Discover Your Perfect Cape Ann Vacation Homes

Best Vacation Homes in Cape Ann

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9.4 (82 Reviews)
Bed & Breakfast
Lantana House
  • Air Conditioner
  • Parking
  • TV
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9.8 (338 Reviews)
Bed & Breakfast
Addison Choate Inn
  • Air Conditioner
  • Parking
  • TV
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9.3 (33 Reviews)
Bed & Breakfast
Beach & King Street Inn
  • Air Conditioner
  • Parking
  • View
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9.8 (278 Reviews)
Bed & Breakfast
The Seafarer Inn
  • Air Conditioner
  • Parking
  • TV
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Why Choose Rent By Owner for your Cape Ann 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 Cape Ann Vacation Rentals

Where are the best neighborhoods to stay in Cape Ann?

When exploring Cape Ann, Rockport, Massachusetts, your choice of neighborhood can greatly enhance your stay. Each area offers its own unique charm and character, whether you're seeking scenic coastal views, artistic neighborhoods, or peaceful seaside retreats. By selecting the right neighborhood to stay in, you can enjoy easy access to local attractions and immerse yourself in the authentic ambiance of this picturesque New England destination. Discover the perfect spot for your next getaway with reliable vacation rentals that cater to your preferences, ensuring a memorable experience in this scenic region.

Annisquam

This charming neighborhood offers a peaceful retreat with scenic views and a close-knit community, making it an ideal choice for those seeking tranquility in Gloucester. Here, you can enjoy the quiet beauty of the area while staying in comfortable vacation rentals that provide easy access to local attractions.

View 270+ Rentals in Annisquam

Great Neck

Located within Ipswich, this scenic area features expansive waterfront views and a relaxed atmosphere perfect for unwinding. The region’s vacation rentals offer a convenient base for exploring the natural beauty and coastal charm that define here.

View 37+ Rentals in Great Neck

Best Times to Visit Cape Ann

When should you plan your Vacation Rentals stay?

Choosing the right time to vacation here can enhance your experience, as the best seasons often depend on whether you prefer vibrant summer activities or tranquil off-peak relaxation in this charming destination.

Peak Season Highlights

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Summer (June to August)

During the warm summer months, you can enjoy the scenic beauty and lively atmosphere of this coastal destination, making it an ideal time for outdoor activities and exploring the area.

Average Temperature Daytime: 75-85°F - Nighttime: 60-70°F
autumn
Fall (September to November)

In the fall, the region transforms with vibrant foliage, offering a picturesque backdrop for your stay and perfect for relaxing seaside strolls and cozy evenings.

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

Off-Season Highlights

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Winter (December to February)

The quiet winter season provides a tranquil escape, with fewer crowds allowing you to enjoy the peaceful charm of this coastal area from your vacation rentals.

Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
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Spring (March to May)

Spring brings mild weather and blooming landscapes, making it a pleasant time for those seeking a less busy experience while exploring what this destination has to offer.

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

Weekly Weather Forecast for Cape Ann

How to Book Your Cape Ann 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 Cape Ann

More Top-Rated Vacation Rentals in Cape Ann 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 outdoor seating areas perfect for relaxing and taking in the coastal views.
  • Look for private patios or decks to dine al fresco and unwind after a day exploring the area.
  • Many properties offer barbecue grills for preparing fresh seafood and local ingredients.
  • Access charming garden spaces or landscaped yards that enhance your outdoor experience.
  • Some rentals feature outdoor showers to rinse off after beach days on the region’s scenic shores.
  • Take advantage of spacious lawns or open areas ideal for outdoor activities or family gatherings.
  • Seek properties with direct access to nearby beaches, allowing effortless seaside strolls and sunbathing.

Top Attractions Around Cape Ann

What attractions are nearby?

While visiting this charming coastal area, you can enjoy a variety of activities such as exploring scenic beaches, discovering local art galleries, and savoring fresh seafood at nearby waterfront restaurants.

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Family Activities

  • Fishermen's Memorial Museum: Learn about the region's maritime history through engaging exhibits and interactive displays that fascinate both kids and adults alike.
  • Bearskin Neck: Explore this charming area filled with unique shops, galleries, and fresh seafood eateries, perfect for a family stroll along the scenic waterfront.
  • Motif No. 1: Visit the iconic fishing shack recognized as one of the most painted buildings in America, offering great photo opportunities and local charm.
  • Reel Mysteries: Experience family-friendly boat tours that reveal the area's rich maritime culture and scenic coastline views from the water.
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Adult Activities

  • Whale Watching Tours: Embark on a scenic cruise to experience the region’s abundant marine wildlife, including the chance to see whales in their natural habitat.
  • Art Galleries and Studios: Explore local artistry by visiting renowned galleries and studios that showcase the creative spirit of this coastal destination.
  • Fishing Excursions: Enjoy a memorable day out on the water with guided fishing trips that cater to both beginners and seasoned anglers.
  • Historic Walking Tours: Discover the area's rich maritime history through guided tours that highlight its unique architectural and cultural heritage.

Cape Ann Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining and shops: Take advantage of the area's charming boutiques and authentic eateries to immerse yourself in the regional culture and support small businesses.
  • Plan outdoor activities early: Schedule visits to scenic spots and beaches during the morning hours to enjoy tranquility and avoid crowds in this popular destination.
  • Stay connected with local events: Check for seasonal festivals and community gatherings to experience the vibrant local scene and enrich your stay here.
  • Choose a strategic location for your vacation rentals: Opt for accommodations near key attractions and amenities to maximize your sightseeing and relaxation time in this inviting region.

Transportation Options

  • Car Rentals: Renting a car provides the flexibility to explore this coastal region at your own pace, ideal for visiting secluded beaches or scenic attractions nearby.
  • Public Transportation: The local bus service offers an affordable and convenient way to get around the area without the need for driving, perfect for day-trippers and casual explorers.
  • Taxis and Rideshare Services: Taxis and rideshare options like Uber or Lyft are readily available here, providing quick transportation for comfortable travel between your vacation rental and popular destinations.
  • Bicycle Rentals: Biking is a popular choice to enjoy the scenic views of the region while staying active, with several bike rental shops located close to most accommodations.

Local Customs Options

  • Sea Shanty Singing: Participating in traditional maritime song sessions is a cherished custom here, reflecting the area's rich fishing history and seafaring culture.
  • Clam Chowder Tradition: Savoring locally prepared clam chowder is a beloved culinary custom that highlights the region’s abundance of fresh seafood.
  • Artisan Craftsmanship: Supporting local artisans by exploring galleries and shops dedicated to handcrafted goods is a common way visitors embrace the area's creative spirit.
  • Fishing Heritage Celebrations: Engaging in or observing community events that honor the longstanding fishing traditions connects you deeply with this coastal area's identity.

Cape Ann Vacation Rental Frequently Asked Questions

1. What are the top vacation rentals in Cape Ann?

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

2. How many Rentbyowner vacation rentals are available in Cape Ann?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 330 in the Cape Ann 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 Cape Ann. 

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

The cancellation policy varies by listing, so it is important to review the specific terms outlined in the property description or contact the owner directly to understand the options available and any applicable fees.

4. How do I confirm my booking for a vacation rental here?

Booking confirmation typically occurs after completing the reservation process on the listing page and receiving a confirmation email from the owner or property manager. Make sure to verify all details before finalizing your reservation.

5. Are there any additional fees I should be aware of when booking a vacation rental in this region?

Additional fees such as cleaning charges, security deposits, or service fees may apply and are usually detailed in the listing. It’s recommended to read the full list of costs or reach out to the owner for clarification.

6. What amenities are generally included in vacation rentals in this destination?

Most properties feature essential amenities like Wi-Fi, kitchen facilities, and parking. To find out about specific features, review the property listing thoroughly or contact the owner for further details.

7. Is it possible to make special requests or accommodations when booking a vacation rental here?

Many owners are willing to consider special requests such as early check-in, late check-out, or particular amenities. Communicate your needs directly with the host through the booking platform to ensure they can accommodate your requirements.

Best Vacation Homes in Cape Ann