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Cape Ann Vacation Rentals

Find 570 available offers from 6 partners
Cape Ann
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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Condo
House
Apartment
Rating
4.5+
4+
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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Best Vacation Home Deals in Cape Ann

Save up to 64%

House Cape Ann
May 4 - May 11
-26%
$400
$297 per night
House ∙ 11 guests ∙ 4 bedrooms
Vacation Home in Rockport with Grill & Yard + Ocean Views
4.8
Outstanding (34 ratings)
Cape Ann, North Shore, Massachusetts, United States
Details
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House Cape Ann
Apr 13 - Apr 20
-26%
$475
$353 per night
House ∙ 9 guests ∙ 3 bedrooms
House in Rockport with Yard & Grill
4.9
Outstanding (129 ratings)
Cape Ann, North Shore, Massachusetts, United States
Details
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House Cape Ann
Dec 9 - Dec 16
-64%
$336
$122 per night
House ∙ 7 guests ∙ 3 bedrooms
Vacation Home in Gloucester with Free Parking
5.0
Outstanding (6 ratings)
Cape Ann, North Shore, Massachusetts, United States
Details
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Compare and find the perfect vacation rental for as little as $106 per night by searching and comparing the 570 properties available in Cape Ann. HomeToGo instantly presents you with the best offers by comparing all of the available properties in Cape Ann from 6 different providers.

Top-Rated Rentals and Accommodations in Cape Ann

Book Vacation Rental Offers with the Highest User Rating

Cottage Cape Ann
Nov 11 - Nov 18
-45%
$549
$300 per night
Cottage ∙ 8 guests ∙ 4 bedrooms
Cottage in Gloucester with Grill & Yard
5.0
Outstanding (202 ratings)
Cape Ann, North Shore, Massachusetts, United States
Details
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Apartment Cape Ann
Nov 21 - Nov 28
$105 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Nice Apartment in Gloucester with Yard & Grill
4.7
Excellent (45 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Cottage Cape Ann
Jun 7 - Jun 14
$179 per night
Cottage ∙ 2 guests ∙ 1 bedroom
Cottage in Rockport with Grill
5.0
Outstanding (27 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 $106 per night

Cottage Cape Ann
Dec 16 - Dec 23
$179 per night
Cottage ∙ 3 guests ∙ 1 bedroom
Cottage in Rockport with Yard
4.9
Outstanding (56 ratings)
Cape Ann, North Shore, Massachusetts, United States
Details
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Apartment Cape Ann
May 4 - May 11
-19%
$134
$109 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Apartment in Rockport + Ocean Views
5.0
Outstanding (6 ratings)
Cape Ann, North Shore, Massachusetts, United States
Details
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Cottage Cape Ann
Nov 18 - Nov 25
-66%
$524
$180 per night
Cottage ∙ 7 guests ∙ 2 bedrooms
Wonderful Cottage in Rockport with Grill
5.0
Outstanding (3 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
Jul 20 - Jul 27
$556 per night
House ∙ 10 guests ∙ 6 bedrooms
House in Gloucester with Grill + Scenic Views
4.9
Outstanding (67 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Apartment Cape Ann
Mar 23 - Mar 30
$185 per night
Apartment ∙ 5 guests ∙ 1 bedroom
Rental Apartment in Gloucester with Grill & Yard + Water Views
4.9
Outstanding (53 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Condo Cape Ann
Jan 5 - Jan 12
$220 per night
Condo ∙ 4 guests ∙ 1 bedroom
Condo in Rockport + Ocean Views + Next to Beach
4.9
Outstanding (44 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
May 4 - May 11
-29%
$638
$456 per night
House ∙ 6 guests ∙ 3 bedrooms
Nice Vacation Home in Gloucester with Second Fireplace + Fantastic Views
5.0
Outstanding (1 rating)
Cape Ann, North Shore, Massachusetts, United States
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Cottage Cape Ann
Aug 24 - Aug 31
$179 per night
Cottage ∙ 3 guests ∙ 1 bedroom
Cottage in Rockport with Grill & Yard + Ocean Views
4.9
Outstanding (106 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Cottage Cape Ann
Jan 13 - Jan 20
-65%
$600
$208 per night
Cottage ∙ 8 guests ∙ 3 bedrooms
Lovely Cottage in Gloucester with Yard & Grill
4.9
Outstanding (34 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Budget-friendly Vacation Rentals in Cape Ann

Find Fantastic yet Inexpensive Offers

House Cape Ann
Apr 20 - Apr 27
$712 per night
House ∙ 16 guests ∙ 8 bedrooms
House in Gloucester with Exterior Patio + Ocean Views + Close to Beach
4.6
Excellent (65 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
Oct 14 - Oct 21
-18%
$425
$350 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Gloucester with Grill & Yard + Gorgeous Views
5.0
Outstanding (36 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
Jan 13 - Jan 20
$494 per night
House ∙ 12 guests ∙ 5 bedrooms
House in Gloucester with Yard & Grill + Beach Nearby
4.9
Outstanding (64 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Cape Ann and book a vacation rental with air conditioning.

Apartment  Cape Ann
Dec 9 - Dec 16
-18%
$499
$410 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Rental Apartment in Rockport
5.0
Outstanding (92 ratings)
Cape Ann, North Shore, Massachusetts, United States
Air conditioning
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House  Cape Ann
Nov 11 - Nov 18
-30%
$422
$297 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Gloucester with Grill & Yard + Marsh Views
4.8
Outstanding (74 ratings)
Cape Ann, North Shore, Massachusetts, United States
Air conditioning
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House  Cape Ann
Nov 3 - Nov 10
$347 per night
House ∙ 9 guests ∙ 4 bedrooms
Beautiful House in Rockport with Grill + Ocean Views
5.0
Outstanding (13 ratings)
Cape Ann, North Shore, Massachusetts, United States
Air conditioning
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Vacation Rentals With Fireplaces

Get warm and cozy on cold winter nights in Cape Ann by booking a vacation home with a fireplace.

House  Cape Ann
Dec 16 - Dec 23
-33%
$827
$558 per night
House ∙ 14 guests ∙ 5 bedrooms
House in Rockport with Yard & Grill + Water Views
4.2
Very good (5 ratings)
Cape Ann, North Shore, Massachusetts, United States
Fireplace
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Cottage  Cape Ann
Sep 14 - Sep 21
$302 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Wonderful Cottage in Rockport with Grill & Yard + Beach Nearby
5.0
Outstanding (79 ratings)
Cape Ann, North Shore, Massachusetts, United States
Fireplace
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Apartment  Cape Ann
Jan 13 - Jan 20
-55%
$1,098
$494 per night
Apartment ∙ 8 guests ∙ 4 bedrooms
Apartment in Gloucester with Yard & Grill + Ocean Views
4.9
Outstanding (19 ratings)
Cape Ann, North Shore, Massachusetts, United States
Fireplace
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Cape Ann accommodation with high-speed internet.

Apartment  Cape Ann
Nov 3 - Nov 10
-69%
$511
$161 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Rental Apartment in Gloucester
5.0
Outstanding (6 ratings)
Cape Ann, North Shore, Massachusetts, United States
Internet
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House  Cape Ann
Dec 9 - Dec 16
-81%
$467
$91 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Rockport with Favorite Barbecue
4.0
Very good
Cape Ann, North Shore, Massachusetts, United States
Internet
Details
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Apartment  Cape Ann
Dec 9 - Dec 16
$85 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Rental Apartment in Rockport with Grill & Yard
5.0
Outstanding (9 ratings)
Cape Ann, North Shore, Massachusetts, United States
Internet
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Popular Rental Amenities in Cape Ann

  • Pet-friendly (74)
  • Air conditioning (483)
  • WiFi (579)
  • Parking (20)
  • Pool (167)
  • Kitchen (317)
  • TV (503)
  • Balcony/patio (242)
  • Fireplace (212)
  • No smoking (402)
  • Grill (248)
  • Washing machine (230)

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 travel with your pet or you want to stay cool in your vacation home, as most accommodations provide "Pets allowed" and "Air conditioning." Plan your vacation in advance if you need a fenced-in backyard or you need a special entrance for wheelchairs. There are just 10 listed rentals providing "Fenced" and 19 rentals with "Wheelchair accessible."

Price and Availability Index in Cape Ann

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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 August (8/31 - 9/7). During this week, a night will cost on average $540. Opt for a getaway in March (3/16 - 3/23) 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 (8/31 - 9/7), 70% of the vacation rentals are booked. More accommodations are available in a week of November (11/11 - 11/18) as the booking rate is only 33%.

The Weather in Cape Ann

max.
Min.
37°
21°
13 days 13
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37°
21°
15 days 15
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45°
28°
14 days 14
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57°
39°
14 days 14
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68°
48°
14 days 14
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75°
55°
12 days 12
max.
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82°
64°
11 days 11
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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

Wed, 27 Sep
57°
55°

5%

2 h

14 mi/h

Thu, 28 Sep
57°
53°

15%

0 h

19 mi/h

Fri, 29 Sep
57°
53°

15%

0 h

15 mi/h

Sat, 30 Sep
66°
57°

10%

7 h

6 mi/h

Sun, 1 Oct
60°
57°

0%

5 h

7 mi/h

Mon, 2 Oct
60°
57°

10%

7 h

13 mi/h

Tue, 3 Oct
57°
55°

15%

0 h

20 mi/h

Accommodations for your vacation in Cape Ann

In Cape Ann, nearly half of the 570 vacation properties are house rental, which represent 48.14% of its available accommodations. In addition, house rental there have an average price of $590 per night as well as an average size of 167 m². Furthermore, the majority of house rental in this destination can host 7 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 75 m², 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.

Information about vacation rentals in Cape Ann

🏡 Vacation rentals available 570 homes
💳 Possible discounts up to 26%
🌙 Nightly prices starting at $106
⭐ Popular amenities Pets allowed, Air conditioning and Internet
🐾 Pet friendly homes 70 homes
🏊 Vacation rentals with pools 167 homes

Frequently Asked Questions

What is the typical price per night for a vacation home in Cape Ann?

The price of a night's stay in Cape Ann starts at $106. If you’re interested in a house rental, the average price is $590 per night. A apartment rental Cape Ann will cost on average $339 per night.

How many vacation rentals are available for booking in Cape Ann?

There are currently 570 rentals in Cape Ann to choose from and book for your next trip.

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

If you're looking to book a vacation rental in Cape Ann, others search for accommodation with Air conditioning, Pets allowed and Internet.

How many vacation homes with pools are in Cape Ann?

There are 167 vacation rentals from 6 providers in Cape Ann.

Are pets allowed in vacation homes in Cape Ann?

Finding a rental in Cape Ann that allows pets is possible, with 70 pet-friendly available.

When is it better to travel to Cape Ann?

July and August are typically the warmest months in Cape Ann with temperatures around 82 °F. January and February in Cape Ann are the coldest, with 21 °F on average.

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