Just under an hour away from Boston, Cape Ann, Massachusetts, juts out into and overlooks the wide, glittering expanse of the Atlantic. Opt for a vacation home here to enjoy the beach setting, see whales play, and visit historical ports and some of America's most definitive Boston establishments.

Top 15 Recommended vacation rentals in Cape Ann
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Popular Rental Amenities in Cape Ann
Many travelers spend more time comparing accommodations including pools. A few of the accommodations offer access to a pool. In addition, rentals with pools in Cape Ann have an average price of $442 per night. Most of the listed accommodations with pools are hotel room. In Cape Ann, more than half of the accommodations providing a pool are situated close to the water.
Oceanfront Vacation Rentals in Cape Ann

Go whale watching
Gloucester is ideally placed for whale watching, and the top observation spot is undoubtedly Stellwagen Bank National Marine Sanctuary. The area is a great place for diving expeditions, and there are cruises throughout the summer that grant you a good chance at spotting the region’s great whales. Kids love Cape Ann's most spectacular beach, Wingaersheek, overlooked by Annisquam Harbor Light Station, a historic lighthouse. You could also make a day trip to Stage Fort Park, which has two beaches and a recreation area with picnic tables, a playground, and hiking trails.
Discover a 400-year-old port
Gloucester Harbor, a fishing port for 400 years, inspired works of fiction by Rudyard Kipling and the novel The Perfect Storm. Fishing boats still bob in the harbor, swamped in nets and other boating paraphernalia, just as they did in 1623 when the town was founded. Visit the Maritime Heritage Center, which restores wooden boats, and the popular Rocky Neck Art Colony, which boasts over a dozen galleries, studios, and restaurants. The artistic tradition of the community stems from that of Luminist painter and printmaker Fitz Henry Lane, a Gloucester inhabitant. See his works at the Cape Ann Museum.
Beautiful Boston
Boston is within easy reach. Come and see the country's first Ivy League school, Harvard. You can also learn about the city’s seminal role in gaining independence from Britain, which is commemorated along the Freedom Trail. Watch the mighty Red Sox play at Fenway Park, the nation's oldest ballpark. Alternatively, dine on local seafood and soak up the rich culture of the city.
Information about vacation rentals in Cape Ann
🏡 Vacation rentals available | 980 rentals |
---|---|
💳 Possible discounts | up to 12% |
🌙 Nightly prices starting at | $83 |
⭐ Popular amenities | Pets allowed, Air conditioning and Internet |
🐾 Pet friendly homes | 172 homes |
🏊 Vacation rentals with pools | 190 homes |
Frequently Asked Questions
What is the average price per night for a vacation rental in Cape Ann?
The price of a night's stay in Cape Ann starts at $83. $640 is the average nightly price for house rentals in Cape Ann. Apartment rentals in Cape Ann cost on average $409 per night.
How many vacation rentals are available to book in Cape Ann?
Currently there are 980 vacation rentals available for booking for your upcoming trip.
What are the most popular amenities for vacation homes in Cape Ann?
The most popular amenities for vacation home rentals in Cape Ann include accommodations that have: Pets allowed, Air conditioning, and Internet.
How many vacation homes with a pool are there in Cape Ann?
Discover 190 vacation rentals available in Cape Ann.
Are pets allowed in vacation rentals in Cape Ann?
If you are traveling with a pet in Cape Ann - 18% of vacation rentals are pet-friendly.
What are the best months to travel to Cape Ann?
When choosing a vacation home in Cape Ann, keep in mind that rainy season is typically in December or February, with September often being the driest.
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