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Cape Ann Vacation Rentals

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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.

Save up to 72%

Best Vacation Home Deals in Cape Ann

Apr 8 - Apr 15

-72%

~~$540~~

$150 per night

Apartment ∙ 2 guests ∙ 1 bedroom

Rental Apartment in Rockport with Electric Fireplace + House View

5.0

"Excellent" (126 ratings)

Cape Ann, North Shore, Massachusetts, United States

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Dec 9 - Dec 16

-52%

~~$549~~

$263 per night

House ∙ 12 guests ∙ 4 bedrooms

Nice Vacation Home in Gloucester with Yard & Grill + Water Views + Next to Beach

5.0

"Excellent" (80 ratings)

Cape Ann, North Shore, Massachusetts, United States

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Jun 1 - Jun 8

-27%

~~$650~~

$475 per night

House ∙ 4 guests ∙ 3 bedrooms

Vacation Home in Gloucester with Easy Parking + Incredible Views

5.0

"Excellent" (62 ratings)

Cape Ann, North Shore, Massachusetts, United States

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Compare and find the perfect vacation rental for as little as $116 per night by searching and comparing the 659 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

May 13 - May 20

-16%

~~$376~~

$315 per night

Cottage ∙ 4 guests ∙ 3 bedrooms

Wonderful Cottage in Rockport with Grill & Yard + Beach Nearby

5.0

"Excellent" (76 ratings)

Cape Ann, North Shore, Massachusetts, United States

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Sep 24 - Oct 1

-23%

~~$651~~

$500 per night

House ∙ 4 guests ∙ 3 bedrooms

Vacation Home in Gloucester with Easy Parking + Incredible Views

5.0

"Excellent" (62 ratings)

Cape Ann, North Shore, Massachusetts, United States

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Feb 10 - Feb 17

-65%

~~$1,080~~

$381 per night

House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Rockport with Yard & Grill

5.0

"Excellent" (35 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 $116 per night

May 20 - May 27

-24%

~~$491~~

$380 per night

House ∙ 4 guests ∙ 3 bedrooms

House in Rockport with Yard & Grill

4.9

"Excellent" (132 ratings)

Cape Ann, North Shore, Massachusetts, United States

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Feb 17 - Feb 24

-22%

~~$240~~

$188 per night

Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Rockport with Grill & Yard

4.9

"Excellent" (140 ratings)

Cape Ann, North Shore, Massachusetts, United States

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Mar 27 - Apr 3

-44%

~~$475~~

$297 per night

Cottage ∙ 8 guests ∙ 4 bedrooms

Cottage in Gloucester with Grill & Yard

5.0

"Excellent" (186 ratings)

Cape Ann, North Shore, Massachusetts, United States

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Feb 17 - Feb 24

-23%

~~$405~~

$313 per night

House ∙ 11 guests ∙ 4 bedrooms

Vacation Home in Rockport with Grill & Yard + Ocean Views

4.7

"Outstanding" (35 ratings)

Cape Ann, North Shore, Massachusetts, United States

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Apr 8 - Apr 15

-72%

~~$539~~

$151 per night

Apartment ∙ 2 guests ∙ 1 bedroom

Rental Apartment in Rockport with Electric Fireplace + House View

5.0

"Excellent" (126 ratings)

Cape Ann, North Shore, Massachusetts, United States

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Sep 7 - Sep 14

$179 per night

Cottage ∙ 3 guests ∙ 1 bedroom

Cottage in Rockport with Grill & Yard + Ocean Views

5.0

"Excellent" (94 ratings)

Cape Ann, North Shore, Massachusetts, United States

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Dec 2 - Dec 9

-52%

~~$550~~

$261 per night

House ∙ 12 guests ∙ 4 bedrooms

Nice Vacation Home in Gloucester with Yard & Grill + Water Views + Next to Beach

5.0

"Excellent" (80 ratings)

Cape Ann, North Shore, Massachusetts, United States

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May 22 - May 29

-21%

~~$200~~

$157 per night

Apartment ∙ 4 guests ∙ 1 bedroom

Lovely Apartment in Gloucester with Private Balcony

5.0

"Excellent" (110 ratings)

Cape Ann, North Shore, Massachusetts, United States

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Aug 12 - Aug 19

$1,428 per night

House ∙ 12 guests ∙ 5 bedrooms

House in Rockport with Juliet Balcony + Spectacular View

5.0

"Excellent" (53 ratings)

Cape Ann, North Shore, Massachusetts, United States

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Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Cape Ann

Feb 17 - Feb 24

-22%

~~$240~~

$188 per night

Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Rockport with Grill & Yard

4.9

"Excellent" (140 ratings)

Cape Ann, North Shore, Massachusetts, United States

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May 20 - May 27

-23%

~~$495~~

$380 per night

House ∙ 4 guests ∙ 3 bedrooms

House in Rockport with Yard & Grill

4.9

"Excellent" (132 ratings)

Cape Ann, North Shore, Massachusetts, United States

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Aug 3 - Aug 10

$1,428 per night

House ∙ 12 guests ∙ 5 bedrooms

House in Rockport with Juliet Balcony + Spectacular View

5.0

"Excellent" (53 ratings)

Cape Ann, North Shore, Massachusetts, United States

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Vacation Houses With Pools

Make a splash on your next vacation! Over 23% of in Cape Ann vacation rentals have a swimming pool.

Jun 3 - Jun 10

$270 per night

Apartment ∙ 8 guests ∙ 3 bedrooms

Apartment in Rockport with Yard, Grill & Pool + Sunrise Views

5.0

"Excellent" (48 ratings)

Cape Ann, North Shore, Massachusetts, United States

Pool

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May 25 - Jun 1

-46%

~~$624~~

$339 per night

House ∙ 4 guests ∙ 2 bedrooms

Wonderful Vacation Home in Gloucester with Pool, Grill & Yard

Cape Ann, North Shore, Massachusetts, United States

Pool

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Sep 16 - Sep 23

$286 per night

Motel ∙ 4 guests ∙ 1 bedroom

Motel in Gloucester with Patio, Yard & Pool

4.8

"Excellent" (78 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!

Mar 27 - Apr 3

-44%

~~$473~~

$267 per night

Cottage ∙ 8 guests ∙ 4 bedrooms

Cottage in Gloucester with Grill & Yard

5.0

"Excellent" (187 ratings)

Cape Ann, North Shore, Massachusetts, United States

Pet-friendly

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Apr 1 - Apr 8

-40%

~~$996~~

$598 per night

House ∙ 8 guests ∙ 3 bedrooms

House in Rockport with Granite Fireplace + Gorgeous Views

5.0

"Excellent" (38 ratings)

Cape Ann, North Shore, Massachusetts, United States

Pet-friendly

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Dec 9 - Dec 16

-21%

~~$366~~

$287 per night

House ∙ 9 guests ∙ 3 bedrooms

Vacation Home in Rockport with Yard & Grill

4.9

"Excellent" (17 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.

May 24 - May 31

-21%

~~$200~~

$158 per night

Apartment ∙ 4 guests ∙ 1 bedroom

Lovely Apartment in Gloucester with Private Balcony

5.0

"Excellent" (110 ratings)

Cape Ann, North Shore, Massachusetts, United States

Balcony

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Dec 27 - Jan 3

-22%

~~$406~~

$315 per night

House ∙ 11 guests ∙ 4 bedrooms

Vacation Home in Rockport with Grill & Yard + Ocean Views

4.7

"Outstanding" (35 ratings)

Cape Ann, North Shore, Massachusetts, United States

Balcony

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Nov 25 - Dec 2

$179 per night

Cottage ∙ 3 guests ∙ 1 bedroom

Cottage in Rockport with Grill & Yard + Ocean Views

5.0

"Excellent" (94 ratings)

Cape Ann, North Shore, Massachusetts, United States

Balcony

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Popular Rental Amenities in Cape Ann

Internet (604)
TV (571)
Air conditioning (539)
No smoking (483)
Microwave (414)
No pets (403)
Kitchen (382)
Yard (375)
Grill (303)
Washer (282)
Dishwasher (239)
Balcony/Patio (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 can't imagine a vacation without internet or you never miss an episode of your favorite show, as most accommodations provide "Internet" and "TV." Plan your vacation in advance if you want a rental providing a crib or you bring your pet everywhere. There are just 43 listed rentals providing "Smoking" and 91 rentals with "Fenced."

The Weather in Cape Ann

- 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

Mon, 27 Mar

42°

37°

Tue, 28 Mar

39°

37°

Wed, 29 Mar

41°

35°

Thu, 30 Mar

39°

32°

Fri, 31 Mar

41°

33°

Sat, 1 Apr

48°

44°

Sun, 2 Apr

46°

39°

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Accommodations for your vacation in Cape Ann

In Cape Ann, more than half of the 659 vacation properties are house rental, which represent 50.25% of its available accommodations. In addition, house rental there have an average price of $637 per night as well as an average size of 158 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 80 m², and the average price is $369 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	659 properties
💳 Possible discounts	up to 27%
🌙 Nightly prices starting at	$116
⭐ Popular amenities	Internet, TV and Air conditioning
🐾 Pet friendly accommodations	94 properties
🏊 Vacation rentals with pools	150 properties

Frequently Asked Questions

What is the average price per night for a vacation rental in Cape Ann?

The nightly price of accommodations in Cape Ann starts at $116. If you would like to stay in a house rental, the average price is $637 per night. A apartment rental Cape Ann will cost on average $369 per night.

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

There are currently 659 vacation homes to choose from for your trip.

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

If you're looking to book a vacation rental in Cape Ann, the most popular amenities are: Internet, TV and Air conditioning.

How many vacation homes with pools are there in Cape Ann?

Discover 150 vacation rentals available in Cape Ann for renting.

Are dogs allowed in vacation rentals in Cape Ann?

If you are traveling with a pet in Cape Ann - 14% of vacation homes are pet-friendly.

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

July and August are usually 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.

We list offers from thousands of providers, including:

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.

Cape Ann Vacation Rentals

Choose the perfect vacation rental

Enjoy fresh Atlantic air with a Cape Ann vacation rental

Best Vacation Home Deals in Cape Ann

Top-Rated Rentals and Accommodations in Cape Ann

Recommended Vacation Rentals in Cape Ann

Budget-friendly Vacation Rentals in Cape Ann

Vacation Houses With Pools

Dog-Friendly Vacation Rentals

Best vacation rentals with a balcony

Popular Rental Amenities in Cape Ann

The Weather in Cape Ann

7-Day Weather Forecast in Cape Ann

Accommodations for your vacation in Cape Ann

Discover a 400-year-old port

Go whale watching

Beautiful Boston

Information about vacation rentals in Cape Ann

Frequently Asked Questions

What is the average price per night for a vacation rental in Cape Ann?

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

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

How many vacation homes with pools are there in Cape Ann?

Are dogs allowed in vacation rentals in Cape Ann?

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

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