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Cape Ann Vacation Rentals

Find 643 available offers from 6 partners
Cape Ann
Anytime
Guests
Cape Ann
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Condo
House
Apartment
Rating
4.5+
4+

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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Vacation Houses With Pools

Make a splash on your next vacation! Over 29% of in Cape Ann vacation rentals have a swimming pool.

Motel  Cape Ann
Apr 20 - Apr 27
$150 per night
Motel ∙ 8 guests ∙ 1 bedroom

Motel in Gloucester with Patio, Yard & Grill

4.4
Very good (337 ratings)
Cape Ann, North Shore, Massachusetts, United States
Pool
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Bed and breakfast  Cape Ann
Mar 2 - Mar 9
-53%
$257
$120 per night
Bed and breakfast ∙ 8 guests ∙ 1 bedroom

B&B in Rockport with Pool, Yard & Patio

4.3
Very good (1058 ratings)
Cape Ann, North Shore, Massachusetts, United States
Free cancellation
Pool
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Motel  Cape Ann
May 4 - May 11
-41%
$424
$250 per night
Motel ∙ 8 guests ∙ 1 bedroom

Motel in Gloucester with Pool, Patio & Yard + Close to Beach

4.8
Outstanding (382 ratings)
Cape Ann, North Shore, Massachusetts, United States
Free cancellation
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!

House  Cape Ann
Apr 19 - Apr 26
-64%
$612
$222 per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home in Rockport with Free Parking + Ocean View

4.2
Very good (62 ratings)
Cape Ann, North Shore, Massachusetts, United States
Pet-friendly
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House  Cape Ann
May 3 - May 10
-38%
$650
$400 per night
House ∙ 11 guests ∙ 5 bedrooms

Vacation Home in Gloucester with Yard, Grill & Patio + Water Views

5.0
Outstanding (22 ratings)
Cape Ann, North Shore, Massachusetts, United States
Pet-friendly
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Apartment  Cape Ann
Mar 2 - Mar 9
-33%
$200
$135 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Rental Apartment in Gloucester with Yard, Patio & Grill

4.9
Outstanding (84 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  Cape Ann
Mar 2 - Mar 9
$800 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Gloucester with Grill & Patio + Fantastic View

5.0
Outstanding (2 ratings)
Cape Ann, North Shore, Massachusetts, United States
Balcony
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House  Cape Ann
Aug 24 - Aug 31
$315 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Gloucester with Private Parking

5.0
Outstanding (36 ratings)
Cape Ann, North Shore, Massachusetts, United States
Balcony
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House  Cape Ann
Feb 15 - Feb 22
-21%
$950
$750 per night
House ∙ 10 guests ∙ 5 bedrooms

House in Rockport with Yard, Patio & Grill

5.0
Outstanding (37 ratings)
Cape Ann, North Shore, Massachusetts, United States
Balcony
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Best Vacation Home Deals in Cape Ann

Save up to 72%

House Cape Ann
May 3 - May 10
-20%
$375
$300 per night
House ∙ 11 guests ∙ 4 bedrooms

Vacation Home in Rockport with Patio, Grill & Yard + Ocean Views

4.8
Outstanding (36 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
Mar 2 - Mar 9
-41%
$672
$394 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Rockport with Serene Garden + Beautiful Views

4.6
Excellent (17 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
Mar 2 - Mar 9
-72%
$356
$100 per night
House ∙ 7 guests ∙ 3 bedrooms

Vacation Home in Gloucester with Free Parking

5.0
Outstanding (20 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Compare and find the perfect vacation rental for as little as $93 per night by searching and comparing the 643 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.

Recommended Vacation Rentals in Cape Ann

Find your perfect vacation rental in Cape Ann: from $93 per night

House Cape Ann
Sep 21 - Sep 28
$425 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Gloucester with Grill, Yard & Patio + Gorgeous Views

5.0
Outstanding (37 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
May 4 - May 11
$206 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Gloucester with Patio, Grill & Yard + Marsh Views

4.8
Outstanding (78 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Apartment Cape Ann
Mar 2 - Mar 9
$105 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Nice Rental Apartment in Gloucester with Yard & Grill

5.0
Outstanding (4 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Cottage Cape Ann
Mar 2 - Mar 9
$93 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Pleasant Cottage in Gloucester with Yard, Grill & Patio + Ocean Views

4.7
Excellent (24 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
May 3 - May 10
$357 per night
House ∙ 9 guests ∙ 3 bedrooms

House in Rockport with Yard, Patio & Grill

4.9
Outstanding (138 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
Nov 16 - Nov 23
$454 per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home in Gloucester with Yard, Grill & Patio

4.9
Outstanding (19 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Cottage Cape Ann
Jun 1 - Jun 8
$127 per night
Cottage ∙ 2 guests ∙ 1 bedroom

Cottage in Rockport with Patio + Ocean View

4.7
Excellent (93 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Cottage Cape Ann
Apr 27 - May 4
$179 per night
Cottage ∙ 3 guests ∙ 1 bedroom

Cottage in Rockport with Grill, Patio & Yard + Ocean Views

4.9
Outstanding (124 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Cottage Cape Ann
Mar 2 - Mar 9
$153 per night
Cottage ∙ 3 guests ∙ 1 bedroom

Cottage in Rockport with Yard & Patio

5.0
Outstanding (66 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
Jun 15 - Jun 22
$151 per night
House ∙ 3 guests ∙ 1 bedroom

Beautiful Vacation Home in Gloucester with Private Parking + Water Views

4.9
Outstanding (86 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Apartment Cape Ann
Nov 9 - Nov 16
$175 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Rental Apartment in Gloucester with Private Patio + Ocean Views

5.0
Outstanding (115 ratings)
Cape Ann, North Shore, Massachusetts, United States
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House Cape Ann
May 4 - May 11
$414 per night
House ∙ 9 guests ∙ 4 bedrooms

Beautiful House in Rockport with Grill & Patio + Ocean Views

5.0
Outstanding (27 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Top-Rated Rentals and Accommodations in Cape Ann

Book Vacation Rental Offers with the Highest User Rating

House Cape Ann
May 25 - Jun 1
-34%
$518
$343 per night
House ∙ 5 guests ∙ 3 bedrooms

House in Gloucester with Grill, Patio & Yard

5.0
Outstanding (13 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Cottage Cape Ann
Nov 2 - Nov 9
$180 per night
Cottage ∙ 7 guests ∙ 2 bedrooms

Wonderful Cottage in Rockport with Grill & Patio

5.0
Outstanding (4 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Apartment Cape Ann
Aug 24 - Aug 31
$103 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Nice Apartment in Gloucester with Yard & Grill

4.8
Outstanding (52 ratings)
Cape Ann, North Shore, Massachusetts, United States
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Popular Rental Amenities in Cape Ann

  • Pet-friendly (94)
  • Air conditioning (598)
  • WiFi (642)
  • Parking (20)
  • Pool (186)
  • Kitchen (370)
  • TV (611)
  • Balcony/patio (454)
  • Fireplace (273)
  • No smoking (624)
  • Grill (285)
  • Washing machine (276)

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 need a vacation home with air conditioning, 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 wheelchair accessible vacation rental. There are just 10 listed rentals providing "Fenced" and 94 rentals with "Wheelchair accessible."

The Weather in Cape Ann

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37°
21°
13 days 13
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21°
15 days 15
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28°
14 days 14
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39°
14 days 14
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48°
14 days 14
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75°
55°
12 days 12
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82°
64°
11 days 11
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81°
63°
9 days 9
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73°
54°
8 days 8
max.
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63°
45°
12 days 12
max.
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50°
34°
10 days 10
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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

Mon, 26 Feb
44°
42°

0%

6 h

11 mi/h

Tue, 27 Feb
42°
39°

55%

1 h

14 mi/h

Wed, 28 Feb
50°
48°

15%

0 h

25 mi/h

Thu, 29 Feb
32°
30°

15%

5 h

17 mi/h

Fri, 1 Mar
44°
44°

10%

5 h

16 mi/h

Sat, 2 Mar
42°
42°

10%

6 h

4 mi/h

Sun, 3 Mar
41°
41°

0%

6 h

11 mi/h

Accommodations for your vacation in Cape Ann

In Cape Ann, more than half of the 643 vacation properties are house rental, which represent 50.46% of its available accommodations. In addition, house rental there have an average price of $622 per night as well as an average size of 164 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 83 m², and the average price is $383 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 643 rentals
💳 Possible discounts up to 60%
🌙 Nightly prices starting at $93
⭐ Popular amenities Pets allowed, Air conditioning and Internet
🐾 Pet friendly homes 91 homes
🏊 Vacation rentals with pools 186 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 $93. If you’re interested in a house rental, the average price is $622 per night. A apartment rental Cape Ann will cost on average $383 per night.

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

There are currently 643 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 186 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 91 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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