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Cape Ann Vacation Rentals

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Cape Ann
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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Bed & Breakfast
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

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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Save up to 67%

Best Vacation Home Deals in Cape Ann

House Cape Ann
Dec 2 - Dec 9
-67%
$240
$80 per night
House ∙ 6 guests ∙ 3 bedrooms
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
Dec 10 - Dec 17
-38%
$400
$250 per night
House ∙ 7 guests ∙ 3 bedrooms
3.5
"Good" (2 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
Dec 10 - Dec 17
-44%
$394
$220 per night
House ∙ 6 guests ∙ 2 bedrooms
4.9
"Excellent" (27 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Compare and find the perfect vacation rental for as little as $80 per night by searching and comparing the 653 properties available in Cape Ann. HomeToGo instantly presents you with the best offers by comparing all of the available properties in Cape Ann from 5 different providers.

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Top-Rated Rentals and Accommodations in Cape Ann

Cottage Cape Ann
Nov 11 - Nov 18
-40%
$450
$272 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (30 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
Feb 18 - Feb 25
$399 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (5 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
Feb 25 - Mar 4
-44%
$734
$413 per night
House ∙ 7 guests ∙ 4 bedrooms
5.0
"Excellent" (2 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Recommended Vacation Rentals in Cape Ann

Find your perfect vacation rental in Cape Ann: from $120 per night

House Cape Ann
Jan 7 - Jan 14
-38%
$400
$250 per night
House ∙ 7 guests ∙ 3 bedrooms
3.5
"Good" (2 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Cottage Cape Ann
Nov 11 - Nov 18
-40%
$450
$272 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (30 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Cottage Cape Ann
May 20 - May 27
$295 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (19 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
Nov 26 - Dec 3
$543 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (22 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
Feb 25 - Mar 4
-53%
$677
$319 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (1 rating)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
Oct 18 - Oct 25
$396 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (3 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
Feb 25 - Mar 4
-52%
$830
$395 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (12 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
Dec 17 - Dec 24
-18%
$550
$450 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (6 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Apartment Cape Ann
Dec 17 - Dec 24
-37%
$190
$120 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0
"Excellent" (6 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Cape Ann

Apartment Cape Ann
Nov 11 - Nov 18
$175 per night
Apartment ∙ 3 guests ∙ 1 bedroom
5.0
"Excellent" (68 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
Dec 27 - Jan 3
$185 per night
House ∙ 5 guests ∙ 3 bedrooms
4.9
"Excellent" (38 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Apartment Cape Ann
Dec 10 - Dec 17
-37%
$190
$120 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0
"Excellent" (6 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Vacation Houses With Pools

Make a splash on your next vacation! Over 30% of in Cape Ann vacation rentals have a swimming pool.

Apartment Pool Cape Ann
Dec 17 - Dec 24
-70%
$550
$165 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.8
"Excellent" (205 ratings)
Cape Ann, North Shore, Massachusetts, United States
Pool
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House Pool Cape Ann
Nov 11 - Nov 18
-62%
$538
$207 per night
House ∙ 4 guests ∙ 2 bedrooms
Cape Ann, North Shore, Massachusetts, United States
Pool
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Bed & Breakfast Pool Cape Ann
Dec 14 - Dec 21
-29%
$228
$162 per night
Bed & Breakfast ∙ 14 guests ∙ 1 bedroom
4.2
"Very good" (2588 ratings)
Cape Ann, North Shore, Massachusetts, United States
Pool
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Dog-Friendly Vacation Rentals

Bring Fido on your next trip and book a stay in one of these pet-friendly rentals in Cape Ann!

Cottage Pet-friendly Cape Ann
May 20 - May 27
$295 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (19 ratings)
Cape Ann, North Shore, Massachusetts, United States
Pet-friendly
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House Pet-friendly Cape Ann
Feb 25 - Mar 4
-53%
$677
$319 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (1 rating)
Cape Ann, North Shore, Massachusetts, United States
Pet-friendly
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House Pet-friendly Cape Ann
Feb 25 - Mar 4
-41%
$675
$395 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (12 ratings)
Cape Ann, North Shore, Massachusetts, United States
Pet-friendly
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Best vacation rentals with a balcony

Looking for a home with a balcony? Check out these vacation homes in Cape Ann with their own private patios and balconies.

House Balcony Cape Ann
Nov 26 - Dec 3
$543 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (22 ratings)
Cape Ann, North Shore, Massachusetts, United States
Balcony
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House Balcony Cape Ann
Dec 17 - Dec 24
-18%
$550
$450 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (6 ratings)
Cape Ann, North Shore, Massachusetts, United States
Balcony
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Apartment Balcony Cape Ann
Dec 17 - Dec 24
-37%
$190
$120 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0
"Excellent" (6 ratings)
Cape Ann, North Shore, Massachusetts, United States
Balcony
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Popular Rental Amenities in Cape Ann

  • Internet (613)
  • TV (553)
  • Air conditioning (513)
  • No smoking (460)
  • Yard (426)
  • Microwave (402)
  • No pets (398)
  • Kitchen (364)
  • Grill (309)
  • Washer (271)
  • Balcony/Patio (234)
  • Dishwasher (221)

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 "TV." Plan your vacation in advance if you want a rental with a jacuzzi or you need a crib for your baby. There are just 3 listed rentals providing "Hot tub" and 46 rentals with "Crib."

The Weather in Cape Ann

max.
Min.
37°
21°
13 days 13
max.
Min.
37°
21°
15 days 15
max.
Min.
45°
28°
14 days 14
max.
Min.
57°
39°
14 days 14
max.
Min.
68°
48°
14 days 14
max.
Min.
75°
55°
12 days 12
max.
Min.
82°
64°
11 days 11
max.
Min.
81°
63°
9 days 9
max.
Min.
73°
54°
8 days 8
max.
Min.
63°
45°
12 days 12
max.
Min.
50°
34°
10 days 10
max.
Min.
43°
28°
16 days 16
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 December while the driest month is September.

7-Day Weather Forecast in Cape Ann

Sun, 27 Nov
51°
46°

15%

3 h

14 mi/h

Mon, 28 Nov
51°
39°

15%

7 h

17 mi/h

Tue, 29 Nov
42°
33°

0%

9 h

7 mi/h

Wed, 30 Nov
55°
44°

15%

5 h

20 mi/h

Thu, 1 Dec
46°
33°

15%

9 h

24 mi/h

Fri, 2 Dec
41°
32°

0%

9 h

9 mi/h

Sat, 3 Dec
48°
42°

15%

2 h

19 mi/h

Accommodations for your vacation in Cape Ann

In Cape Ann, more than half of the 653 vacation properties are house rental, which represent 51.04% of its available accommodations. In addition, house rental there have an average price of $650 per night as well as an average size of 1,780 ft². Furthermore, the majority of house rental in this destination can host 8 guests, which makes it an ideal vacation spot for large groups. If you would prefer to compare another accommodation type, you could check apartment rental, which are the other most typical accommodation type in Cape Ann. The average size of apartment rental in Cape Ann is 830 ft², and the average price is $339 per night.
What are the best places to discover the arts and culture of Cape Ann?

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.

What are the best activities for families 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.

Where are the unique attractions in Cape Ann?

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.

Frequently Asked Questions

How much does it cost to rent a vacation rental in Cape Ann?

The price for House rental and Apartment rental in Cape Ann is $80 per night.

How many vacation rentals are available to book in Cape Ann?

December has the highest amount of available House rental and Apartment rental in Cape Ann, so you can expect plenty of offers, even for last-minute bookings.

What amenities are most popular for vacation homes in Cape Ann?

Most travelers search for Internet, TV, and Yard when booking a vacation rental in Cape Ann.

How many vacation rentals are in Cape Ann?

Cape Ann has 653 House rental and Apartment rental on offer to rent.

Are pets allowed in vacation rentals in Cape Ann?

Finding a cabin rental in Cape Ann that allows dogs is definitely possible, with 75 pet-friendly homes on offfer.

What's the best time of year to travel to Cape Ann?

If booking a vacation rental in Cape Ann, consider that rainy season is usually in December or February, with September often being the driest.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Cape Ann TripAdvisor Vacation Rentals in Cape Ann Vrbo Vacation Rentals in Cape Ann VacationRentals.com Vacation Rentals in Cape Ann HouseTrip Vacation Rentals in Cape Ann FlipKey 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 Novasol Vacation Rentals in Cape Ann HomeEscape Vacation Rentals in Cape Ann

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