Cape Ann Vacation Rentals

Compare 663 available properties from 17 providers
Cape Ann
Save up to 28%

Best Vacation Home Deals in Cape Ann

-28%
Apartment ∙ 3 guests
Rockport, Gloucester, Massachusetts, United States
from $154 $215
VRBO
4.9
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-28%
Apartment ∙ 3 guests ∙ 1 bedroom
Gloucester, Essex County, Massachusetts, United States
from $158 $219
VRBO
5.0
View deal
-21%
House ∙ 4 guests ∙ 2 bedrooms
Rockport, Gloucester, Massachusetts, United States
from $186 $235
VRBO
5.0
View deal

Compare and find the perfect vacation rental for as little as $58 per night by searching and comparing the 663 properties available in Cape Ann. HomeToGo instantly presents you with the best offers by comparing all of the available acommodations in Cape Ann from 17 different providers.

Recommended Vacation Rentals in Cape Ann

Find your perfect vacation rental in Cape Ann: from $58 per night

House ∙ 2 guests ∙ 1 bedroom
Rockport, Gloucester, Massachusetts, United States
from $125
VRBO
4.9
View deal
House ∙ 2 guests ∙ 1 bedroom
Rockport, Gloucester, Massachusetts, United States
from $125
VRBO
5.0
View deal
Apartment ∙ 4 guests ∙ 2 bedrooms
Rockport, Gloucester, Massachusetts, United States
from $219
VRBO
5.0
View deal
House ∙ 6 guests ∙ 3 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $250
VRBO
4.9
View deal
Apartment ∙ 4 guests ∙ 2 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $150
VRBO
4.9
View deal
Apartment ∙ 2 guests ∙ 1 bedroom
Gloucester, Essex County, Massachusetts, United States
from $145
VRBO
5.0
View deal
Apartment ∙ 3 guests
Rockport, Gloucester, Massachusetts, United States
from $154
VRBO
4.9
View deal
House ∙ 6 guests ∙ 2 bedrooms
Rockport, Gloucester, Massachusetts, United States
from $98
VRBO
4.7
View deal
Condo ∙ 2 guests
Rockport, Gloucester, Massachusetts, United States
from $59
Airbnb
4.5
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Vacation Homes With Fishing Spots Nearby

Fishing
Apartment ∙ 2 guests
Gloucester, Essex County, Massachusetts, United States
from $175
VRBO
5.0
View deal
Fishing
Apartment ∙ 7 guests ∙ 2 bedrooms
Rockport, Gloucester, Massachusetts, United States
from $201
VRBO
5.0
View deal
Fishing
House ∙ 4 guests ∙ 1 bedroom
Gloucester, Essex County, Massachusetts, United States
from $168
VRBO
4.9
View deal
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Vacation Rentals With Fireplaces

Fireplace
Cabin ∙ 4 guests ∙ 2 bedrooms
Rockport, Gloucester, Massachusetts, United States
from $221
Airbnb
4.5
View deal
Fireplace
House ∙ 2 guests ∙ 1 bedroom
Gloucester, Essex County, Massachusetts, United States
from $110
Airbnb
5.0
View deal
Fireplace
House ∙ 2 guests ∙ 2 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $132
Airbnb
5.0
View deal
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Dog-Friendly Vacation Rentals

Pet-friendly
Apartment ∙ 3 guests ∙ 1 bedroom
Gloucester, Essex County, Massachusetts, United States
from $171
Airbnb
5.0
View deal
Pet-friendly
Apartment ∙ 2 guests ∙ 1 bedroom
Gloucester, Essex County, Massachusetts, United States
from $184
Airbnb
5.0
View deal
Pet-friendly
House ∙ 8 guests ∙ 4 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $789
Airbnb
5.0
View deal
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Popular Rental Amenities in Cape Ann

  • Internet (610)
  • Kitchen (606)
  • TV (568)
  • AC (430)
  • Washer (425)
  • Microwave (395)
  • Grill (318)
  • No smoking (285)
  • Parking (279)
  • Yard (262)
  • Dishwasher (259)
  • No pets (199)
Filters are provided to help you find a great vacation rental in Cape Ann. You can easily compare and find a property fitting your expectations in Cape Ann if you need internet access during your vacation or you want to tune out with some TV time, as most accommodations provide "internet" and "TVs." Plan your vacation in advance if you love sweating the stress away in saunas or you enjoy soaking in the hot tub. There are just 1 listed rentals providing "saunas" and 5 rentals with "Jacuzzis."

Price and Availability Index in Cape Ann

Vacation Rental Price Information in Cape Ann

This graph displays average prices of the vacation rentals and holiday apartments located in Cape Ann. The week with the highest average prices is in January (1/4 - 1/11). During this week, a night will cost on average $286. Opt for a getaway in July (7/20 - 7/27) for optimal savings when heading to Cape Ann.

Rental Availability Information in Cape Ann

The availability graph shows the percentage of available rentals in Cape Ann. In a week of August (8/3 - 8/10), 45% of the vacation rentals are booked. More accommodations are available in a week of May (5/25 - 6/1) as the booking rate is only 23%.

The Weather in Cape Ann

37°
21°
37°
21°
45°
28°
57°
39°
68°
48°
75°
55°
82°
64°
81°
63°
73°
54°
63°
45°
50°
34°
43°
28°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out our climate diagram to find the perfect month for your vacation. July is the warmest month in Cape Ann with average maximum temperatures of 82°. Conversely, January is the coolest month in Cape Ann, with temperatures going under 21° The rainiest month is July while the driest month is September.

Accommodations in Cape Ann

In Cape Ann, more than half of the 663 vacation properties are house rentals, which represent 55.15% of its available accommodations. In addition, house rentals there have an average price of $400 per night as well as an average size of 2,060 ft². Furthermore, the majority of house rentals in this destination can host 6 guests, which makes it an ideal vacation spot for medium-sized groups and families. If you would prefer to compare another accommodation type, you could check apartment rentals, which are the other most typical accommodation type in Cape Ann. The average size of apartment rentals in Cape Ann is 840 ft², and the average price is $208 per night.

Enjoy fresh Atlantic air with a Cape Ann vacation rental

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.

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Art & Culture

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.

Family Activities

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.

Local Attractions

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.

We compare more than 300 providers, including:

Booking.com Vacation Rentals in Cape Ann VRBO Vacation Rentals in Cape Ann HomeAway Vacation Rentals in Cape Ann TripAdvisor Vacation Rentals in Cape Ann VacationRentals.com Vacation Rentals in Cape Ann HouseTrip Vacation Rentals in Cape Ann FlipKey Vacation Rentals in Cape Ann 9flats.com Vacation Rentals in Cape Ann VaycayHero Vacation Rentals in Cape Ann PerfectPlaces.com Vacation Rentals in Cape Ann Homestay.com Vacation Rentals in Cape Ann Only-apartments Vacation Rentals in Cape Ann Interhome Vacation Rentals in Cape Ann Bedycasa Vacation Rentals in Cape Ann Novasol Vacation Rentals in Cape Ann HomeEscape Vacation Rentals in Cape Ann