75°F - Nighttime: 50°F - 60°F
Off-Season Highlights
Late Fall to Early Winter (November to December)
As the region transitions into winter, you'll find quieter surroundings in this destination, ideal for those seeking peace and solitude in oceanfront accommodations.
Average Temperature Daytime: 45°F - 55°F - Nighttime: 35°F - 45°F
Winter (January to February)
During the colder months, the area becomes a serene retreat perfect for cozying up in oceanfront rentals while enjoying the quiet winter landscape.
Average Temperature Daytime: 35°F - 45°F - Nighttime: 25°F - 35°F
Weekly Weather Forecast for Gloucester
How to Book Your Gloucester Oceanfront Vacation Rentals
What's our booking process?
Our platform allows you to browse a curated selection of oceanfront 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
Common Oceanfront Vacation Rentals Amenities
What amenities can you expect?
Our Oceanfront 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 private outdoor seating areas, perfect for relaxing while taking in scenic water views.
- Take advantage of communal barbecue grills to prepare fresh seafood and local delicacies al fresco.
- Stroll along designated walking paths or private beaches accessible directly from your rental.
- Make the most of well-maintained outdoor patios or decks for dining with an ocean backdrop.
- Utilize outdoor showers to rinse off after a day at the nearby shoreline.
- Benefit from on-site boat docks or launch areas if you wish to explore the region by water.
- Relax in shaded gazebos or pergolas designed for enjoying the salty sea air comfortably.
Top Attractions Around Gloucester
What attractions are nearby?
Within this charming coastal region, you can enjoy a variety of outdoor activities such as kayaking, fishing, and scenic walks along the shoreline, making it an ideal destination for those seeking relaxing oceanfront rentals that offer easy access to the natural beauty and maritime heritage of Gloucester, Massachusetts.
Family Activities
- Whale Watching Tours: Embark on an exciting adventure to see majestic whales in their natural habitat, a highlight for families staying in beachfront accommodations here.
- Fishing Charters: Enjoy a family-friendly fishing experience off the coast, perfect for creating memorable moments amidst stunning ocean views.
- Plum Cove Beach: Spend a relaxing day at this scenic beach, ideal for building sandcastles and shoreline exploration with loved ones.
- Fishermen’s Memorial Tower: Visit this historical site offering panoramic views of the region and insights into its rich maritime heritage, enriching your family trip here.
Adult Activities
- Whale Watching Tours: Embark on an unforgettable adventure to observe majestic whales in their natural habitat along the coastline, a must-do activity for ocean lovers staying in Gloucester.
- Fishing Charters: Experience the thrill of deep-sea fishing with guided charters that cater to all skill levels, offering a fantastic way to enjoy the region’s rich maritime culture.
- Beach Relaxation and Walking: Unwind on the sandy shores or take scenic walks along the coastline, perfect for enjoying the sea breeze while staying in comfort at nearby oceanfront rentals.
- Historical Maritime Tours: Discover the area's rich seafaring history through guided boat tours and visits to local maritime museums, enriching your visit with cultural insights.
Other Places to Stay in Gloucester, MA
Dogtown
Good Harbor Beach
Annisquam
Plum Cove Beach
Northeast Hospital Corporation - Addison Gilbert Campus
Cape Ann Museum
Cape Ann Historical Museum
Sargent House Museum
Schooner Adventure
Gloucester Unitarian Universalist Church
Lucky 7 Arcade
Magnolia
Gloucester Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Stunning Sunrises and Sunsets: Make sure to schedule your days to enjoy the breathtaking views from your oceanfront rental, especially during early mornings and evenings.
- Explore Local Seafood and Coastal Cuisine: Take advantage of the region's fresh seafood offerings by visiting nearby eateries or preparing delicious meals in your rental’s kitchen.
- Take Advantage of Water Activities: Engage in activities such as kayaking, paddleboarding, or simply relaxing on the beach to fully immerse yourself in the coastal atmosphere.
- Discover Hidden Coastal Trails: Use your stay as an opportunity to explore scenic trails along the shoreline, offering unique perspectives of this charming destination's natural beauty.
Transportation Options
- Gloucester Transportation Services: You can easily access local bus routes and shuttle services that connect you to key destinations within the region, making travel around this coastal area convenient.
- Rental Car Agencies: Numerous rental car providers are available for you to explore Gloucester at your own pace and visit nearby attractions along the scenic Massachusetts coastline.
- Taxi and Rideshare Options: Reliable taxi companies and rideshare services like Uber and Lyft are accessible here, providing quick and comfortable transportation from your oceanfront rental.
- Maritime and Ferry Services: For a unique experience, consider maritime transport options that connect you to neighboring islands and coastal points, enhancing your exploration of this region's maritime heritage.
Local Customs Options
- Local Seafood Traditions: You’ll find that fresh, locally caught seafood is a cornerstone of the region's culinary customs, often enjoyed in traditional ways like clam bakes and lobster boils.
- Fishing Heritage: The area's rich fishing history influences local customs, with many residents participating in or celebrating maritime activities that have been part of the community for generations.
- Harbor Festivals: Seasonal harbor festivals are a cherished tradition here, offering a chance to experience the area's vibrant maritime culture through parades, boat races, and seafood events.
- Preservation of Maritime Crafts: You'll notice a strong respect for maritime craftsmanship, with local artisans maintaining traditions such as boat building, net making, and lighthouse preservation.
Frequently Asked Questions About Gloucester Oceanfront Rentals
1. What are the top Oceanfront 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 Oceanfront Rentals in Gloucester:
- Good Harbor Beach House - walk to beach, close to restaurants and shopping!
- 4 Bedroom LUX House/with Pool Next Door
- WaterViews Overlooking Gloucester Inner Harbor/Sunroom/Deck/Walk to Town/AC
- Walk to Good Harbor Beach. 3BR home, NEW Kitchen
- Sunset Views, Waterfront Property, Dock - Sleeps 12
- Elegant Gloucester Beach Getaway with Ocean Views!
- Stunning Views from Beachfront House in Manchester-by-the-Sea!
- Gloucester Ocean View Escape! Calm, Design-Forward & Minutes to Downtown
- Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive
- 5-star home with quick walk to 2 beaches!
2. How many Oceanfront Rentals are available in Gloucester?
Currently, the total number of properties listed by RBO in 2026 is over 251 in the Gloucester area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Oceanfront Rentals in Gloucester.
3. What is the cancellation policy for oceanfront rentals in Gloucester, Massachusetts?
Cancellation policies vary by property, so it’s best to review the specific listing details or contact the property owner directly to understand their terms and any applicable fees.
4. Are there any extra fees or charges associated with booking oceanfront accommodations in Gloucester?
Additional fees, such as cleaning or service charges, are outlined in each listing. Be sure to check the detailed property description or reach out to the owner for clarification before confirming your reservation.
5. What amenities are typically included in oceanfront rentals in Gloucester?
Most properties offer amenities like Wi-Fi, parking, kitchen facilities, and outdoor spaces. To find out about specific features, review the property's listing details or contact the owner directly.
6. How do I secure my booking for an oceanfront rental in Gloucester?
Booking can usually be completed through the listing platform with a secure payment process. For additional assistance or special requests, contact the owner directly to ensure a smooth reservation.
7. Is it possible to make changes or cancel my reservation for an oceanfront rental in Gloucester?
Changes or cancellations depend on the property's policies. Please refer to the specific listing details or contact the owner to discuss options and any potential penalties.
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9.5(43 Reviews)
1 Bedroom
1 Bath
4 Guests
1001.04 ft²
- Oceanfront
- Fireplace/Heating
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- Balcony/Terrace
AU $717/Night
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10.0(11 Reviews)
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10.0(9 Reviews)
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